desethylamiodarone profile

desethylamiodarone: metabolite of amiodarone; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	104774
CHEMBL ID	1600
CHEBI ID	180711
SCHEMBL ID	4535165
MeSH ID	M0110249

Synonym
(2-butyl-1-benzouran-3-yl)-[4-[2-(ethylamino)ethoxy]-3,5-diiodophenyl]methanone
CHEBI:180711
methanone, (2-butyl-3-benzofuranyl)(4-(2-(ethylamino)ethoxy)-3,5-diiodophenyl)-
n-desethylamiodarone
n-deethylamiodarone
n-monodesethylamiodarone
(2-butyl-3-benzofuranyl)(4-(2-(ethylamino)ethoxy)-3,5-diiodophenyl)methanone
lb 33020
bdbm18958
deethylamiodarone
chembl1600 ,
desethylamiodarone
l 33520
(2-{4-[(2-butyl-1-benzofuran-3-yl)carbonyl]-2,6-diiodophenoxy}ethyl)(ethyl)amine
83409-32-9
mono-n-desethylamiodarone
FT-0665924
(2-butyl-1-benzofuran-3-yl)-[4-[2-(ethylamino)ethoxy]-3,5-diiodophenyl]methanone
m31fu99e3y ,
unii-m31fu99e3y
dami
amiodarone hydrochloride impurity b [ep impurity]
lb-33020
(2-butylbenzofuran-3-yl)(4-(2-(ethylamino)ethoxy)-3,5-diiodophenyl)methanone
desethylaminodarone [who-dd]
amiodarone metabolite m7
desethylaminodarone
DTXSID00232344
SCHEMBL4535165
(2-butyl-3-benzofuranyl)[4-[2-(ethylamino)ethoxy]-3,5-diiodophenyl]-methanone
VXOKDLACQICQFA-UHFFFAOYSA-N
AKOS027383912
amiodarone-m n-desethyl
desethyl amiodarone
Q27283413
discontinued see: d288731

Research Excerpts

Overview

Desethylamiodarone (DEA) acts as a competitive inhibitor of triiodothyronine (T3) binding to the alpha1-thyroid hormone receptor (TR alpha1) but as a non-competitive inhibitor with respect to TR beta1.

Excerpt	Reference	Relevance
"Desethylamiodarone (DEA) acts as a competitive inhibitor of triiodothyronine (T3) binding to the alpha1-thyroid hormone receptor (TR alpha1) but as a non-competitive inhibitor with respect to TR beta1. "	( Effect of mutations in the beta1-thyroid hormone receptor on the inhibition of T3 binding by desethylamiodarone. Bakker, O; Chatterjee, VK; van Beeren, HC; Wiersinga, WM, 1999)	1.97
"Desethylamiodarone (DA) is a major metabolite of amiodarone (AM), a Class III antiarrhythmic drug. "	( A comparison of plasma, white blood cell, red blood cell, and tissue distribution of amiodarone and desethylamiodarone in anesthetized dogs. Bandyopadhyay, S; Somani, P, 1987)	1.93

Effects

Excerpt	Reference	Relevance
"Desethylamiodarone has been identified as the principal lipophilic metabolite of amiodarone present in plasma specimens from amiodarone-treated patients. "	( Identification and measurement of desethylamiodarone in blood plasma specimens from amiodarone-treated patients. Farmer, PB; Flanagan, RJ; Holt, DW; Storey, GC, 1982)	1.99

Treatment

Desethylamiodarone treatment resulted in a neutrophilic alveolitis, but the levels of TNF-alpha and TGF-beta were not significantly different from control animals. Treatment with desethylamodarone also induced phospholipidosis in AM.

Excerpt	Reference	Relevance
"Desethylamiodarone treatment resulted in a neutrophilic alveolitis, but the levels of TNF-alpha and TGF-beta were not significantly different from control animals."	( Amiodarone-induced pulmonary toxicity in Fischer rats: release of tumor necrosis factor alpha and transforming growth factor beta by pulmonary alveolar macrophages. Gairola, CG; Reinhart, PG, 1997)	1.02
"Desethylamiodarone pretreatment improved survival without altering the occurrence of different types of arrhythmias during the first 20 min after coronary ligation."	( Antiarrhythmic effect of desethylamiodarone in conscious rats. Bódi, I; Rabloczky, G; Varró, A, 1987)	1.3
"Treatment with desethylamiodarone also induced phospholipidosis in AM."	( Amiodarone-induced phospholipidosis in rat alveolar macrophages. Kacew, S; Ogle, CL; Reasor, MJ; Walker, ER, 1988)	0.61

Toxicity

Benzofuran antiarrhythmic drug amiodarone has a direct toxic effect on the human thyroid gland. The relationship of steady-state serum levels of amiodrone and its major metabolite was assessed. Desethylamodarone was more toxic than amiodlarone in the cultured hepatocytes.

Excerpt	Reference	Relevance
" Desethylamiodarone was more toxic than amiodarone in the cultured hepatocytes."	( Amiodarone- and desethylamiodarone-induced myelinoid inclusion bodies and toxicity in cultured rat hepatocytes. Bandyopadhyay, S; Gross, SA; Klaunig, JE; Somani, P, 1990)	1.54
" Using lactate dehydrogenase release into the medium to quantitate cell death, both drugs were found to cause cell death in a concentration-dependent manner within 24 hr of incubation; this data showed desethylamiodarone to be significantly more toxic than amiodarone."	( Amiodarone and desethylamiodarone toxicity in isolated hepatocytes in culture. Bandyopadhyay, S; Gross, SA; Klaunig, JE; Somani, P, 1989)	0.82
"Since recent in vivo evidence suggests that the benzofuran antiarrhythmic drug amiodarone has a direct toxic effect on the human thyroid gland, we have investigated the effects of both amiodarone and its metabolite desethylamiodarone on a novel immortalized functional human thyrocyte line (SGHTL-34 cells)."	( Cytotoxic effects of amiodarone and desethylamiodarone on human thyrocytes. Beddows, SA; Johnstone, AP; McNerney, R; Nussey, SS; Page, SR; Taylor, AH; Whitley, GS, 1989)	0.74
"Amiodarone pulmonary toxicity represents an example of a life-threatening adverse drug reaction."	( Amiodarone pulmonary toxicity: biochemical evidence for a cellular phospholipidosis in the bronchoalveolar lavage of human subjects. Martin, WJ; Standing, JE, 1988)	0.27
" Sixty-three patients (55%) had one or more adverse effects attributed to amiodarone."	( Relation between amiodarone and desethylamiodarone plasma concentrations and electrophysiologic effects, efficacy and toxicity. DiMarco, JP; Greenberg, ML; Kaiser, DL; Lerman, BB; Shipe, JR, 1987)	0.56
"The relationship of steady-state serum levels of amiodarone and its major metabolite, desethylamiodarone, to therapeutic and toxic effects was evaluated in 111 patients treated for supraventricular and ventricular arrhythmias."	( Relationship of steady-state serum concentrations of amiodarone and desethylamiodarone to therapeutic efficacy and adverse effects. Falik, R; Flores, BT; Gibson, GA; Josephson, ME; Marchlinski, FE; Shaw, L, 1987)	0.73
"The relationship of apparent steady-state serum concentrations of amiodarone and its metabolite, desethylamiodarone, to therapeutic and toxic effects was assessed in 127 patients who had treatment-resistant ventricular or supraventricular arrhythmias or were intolerant to other agents."	( Steady-state serum amiodarone concentrations: relationships with antiarrhythmic efficacy and toxicity. Belhassen, B; Greenspan, AM; Greenspon, AJ; Horowitz, LN; Rotmensch, HH; Shoshani, D; Spielman, SR; Swanson, BN; Vlasses, PH, 1984)	0.49
"The relationships between size of loading dose and drug concentration, size of maintenance dose and drug concentration, and pulmonary and cutaneous adverse side effects and drug dosage were examined in patients given amiodarone."	( Relationships between amiodarone dosage, drug concentrations, and adverse side effects. Heger, JJ; Prystowsky, EN; Zipes, DP, 1983)	0.27
" Amiodarone appeared to be safe and did not have to be discontinued because of intolerable side effects."	( Efficacy, safety, and determinants of conversion of atrial fibrillation and flutter with oral amiodarone. Crijns, HJ; de Kam, PJ; Gosselink, AT; Lie, KI; Tieleman, RG; van den Berg, MP; van Gelder, IC; van Gilst, WH, 1997)	0.3
"Amiodarone (AM), a drug used in the treatment of cardiac dysrrhythmias, can produce severe pulmonary adverse effects, including fibrosis."	( Direct mitochondrial dysfunction precedes reactive oxygen species production in amiodarone-induced toxicity in human peripheral lung epithelial HPL1A cells. Brien, JF; Comeau, JL; Hill, BC; Ji, Y; Massey, TE; Nicolescu, AC; Racz, WJ; Takahashi, T, 2008)	0.35
" First, we showed that 50μM amiodarone is more toxic to primary human hepatocytes after CYP induction with rifampicin."	( The role of CYP3A4 in amiodarone-associated toxicity on HepG2 cells. Brecht, K; Krähenbühl, S; Lindinger, PW; Maseneni, S; Morand, R; Török, M; Zahno, A, 2011)	0.37
"Amiodarone is a widely used potent antiarrhythmic for the treatment of cardiac disease; however, its use is often discontinued due to numerous adverse effects, including hepatotoxicity."	( The role of CYP 3A4 and 1A1 in amiodarone-induced hepatocellular toxicity. Bryant, MS; Guo, L; Ning, B; Ren, Z; Wu, Q; Xuan, J, 2016)	0.43

Pharmacokinetics

Excerpt	Reference	Relevance
" Because of the long elimination half-life for amiodarone previously reported in healthy volunteers after single doses of amiodarone and the frequent administration of amiodarone associated with this half-life, a modified equation for a continuous infusion was used to describe each subject's ASC versus time data."	( Effect of phenytoin on the clinical pharmacokinetics of amiodarone. Gear, K; Hoyer, GL; Karol, MD; Marcus, FI; Nolan, PE, 1990)	0.28
"Phenobarbitone pretreatment has been shown to increase amiodarone total clearance and decrease amiodarone elimination half-life after a single intravenous amiodarone dose in the rat."	( Effect of phenobarbitone on the pharmacokinetics and tissue levels of amiodarone in the rat. Bernhard, R; Ferguson, RK; Fruncillo, RJ; Swanson, BN; Vlasses, PH, 1985)	0.27
" Terminal half-life (t1/2 el) of amiodarone increased from a mean (SD) 24."	( Amiodarone pharmacokinetics in coronary patients: differences between acute and one-month chronic dosing. Cheymol, G; Coumel, P; Escoubet, B; Jaillon, P; Poirier, JM; Richard, MO, )	0.13
" The administration of a single intravenous dose of amiodarone hydrochloride, 50 mg/kg, reduced antipyrine clearance by 32% and increased the half-life by 46%."	( Effect of amiodarone and desethylamiodarone on the pharmacokinetics of antipyrine in the rat. Knowlton, PW; Liu, LL; Svensson, CK, 1987)	0.58
" The decline in amiodarone plasma concentration after a single intravenous 400 mg dose was described by a triexponential decay equation, with a mean terminal half-life (t1/2) of 34."	( Pharmacokinetics and body distribution of amiodarone in man. Maes, RA; Plomp, TA; Robles de Medina, EO; van Lier, T; van Rossum, JM, 1984)	0.27
" In patients the terminal elimination half-life was on the order of 40 days, with a more rapid phase of elimination in the first few days following the withdrawal of therapy."	( Amiodarone pharmacokinetics. Holt, DW; Jackson, PR; Storey, GC; Tucker, GT, 1983)	0.27
"Amiodarone is an increasingly popular and uniquely effective antiarrhythmic agent for which population pharmacokinetic parameters in patients receiving long-term oral therapy have not been defined previously."	( Population pharmacokinetics of long-term oral amiodarone therapy. Bouillon, T; Pollak, PT; Shafer, SL, 2000)	0.31
" Rapid distribution half-life was 17 hours, and terminal half-life was 55 days."	( Population pharmacokinetics of long-term oral amiodarone therapy. Bouillon, T; Pollak, PT; Shafer, SL, 2000)	0.31
" Evaluation of the safety of the combination is needed to confirm that the relatively small pharmacokinetic changes in this study are of no clinical significance."	( A pharmacokinetic study of the combined administration of amiodarone and ximelagatran, an oral direct thrombin inhibitor. Carlson, GF; Eriksson, UG; Gillette, S; Hamer, JE; Kowey, PR; Sarich, TC; Schützer, KM; Teng, R, 2004)	0.32
" Amiodarone had a significantly lower (approximately 50%) clearance than DEA, although the volume of distribution and terminal phase half-life did not differ significantly."	( Pharmacokinetics of desethylamiodarone in the rat after its administration as the preformed metabolite, and after administration of amiodarone. Brocks, DR; Hamdy, DA; Shayeganpour, A, 2008)	0.67
" The pharmacokinetic profile, blood pressure and electrocardiographic analyses were obtained on a timely basis after up to 77 days."	( Pharmacokinetics of intravenous amiodarone and its electrocardiographic effects on healthy Japanese subjects. Hagiwara, N; Irie, S; Kasanuki, H; Shiga, T; Tanaka, T, 2011)	0.37
" Here, using amiodarone (AMIO) as an example, we demonstrate the use of physiologically based pharmacokinetic (PBPK) modeling to assess how a potential inhibitory metabolite can contribute to clinically significant DDIs."	( Physiologically based pharmacokinetic modeling to predict drug-drug interactions involving inhibitory metabolite: a case study of amiodarone. Chen, Y; Hop, CE; Mao, J, 2015)	0.42
" The present study aimed to build a whole-body physiologically based pharmacokinetic (PBPK) model for AMD and DEA in rats."	( A Physiologically Based Pharmacokinetic Model of Amiodarone and its Metabolite Desethylamiodarone in Rats: Pooled Analysis of Published Data. Cai, Y; Chen, F; Hu, ZY; Jia, WW; Lu, JT; Zhao, YS, 2016)	0.66
" The key pharmacokinetic properties of AMD, such as extensive tissue distribution, substantial storage in the fat tissue, and long half-lives in many tissues, were closely reflected."	( A Physiologically Based Pharmacokinetic Model of Amiodarone and its Metabolite Desethylamiodarone in Rats: Pooled Analysis of Published Data. Cai, Y; Chen, F; Hu, ZY; Jia, WW; Lu, JT; Zhao, YS, 2016)	0.66
"Some population pharmacokinetic models for amiodarone (AMD) did not incorporate N-desethylamiodarone (DEA) concentration."	( Population Pharmacokinetic Model of Amiodarone and N-Desethylamiodarone Focusing on Glucocorticoid and Inflammation. Akai, N; Hanada, K; Hirai, T; Itoh, T; Iwamoto, T; Kasai, H; Takahashi, M; Uchida, S, 2022)	1.2

Compound-Compound Interactions

Excerpt	Reference	Relevance
"A rapid method for the quantification of amiodarone and desethylamiodarone in animal plasma using high-performance liquid chromatography combined with UV detection (HPLC-UV) is presented."	( Determination of amiodarone and desethylamiodarone in horse plasma and urine by high-performance liquid chromatography combined with UV detection and electrospray ionization mass spectrometry. Baert, K; Croubels, S; De Backer, P; De Clercq, D; Deprez, P; Maes, A; van Loon, G, 2006)	0.86
"Evaluation of drug-drug interaction (DDI) involving circulating inhibitory metabolites of perpetrator drugs has recently drawn more attention from regulatory agencies and pharmaceutical companies."	( Physiologically based pharmacokinetic modeling to predict drug-drug interactions involving inhibitory metabolite: a case study of amiodarone. Chen, Y; Hop, CE; Mao, J, 2015)	0.42

Bioavailability

Excerpt	Reference	Relevance
" Assuming there were no changes in the bioavailability of amiodarone during continuous administration, these findings strongly suggest induction of amiodarone metabolism by phenytoin."	( Effect of phenytoin on the clinical pharmacokinetics of amiodarone. Gear, K; Hoyer, GL; Karol, MD; Marcus, FI; Nolan, PE, 1990)	0.28
" The mean bioavailability of oral amiodarone ranged from 17% to 60% with an average of 39%."	( Pharmacokinetics and body distribution of amiodarone and desethylamiodarone in rats after oral administration. Maes, RA; Plomp, TA; Van Rossum, JM; Wiersinga, WM, )	0.38
"The relative and absolute bioavailability of different oral forms of amiodarone was examined in 12 subjects."	( Absolute bioavailability of amiodarone in normal subjects. Berger, Y; Desager, JP; Harvengt, C; Pacco, M; Pourbaix, S, 1985)	0.27
" The bioavailability of oral amiodarone was only 31 +/- 26%, in part due to first-pass metabolism."	( Pharmacokinetics and body distribution of amiodarone in man. Maes, RA; Plomp, TA; Robles de Medina, EO; van Lier, T; van Rossum, JM, 1984)	0.27
"1 fold) than oral DEA and oral bioavailability of AM (46%) was greater than DEA (17%)."	( Pharmacokinetics of desethylamiodarone in the rat after its administration as the preformed metabolite, and after administration of amiodarone. Brocks, DR; Hamdy, DA; Shayeganpour, A, 2008)	0.67

Dosage Studied

The defibrillation energy requirement does not correlate with the plasma concentrations of amiodarone, desethylamiodar one, or amiodrone plus desethylation. Desethylamodarone serum and tissue concentrations were substantially lower than the corresponding amiodArone concentrations.

Excerpt	Relevance	Reference
"Two intravenous amiodarone dosing schedules in 28 patients with atrial fibrillation arisen less than 10 days before, were evaluated."	( [Amiodarone and its infusion velocity in recent-onset atrial fibrillation]. Bonino, ML; Ramus, GV; Tonda, L; Veglio, F, 1991)	0.28
"A comparative study of the plasma disposition and tissue distribution of amiodarone and its proximate metabolite, desethylamiodarone, for a single oral dose and short-term oral dosage regimens was conducted in the dog."	( Disposition of amiodarone and its proximate metabolite, desethylamiodarone, in the dog for oral administration of single-dose and short-term drug regimens. Abdollah, H; Armstrong, PW; Brennan, FJ; Brien, JF; Jimmo, S, )	0.59
" The tissue ultrastructural changes after repeated DEA dosing were qualitatively similar to our previous findings with amiodarone."	( Amiodarone toxicity. II. Desethylamiodarone-induced phospholipidosis and ultrastructural changes during repeated administration in rats. Guha, M; Kannan, R; Sarma, JS; Venkataraman, K, 1991)	0.58
" The ultrastructural changes in liver, lung, and alveolar macrophages in saline controls and in rats on the two amiodarone dosage regimens were investigated."	( Tissue drug accumulation and ultrastructural changes during amiodarone administration in rats. Guha, M; Kannan, R; Sarma, JS; Venkataraman, K, 1989)	0.28
" These data emphasize the highly variable cellular distribution of amiodarone and desethylamiodarone in the same patient on stable dosage over time."	( Individual variability of amiodarone distribution in plasma and erythrocytes: implications for therapeutic monitoring. Burgess, CD; Maling, TJ; Purdie, G; Siebers, RW; Taylor, C, 1989)	0.5
" A standardized oral loading dosage was used for all patients (1,200 mg/day for 14 days; 800 mg/day for 7 days; and 400 mg/day thereafter)."	( Electropharmacology of amiodarone therapy initiation. Time courses of onset of electrophysiologic and antiarrhythmic effects. Duff, HJ; Gillis, AM; Mitchell, LB; Wyse, DG, 1989)	0.28
"83 h for both dosages and the mean elimination half-life was 15 h after the 100 mg/kg dosage and 105 h after the 200 mg/kg dosage."	( Pharmacokinetics and body distribution of amiodarone and desethylamiodarone in rats after oral administration. Maes, RA; Plomp, TA; Van Rossum, JM; Wiersinga, WM, )	0.38
" After one-month dosing apparent t1/2 el of desethylamiodarone increased to 29."	( Amiodarone pharmacokinetics in coronary patients: differences between acute and one-month chronic dosing. Cheymol, G; Coumel, P; Escoubet, B; Jaillon, P; Poirier, JM; Richard, MO, )	0.39
" There was no significant correlation between serum amiodarone or desethylamiodarone levels and dosage of amiodarone."	( Amiodarone efficacy in a young population: relationship to serum amiodarone and desethylamiodarone levels. Garson, A; Kannan, R; McVey, P; Miller, S; Singh, BN; Yabek, SM, 1987)	0.74
"Thirty-three patients treated with an abbreviated oral amiodarone loading regimen for ventricular tachycardia underwent electrophysiologic testing in the control state, after 1 week of high-dose (1170 +/- 88 mg/day) inpatient therapy; and after an 8-week intermediate (669 +/- 129 mg/day) dosing phase."	( Dissociation of electrophysiologic and pharmacologic stability during an abbreviated oral loading regimen of amiodarone. Batsford, WP; Bookbinder, MJ; Kennedy, EE; McPherson, CA; Perlmutter, RA; Rosenfeld, LF, 1987)	0.27
"Thirty-eight patients with refractory supraventricular and ventricular tachyarrhythmias were administered a mean oral dosage of 400 mg amiodarone daily (200-600 mg)."	( [Amiodarone therapy--behavior of serum and fatty tissue concentrations]. Bethge, KP; Bosse, K; Gonska, BD; Köbberling, J; Kreuzer, H; Quentin, CD; Wagner, H, 1986)	0.27
" The absolute bioavailability of oral amiodarone was calculated by comparison of AUCs after oral dosing with those after intravenous injection."	( Absolute bioavailability of amiodarone in normal subjects. Berger, Y; Desager, JP; Harvengt, C; Pacco, M; Pourbaix, S, 1985)	0.27
" Desethylamiodarone serum and tissue concentrations were substantially lower than the corresponding amiodarone concentrations and varied from 1 to 48% (mean 15%) depending on the dosage used and the kind of tissue."	( Tissue distribution of amiodarone and desethylamiodarone in rats after multiple intraperitoneal administration of various amiodarone dosages. Maes, RA; Plomp, TA; Wiersinga, WM, 1985)	1.45
"In eight patients who had previously responded to treatment with oral amiodarone for prevention of recurrent supraventricular paroxysmal tachycardia, a new regimen of oral amiodarone dosing was evaluated."	( Once per week oral administration of amiodarone in the prophylaxis of supraventricular paroxysmal tachycardia. Furlanello, F; Inama, G; Padrini, R; Piovan, D, 1985)	0.27
" The responsiveness was maintained with the smaller dosage of 200 mg in 68% of this group."	( Multicenter controlled observation of a low-dose regimen of amiodarone for treatment of severe ventricular arrhythmias. Collaborative Group for Amiodarone Evaluation. , 1984)	0.27
" The dosage was 400 to 600 mg/d following a loading dosage of 1000 mg for 8 to 12 days."	( [Control of anti-arrhythmia therapy with amiodarone. Value of the determination of blood levels]. Lüderitz, B; Nitsch, J, 1984)	0.27
" Monitoring serum amiodarone concentrations may differentiate failure of drug therapy from suboptimal dosing and reduce the incidence of concentration-related side effects."	( Steady-state serum amiodarone concentrations: relationships with antiarrhythmic efficacy and toxicity. Belhassen, B; Greenspan, AM; Greenspon, AJ; Horowitz, LN; Rotmensch, HH; Shoshani, D; Spielman, SR; Swanson, BN; Vlasses, PH, 1984)	0.27
" On the other hand digitalis administered according to age, sex, weight, kidney function, together with amiodarone, can be given at full dosage in patients without cardiac failure."	( [Pharmacological and clinical research on the interaction of digitalis and amiodarone in heart disease patients with varying degrees of cardiac insufficiency]. Aquili, C; Ferrari, M; Fornaro, G; Fortina, A; Padrini, R; Piovan, D; Rossi, P; Tomassini, G, 1984)	0.27
" Drug or metabolite concentrations in plasma and RBCs correlated directly with daily dosage of amiodarone."	( Plasma and red blood cell concentrations of amiodarone during chronic therapy. Heger, JJ; Prystowsky, EN; Solow, EB; Zipes, DP, 1984)	0.27
"The concentrations of amiodarone (Cordarone) and desethylamiodarone in plasma after single oral and intravenous and long-term oral dosing were determined in seven normal subjects and 106 patients with various cardiac arrhythmias, respectively, using a high-performance liquid chromatographic method."	( Pharmacokinetics and body distribution of amiodarone in man. Maes, RA; Plomp, TA; Robles de Medina, EO; van Lier, T; van Rossum, JM, 1984)	0.52
"The relationships between size of loading dose and drug concentration, size of maintenance dose and drug concentration, and pulmonary and cutaneous adverse side effects and drug dosage were examined in patients given amiodarone."	( Relationships between amiodarone dosage, drug concentrations, and adverse side effects. Heger, JJ; Prystowsky, EN; Zipes, DP, 1983)	0.27
" The concentrations of all four drugs in the sample collected during life were consistent with the dosage given and in the range accepted for normal therapy."	( Differences in amiodarone, digoxin, flecainide and sotalol concentrations between antemortem serum and femoral postmortem blood. McCarthy, PT; O'Sullivan, JJ; Wren, C, 1995)	0.29
"A 24 h intravenous dosing regimen of amiodarone was designed to reach a peak plasma concentration at 1 h and to maintain the concentration above a certain level during the infusion period."	( Acute treatment of recent-onset atrial fibrillation and flutter with a tailored dosing regimen of intravenous amiodarone. A randomized, digoxin-controlled study. Chang, MS; Chen, CY; Chiang, HT; Hou, ZY; Lin, SL; Tu, MS; Woosley, RL, 1995)	0.29
" Thus, dosage adjustment in patients with renal impairment is not necessary based on this pharmacokinetic analysis."	( Disposition of intravenous amiodarone in subjects with normal and impaired renal function. Chow, MS; Izard, M; Klamerus, KJ; Neefe, DL; O'Rangers, E; Ujhelyi, MR; Vadiei, K; Zimmerman, JJ, 1996)	0.29
" The heart rate, PQ, QR, QS, QT, RR intervals, and P,R,S, and T amplitudes were also measured after dosing using telemetry."	( Effects of desethylamiodarone on the electrocardiogram in conscious freely moving animals: pharmacokinetic and pharmacodynamic modeling using computer-assisted radio telemetry. Eddington, ND; Kharidia, J, 1996)	0.68
" The defibrillation energy requirement does not correlate with the plasma concentrations of amiodarone, desethylamiodarone, amiodarone plus desethylamiodarone, or with the duration or daily dosage of amiodarone therapy."	( Relation between amiodarone and desethylamiodarone plasma concentrations and ventricular defibrillation energy requirements. Daoud, EG; Horwood, L; Man, KC; Morady, F; Strickberger, SA, 1997)	0.79
"Amiodarone caused a dose-response increase in DFT (mean +/- SD) from 22."	( Effects of amiodarone and its active metabolite desethylamiodarone on the ventricular defibrillation threshold. Chen, BP; Chow, MS; Fan, C; Kluger, J; Zhou, L, 1998)	0.56
" A practical dosing regimen of 1600 mg/d for 2 days, 1,200 mg/d for 5 days, 1,000 mg/d for 7 days, 800 mg/d for 7 days, 600 mg/d for 7 days, and 400 mg/d for 62 days followed by a maintenance dose of 343 mg/d (400 mg/d for 6 of 7 days) is proposed."	( Population pharmacokinetics of long-term oral amiodarone therapy. Bouillon, T; Pollak, PT; Shafer, SL, 2000)	0.31
" However, based on the estimated variability, the proposed dosing regimen would produce steady-state concentrations within the therapeutic window for 90% of patients."	( Population pharmacokinetics of long-term oral amiodarone therapy. Bouillon, T; Pollak, PT; Shafer, SL, 2000)	0.31
"To achieve similar concentrations, an approximately 3-fold increase in dosage of amiodarone was required when patients were given the drug nasogastrically rather than orally."	( Serum amiodarone and desethylamiodarone concentrations following nasogastric versus oral administration. Goto, T; Kamakura, S; Komamura, K; Kotake, T; Morishita, H; Takada, M, 2006)	0.65
" Venous blood samples were taken periodically during the first 72 hours after dosing to determine standard pharmacokinetic parameters."	( Comparative bioavailability of a premixed, ready-to-use formulation of intravenous amiodarone with traditional admixture in healthy subjects. Adams, MP; Agha, B; Cooper, WD; Cushing, DJ; Souney, PF, 2012)	0.38
" Model simulations were in good agreement with the observed time courses of the drug-metabolite pair in tissues, under various dosing scenarios."	( A Physiologically Based Pharmacokinetic Model of Amiodarone and its Metabolite Desethylamiodarone in Rats: Pooled Analysis of Published Data. Cai, Y; Chen, F; Hu, ZY; Jia, WW; Lu, JT; Zhao, YS, 2016)	0.66

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Class	Description
aromatic ketone	A ketone in which the carbonyl group is attached to an aromatic ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
ATP-dependent translocase ABCB1	Homo sapiens (human)	IC50 (µMol)	20.3000	0.0002	2.3185	10.0000	AID679131; AID679132
Thyroid hormone receptor beta	Rattus norvegicus (Norway rat)	IC50 (µMol)	27.0000	0.0002	0.0083	0.0350	AID1797808
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Trace amine-associated receptor 1	Rattus norvegicus (Norway rat)	EC50 (µMol)	0.0330	0.0139	0.4263	2.0440	AID409815
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
positive regulation of thyroid hormone mediated signaling pathway	Thyroid hormone receptor alpha	Gallus gallus (chicken)
negative regulation of RNA polymerase II transcription preinitiation complex assembly	Thyroid hormone receptor alpha	Gallus gallus (chicken)
mRNA transcription by RNA polymerase II	Thyroid hormone receptor alpha	Gallus gallus (chicken)
positive regulation of transcription by RNA polymerase II	Thyroid hormone receptor alpha	Gallus gallus (chicken)
cell differentiation	Thyroid hormone receptor alpha	Gallus gallus (chicken)
retinoic acid receptor signaling pathway	Thyroid hormone receptor alpha	Gallus gallus (chicken)
negative regulation of transcription by RNA polymerase II	Thyroid hormone receptor alpha	Gallus gallus (chicken)
thyroid hormone mediated signaling pathway	Thyroid hormone receptor alpha	Gallus gallus (chicken)
G2/M transition of mitotic cell cycle	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic metabolic process	ATP-dependent translocase ABCB1	Homo sapiens (human)
response to xenobiotic stimulus	ATP-dependent translocase ABCB1	Homo sapiens (human)
phospholipid translocation	ATP-dependent translocase ABCB1	Homo sapiens (human)
terpenoid transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
regulation of response to osmotic stress	ATP-dependent translocase ABCB1	Homo sapiens (human)
transmembrane transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
transepithelial transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
stem cell proliferation	ATP-dependent translocase ABCB1	Homo sapiens (human)
ceramide translocation	ATP-dependent translocase ABCB1	Homo sapiens (human)
export across plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
transport across blood-brain barrier	ATP-dependent translocase ABCB1	Homo sapiens (human)
positive regulation of anion channel activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
carboxylic acid transmembrane transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic detoxification by transmembrane export across the plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic transport across blood-brain barrier	ATP-dependent translocase ABCB1	Homo sapiens (human)
regulation of chloride transport	ATP-dependent translocase ABCB1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nuclear receptor activity	Thyroid hormone receptor alpha	Gallus gallus (chicken)
protein binding	Thyroid hormone receptor alpha	Gallus gallus (chicken)
zinc ion binding	Thyroid hormone receptor alpha	Gallus gallus (chicken)
TBP-class protein binding	Thyroid hormone receptor alpha	Gallus gallus (chicken)
protein domain specific binding	Thyroid hormone receptor alpha	Gallus gallus (chicken)
thyroid hormone binding	Thyroid hormone receptor alpha	Gallus gallus (chicken)
sequence-specific double-stranded DNA binding	Thyroid hormone receptor alpha	Gallus gallus (chicken)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Thyroid hormone receptor alpha	Gallus gallus (chicken)
protein binding	ATP-dependent translocase ABCB1	Homo sapiens (human)
ATP binding	ATP-dependent translocase ABCB1	Homo sapiens (human)
ABC-type xenobiotic transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
efflux transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
ATP hydrolysis activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
ubiquitin protein ligase binding	ATP-dependent translocase ABCB1	Homo sapiens (human)
ATPase-coupled transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
xenobiotic transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
carboxylic acid transmembrane transporter activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
phosphatidylcholine floppase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
phosphatidylethanolamine flippase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
ceramide floppase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
floppase activity	ATP-dependent translocase ABCB1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	Thyroid hormone receptor alpha	Gallus gallus (chicken)
cytosol	Thyroid hormone receptor alpha	Gallus gallus (chicken)
RNA polymerase II transcription regulator complex	Thyroid hormone receptor alpha	Gallus gallus (chicken)
nucleus	Thyroid hormone receptor alpha	Gallus gallus (chicken)
cytoplasm	ATP-dependent translocase ABCB1	Homo sapiens (human)
plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
cell surface	ATP-dependent translocase ABCB1	Homo sapiens (human)
membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
apical plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
extracellular exosome	ATP-dependent translocase ABCB1	Homo sapiens (human)
external side of apical plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
plasma membrane	ATP-dependent translocase ABCB1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1797808	TRbeta-Binding Assay from Article 10.1210/endo.137.7.8770901: \\Structure-function relationship of the inhibition of the 3,5,3'-triiodothyronine binding to the alpha1- and beta1-thyroid hormone receptor by amiodarone analogs.\\	1996	Endocrinology, Jul, Volume: 137, Issue:7	Structure-function relationship of the inhibition of the 3,5,3'-triiodothyronine binding to the alpha1- and beta1-thyroid hormone receptor by amiodarone analogs.
AID1797807	TRalpha-Binding Assay. from Article 10.1210/endo.137.7.8770901: \\Structure-function relationship of the inhibition of the 3,5,3'-triiodothyronine binding to the alpha1- and beta1-thyroid hormone receptor by amiodarone analogs.\\	1996	Endocrinology, Jul, Volume: 137, Issue:7	Structure-function relationship of the inhibition of the 3,5,3'-triiodothyronine binding to the alpha1- and beta1-thyroid hormone receptor by amiodarone analogs.
AID1217052	Drug level in human liver microsomes assessed as compound formation treated with 50 uM amiodarone for 60 mins by UPLC-Q/TOF mass spectrometry in presence of NADPH	2011	Drug metabolism and disposition: the biological fate of chemicals, Jun, Volume: 39, Issue:6	Identification of amiodarone metabolites in human bile by ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry.
AID445746	Effect on calcium mobilization in CHO cells stably expressing Galpha16 at 10 uM relative to beta-phenethylamine	2009	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 19, Issue:20	Amiodarone and its putative metabolites fail to activate wild type hTAAR1.
AID445741	Activation of human TAAR1 expressed in CHOK1 cells coexpressing Galpha16 assessed as calcium accumulation at 0.1 to 1 uM relative to beta-phenethylamine	2009	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 19, Issue:20	Amiodarone and its putative metabolites fail to activate wild type hTAAR1.
AID1217046	Retention time of the compound by UPLC-Q/TOF mass spectrometry	2011	Drug metabolism and disposition: the biological fate of chemicals, Jun, Volume: 39, Issue:6	Identification of amiodarone metabolites in human bile by ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry.
AID679131	TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical) (Digoxin: 0.025 uM) in MDR1-expressing LLC-PK1 cells	2001	European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, Feb, Volume: 12, Issue:4	Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport.
AID679132	TP_TRANSPORTER: inhibition of Daunorubicin transepithelial transport (basal to apical) (Daunorubicin: 0.035 uM) in MDR1-expressing LLC-PK1 cells	2001	European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, Feb, Volume: 12, Issue:4	Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport.
AID445740	Activation of human TAAR1 expressed in CHOK1 cells assessed as cAMP accumulation at 0.1 to 1 uM	2009	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 19, Issue:20	Amiodarone and its putative metabolites fail to activate wild type hTAAR1.
AID1217061	Drug level in human liver S9 fraction assessed as compound formation treated with 50 uM amiodarone for 60 mins by UPLC-Q/TOF mass spectrometry in presence of NADPH	2011	Drug metabolism and disposition: the biological fate of chemicals, Jun, Volume: 39, Issue:6	Identification of amiodarone metabolites in human bile by ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry.
AID1217045	Drug level in arrhythmia patient bile treated with amiodarone at 200 mg/day, po for 7 days by UPLC-Q/TOF mass spectrometry	2011	Drug metabolism and disposition: the biological fate of chemicals, Jun, Volume: 39, Issue:6	Identification of amiodarone metabolites in human bile by ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry.
AID445744	Activation of human TAAR1 expressed in CHOK1 cells coexpressing Galpha16 assessed as calcium accumulation at 10 uM relative to beta-phenethylamine	2009	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 19, Issue:20	Amiodarone and its putative metabolites fail to activate wild type hTAAR1.
AID409814	Antagonist activity at rat TAAR1 expressed in HEK293 cells assessed as intracellular cAMP level at 10 uM after 1 hr	2008	Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22	Trace amine-associated receptor 1 (TAAR1) is activated by amiodarone metabolites.
AID1217031	Drug level in human liver S9 fraction assessed as compound formation treated with 50 uM amiodarone for 60 mins by LC-UV analysis in presence of NADPH	2011	Drug metabolism and disposition: the biological fate of chemicals, Jun, Volume: 39, Issue:6	Identification of amiodarone metabolites in human bile by ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry.
AID409815	Antagonist activity at rat TAAR1 expressed in HEK293 cells assessed as intracellular cAMP level	2008	Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22	Trace amine-associated receptor 1 (TAAR1) is activated by amiodarone metabolites.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	117 (40.07)	18.7374
1990's	82 (28.08)	18.2507
2000's	56 (19.18)	29.6817
2010's	29 (9.93)	24.3611
2020's	8 (2.74)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	16 (5.11%)	5.53%
Reviews	4 (1.28%)	6.00%
Case Studies	11 (3.51%)	4.05%
Observational	1 (0.32%)	0.25%
Other	281 (89.78%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	1.96	1	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
choline [no description available]	6.97	1	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	1.97	1	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	1.97	1	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	8.08	5	0	diatomic iodine	nutrient
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	1.96	1	0	sulfur oxide; sulfur oxoanion
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	1.97	1	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.39	2	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	2.04	1	0	bipyridine	chelator; ferroptosis inhibitor
5,5-dimethyl-1-pyrroline-1-oxide 5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : A member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation.	2.04	1	0	1-pyrroline nitrones	neuroprotective agent; spin trapping reagent
phenytoin [no description available]	1.97	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
albendazole [no description available]	2.07	1	0	aryl sulfide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	anthelminthic drug; microtubule-destabilising agent; tubulin modulator
theophylline [no description available]	1.99	1	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
amiodarone Amiodarone: An antianginal and class III antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting POTASSIUM CHANNELS and VOLTAGE-GATED SODIUM CHANNELS. There is a resulting decrease in heart rate and in vascular resistance.. amiodarone : A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.	15.73	290	16	1-benzofurans; aromatic ketone; organoiodine compound; tertiary amino compound	cardiovascular drug
amodiaquine Amodiaquine: A 4-aminoquinoline compound with anti-inflammatory properties.. amodiaquine : A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position.	1.97	1	0	aminoquinoline; organochlorine compound; phenols; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; drug allergen; EC 2.1.1.8 (histamine N-methyltransferase) inhibitor; non-steroidal anti-inflammatory drug; prodrug
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	7.37	2	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
atenolol Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.	1.97	1	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
azelastine azelastine: azeptin is azelastine hydrochloride; structure; eye drop formulation effective in relieving symptoms of allergic conjunctivitis; do not confuse with 5-loxin which is an extract of Boswellia. azelastine : A phthalazine compound having an oxo substituent at the 1-position, a 1-methylazepan-4-yl group at the 2-position and a 4-chlorobenzyl substituent at the 4-position.	2	1	0	monochlorobenzenes; phthalazines; tertiary amino compound	anti-allergic agent; anti-asthmatic drug; bronchodilator agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; H1-receptor antagonist; platelet aggregation inhibitor
benzbromarone Benzbromarone: Uricosuric that acts by increasing uric acid clearance. It is used in the treatment of gout.. benzbromarone : 1-Benzofuran substituted at C-2 and C-3 by an ethyl group and a 3,5-dibromo-4-hydroxybenzoyl group respectively. An inhibitor of CYP2C9, it is used as an anti-gout medication.	2.03	1	0	1-benzofurans; aromatic ketone	uricosuric drug
bepridil Bepridil: A long-acting calcium-blocking agent with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist.. bepridil : A tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl.	3.48	2	0	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	2.71	3	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
bisoprolol Bisoprolol: A cardioselective beta-1 adrenergic blocker. It is effective in the management of HYPERTENSION and ANGINA PECTORIS.	7.1	1	0	secondary alcohol; secondary amine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
caffeine [no description available]	1.99	1	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.38	2	0	aromatic ether; nitrile; polyether; tertiary amino compound
calmidazolium calmidazolium: powerful inhibitor of or red blood cell Ca++-ATPase & Ca++ transport into inside-out red blood cell vesicles; RN refers to chloride; structure in first source; an antagonist of calmodulin. calmidazolium : An imidazolium ion that is imidazolium cation substituted by a bis(4-chlorophenyl)methyl group at position 1 and a 2-[(2,4-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl group at position 3. It acts as an antagonist of calmodulin, a calcium binding messenger protein.	1.97	1	0	imidazolium ion	apoptosis inducer; calmodulin antagonist
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.03	1	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
celecoxib [no description available]	2.41	1	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	1.97	1	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	2	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
clofilium clofilium: RN given refers to parent cpd; structure	1.97	1	0	benzenes; organic amino compound
profenamine profenamine: was heading 1972-94 (see under PHENOTHIAZINES 1972-90); use PHENOTHIAZINES to search ETHOPROPAZINE 1972-94. profenamine : A member of the class of phenothiazines that is phenothiazine in which the hydrogen attached to the nitrogen is substituted by a 2-(diethylamino)propyl group. An antimuscarinic, it is used as the hydrochloride for the symptomatic treatment of Parkinson's disease.	2.03	1	0	phenothiazines; tertiary amino compound	adrenergic antagonist; antidyskinesia agent; antiparkinson drug; histamine antagonist; muscarinic antagonist
carbonyl cyanide p-trifluoromethoxyphenylhydrazone Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone: A proton ionophore that is commonly used as an uncoupling agent in biochemical studies.. carbonyl cyanide p-trifluoromethoxyphenylhydrazone : A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.	2.04	1	0	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore
flecainide Flecainide: A potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial ARRHYTHMIAS and TACHYCARDIAS.. flecainide : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid with the primary amino group of piperidin-2-ylmethylamine. An antiarrhythmic agent used (in the form of its acetate salt) to prevent and treat tachyarrhythmia (abnormal fast rhythm of the heart).	1.98	1	0	aromatic ether; monocarboxylic acid amide; organofluorine compound; piperidines	anti-arrhythmia drug
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	2.41	2	0	carbohydrazide	antitubercular agent; drug allergen
isradipine Isradipine: A potent antagonist of CALCIUM CHANNELS that is highly selective for VASCULAR SMOOTH MUSCLE. It is effective in the treatment of chronic stable angina pectoris, hypertension, and congestive cardiac failure.	1.97	1	0	benzoxadiazole; dihydropyridine; isopropyl ester; methyl ester
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	2.96	4	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
mephenytoin Mephenytoin: An anticonvulsant effective in tonic-clonic epilepsy (EPILEPSY, TONIC-CLONIC). It may cause blood dyscrasias.. mephenytoin : An imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism.	1.97	1	0	imidazolidine-2,4-dione	anticonvulsant
nocodazole [no description available]	2.06	1	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	3.41	1	1	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	2.41	2	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.4	2	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2.37	2	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
procainamide Procainamide: A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.. procainamide : A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.	1.97	1	0	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker
propafenone Propafenone: An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity.. propafenone : An aromatic ketone that is 3-(propylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is replaced by a 2-(3-phenylpropanoyl)phenyl group. It is a class 1C antiarrhythmic drug with local anesthetic effects, and is used as the hydrochloride salt in the management of supraventricular and ventricular arrhythmias.	2.07	1	0	aromatic ketone; secondary alcohol; secondary amino compound	anti-arrhythmia drug
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	1.97	1	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
sotalol Sotalol: An adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias.. sotalol : A sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is substituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and cardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias.	2.67	3	0	ethanolamines; secondary alcohol; secondary amino compound; sulfonamide	anti-arrhythmia drug; beta-adrenergic antagonist; environmental contaminant; xenobiotic
trifluoperazine [no description available]	3.48	2	0	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	1.98	1	0	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	2	1	0	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.68	3	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	8.69	10	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	1.97	1	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	9.29	19	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2	1	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	1.97	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	1.97	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	2.4	2	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
benziodarone benziodarone: minor descriptor (75-89); on-line & INDEX MEDICUS search BENZOFURANS (68-89) & IODOBENZOATES (74)	1.97	1	0	aromatic ketone
n,n'-diphenyl-4-phenylenediamine N,N'-diphenyl-4-phenylenediamine: in veterinary medicine, has been used to prevent vitamin E deficiency in lambs; structure. N,N'-diphenyl-1,4-phenylenediamine : An N-substituted diamine that is 1,4-phenylenediamine in which one hydrogen from each amino group is replaced by a phenyl group.	1.97	1	0	N-substituted diamine; secondary amino compound	antioxidant
diethylamine [no description available]	2	1	0	secondary aliphatic amine
tetraphenylborate Tetraphenylborate: An anionic compound that is used as a reagent for determination of potassium, ammonium, rubidium, and cesium ions. It also uncouples oxidative phosphorylation and forms complexes with biological materials, and is used in biological assays.	1.97	1	0
thiazoles [no description available]	2.04	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
chlorphentermine Chlorphentermine: A sympathomimetic agent that was formerly used as an anorectic. It has properties similar to those of DEXTROAMPHETAMINE. It has been implicated in lipid storage disorders and pulmonary hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1223)	2.38	2	0	amphetamines
methoxyhydroxyphenylglycol Methoxyhydroxyphenylglycol: Synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover.	2	1	0	methoxybenzenes; phenols
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	2.45	2	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	1.97	1	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	3.11	5	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
iodine [no description available]	7.37	2	0	halide anion; monoatomic iodine	human metabolite
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	1.97	1	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.01	1	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.04	1	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	2	1	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.04	1	0	organic bromide salt	colorimetric reagent; dye
3,4-dihydroxyphenylglycol 3,4-dihydroxyphenylglycol: noradrenaline metabolite in mouse brain; RN given refers to cpd without isomeric designation. 3,4-dihydroxyphenylethyleneglycol : A tetrol composed of ethyleneglycol having a 3,4-dihydroxyphenyl group at the 1-position.	2	1	0	catechols; tetrol	metabolite; mouse metabolite
1,4-dihydropyridine [no description available]	1.98	1	0
1-hydroxymethylmidazolam 1-hydroxymethylmidazolam: metabolite of midazolam. 1-hydroxymidazolam : An imidazobenzodiazepine that is midazolam in which one of the hydrogens of the methyl group is substituted by a hydroxy group. It is the major metabolite of the anesthetic, midazolam.	2	1	0	aromatic primary alcohol; imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	drug metabolite; human blood serum metabolite; human urinary metabolite
4-hydroxymidazolam 4-hydroxymidazolam: metabolite of midazolam; structure given in first source. 4-hydroxymidazolam : An imidazobenzodiazepine that is midazolam which is substituted by a hydroxy group at position 4. It is the minor hydroxylated metabolite of the anesthetic, midazolam.	2	1	0	imidazobenzodiazepine; monofluorobenzenes; organic hydroxy compound; organochlorine compound	drug metabolite; human blood serum metabolite; human urinary metabolite
di-n-desethylamiodarone di-N-desethylamiodarone: amiodarone metabolite in dogs; structure given in first source	2.94	4	0
dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate: stable deriv of nifedipine; structure given in first source	2	1	0	phenylpyridine
n-depropylpropafenone N-depropylpropafenone: propafenone metabolite; structure given in first source	2.07	1	0
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	2.03	1	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
desmethylazelastine desmethylazelastine: azelastine metabolite	2	1	0	phthalazines
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.06	1	0	amino acid zwitterion; angiotensin II	human metabolite
dronedarone Dronedarone: A non-iodinated derivative of amiodarone that is used for the treatment of ARRHYTHMIA.. dronedarone : A member of the class of 1-benzofurans used for the treatment of cardiac arrhythmias.	4.24	5	0	1-benzofurans; aromatic ether; aromatic ketone; sulfonamide; tertiary amino compound	anti-arrhythmia drug; environmental contaminant; xenobiotic
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	9.79	59	2
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	1.98	1	0
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	2	1	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
amiodarone hydrochloride [no description available]	2.06	1	0	aromatic ketone
medigoxin Medigoxin: A semisynthetic digitalis glycoside with the general properties of DIGOXIN but more rapid onset of action. Its cardiotonic action is prolonged by its demethylation to DIGOXIN in the liver. It has been used in the treatment of congestive heart failure (HEART FAILURE).	1.96	1	0	cardenolide glycoside
1,2-dilauroylphosphatidylcholine 1,2-dilauroylphosphatidylcholine: RN given refers to cpd without isomeric designation. 1,2-dilauroyl-sn-glycero-3-phosphocholine(1+) : A A 1,2-diacyl-sn-glycero-3-phosphocholine(1+) that is the dilauroyl diester of phosphatidiylcholine.	2.03	1	0	1,2-diacyl-sn-glycero-3-phosphocholine(1+)
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	2	1	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	1.99	1	0	actinomycin	mutagen
potassium perchlorate potassium perchlorate: thyroid antagonist; structure	2.03	1	0
propylthiouracil Propylthiouracil: A thiourea antithyroid agent. Propythiouracil inhibits the synthesis of thyroxine and inhibits the peripheral conversion of throxine to tri-iodothyronine. It is used in the treatment of hyperthyroidism. (From Martindale, The Extra Pharmacopeoia, 30th ed, p534). 6-propyl-2-thiouracil : A pyrimidinethione consisting of uracil in which the 2-oxo group is substituted by a thio group and the hydrogen at position 6 is substituted by a propyl group.	2	1	0	pyrimidinethione	antidote to paracetamol poisoning; antimetabolite; antioxidant; antithyroid drug; carcinogenic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; hormone antagonist
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	4.28	4	1	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
tamoxifen [no description available]	3.09	1	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
nadp [no description available]	2.74	3	0
bilirubin [no description available]	1.99	1	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	1.98	1	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
dextromethorphan Dextromethorphan: Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.. dextromethorphan : A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.	7.38	2	0	6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene	antitussive; environmental contaminant; neurotoxin; NMDA receptor antagonist; oneirogen; prodrug; xenobiotic
diphenylhexatriene Diphenylhexatriene: A fluorescent compound that emits light only in specific configurations in certain lipid media. It is used as a tool in the study of membrane lipids.	1.98	1	0	alkatriene	fluorochrome
ximelagatran ximelagatran: prodrug (via hydroxylation) of melagatran & a direct thrombin inhibitor; liver toxicity concerns so AZD0837 being developed to replace this. ximelagatran : A member of the class of azetidines that is melagatran in which the carboxylic acid group has been converted to the corresponding ethyl ester and in which the amidine group has been converted into the corresponding amidoxime. A prodrug for melagatran, ximelagatran was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.	3.4	1	1	amidoxime; azetidines; carboxamide; ethyl ester; hydroxylamines; secondary amino compound; secondary carboxamide; tertiary carboxamide	anticoagulant; EC 3.4.21.5 (thrombin) inhibitor; prodrug; serine protease inhibitor
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	1.98	1	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	1.98	1	0	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
celivarone celivarone: antiarrhythmic agent; structure in first source	3.14	1	0
u 18666a 3-beta-(2-(diethylamino)ethoxy)androst-5-en-17-one: inhibits cycloartenol synthase. 3beta-(2-diethylaminoethoxy)androst-5-en-17-one hydrochloride : A hydrochloride obtained by reaction of 3beta-(2-diethylaminoethoxy)androst-5-en-17-one with one equivalent of hydrochloric acid. It is a cholesterol synthesis and transport inhibitor.	2.06	1	0	hydrochloride	antiviral agent; EC 1.3.1.72 (Delta(24)-sterol reductase) inhibitor; Hedgehog signaling pathway inhibitor; nicotinic antagonist; sterol biosynthesis inhibitor
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	1.97	1	0
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.5	2	0
angiotensinogen Angiotensinogen: An alpha-globulin of about 453 amino acids, depending on the species. It is produced by the liver in response to lowered blood pressure and secreted into blood circulation. Angiotensinogen is the inactive precursor of the ANGIOTENSINS produced in the body by successive enzyme cleavages. Cleavage of angiotensinogen by RENIN yields the decapeptide ANGIOTENSIN I. Further cleavage of angiotensin I (by ANGIOTENSIN CONVERTING ENZYME) yields the potent vasoconstrictor octapeptide ANGIOTENSIN II; and then, via other enzymes, other angiotensins also involved in the hemodynamic-regulating RENIN-ANGIOTENSIN SYSTEM.	2.06	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.4	2	0	1,2-diacyl-sn-glycero-3-phosphocholine
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2.04	1	0
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	2.11	1	0
triiodothyronine, reverse Triiodothyronine, Reverse: A metabolite of THYROXINE, formed by the peripheral enzymatic monodeiodination of T4 at the 5 position of the inner ring of the iodothyronine nucleus.. 3,3',5'-triiodo-L-thyronine zwitterion : Zwitterionic form of 3,3',5'-triiodo-L-thyronine.	2.89	4	0	3,3',5'-triiodothyronine; amino acid zwitterion
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.07	1	0
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	8.77	2	1	benzenes; hydroxycoumarin; methyl ketone
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.41	2	0
oligomycins Oligomycins: A closely related group of toxic substances elaborated by various strains of Streptomyces. They are 26-membered macrolides with lactone moieties and double bonds and inhibit various ATPases, causing uncoupling of phosphorylation from mitochondrial respiration. Used as tools in cytochemistry. Some specific oligomycins are RUTAMYCIN, peliomycin, and botrycidin (formerly venturicidin X).	1.97	1	0
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2	1	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2.69	3	0
thromboplastin Thromboplastin: Constituent composed of protein and phospholipid that is widely distributed in many tissues. It serves as a cofactor with factor VIIa to activate factor X in the extrinsic pathway of blood coagulation.	2.04	1	0
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2	1	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor

Condition	Relationship Strength	Studies	Trials
Arrhythmia [description not available]	9.69	39	5
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	9.69	39	5
Auricular Fibrillation [description not available]	7.08	9	4
Atrial Fibrillation Abnormal cardiac rhythm that is characterized by rapid, uncoordinated firing of electrical impulses in the upper chambers of the heart (HEART ATRIA). In such case, blood cannot be effectively pumped into the lower chambers of the heart (HEART VENTRICLES). It is caused by abnormal impulse generation.	7.08	9	4
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.41	1	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.41	1	0
Innate Inflammatory Response [description not available]	2.41	1	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	7.41	1	0
Cancer of Lung [description not available]	2.46	2	0
B16 Melanoma [description not available]	2.66	2	0
Cancer of Skin [description not available]	2.25	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	2.46	2	0
Skin Neoplasms Tumors or cancer of the SKIN.	2.25	1	0
Lysosomal Enzyme Disorders [description not available]	2.25	1	0
Central Hypothyroidism [description not available]	5.91	9	1
Hypothyroidism A syndrome that results from abnormally low secretion of THYROID HORMONES from the THYROID GLAND, leading to a decrease in BASAL METABOLIC RATE. In its most severe form, there is accumulation of MUCOPOLYSACCHARIDES in the SKIN and EDEMA, known as MYXEDEMA. It may be primary or secondary due to other pituitary disease, or hypothalamic dysfunction.	5.91	9	1
Thyrotoxicosis A hypermetabolic syndrome caused by excess THYROID HORMONES which may come from endogenous or exogenous sources. The endogenous source of hormone may be thyroid HYPERPLASIA; THYROID NEOPLASMS; or hormone-producing extrathyroidal tissue. Thyrotoxicosis is characterized by NERVOUSNESS; TACHYCARDIA; FATIGUE; WEIGHT LOSS; heat intolerance; and excessive SWEATING.	3.41	2	0
Bladder Cancer [description not available]	7.15	1	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.15	1	0
Cancer of Cervix [description not available]	2.17	1	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.17	1	0
Ventricular Fibrillation A potentially lethal cardiac arrhythmia that is characterized by uncoordinated extremely rapid firing of electrical impulses (400-600/min) in HEART VENTRICLES. Such asynchronous ventricular quivering or fibrillation prevents any effective cardiac output and results in unconsciousness (SYNCOPE). It is one of the major electrocardiographic patterns seen with CARDIAC ARREST.	3.48	8	0
Coronary Occlusion Complete blockage of blood flow through one of the CORONARY ARTERIES, usually from CORONARY ATHEROSCLEROSIS.	2.11	1	0
Acute Liver Injury, Drug-Induced [description not available]	3.12	5	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	3.12	5	0
Hyperthyroid [description not available]	4.08	3	1
Hyperthyroidism Hypersecretion of THYROID HORMONES from the THYROID GLAND. Elevated levels of thyroid hormones increase BASAL METABOLIC RATE.	4.08	3	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.39	7	0
Hyperlipemia [description not available]	2.45	2	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.45	2	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	3.26	6	0
Thyroid Diseases Pathological processes involving the THYROID GLAND.	3.61	3	0
Atrial Ectopic Tachycardia [description not available]	2.06	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.06	1	0
Granulocytic Leukemia [description not available]	2.07	1	0
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	2.07	1	0
Alveolitis, Fibrosing [description not available]	3.37	7	0
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	8.37	7	0
Liver Dysfunction [description not available]	2.39	2	0
Liver Diseases Pathological processes of the LIVER.	2.39	2	0
Injury, Ischemia-Reperfusion [description not available]	2.01	1	0
Heart Disease, Ischemic [description not available]	2.01	1	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2.01	1	0
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	2.01	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.23	6	0
Enlarged Liver [description not available]	2.02	1	0
Cancer of Liver [description not available]	2.41	2	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.41	2	0
Hyperlipoproteinemia [description not available]	7.03	1	0
Hyperlipoproteinemias Conditions with abnormally elevated levels of LIPOPROTEINS in the blood. They may be inherited, acquired, primary, or secondary. Hyperlipoproteinemias are classified according to the pattern of lipoproteins on electrophoresis or ultracentrifugation.	2.03	1	0
Tachyarrhythmia [description not available]	5.3	13	0
Tachycardia Abnormally rapid heartbeat, usually with a HEART RATE above 100 beats per minute for adults. Tachycardia accompanied by disturbance in the cardiac depolarization (cardiac arrhythmia) is called tachyarrhythmia.	5.3	13	0
Peripheral Nerve Diseases [description not available]	2.37	2	0
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	2.37	2	0
Recrudescence [description not available]	4.28	4	0
Cardiac Diseases [description not available]	4.05	3	1
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	4.05	3	1
Impotence [description not available]	1.96	1	0
Anorexia The lack or loss of APPETITE accompanied by an aversion to food and the inability to eat. It is the defining characteristic of the disorder ANOREXIA NERVOSA.	1.96	1	0
Erectile Dysfunction The inability in the male to have a PENILE ERECTION due to psychological or organ dysfunction.	1.96	1	0
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	1.96	1	0
Disease, Pulmonary [description not available]	2.89	4	0
Incontinentia Pigmenti Achromians [description not available]	1.96	1	0
Lung Diseases Pathological processes involving any part of the LUNG.	2.89	4	0
Chronic Kidney Failure [description not available]	3.29	2	0
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	3.29	2	0
Actinic Reticuloid Syndrome [description not available]	2.37	2	0
Adipocere [description not available]	1.98	1	0
Auricular Flutter [description not available]	5.2	4	1
Atrial Flutter Rapid, irregular atrial contractions caused by a block of electrical impulse conduction in the right atrium and a reentrant wave front traveling up the inter-atrial septum and down the right atrial free wall or vice versa. Unlike ATRIAL FIBRILLATION which is caused by abnormal impulse generation, typical atrial flutter is caused by abnormal impulse conduction. As in atrial fibrillation, patients with atrial flutter cannot effectively pump blood into the lower chambers of the heart (HEART VENTRICLES).	5.2	4	1
Lipidoses Conditions characterized by abnormal lipid deposition due to disturbance in lipid metabolism, such as hereditary diseases involving lysosomal enzymes required for lipid breakdown. They are classified either by the enzyme defect or by the type of lipid involved.	3.23	6	0
Hepatocellular Carcinoma [description not available]	1.99	1	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	1.99	1	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	2.39	2	0
Adenocarcinoma, Basal Cell [description not available]	2	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2	1	0
Extrasystole, Ventricular [description not available]	2	1	0
Atrioventricular Nodal Re-Entrant Tachycardia [description not available]	2	1	0
Tachycardia, Ventricular An abnormally rapid ventricular rhythm usually in excess of 150 beats per minute. It is generated within the ventricle below the BUNDLE OF HIS, either as autonomic impulse formation or reentrant impulse conduction. Depending on the etiology, onset of ventricular tachycardia can be paroxysmal (sudden) or nonparoxysmal, its wide QRS complexes can be uniform or polymorphic, and the ventricular beating may be independent of the atrial beating (AV dissociation).	2	1	0
Cardiovascular Pregnancy Complications [description not available]	2.37	2	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.66	3	0
Cardiovascular Stroke [description not available]	3.22	6	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	3.22	6	0
Birth Weight The mass or quantity of heaviness of an individual at BIRTH. It is expressed by units of pounds or kilograms.	1.97	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	1.97	1	0
Coronary Heart Disease [description not available]	3.8	4	0
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	3.8	4	0
Cirrhosis [description not available]	1.97	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	1.97	1	0
Cardiac Complex, Premature [description not available]	1.97	1	0
Injury, Myocardial Reperfusion [description not available]	1.97	1	0
Tachycardia, Supraventricular A generic expression for any tachycardia that originates above the BUNDLE OF HIS.	2.37	2	0
Cardiomyopathy, Hypertrophic Obstructive [description not available]	1.96	1	0
Long Sleeper Syndrome [description not available]	1.96	1	0
Cardiomyopathy, Hypertrophic A form of CARDIAC MUSCLE disease, characterized by left and/or right ventricular hypertrophy (HYPERTROPHY, LEFT VENTRICULAR; HYPERTROPHY, RIGHT VENTRICULAR), frequent asymmetrical involvement of the HEART SEPTUM, and normal or reduced left ventricular volume. Risk factors include HYPERTENSION; AORTIC STENOSIS; and gene MUTATION; (FAMILIAL HYPERTROPHIC CARDIOMYOPATHY).	1.96	1	0
Sleep Wake Disorders Abnormal sleep-wake schedule or pattern associated with the CIRCADIAN RHYTHM which affect the length, timing, and/or rigidity of the sleep-wake cycle relative to the day-night cycle.	1.96	1	0
Epididymitis Inflammation of the EPIDIDYMIS. Its clinical features include enlarged epididymis, a swollen SCROTUM; PAIN; PYURIA; and FEVER. It is usually related to infections in the URINARY TRACT, which likely spread to the EPIDIDYMIS through either the VAS DEFERENS or the lymphatics of the SPERMATIC CORD.	6.97	1	0
Infections, Plasmodium [description not available]	1.97	1	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	1.97	1	0
Complication, Postoperative [description not available]	3.35	1	1
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	3.35	1	1
Paroxysmal Reciprocal Tachycardia [description not available]	1.96	1	0
Tachycardia, Paroxysmal Abnormally rapid heartbeats with sudden onset and cessation.	1.96	1	0
Angor Pectoris [description not available]	1.96	1	0
Angina Pectoris The symptom of paroxysmal pain consequent to MYOCARDIAL ISCHEMIA usually of distinctive character, location and radiation. It is thought to be provoked by a transient stressful situation during which the oxygen requirements of the MYOCARDIUM exceed that supplied by the CORONARY CIRCULATION.	1.96	1	0
Carotid Arteriopathies, Traumatic [description not available]	2.04	1	0
Carotid Artery Thrombosis Blood clot formation in any part of the CAROTID ARTERIES. This may produce CAROTID STENOSIS or occlusion of the vessel, leading to TRANSIENT ISCHEMIC ATTACK; CEREBRAL INFARCTION; or AMAUROSIS FUGAX.	2.04	1	0
Niemann-Pick Disease [description not available]	2.06	1	0
Niemann-Pick Diseases A group of autosomal recessive disorders in which harmful quantities of lipids accumulate in the viscera and the central nervous system. They can be caused by deficiencies of enzyme activities (SPHINGOMYELIN PHOSPHODIESTERASE) or defects in intracellular transport, resulting in the accumulation of SPHINGOMYELINS and CHOLESTEROL. There are various subtypes based on their clinical and genetic differences.	2.06	1	0

desethylamiodarone

Description

Cross-References

Synonyms (36)

Research Excerpts

Overview

Effects

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Drug Classes (1)

Protein Targets (4)

Inhibition Measurements

Activation Measurements

Biological Processes (25)

Molecular Functions (21)

Ceullar Components (10)

Bioassays (15)

Research

Studies (292)

Market Indicators

Research Demand Index: 29.57

Study Types

desethylamiodarone

Description

Cross-References

Synonyms (36)

Research Excerpts

Overview

Effects

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Drug Classes (1)

Protein Targets (4)

Inhibition Measurements

Activation Measurements

Biological Processes (25)

Molecular Functions (21)

Ceullar Components (10)

Bioassays (15)

Research

Studies (292)

Market Indicators

Research Demand Index: 29.57

Study Types

Related Drugs (121)

Related Conditions (109)