deacetyldiltiazem: metabolite of diltiazem; RN given refers to (cis-(+-))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 91638 |
| CHEBI ID | 169833 |
| SCHEMBL ID | 7348984 |
| MeSH ID | M0114052 |
| Synonym |
|---|
| (2s,3s)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4-one |
| CHEBI:169833 |
| 42399-40-6 |
| deacetyldiltiazem |
| A7196 |
| einecs 255-795-9 |
| 849ut193yj , |
| unii-849ut193yj |
| (2s-cis)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5h)-one |
| 1,5-benzothiazepin-4(5h)-one, 5-(2-(dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-, (2s,3s)- |
| desacetyldiltiazem |
| diltiazem hydrochloride impurity f [ep impurity] |
| (+)-desacetyldiltiazem |
| desacetyldiltiazem [who-ip] |
| desacetyldiltiazem [who-dd] |
| desacetyl diltiazem |
| (2s-cis)-5-[(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5h)-one |
| deacetyl-d-diltiazem |
| SCHEMBL7348984 |
| NZHUXMZTSSZXSB-MOPGFXCFSA-N |
| (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5h)-one |
| cis-(+)-2-(4'-methoxyphenyl)-3-hydroxy-5-(2'-dimethylaminoethyl)-2,3-dihydro-1,5-benzothiazepine-4(5h)-one |
| (+)-(2s,3s)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5h)-one |
| cis-(+)-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5h)-one |
| (+/-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5h)-one |
| (2s,3s)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one |
| AKOS027378048 |
| diltiazem-m deacetyl |
| (2s,3s)-5-[2-(dimethylamino)-ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5h)-one; diltiazem hydrochloride imp. f (ep); desacetyldiltiazem; diltiazem hydrochloride impurity f; diltiazem impurity f |
| (2s,3s)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5h)-one |
| desacetyldiltiazem 1.0 mg/ml in acetonitrile |
| (2s,3s)-5-(2-(dimethylamino)ethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5h)-one |
| (2s,3s)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5h)-one; cas: 75472-91-2 hcl |
| diltiazem ep impurity f; desacetyl diltiazem |
| Q27269511 |
| DTXSID00881093 |
| 1,5-benzothiazepin-4(5h)-one, 5-[2-(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-, (2s,3s)- |
The pharmacokinetic changes of diltiazem (DTZ) and its main metabolite, deacetyldiltiazm (DAD) were studied after oral administration of DTZ to normal rabbits and mild and medium folate-induced renal failure rabbits. The half-life of the metabolite N-demethyldilt Diazem was similar to that of diltsiazem.
| Excerpt | Reference | Relevance |
|---|---|---|
| " In vivo pharmacokinetic studies following intravenous (iv) and portal venous (pv) administration revealed that UN-ARF increased the intrinsic clearance (CLi) of DTZ from 243." | ( Decreased systemic clearance of diltiazem with increased hepatic metabolism in rats with uranyl nitrate-induced acute renal failure. Lee, MH; Lee, YH; Shim, CK, 1992) | 0.28 |
| " Serial blood samples were collected up to 24 h after dose 13 on day 5 to determine possible pharmacokinetic interactions between the two drugs." | ( Pharmacokinetics of diltiazem and propranolol when administered alone and in combination. Dimmitt, DC; Elvin, AT; Giesing, DH; Lanman, RC; Yu, DK, 1991) | 0.28 |
| " Elimination half-life increases and gives AUC's and Cmax higher than those predicted from single dose data." | ( Diltiazem pharmacokinetics in elderly volunteers after single and multiple doses. Boucher, S; Caillé, G; Grace, MG; Lakhani, Z; Russell, A; Spénard, J; Thiffault, J, ) | 0.13 |
| " These findings suggest that some form of acute tolerance to the electrophysiologic effect of diltiazem develops, but the results of pharmacodynamic modeling suggest that this is not caused by the antagonistic effects the metabolites." | ( The pharmacokinetics and pharmacodynamics of diltiazem and its metabolites in healthy adults after a single oral dose. Boyd, RA; Chin, SK; Don-Pedro, O; Giacomini, KM; Sheiner, LB; Verotta, D; Williams, RL, 1989) | 0.28 |
| " The half-life of the metabolite N-demethyldiltiazem (MA) was similar to that of diltiazem, whereas the half-lives of deacetyldiltiazem (M1) and N-demethyldeacetyldiltiazem (M2) were longer." | ( Pharmacokinetics of diltiazem and its metabolites after repeated multiple-dose treatments in healthy volunteers. Höglund, P; Nilsson, LG, 1989) | 0.49 |
| " The half-life of the metabolite N-demethyldiltiazem was similar to that of diltiazem whereas the half-lives of the metabolites deacetyldiltiazem and N-demethyldeacetyldiltiazem were longer." | ( Pharmacokinetics of diltiazem and its metabolites after single and multiple dosing in healthy volunteers. Höglund, P; Nilsson, LG, 1989) | 0.48 |
| "05) increase in diltiazem levels at most time points, in peak concentration and area under the concentration-time curve." | ( The effect of ranitidine and cimetidine on single-dose diltiazem pharmacokinetics. Goodman, RP; McKenney, JM; Winship, LC; Wood, JH; Wright, JT, ) | 0.13 |
| "The pharmacokinetic and pharmacodynamic effects of diltiazem were studied in 8 patients after a short intravenous infusion (20 mg over 10 minutes), a single oral dose (60 or 90 mg), and repeated oral administration (60 or 90 mg every 6 hours for 16 doses)." | ( Pharmacokinetic and pharmacodynamic effects of diltiazem. Pritchett, EL; Shand, DG; Smith, MS; Verghese, CP, 1983) | 0.27 |
| "The objective of this randomized five-way cross-over study with healthy male volunteers was to determine, one the one hand, the bioavailability and main pharmacokinetic parameters of 4 sustained release diltiazem (Surecaps, CAS 42399-41-7) test preparations with ascending doses (180, 240, 300, 360 mg), administered as single application, versus an immediate release 60 mg diltiazem reference preparation, which was given thrice a day at 8-h intervals." | ( Evaluation of pharmacokinetics, bioavailability and dose linearity of diltiazem in healthy volunteers. Hutt, V; Jaeger, H; Janik, F; Kappler, J; Maccari, M; Pabst, G; Ravelli, V, 1993) | 0.29 |
| " The slope of the alpha- and beta-phases increased slightly in six of the eight pregnant rabbits as compared with the non-pregnant animal, but the other pharmacokinetic parameters that largely determine drug disposition (AUC, V(n), CL) showed no significant differences." | ( Diltiazem blood pharmacokinetics in the pregnant and non-pregnant rabbit: maternal and foetal tissue levels. Aramayona, JJ; Bregante, MA; Fraile, LJ; Garcia, MA; Solans, C, 2000) | 0.31 |
| "The pharmacokinetic changes of diltiazem (DTZ) and its main metabolite, deacetyldiltiazem (DAD) were studied after oral administration of DTZ to normal rabbits and mild and medium folate-induced renal failure rabbits." | ( Pharmacokinetics of diltiazem and its major metabolite, deacetyidiltiazem after oral administration of diltiazem in mild and medium folate-induced renal failure rabbits. Burm, JP; Choi, JS; Lee, JH, 2001) | 0.54 |
| " However, other pharmacokinetic parameters of DAD were not significantly different among three groups of rabbits." | ( Pharmacokinetic changes of diltiazem and desacetyldiltiazem after oral administration of diltiazem in rabbits with diabetes mellitus induced by alloxan. Choi, JS; Kim, YG, 2002) | 0.31 |
| " The first 5 individuals identified with genotypes corresponding to a homozygous extensive, heterozygous extensive, or homozygous poor CYP2D6-metabolizing phenotype, respectively, were voluntarily enrolled in the pharmacokinetic study." | ( Pharmacokinetics of diltiazem and its metabolites in relation to CYP2D6 genotype. Bergan, S; Bøe, GH; Christensen, H; Johansen, PW; Lehne, G; Molden, E; Reubsaet, L; Rootwelt, H; Rugstad, HE, 2002) | 0.31 |
| "The purpose of this study was to investigate the pharmacokinetic alteration of diltiazem and its main metabolite, deacetyldiltiazem, after oral administration of diltiazem in rabbits with or without cimetidine co-administration." | ( The influence of cimetidine on the pharmacokinetics of diltiazem and its main metabolite in rabbits. Burm, JP; Choi, JS, 2004) | 0.53 |
| " Pharmacokinetic parameters of diltiazem and desacetyldiltiazem were determined after oral administration of diltiazem (15 mg/kg) in rats pretreated with morin (1." | ( Effects of morin pretreatment on the pharmacokinetics of diltiazem and its major metabolite, desacetyldiltiazem in rats. Choi, HJ; Choi, JS, 2005) | 0.33 |
| " Pharmacokinetic parameters of diltiazem and desacetyldiltiazem were determined in rats after oral administration of diltiazem (15 mg x kg(-1)) to rats pretreated with atorvastatin (0." | ( Effect of atorvastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats. Chang, KS; Choi, DH; Choi, JS; Hong, SP, 2007) | 0.34 |
| " The pharmacokinetic parameters of diltiazem and desacetyldiltiazem were determined after an oral administration of diltiazem (15 mg/kg) to rats in the presence and absence of resveratrol (0." | ( Effects of resveratrol on the pharmacokinetics of diltiazem and its major metabolite, desacetyldiltiazem, in rats. Choi, DH; Choi, JS; Hong, SP, 2008) | 0.35 |
| " Pharmacokinetic parameters of diltiazem and desacetyldiltiazem were determined following the oral administration of diltiazem (15 mg x kg(-1)) in the presence or absence of EGCG (1, 4 and 12 mg x kg(-1))." | ( Effects of epigallocatechin gallate on the bioavailability and pharmacokinetics of diltiazem in rats. Choi, JS; Li, C, 2008) | 0.35 |
| "Compared with the control group (given diltiazem alone), hesperidin (5 or 15 mg/kg) significantly altered the pharmacokinetic parameters of diltiazem, except for 1 mg/kg hesperidin." | ( Effect of hesperidin on the oral pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats. Cho, YA; Choi, DH; Choi, JS, 2009) | 0.35 |
| "The pharmacokinetic parameters of diltiazem and desacetyldiltiazem were determined after orally administering diltiazem (12 mg/kg) to rats in the presence and absence of lovastatin (0." | ( Effects of lovastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats: possible role of cytochrome P450 3A4 and P-glycoprotein inhibition by lovastatin. Chang, KS; Choi, DH; Chung, JW; Ha, SI; Han, JY; Hong, SP; Koh, YY; Yang, JS, 2011) | 0.37 |
| " Compared with the control (given diltiazem alone), the presence of lovastatin significantly altered the pharmacokinetic parameters of diltiazem." | ( Effects of lovastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats: possible role of cytochrome P450 3A4 and P-glycoprotein inhibition by lovastatin. Chang, KS; Choi, DH; Chung, JW; Ha, SI; Han, JY; Hong, SP; Koh, YY; Yang, JS, 2011) | 0.37 |
| " The pharmacokinetic parameters of diltiazem and desacetyldiltiazem were determined after oral and intravenous administration of diltiazem to rats in the presence and absence of simvastatin (0." | ( Effects of simvastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, after oral and intravenous administration in rats: possible role of P-glycoprotein and CYP3A4 inhibition by simvastatin. Choi, DH; Choi, JS; Li, C, 2011) | 0.37 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " The absolute bioavailability of pv DTZ (Fpv) was decreased by UN-ARF from 37." | ( Decreased systemic clearance of diltiazem with increased hepatic metabolism in rats with uranyl nitrate-induced acute renal failure. Lee, MH; Lee, YH; Shim, CK, 1992) | 0.28 |
| "The influence of food on the bioavailability of a conventional tablet and of a slow-release capsule of diltiazem was investigated in two separate groups of 24 healthy volunteers in two open crossover studies." | ( Influence of food on the bioavailability of diltiazem and two of its metabolites following the administration of conventional tablets and slow-release capsules. Boucher, S; Caillé, G; Du Souich, P; Lery, L; Lery, N; Pilon, D; Spenard, J; Varin, F; Vezina, M, 1990) | 0.28 |
| " The area under the curve of diltiazem in a dosing interval at steady state increased significantly compared with the single dose, indicating an increased bioavailability after repeated dosing, probably because of decreased presystemic elimination." | ( Pharmacokinetics of diltiazem and its metabolites after single and multiple dosing in healthy volunteers. Höglund, P; Nilsson, LG, 1989) | 0.28 |
| " The rate of absorption is also slower." | ( A new extended-release formulation of diltiazem HCl for the treatment of mild-to-moderate hypertension. Frishman, WH, 1993) | 0.29 |
| "The objective of this randomized five-way cross-over study with healthy male volunteers was to determine, one the one hand, the bioavailability and main pharmacokinetic parameters of 4 sustained release diltiazem (Surecaps, CAS 42399-41-7) test preparations with ascending doses (180, 240, 300, 360 mg), administered as single application, versus an immediate release 60 mg diltiazem reference preparation, which was given thrice a day at 8-h intervals." | ( Evaluation of pharmacokinetics, bioavailability and dose linearity of diltiazem in healthy volunteers. Hutt, V; Jaeger, H; Janik, F; Kappler, J; Maccari, M; Pabst, G; Ravelli, V, 1993) | 0.29 |
| "Since the ability of the small intestine to biotransform a drug may decrease in distal segments of the intestine, this study aimed to assess whether the site of administration in the small intestine could affect the systemic bioavailability of diltiazem and its two active metabolites, N-desmethyldiltiazem (MA) and desacetyl-diltiazem (M1)." | ( The site of absorption in the small intestine determines diltiazem bioavailability in the rabbit. Caillé, G; du Souich, P; Homsy, W, 1995) | 0.29 |
| "The site of absorption into the intestine modulates the bioavailability of diltiazem and its two active metabolites." | ( The site of absorption in the small intestine determines diltiazem bioavailability in the rabbit. Caillé, G; du Souich, P; Homsy, W, 1995) | 0.29 |
| " Diltiazem HCl ER tablets administered in the evening exhibited 17% and 22% greater bioavailability compared to morning administration under single-dose and steady-state conditions, respectively." | ( Pharmacokinetics of a novel diltiazem HCl extended-release tablet formulation for evening administration. Albert, KS; Eradiri, O; Lai, JC; Sista, S, 2003) | 0.32 |
| " Apparent volume of distribution normalized by the bioavailability (Vd/F) of diltiazem increased significantly in rabbits pretreated with cimetidine increased." | ( The influence of cimetidine on the pharmacokinetics of diltiazem and its main metabolite in rabbits. Burm, JP; Choi, JS, 2004) | 0.32 |
| " Compared with the control group (given diltiazem alone), pretreatment of morin significantly increased the absorption rate constant (Ka) and peak concentration (Cmax) of diltiazem (p<0." | ( Effects of morin pretreatment on the pharmacokinetics of diltiazem and its major metabolite, desacetyldiltiazem in rats. Choi, HJ; Choi, JS, 2005) | 0.33 |
| " Consequently, absolute and relative bioavailability values of diltiazem in the presence of naringin were significantly higher (p<0." | ( Enhanced oral exposure of diltiazem by the concomitant use of naringin in rats. Choi, JS; Han, HK, 2005) | 0.33 |
| " Consequently, absolute bioavailability values of diltiazem pretreated with atorvastatin (8." | ( Effect of atorvastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats. Chang, KS; Choi, DH; Choi, JS; Hong, SP, 2007) | 0.34 |
| " Consequently, the absolute bioavailability (AB) of diltiazem in the presence of resveratrol (2." | ( Effects of resveratrol on the pharmacokinetics of diltiazem and its major metabolite, desacetyldiltiazem, in rats. Choi, DH; Choi, JS; Hong, SP, 2008) | 0.35 |
| "This study investigated the effect of orally administered epigallocatechin gallate (EGCG), a flavonoid, on the bioavailability or pharmacokinetics of diltiazem and its main active metabolites desacetyldiltiazem in rats." | ( Effects of epigallocatechin gallate on the bioavailability and pharmacokinetics of diltiazem in rats. Choi, JS; Li, C, 2008) | 0.35 |
| "This study was to investigate the effect of hesperidin, an antioxidant, on the bioavailability and pharmacokinetics of diltiazem and its active major metabolite, desacetyldiltiazem, in rats." | ( Effect of hesperidin on the oral pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats. Cho, YA; Choi, DH; Choi, JS, 2009) | 0.35 |
| "Hesperidin significantly enhanced the oral bioavailability of diltiazem in rats." | ( Effect of hesperidin on the oral pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats. Cho, YA; Choi, DH; Choi, JS, 2009) | 0.35 |
| " Consequently, the absolute bioavailability values of diltiazem in the presence of lovastatin (11." | ( Effects of lovastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, in rats: possible role of cytochrome P450 3A4 and P-glycoprotein inhibition by lovastatin. Chang, KS; Choi, DH; Chung, JW; Ha, SI; Han, JY; Hong, SP; Koh, YY; Yang, JS, 2011) | 0.37 |
| " Consequently, the absolute bioavailability (AB) values of diltiazem in the presence of simvastatin (1." | ( Effects of simvastatin on the pharmacokinetics of diltiazem and its main metabolite, desacetyldiltiazem, after oral and intravenous administration in rats: possible role of P-glycoprotein and CYP3A4 inhibition by simvastatin. Choi, DH; Choi, JS; Li, C, 2011) | 0.37 |
| "This study investigated the effect of piperine on the gene expression of P-glycoprotein (P-gp) as well as pregnane-X-receptor (PXR) activity and also its implication on the bioavailability of diltiazem, a P-gp substrate." | ( Repeated dosing of piperine induced gene expression of P-glycoprotein via stimulated pregnane-X-receptor activity and altered pharmacokinetics of diltiazem in rats. Han, HK; Kang, KW; Qiang, F, 2012) | 0.38 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Chronic oral dosing significantly lowered both the systemic and oral clearance of diltiazem, with no changes in either the volume of distribution or blood binding of diltiazem." | ( The effects of chronic oral diltiazem and cimetidine dosing on the pharmacokinetics and negative dromotropic action of intravenous and oral diltiazem in the dog. Bai, SA; Lankford, S; Maskasame, C, 1992) | 0.28 |
| " The area under the curve of diltiazem in a dosing interval at steady state increased significantly compared with the single dose, indicating an increased bioavailability after repeated dosing, probably because of decreased presystemic elimination." | ( Pharmacokinetics of diltiazem and its metabolites after single and multiple dosing in healthy volunteers. Höglund, P; Nilsson, LG, 1989) | 0.28 |
| " Plasma concentrations of diltiazem and its major metabolite desacetyl-diltiazem were measured by high pressure liquid chromatography (HPLC) up to 48 h after single dosing of the sustained release preparations as well as after repeated doses of the immediate release formulation." | ( Evaluation of pharmacokinetics, bioavailability and dose linearity of diltiazem in healthy volunteers. Hutt, V; Jaeger, H; Janik, F; Kappler, J; Maccari, M; Pabst, G; Ravelli, V, 1993) | 0.29 |
| " These observations suggested that the metabolism of diltiazem to deacetyldiltiazem was reduced by cimetidine treatment and that the dosage of diltiazem should be adjusted when the drug is co-administered chronically with cimetidine in a clinical setting." | ( The influence of cimetidine on the pharmacokinetics of diltiazem and its main metabolite in rabbits. Burm, JP; Choi, JS, 2004) | 0.56 |
| " Based on these results, if these results would be confirmed in clinical experiments, the dosage of diltiazem should be readjusted when diltiazem is used concomitantly with resveratrol." | ( Effects of resveratrol on the pharmacokinetics of diltiazem and its major metabolite, desacetyldiltiazem, in rats. Choi, DH; Choi, JS; Hong, SP, 2008) | 0.35 |
| Class | Description |
|---|---|
| benzothiazepine | |
| [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] | |
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 18 (31.58) | 18.7374 |
| 1990's | 19 (33.33) | 18.2507 |
| 2000's | 16 (28.07) | 29.6817 |
| 2010's | 4 (7.02) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (10.01) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 6 (9.52%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 2 (3.17%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 55 (87.30%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||