Page last updated: 2024-12-06

cilazapril, anhydrous

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Description

Cilazapril is an angiotensin-converting enzyme (ACE) inhibitor used to treat high blood pressure and heart failure. It is a prodrug that is metabolized to its active form, cilazaprilat, which inhibits ACE, an enzyme that converts angiotensin I to angiotensin II. Angiotensin II is a potent vasoconstrictor, and its inhibition leads to vasodilation, which lowers blood pressure. The anhydrous form of cilazapril is a stable and more easily handled form of the drug. Cilazapril is synthesized through a multi-step process that involves the use of various organic reagents and catalysts. The study of cilazapril is important because it provides insights into the role of ACE in regulating blood pressure and other physiological processes. Research on cilazapril has contributed to the development of new and effective treatments for hypertension and heart failure.'

Cilazapril: One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors) used for hypertension. It is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cilazapril : A pyridazinodiazepine resulting from the formal condensation of the carboxy group of cilazaprilat with ethanol. It is a drug used in the treatment of hypertension and heart failure. [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]

Cross-References

ID SourceID
PubMed CID56330
CHEMBL ID515606
CHEBI ID3698
SCHEMBL ID24962
MeSH IDM0329303

Synonyms (59)

Synonym
AC-269
vascace
inibace
ro-312848
cilazil
inhibace
dynorm
ro 31-2848
cilazapril (inn)
D07699
88768-40-5
cilazapril
cilazapril anhydrous
DB01340
cilazaprilum [latin]
6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic acid, 9-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)octahydro-10-oxo-, (1s-(1alpha,9alpha(r*)))-
6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic acid, 9-(((1s)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)octahydro-10-oxo-, (1s,9s)-
ro 34-2848
cilazapril (anhydrous)
anhydrous cilazapril
ro-312848006
CHEMBL515606
cilazaprilum
(4s,7s)-7-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-6-oxo-1,2,3,4,7,8,9,10-octahydropyridazino[1,2-a]diazepine-4-carboxylic acid
NCGC00182039-01
8q9454114q ,
cilazapril [inn]
unii-8q9454114q
dtxcid8028555
tox21_112971
dtxsid1048629 ,
cas-88768-40-5
AKOS015951168
cilazapril [mi]
ro-31-2848/006
6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic acid, 9-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)octahydro-10-oxo-, monohydrate, (1s-(1.alpha.,9.alpha.(r*)))
cilazapril [who-dd]
cilazapril [vandf]
(1s,9s)-9-(((s)-1-carboxy-3-phenylpropyl)amino)octahydro-10-oxo-6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic acid 9-ethyl ester
gtpl6459
ro 31-2848006
(1s,9s)-9-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-10-oxo-1,2,3,4,6,7,8,9-octahydropyridazino[1,2-a]diazepine-1-carboxylic acid
HY-A0043
SCHEMBL24962
NCGC00182039-02
AB01565812_02
(1s,9s)-9-{[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxo-octahydro-1h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
CHEBI:3698
vascase
(1s,9s)-9-{[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxooctahydro-6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
(5s,8s)-5-{[(1s)-1-ethoxycarbonyl-3-phenyl-propyl]-amino}-6-oxo-1,7-diazabicyclo[5.4.0]undecane-8-carboxylic acid
(1s,9s)-9-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-10-oxooctahydro-6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
Q867350
BRD-K96177243-002-01-9
(1s,9s)-9-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
ro-34-2848
ro34-2848
A916338
EN300-19766662

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Adverse events were mostly observed within the first 8-16 weeks of treatment, with headache, dizziness, fatigue, nausea, cough and chest pain being the most frequent."( Cilazapril: an overview of its efficacy and safety in hypertension.
Schneeweiss, A; Szucs, T, 1992
)
0.28
"9 percent) reported adverse events, but most of these were judged unlikely to be related to therapy."( Efficacy and safety of cilazapril in elderly patients with essential hypertension. A multicenter study.
Ben-Ishay, D; Bompani, R; Dixon, R; Hoverman, RJ; Jones, RW; Kobrin, I; Kögler, P; Sanchez, R, 1989
)
0.28
" No serious adverse reactions were observed."( Efficacy and safety of cilazapril in hypertensive patients with moderate to severe renal impairment.
Carlsen, JE; Hansen, FM; Jensen, HA, 1989
)
0.28
" Adverse biochemical effects were not observed in any group."( [Comparative and double-blind study of the efficacy and safety of cilazapril compared to nifedipine retard in the treatment of mild and moderate arterial hypertension].
Athanázio-Heliodoro, RC; Franco, RJ; Marcondes, M; Martin, LC; Mion Júnior, D; Pascoal, IJ; Sampaio, M; Tinucci, T; Velasco-Cornejo, IF, 1994
)
0.29
" Cilazapril had no adverse effects on the biochemical parameters with low incidence of collateral effects."( [Comparative and double-blind study of the efficacy and safety of cilazapril compared to nifedipine retard in the treatment of mild and moderate arterial hypertension].
Athanázio-Heliodoro, RC; Franco, RJ; Marcondes, M; Martin, LC; Mion Júnior, D; Pascoal, IJ; Sampaio, M; Tinucci, T; Velasco-Cornejo, IF, 1994
)
0.29
" The monitoring period was six months and practitioners were asked to report all adverse events."( Short term safety assessment of cilazapril.
Coulter, DM, 1993
)
0.29
"4%) reports describing 133 adverse events; 124 (93%) were assessed as reactions."( Short term safety assessment of cilazapril.
Coulter, DM, 1993
)
0.29
" Although there was a high rate of reporting of known adverse reactions, other events were reported at a very low rate and spontaneous reporting is thus confirmed as an unreliable method of monitoring for unexpected adverse reactions."( Short term safety assessment of cilazapril.
Coulter, DM, 1993
)
0.29

Pharmacokinetics

ExcerptReferenceRelevance
"The antihypertensive effects and pharmacokinetic properties of cilazapril, a long-acting angiotensin-converting enzyme (ACE) inhibitor, were investigated in hypertensive patients with normal renal function (NRF; n = 5) and those with impaired renal function (IRF; n = 7)."( Antihypertensive effects and pharmacokinetics of single and consecutive doses of cilazapril in hypertensive patients with normal and impaired renal function.
Gotoh, E; Kaneko, Y; Shionoiri, H; Takagi, N; Takeda, K; Yabana, M, 1988
)
0.27
" For cilazapril, Cmax and tmax were independent of creatinine clearance."( Pharmacokinetics of cilazapril in patients with renal failure.
Brown, AN; Fillastre, JP; Francis, RJ; Godin, M; Manfredi, R; Moulin, B; Pinta, P; Williams, PE, 1989
)
0.28
" No clinically relevant pharmacokinetic interactions between cilazapril and propranolol were found."( Pharmacokinetic and pharmacodynamic interactions between the ACE inhibitor cilazapril and beta-adrenoceptor antagonist propranolol in healthy subjects and in hypertensive patients.
Belz, GG; Breithaupt, K; Erb, K; Essig, J; Hoogkamer, JF; Kleinbloesem, CH; Kneer, J, 1989
)
0.28
" No significant pharmacokinetic interaction was found between cilazapril and hydrochlorothiazide."( Pharmacokinetics and effects on renal function following cilazapril and hydrochlorothiazide alone and in combination in healthy subjects and hypertensive patients.
Grynne, B; Kleinbloesem, CH; Nilsen, OG; Romfo, OS; Sellevold, OF; Smedsrud, A; Williams, PE, 1989
)
0.28
"The pharmacokinetic properties and antihypertensive effects of cilazapril, a long-acting converting enzyme inhibitor, were investigated in seven hypertensive patients with renal failure."( Pharmacokinetics of single and consecutive doses of cilazapril and its depressor effects in hypertensive patients with renal dysfunction.
Gotoh, E; Kaneko, Y; Miyakawa, T; Oda, H; Shionoiri, H; Takasaki, I; Ueda, S, 1988
)
0.27
" We assessed pharmacokinetic and pharmacodynamic interactions of the ACE inhibitor cilazapril and the beta-blocker propranolol in healthy volunteers and patients with essential hypertension."( Review of studies on the clinical pharmacodynamics of cilazapril.
Belz, GG; Breithaupt, K; Erb, K, 1994
)
0.29
" A significantly increased mean plasma peak concentration (40."( Angiotensin-converting enzyme (ACE)-inhibition in cirrhosis. Pharmacokinetics and dynamics of the ACE-inhibitor cilazapril (Ro 31-2848).
Gross, V; Haag, K; Neis, W; Schölmerich, J; Treher, E; Wiegand, U, 1993
)
0.29
"The pharmacokinetic parameters of cilazaprilat were similar in the two ethnic groups."( A comparison of the pharmacokinetics and pharmacodynamics of cilazapril between Chinese and Caucasian healthy, normotensive volunteers.
Anderson, PJ; Critchley, JA; Tomlinson, B, 1996
)
0.29
" The pharmacokinetic and pharmacodynamic properties of the angiotensin converting enzyme (ACE) inhibitor cilazapril were studied in 30 hypertensive patients with various degrees of renal function."( Pharmacokinetics and haemodynamic effects of the angiotensin converting enzyme inhibitor cilazapril in hypertensive patients with normal and impaired renal function.
Ambros, RJ; Huysmans, FT; Kloke, HJ; Koene, RA; Van Hamersvelt, HW; Wetzels, JF, 1996
)
0.29

Compound-Compound Interactions

ExcerptReferenceRelevance
"The purpose of the present study was to examine the effects of salt-restriction alone and in combination with an angiotensin-converting enzyme (ACE) inhibitor (cilazapril) on both office and ambulatory blood pressure (BP) levels in free living subjects with elevated BP."( Effects of moderate salt restriction alone and in combination with cilazapril on office and ambulatory blood pressure.
Korhonen, M; Litmanen, H; Niskanen, L; Rauramaa, R; Uusitupa, M; Väisänen, S, 1996
)
0.29
" The present study was conducted to examine whether spironolactone, a mineralocorticoid receptor antagonist, alone or in combination with cilazapril, an angiotensin converting enzyme (ACE) inhibitor, ameliorates proteinuria and renal lesions in an immune-initiated progressive nephritis model."( Spironolactone in combination with cilazapril ameliorates proteinuria and renal interstitial fibrosis in rats with anti-Thy-1 irreversible nephritis.
Asai, M; Fukuda, S; Hayashi, M; Kawachi, H; Marumo, T; Monkawa, T; Saruta, T; Shimizu, F; Tsuji, M; Yoshino, J, 2004
)
0.32

Bioavailability

ExcerptReferenceRelevance
" Parent drug absorption and diacid bioavailability in the rat were higher than for enalapril, and the inhibition of plasma ACE of longer duration."( Biological properties of the angiotensin-converting enzyme inhibitor cilazapril.
Brewster, M; Budd, J; Francis, RJ; Klevans, LR; Natoff, IL; Nixon, JS; Patel, AT; Wenger, J; Worth, E,
)
0.13
" Cilazapril is exceptionally well absorbed by the oral route (98% in rats)."( A review of the preclinical cardiovascular pharmacology of cilazapril, a new angiotensin converting enzyme inhibitor.
Waterfall, JF, 1989
)
0.28
" Urinary recovery data indicated an absolute bioavailability for cilazaprilat of 57% (range 45-75%) from oral cilazapril, but only 19% (range 8-40%) from oral cilazaprilat."( The pharmacokinetics and bioavailability of cilazapril in normal man.
Brown, AN; Durnin, C; Francis, RJ; McEwen, J; Rajaguru, S; Walters, GE; Williams, PE, 1989
)
0.28
" The effect of food on the bioavailability of cilazapril at this dose would not be expected to be clinically significant."( The influence of food on the pharmacokinetics and ACE inhibition of cilazapril.
Brown, AN; DeFeo, TM; Lin, A; Massarella, JW; Wills, RJ, 1989
)
0.28
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
"5 mm Hg, but had no effect on the dose-response curves of dose of PE or Ang II vs."( Alpha-adrenergic and angiotensin II pressor sensitivity in hypertensive patients treated with an angiotensin-converting enzyme inhibitor.
Kalliatakis, B; Patton, J; Radford, HM; Rosendorff, C, 1992
)
0.28
" Results of various dose-response studies established the indirect relationship between dose, the plasma concentration of the drug, and the blood pressure response, and identified the dose producing the maximal effect to be 5mg."( Clinical pharmacology of cilazapril.
Francis, RJ; Kleinbloesem, CH; van Brummelen, P; Wiegand, UW, 1991
)
0.28
"The efficacy of cilazapril monotherapy was evaluated in 2 multicentre double-blind dose-response trials."( Antihypertensive duration of action of cilazapril in patients with mild to moderate essential hypertension.
Güntzel, P; Kobrin, I; Paran, E; Viskoper, R; Zimlichman, R, 1991
)
0.28
"5 and 5 mg doses of cilazapril have equivalent antihypertensive efficacy using ABP and that 24-h ABP monitoring should also be performed in dose-response studies."( Antihypertensive effects of cilazapril, 2.5 and 5 mg, once daily versus placebo on ambulatory blood pressure following single- and repeat-dose administration.
Lacourcière, Y; Poirier, L; Provencher, P; Pyzyk, M, 1991
)
0.28
" On repeated daily oral dosing to SHR, both compounds had a cumulative antihypertensive effect."( Biological properties of the angiotensin-converting enzyme inhibitor cilazapril.
Brewster, M; Budd, J; Francis, RJ; Klevans, LR; Natoff, IL; Nixon, JS; Patel, AT; Wenger, J; Worth, E,
)
0.13
"According to classic pharmacologic theory, agonist/antagonist competition can be used to quantify an antagonist's potency by measurement of agonist dose-response curves in the presence of varying doses of the antagonist."( Hemodynamic responses to angiotensin I in normal volunteers and the antagonism by the angiotensin-converting enzyme inhibitor cilazapril.
Belz, GG; Essig, J; Wellstein, A, 1987
)
0.27
" Plasma and urinary cilazaprilat concentrations, and plasma ACE activities were measured up to 72 h after dosing by radioenzymatic methods."( A pharmacokinetic study of cilazapril in elderly and young volunteers.
Brown, AN; Durnin, C; McEwen, J; Rajaguru, S; Walters, GE; Williams, PE, 1989
)
0.28
" A reduced dosage is indicated for these patients."( Pharmacokinetics of cilazapril in patients with renal failure.
Brown, AN; Fillastre, JP; Francis, RJ; Godin, M; Manfredi, R; Moulin, B; Pinta, P; Williams, PE, 1989
)
0.28
") were investigated on the dose-response curves to angiotensin I and to noradrenaline, administered locally in the hand veins in six healthy male volunteers in doses not producing systemic effects."( The effect of oral cilazapril and prazosin on the constrictor effects of locally infused angiotensin I and noradrenaline in human dorsal hand veins.
Beermann, C; Belz, GG; Kleinbloesem, CH; Schloos, J, 1989
)
0.28
" The result of various dose-response studies established the indirect relationship between dose, plasma concentration of the drug, and the blood pressure response and identified the dose producing maximal effect (i."( Clinical pharmacology of cilazapril.
Francis, RJ; Kleinbloesem, CH; Van Brummelen, P; Wiegand, UW, 1989
)
0.28
" Angiotensin I dose-response curves were derived by continuous infusion of angiotensin I in increasing dose steps; steady state was reached within 3 min."( The assessment of ACE activity in man following angiotensin I challenges: a comparison of cilazapril, captopril and enalapril.
Belz, GG; Essig, J; Wellstein, A, 1989
)
0.28
" The angiotensin I dependent increase in systemic and pulmonary resistance and pulmonary capillary wedge pressure was attenuated by cilazapril, as indicated by the shift of the dose-response curves to the right."( Effects of ACE inhibition with cilazapril on splanchnic and systemic haemodynamics in man.
Gasic, S; Heinz, G; Kleinbloesem, C; Korn, A, 1989
)
0.28
" Historical comparison of the first-dose data with those for healthy young volunteers at identical dosage revealed only minor differences in kinetic parameters."( A pharmacokinetic study of cilazapril in patients with congestive heart failure.
Brown, AN; Curry, PV; Francis, RJ; Rajaguru, S; Rosenthal, E; Steiner, J; Williams, PE, 1989
)
0.28
"In pentobarbital-anesthetized dogs, the increase in the renal norepinephrine secretion rate elicited by renal nerve stimulation (1 Hz) during infusion of angiotensin I (15 ng/kg/min) was partially but significantly inhibited (by 21-37%) after dosing with cilazaprilat (0."( Inhibitory effect of cilazaprilat on norepinephrine release induced by renal nerve stimulation in anesthetized dogs.
Chiba, K; Matsuoka, T; Satoh, S; Suzuki-Kusaba, M, 1988
)
0.27
"A multistage sampling method is proposed in dose-response trials, where dose adaptions can be performed in the preplanned adaptive interim analyses."( An adaptive method for establishing a dose-response relationship.
Bauer, P; Röhmel, J, 1995
)
0.29
" The higher dosage level was administered to 42% of patients in the cilazapril-treated group and to 47% in the nitrendipine-treated group."( Effects of cilazapril and nitrendipine on blood pressure, mood, sleep, and cognitive function in elderly hypertensive patients: an Italian multicenter study.
Leonetti, G; Salvetti, A, 1994
)
0.29
"75, 10, and 30 mg) of cilazapril reduced diastolic blood pressure dose-dependently and shifted the angiotensin I dose-response curves to the right."( Review of studies on the clinical pharmacodynamics of cilazapril.
Belz, GG; Breithaupt, K; Erb, K, 1994
)
0.29
"Cilazapril in either dosage induced significant and similar antihypertensive effects on clinic blood pressure shortly after dosing (2 to 4 h), persisting during chronic treatment; however, no relevant effect persisted at the end of dosing (24 h)."( Discrepancies between clinic and ambulatory blood pressure responses to cilazapril therapy.
Lacourcière, Y; Leenen, F; Lenis, JH; Myers, MG; Rangno, R; Spence, JD,
)
0.13
" C or D alone shifted dose-response curves to capsaicin (from 10(-7) M to 10(-3) M) to lower concentrations compared with the control, and C+D further shifted them."( Angiotensin-converting enzyme inhibitor and danazol increase sensitivity of cough reflex in female guinea pigs.
Ebihara, T; Nakazawa, H; Ohrui, T; Sasaki, H; Sekizawa, K, 1996
)
0.29
" When applied locally to the sciatic nerve, the dose-response curve of angiotensin II was more potent in experimental diabetic neuropathy (EDN) than control rats."( Altered vasoreactivity to angiotensin II in experimental diabetic neuropathy: role of nitric oxide.
Kihara, M; Mitsui, MK; Mitsui, Y; Nakasaka, Y; Okuda, K; Schmelzer, JD; Takahashi, M, 1999
)
0.3
" In conclusion, this reappraisal of the conflicting observations reported on ACE inhibitor effects on exercise capacity has highlighted a proposition that there is an optimal dosage of ACE inhibitors which will most enhance exercise capacity, and this will require further well designed cross-over studies to elucidate."( Disparate results of ACE inhibitor dosage on exercise capacity in heart failure: a reappraisal of vasodilator therapy and study design.
Cooke, GA; Tan, LB; Williams, SG; Wright, DJ, 2001
)
0.31
" The method was successfully applied to the determination of the drug and its metabolite in urine samples obtained from three hypertensive patients (detection limits of 115 ng ml(-1) for cilazaprilat and 125 ng ml(-1) for cilazapril) and to pharmaceutical dosage forms."( Capillary zone electrophoresis applied to the determination of the angiotensin-converting enzyme inhibitor cilazapril and its active metabolite in pharmaceuticals and urine.
Akesolo, U; Alonso, RM; Jiménez, RM; Prieto, JA, 2001
)
0.31
" Patients who received a full dosage of ACEI did not have to posses an increasing risk of C-ACEI."( Angiotensin converting enzyme inhibitor induced cough: experience in Siriraj Hospital.
Buranakitjaroen, P; Phoojaroenchanachai, M; Sangprasert, P; Saravich, S; Sriussadaporn, S, 2003
)
0.32
"An increased dosage of cilazapril (twice the maximum recommended dose) in addition to combination therapy with telmisartan was associated with increased blockade of the renin-angiotensin-aldosterone system, with no additional effect on proteinuria, markers of tubular injury or renal fibrosis."( Dual blockade of the renin-angiotensin-aldosterone system with high-dose angiotensin-converting enzyme inhibitor for nephroprotection: an open, controlled, randomized study.
Aleksandrowicz, E; Larczyński, W; Lysiak-Szydlowska, W; Renke, M; Rutkowski, B; Rutkowski, P; Tylicki, L, 2008
)
0.35
" On pharmaceutical market it is available only in inconvenient for pediatric use tablet dosage forms."( Stability of cilazapril in pediatric oral suspensions prepared from commercially available tablet dosage forms.
Paszun, SK; Stanisz, BJ; Zalewska, A,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
prodrugA compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antihypertensive agentAny drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitorAn EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
[role 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]

Drug Classes (3)

ClassDescription
ethyl esterAny carboxylic ester resulting from the formal condensation of the carboxy group of a carboxylic acid with ethanol.
pyridazinodiazepine
dicarboxylic acid monoesterA monoester of a dicarboxylic acid.
[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 Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
cholesterol biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
response to toxic substanceLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol effluxLiver carboxylesterase 1Homo sapiens (human)
negative regulation of cholesterol storageLiver carboxylesterase 1Homo sapiens (human)
epithelial cell differentiationLiver carboxylesterase 1Homo sapiens (human)
cholesterol homeostasisLiver carboxylesterase 1Homo sapiens (human)
reverse cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
medium-chain fatty acid metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cellular response to cholesterolLiver carboxylesterase 1Homo sapiens (human)
cellular response to low-density lipoprotein particle stimulusLiver carboxylesterase 1Homo sapiens (human)
cholesterol ester hydrolysis involved in cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid secretionLiver carboxylesterase 1Homo sapiens (human)
lipid catabolic processLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
sterol esterase activityLiver carboxylesterase 1Homo sapiens (human)
methylumbelliferyl-acetate deacetylase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylesterase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylic ester hydrolase activityLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
cytoplasmLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulum lumenLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
cytosolLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID625283Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for elevated liver function tests2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID625281Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholelithiasis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID625282Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cirrhosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID625287Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatomegaly2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625284Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic failure2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID625285Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic necrosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID456232Activity at human recombinant CES1 expressed in baculovirus-infected Spodoptera frugiperda Sf21 cells assessed as substrate hydrolysis by fluorescence assay2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
In silico prediction of human carboxylesterase-1 (hCES1) metabolism combining docking analyses and MD simulations.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID625280Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholecystitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625286Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625292Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) combined score2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID625291Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver function tests abnormal2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625288Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for jaundice2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID679588TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical)(Digoxin: 0.1 uM, Cilazapril: 50 uM) in MDR1-expressing LLC-PK1 cells2002Life sciences, Feb-15, Volume: 70, Issue:13
Interaction of digoxin with antihypertensive drugs via MDR1.
AID625289Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver disease2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID625279Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for bilirubinemia2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID625290Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver fatty2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (514)

TimeframeStudies, This Drug (%)All Drugs %
pre-199084 (16.34)18.7374
1990's323 (62.84)18.2507
2000's91 (17.70)29.6817
2010's12 (2.33)24.3611
2020's4 (0.78)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.08

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.

MetricThis Compound (vs All)
Research Demand Index8.08 (24.57)
Research Supply Index6.60 (2.92)
Research Growth Index4.68 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.08)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials189 (34.68%)5.53%
Reviews28 (5.14%)6.00%
Case Studies18 (3.30%)4.05%
Observational0 (0.00%)0.25%
Other310 (56.88%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]