Page last updated: 2024-11-06

cilazaprilat

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Cilazaprilat is a potent ACE inhibitor, produced by hydrolysis of the prodrug cilazapril. It is a prodrug of cilazapril, which is a potent, long-acting angiotensin-converting enzyme inhibitor that is used to treat hypertension. It inhibits the enzyme that converts angiotensin I to angiotensin II. Angiotensin II is a potent vasoconstrictor, and its inhibition leads to vasodilation and reduction in blood pressure. Cilazaprilat is a potent ACE inhibitor, but it has a shorter duration of action than cilazapril. It is absorbed rapidly and completely from the gastrointestinal tract, and it is eliminated primarily by the kidneys. Cilazaprilat is used to treat hypertension and heart failure. It is also used in the treatment of diabetic nephropathy. Cilazaprilat is a highly effective drug for the treatment of hypertension, and it is generally well-tolerated. However, it can cause side effects, such as cough, dizziness, and headache. Cilazaprilat is contraindicated in patients with hyperkalemia, bilateral renal artery stenosis, or a history of angioedema. The drug is also contraindicated during pregnancy.'

cilazaprilat: InChIKey: UVAUYSRYXACKSC-ULQDDVLXSA-N [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID64766
CHEMBL ID2104578
CHEBI ID81005
SCHEMBL ID906169
MeSH IDM0133435

Synonyms (36)

Synonym
cilazaprilatum [latin]
ro 31-3113
cilazaprilate [french]
n-((1s,9s)-1-carboxy-10-oxoperhydropyridazino-(1,2-alpha)(1,2)diazepin-9-yl)-4-phenyl-l-homoalanine
cilazaprilat
(1s,9s)-9-((s)-1-carboxy-3-phenylpropylamino)-10-oxo-4,6,7,8,9,10-hexahydro-1h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
C17309
90139-06-3
wbl76fh528 ,
unii-wbl76fh528
cilazaprilat [inn:ban]
cilazaprilatum
cilazaprilate
ro-31-3113
CHEMBL2104578
ro-313113
chebi:81005 ,
cilazapril diacid
cilazaprilat anhydrous
(1s,9s)-9-[[(1s)-1-carboxy-3-phenylpropyl]amino]octahydro-10-oxo-6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
gtpl6461
(1s,9s)-9-[[(2s)-1-hydroxy-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
6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylicacid, 9-[[(1s)-1-carboxy-3-phenylpropyl]amino]octahydro-10-oxo-, (1s,9s)-
(1s,9s)-9-[[(s)-1-carboxy-3-phenylpropyl]amino]-10-oxooctahydro-6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid, 9-[[(1s)-1-carboxy-3-phenylpropyl]amino]octahydro-10-oxo-
cilazaprilat [inn]
n-((1s,9s)-1-carboxy-10-oxoperhydropyridazino-(1,2-.alpha.)(1,2)diazepin-9-yl)-4-phenyl-l-homoalanine
cilazapril diacid [mi]
SCHEMBL906169
3-(4-benzyloxyphenyl)isoxazole-5-carbaldehyde
DTXSID00238043
AKOS030243014
(1s,9s)-9-((s)-1-carboxy-3-phenylpropylamino)-10-oxooctahydro-1h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
DB15565
Q27076049
(4s,7s)-7-[[(1s)-1-carboxy-3-phenylpropyl]amino]-6-oxo-1,2,3,4,7,8,9,10-octahydropyridazino[1,2-a]diazepine-4-carboxylic acid

Research Excerpts

Overview

Cilazaprilat is an inhibitor of angiotensin converting enzyme (ACE) and is the active metabolite of cilAZapril.

ExcerptReferenceRelevance
"1. Cilazaprilat is an inhibitor of angiotensin converting enzyme (ACE) and is the active metabolite of cilazapril. "( A pharmacokinetic study of cilazapril in elderly and young volunteers.
Brown, AN; Durnin, C; McEwen, J; Rajaguru, S; Walters, GE; Williams, PE, 1989
)
0.9

Pharmacokinetics

ExcerptReferenceRelevance
" 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
" 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

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
" 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

Dosage Studied

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. Plasma ACE activities were measured up to 72 h after doses by radioenzymatic methods.

ExcerptRelevanceReference
" 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
" 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
)
0.6
" 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
"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
)
0.77
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
non-proteinogenic alpha-amino acidAny alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
[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]

Pathways (2)

PathwayProteinsCompounds
Cilazapril Action Pathway34
Cilazapril Metabolism Pathway12

Bioassays (1)

Assay IDTitleYearJournalArticle
AID679587TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical)(Digoxin: 0.1 uM, Cilazaprilat: 50 uM) in MDR1-expressing LLC-PK1 cells2002Life sciences, Feb-15, Volume: 70, Issue:13
Interaction of digoxin with antihypertensive drugs via MDR1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (28.95)18.7374
1990's20 (52.63)18.2507
2000's6 (15.79)29.6817
2010's1 (2.63)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 53.99

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index53.99 (24.57)
Research Supply Index3.89 (2.92)
Research Growth Index4.29 (4.65)
Search Engine Demand Index87.16 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (53.99)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (17.07%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other34 (82.93%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]