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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H23NO4S2
Molecular Weight 429.552
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZOFENOPRIL

SMILES

C[C@H](CSC(=O)C1=CC=CC=C1)C(=O)N2C[C@H](C[C@H]2C(O)=O)SC3=CC=CC=C3

InChI

InChIKey=IAIDUHCBNLFXEF-MNEFBYGVSA-N
InChI=1S/C22H23NO4S2/c1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14H2,1H3,(H,25,26)/t15-,18+,19+/m1/s1

HIDE SMILES / InChI

Description

Zofenopril is an inhibitor of Angiotensin Converting Enzyme (ACE), which is approved in Europe for the treatment of hypertension and acute myocardial infarction.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.9 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZOPRANOL
Primary
ZOPRANOL
PubMed

PubMed

TitleDatePubMed
Comparisons in vitro, ex vivo, and in vivo of the actions of seven structurally diverse inhibitors of angiotensin converting enzyme (ACE).
1989
Comparative effects of zofenopril and hydrochlorothiazide on office and ambulatory blood pressures in mild to moderate essential hypertension.
1989 Mar
Effect of Zofenopril on regeneration of sciatic nerve crush injury in a rat model.
2009 Jun 9
Comparison between zofenopril and ramipril in combination with acetylsalicylic acid in patients with left ventricular systolic dysfunction after acute myocardial infarction: results of a randomized, double-blind, parallel-group, multicenter, European study (SMILE-4).
2012
Cost-effectiveness of zofenopril in patients with left ventricular systolic dysfunction after acute myocardial infarction: a post hoc analysis of SMILE-4.
2013
Cardioprotective role of zofenopril in patients with acute myocardial infarction: a pooled individual data analysis of four randomised, double-blind, controlled, prospective studies.
2015
Randomised comparison of zofenopril and ramipril plus acetylsalicylic acid in postmyocardial infarction patients with left ventricular systolic dysfunction: a post hoc analysis of the SMILE-4 Study in patients according to levels of left ventricular ejection fraction at entry.
2015
Blood Pressure Response to Zofenopril or Irbesartan Each Combined with Hydrochlorothiazide in High-Risk Hypertensives Uncontrolled by Monotherapy: A Randomized, Double-Blind, Controlled, Parallel Group, Noninferiority Trial.
2015
Zofenopril Protects Against Myocardial Ischemia-Reperfusion Injury by Increasing Nitric Oxide and Hydrogen Sulfide Bioavailability.
2016 Jul 5
Efficacy of Zofenopril Compared With Placebo and Other Angiotensin-converting Enzyme Inhibitors in Patients With Acute Myocardial Infarction and Previous Cardiovascular Risk Factors: A Pooled Individual Data Analysis of 4 Randomized, Double-blind, Controlled, Prospective Studies.
2017 Jan
Patents

Sample Use Guides

In Vivo Use Guide
The usual effective dose in hypertension is 30 mg/day (in patients without volume or salt depletion) and the starting dose is 7.5 or 15 mg/day (in patients with volume or salt depletion). In acute myocardial infarction the treatment scheme is the following: 7.5 mg every 12 h (1st and 2nd day); 15 mg every 12 h (3rd and 4th day); 30 mg every 12 h (from 5th day).
Route of Administration: Oral
In Vitro Use Guide
Zofenopril (36 uM) significantly increased coronary flow after 5 min of incubation with isolated rat hearts.
Name Type Language
ZOFENOPRIL
INN   MI   WHO-DD  
INN  
Official Name English
R-PROLINE, 1-(3-(BENZOYLTHIO)-2-METHYL-1-OXOPROPYL)-4-(PHENYLTHIO)-, (1(R*),2.ALPHA.,4.ALPHA.)-
Common Name English
ZOFENOPRIL [MI]
Common Name English
(4S)-N-((S)-3-MERCAPTO-2-METHYLPROPIONYL)-4-(PHENYLTHIO)-R-PROLINE BENZOATE (ESTER)
Common Name English
ZOFENIL
Brand Name English
ZOFENOPRIL [INN]
Common Name English
ZOFENOPRIL [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC C09BA15
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
WHO-ATC C09AA15
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
WHO-VATC QC09BA15
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
WHO-VATC QC09AA15
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
Code System Code Type Description
MESH
C044958
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY
EVMPD
SUB00170MIG
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY
EPA CompTox
81872-10-8
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY
CAS
81872-10-8
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY
INN
5535
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY
MERCK INDEX
M11656
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY Merck Index
WIKIPEDIA
ZOFENOPRIL
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY
PUBCHEM
92400
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY SWITZERF
RXCUI
39990
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY RxNorm
NCI_THESAURUS
C82219
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY
IUPHAR
6462
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY
ChEMBL
CHEMBL331378
Created by admin on Tue Mar 06 10:21:46 UTC 2018 , Edited by admin on Tue Mar 06 10:21:46 UTC 2018
PRIMARY