ZOFENOPRIL

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 Search

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

Molecular Formula	C22H23NO4S2
Molecular Weight	429.552
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Bifril_7_5/WC500013887.pdf | http://www.nevapress.com/cdr/full/17/2/115.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 97 Target ID: P12821 Gene ID: 1636.0 Gene Symbol: ACE Target Organism: Homo sapiens (Human) Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Bifril_7_5/WC500013887.pdf	Inhibitor 8297		10.9 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Bifril_7_5/WC500013887.pdf	Primary		Approved 8429	ZOPRANOL Approved Use ZOPRANOL is indicated for the treatment of mild to moderate essential hypertension. Launch Date 9.6465597E11
Acute myocardial infarction 37 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Bifril_7_5/WC500013887.pdf	Primary		Approved 8429	ZOPRANOL Approved Use ZOPRANOL is indicated for the treatment initiated within the first 24 hours of patients with acute myocardial infarction with or without signs and symptoms of heart failure. Launch Date 9.6465597E11

PubMed

Title	Date	PubMed
Comparisons in vitro, ex vivo, and in vivo of the actions of seven structurally diverse inhibitors of angiotensin converting enzyme (ACE).	1989	2557876
Comparative effects of zofenopril and hydrochlorothiazide on office and ambulatory blood pressures in mild to moderate essential hypertension.	1989 Mar	2655685
Zofenopril after anterior myocardial infarction.	1995 Jun 22	7619164
Effect of Zofenopril on regeneration of sciatic nerve crush injury in a rat model.	2009 Jun 9	19508704
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	22707187
Cost-effectiveness of zofenopril in patients with left ventricular systolic dysfunction after acute myocardial infarction: a post hoc analysis of SMILE-4.	2013	23882152
Cardioprotective role of zofenopril in patients with acute myocardial infarction: a pooled individual data analysis of four randomised, double-blind, controlled, prospective studies.	2015	26380097
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	26288740
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	26347187
Zofenopril Protects Against Myocardial Ischemia-Reperfusion Injury by Increasing Nitric Oxide and Hydrogen Sulfide Bioavailability.	2016 Jul 5	27381758
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	27798417

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:14:10 UTC 2023` Edited by `admin` on `Sat Dec 16 17:14:10 UTC 2023`
Record UNII	290ZY759PI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZOFENOPRIL

Official Name

English

R-PROLINE, 1-(3-(BENZOYLTHIO)-2-METHYL-1-OXOPROPYL)-4-(PHENYLTHIO)-, (1(R*),2.ALPHA.,4.ALPHA.)-

Common Name

English

Zofenopril [WHO-DD]

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

Classification Tree Code System Code

WHO-ATC

C09BA15