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 94 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 8504		10.9 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Bifril_7_5/WC500013887.pdf	Primary		Approved 8583	ZOPRANOL Approved Use ZOPRANOL is indicated for the treatment of mild to moderate essential hypertension. Launch Date 2000
Acute myocardial infarction 37 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Bifril_7_5/WC500013887.pdf	Primary		Approved 8583	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 2000

C_max

Value	Dose	Analyte	Population
51.96 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
95.95 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
177.94 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
36.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
71.22 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
339.59 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
689 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1563.89 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
528.34 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
581.16 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
61.04 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
99.02 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
229.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
60.02 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
77.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
804.96 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1453.86 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3550.01 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1577.25 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1041.27 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.74 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.52 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2.55 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.38 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.69 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24935917/	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ZOFENOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
14% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2292772/			ZOFENOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
30 mg 1 times / day steady, oral Studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16789795/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16789795/	Disc. AE: headache, dizziness... Other AEs: cough... AEs leading to discontinuation/dose reduction: headache (1%) dizziness (1%) Other AEs: cough (1%) Sources: https://pubmed.ncbi.nlm.nih.gov/16789795/

AEs

AE	Significance	Dose	Population
cough	1%	30 mg 1 times / day steady, oral Studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16789795/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16789795/
dizziness	1% Disc. AE	30 mg 1 times / day steady, oral Studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16789795/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16789795/
headache	1% Disc. AE	30 mg 1 times / day steady, oral Studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16789795/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16789795/

PubMed

Title	Date	PubMed
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.	2017-01	27798417
Zofenopril Protects Against Myocardial Ischemia-Reperfusion Injury by Increasing Nitric Oxide and Hydrogen Sulfide Bioavailability.	2016-07-05	27381758
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
Cardioprotective role of zofenopril in patients with acute myocardial infarction: a pooled individual data analysis of four randomised, double-blind, controlled, prospective studies.	2014-11-11	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.	2014-09-16	26288740
Cost-effectiveness of zofenopril in patients with left ventricular systolic dysfunction after acute myocardial infarction: a post hoc analysis of SMILE-4.	2013	23882152
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
Effect of Zofenopril on regeneration of sciatic nerve crush injury in a rat model.	2009-06-09	19508704
Zofenopril after anterior myocardial infarction.	1995-06-22	7619164
Comparative effects of zofenopril and hydrochlorothiazide on office and ambulatory blood pressures in mild to moderate essential hypertension.	1989-03	2655685
Comparisons in vitro, ex vivo, and in vivo of the actions of seven structurally diverse inhibitors of angiotensin converting enzyme (ACE).	1989	2557876

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 `Wed Apr 02 08:50:59 GMT 2025` Edited by `admin` on `Wed Apr 02 08:50:59 GMT 2025`
Record UNII	290ZY759PI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZOFENIL

Preferred Name

English

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

zofenopril [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C09BA15