ZOFENOPRIL

Possibly Marketed Outside US

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

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 97	Inhibitor 8,297		10.9 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567	Primary		Approved 8,429	ZOPRANOL
Acute myocardial infarction 37	Primary		Approved 8,429	ZOPRANOL

C_max

Value	Dose	Analyte	Population
51.96 ng/mL	15 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
95.95 ng/mL	30 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
177.94 ng/mL	60 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
36.2 ng/mL	30 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
71.22 ng/mL	30 mg 1 times / day steady-state, oral	ZOFENOPRIL plasma	Homo sapiens
339.59 ng/mL	15 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
689 ng/mL	30 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
1563.89 ng/mL	60 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
528.34 ng/mL	30 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
581.16 ng/mL	30 mg 1 times / day steady-state, oral	ZOFENOPRILAT plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
61.04 ng × h/mL	15 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
99.02 ng × h/mL	30 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
229.8 ng × h/mL	60 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
60.02 ng × h/mL	30 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
77.8 ng × h/mL	30 mg 1 times / day steady-state, oral	ZOFENOPRIL plasma	Homo sapiens
804.96 ng × h/mL	15 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
1453.86 ng × h/mL	30 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
3550.01 ng × h/mL	60 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
1577.25 ng × h/mL	30 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
1041.27 ng × h/mL	30 mg 1 times / day steady-state, oral	ZOFENOPRILAT plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.74 h	15 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
1.52 h	30 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
1.39 h	60 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
1.19 h	30 mg single, oral	ZOFENOPRIL plasma	Homo sapiens
2.55 h	30 mg 1 times / day steady-state, oral	ZOFENOPRIL plasma	Homo sapiens
5.38 h	15 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
6.45 h	30 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
5.69 h	60 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
6.22 h	30 mg single, oral	ZOFENOPRILAT plasma	Homo sapiens
7 h	30 mg 1 times / day steady-state, oral	ZOFENOPRILAT plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
14%			ZOFENOPRIL plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
30 mg 1 times / day steady, oral Studied dose	unhealthy, ADULT	Disc. AE: headache, dizziness... Other AEs: cough...

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AEs

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AE	Significance	Dose	Population
cough	1%	30 mg 1 times / day steady, oral Studied dose	unhealthy, ADULT
dizziness	1% Disc. AE	30 mg 1 times / day steady, oral Studied dose	unhealthy, ADULT
headache	1% Disc. AE	30 mg 1 times / day steady, oral Studied dose	unhealthy, ADULT

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PubMed

Show entries

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
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
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

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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.

Show entries

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