FOSINOPRIL

First approved in 1991

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H46NO7P
Molecular Weight	563.6625
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(=O)O[C@@H](O[P@](=O)(CCCCC1=CC=CC=C1)CC(=O)N2C[C@@H](C[C@H]2C(O)=O)C3CCCCC3)C(C)C

InChI

InChIKey=BIDNLKIUORFRQP-XYGFDPSESA-N

InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30+,39-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C30H46NO7P
Molecular Weight	563.6625
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB00492
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/fosinopril.html

Fosinopril is a phosphinic acid-containing ester prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly hydrolyzed to fosinoprilat, its principle active metabolite. Fosinoprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Fosinopril may be used to treat mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 94 Target ID: CHEMBL1808 Sources: http://www.drugbank.ca/drugs/DB00492	Inhibitor 8504		1.0 nM [IC50]
Angiotensin-converting enzyme 94 Target ID: P12822 Gene ID: 1.00009272E8 Gene Symbol: ACE Target Organism: Oryctolagus cuniculus (Rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2481187	Inhibitor 8504		11.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.drugs.com/pro/fosinopril.html	Primary		Approved 8583	FOSINOPRIL SODIUM Approved Use Fosinopril sodium tablets are indicated for the treatment of hypertension. They may be used alone or in combination with thiazide diuretics. Fosinopril sodium tablets are indicated in the management of heart failure as adjunctive therapy when added to conventional therapy including diuretics with or without digitalis Launch Date 2003

C_max

Value	Dose	Analyte	Population
131 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5598 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	640 mg single, oral dose: 640 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
533 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
711 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	40 mg 2 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1018 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1217 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	80 mg 2 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
112 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1556 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/	7.5 mg single, intravenous dose: 7.5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	FOSINOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
58.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	640 mg single, oral dose: 640 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	40 mg 2 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
7.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/	80 mg 2 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	FOSINOPRILAT serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
920 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	FOSINOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3302 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/	7.5 mg single, intravenous dose: 7.5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	FOSINOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		FOSINOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/	7.5 mg single, intravenous dose: 7.5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		FOSINOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
8% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		FOSINOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/	7.5 mg single, intravenous dose: 7.5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		FOSINOPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1534664/	unhealthy, 28 - 68years Health Status: unhealthy Age Group: 28 - 68years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1534664/	Sources: https://pubmed.ncbi.nlm.nih.gov/1534664/
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf	unhealthy, >65 years Health Status: unhealthy Age Group: >65 years Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf	Disc. AE: Headache, Transaminases increased... AEs leading to discontinuation/dose reduction: Headache (0.4 - 0.9) Transaminases increased (0.4 - 0.9) Fatigue (0.4 - 0.9) Cough (0.4 - 0.9) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf
40 mg 1 times / day steady, oral MTD Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: https://www.rxlist.com/monopril-drug.htm#description	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.rxlist.com/monopril-drug.htm#description	Sources: https://www.rxlist.com/monopril-drug.htm#description

AEs

AE	Significance	Dose	Population
Cough	0.4 - 0.9 Disc. AE	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf	unhealthy, >65 years Health Status: unhealthy Age Group: >65 years Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf
Fatigue	0.4 - 0.9 Disc. AE	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf	unhealthy, >65 years Health Status: unhealthy Age Group: >65 years Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf
Headache	0.4 - 0.9 Disc. AE	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf	unhealthy, >65 years Health Status: unhealthy Age Group: >65 years Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf
Transaminases increased	0.4 - 0.9 Disc. AE	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf	unhealthy, >65 years Health Status: unhealthy Age Group: >65 years Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19915se5-037_monopril_lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 926 P-gp 1741 BCRP 910 MRP2 499	CYP1A1 389 CYP1A2 1197 CYP2B1 12 CYP2B2 3 CYP2E1 729 CYP3A 220 UGT 219 PEPT1 60

Drug as perpetrator

Target	Modality	Activity
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23262422/	yes
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23262422/	yes
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23262422/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20692951/	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20692951/	no
CYP2B1 12	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20692951/	no
CYP2B2 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20692951/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20692951/	no
PEPT1 60	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11560874/	yes [Km 154 uM]
CYP3A 220	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24365260/	yes
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24365260/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:116962	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:116962
ChemicalBook	CB4711162	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4711162
ZINC	ZINC000004213382	http://zinc15.docking.org/substances/ZINC000004213382

PubMed

Title	Date	PubMed
Lithium toxicity after switch from fosinopril to lisinopril.	2005-03	15729089
Effects of fosinopril and pravastatin on carotid intima-media thickness in subjects with increased albuminuria.	2005-03	15692120
[Changes of collagen expression of pulmonary arteries and heart ventricles and intervention of fosinopril and losartan in rats with heart failure].	2004-12-02	15730820
Heart failure and first dose hypotension after angiotensin converting enzyme inhibitors.	2004-12	15744357
Different effects of antihypertensive regimens based on fosinopril or hydrochlorothiazide with or without lipid lowering by pravastatin on progression of asymptomatic carotid atherosclerosis: principal results of PHYLLIS--a randomized double-blind trial.	2004-12	15514192
Lumbar incisional hernias: diagnostic and management dilemma.	2004-11-24	15554289
Effects of fosinopril and pravastatin on cardiovascular events in subjects with microalbuminuria.	2004-11-02	15492322
Framingham score and microalbuminuria: combined future targets for primary prevention?	2004-11	15485402
Possible induction of diabetes by treatment of hypertension with indapamide (with four case reports).	2004-09	15331204
Therapeutic approaches in the prevention of cardiovascular disease in metabolic syndrome and in patients with type 2 diabetes.	2004-09	15316457
Is the extrapolated adult dose of fosinopril safe and effective in treating hypertensive children?	2004-09	15262902
Fosinopril and amlodipine in the treatment of isolated systolic hypertension.	2004-08-26	15327190
Clinical trials update from the European Society of Cardiology Heart Failure meeting: SHAPE, BRING-UP 2 VAS, COLA II, FOSIDIAL, BETACAR, CASINO and meta-analysis of cardiac resynchronisation therapy.	2004-08	15302018
Studies on the glycemic and lipidemic effect of monopril and losartan in normal and diabetic rats.	2004-08	15177300
Mortality rates in elderly patients who take different angiotensin-converting enzyme inhibitors after acute myocardial infarction: a class effect?	2004-07-20	15262665
Comparative effects of fosinopril and irbesartan on hematopoiesis in essential hypertensives.	2004-07	15462108
American Heart Association scientific sessions.	2004-04	15102593
Normalization of renal aquaporin-2 water channel expression by fosinopril, valsartan, and combination therapy in congestive heart failure: a new mechanism of action.	2004-03	15010283
Cardiorenal protective effects of vasopeptidase inhibition with omapatrilat in hypertensive transgenic (mREN-2)27 rats.	2004-01	15000298
[Effect of fosinopril on the rate of neurohumoral and proinflammatory activation in patients with heart failure].	2004	15540418
[Effects of carvedilol, atenolol and their combination with fosinopril on cardiac rhythm variability, clinicofunctional status and quality of life in patients with postinfarction left ventricular dysfunction].	2004	15532380
Systemic contact dermatitis due to captopril without cross-sensitivity to fosinopril, quinapril and benazepril.	2004	15040496
Effect of dual angiotensin converting enzyme/neutral endopeptidase inhibition, angiotensin converting enzyme inhibition, or AT1 antagonism on coronary microvasculature in spontaneously hypertensive rats.	2003-11	14573331
Angiotensin-converting enzyme inhibition but not angiotensin II receptor blockade regulates matrix metalloproteinase activity in patients with glomerulonephritis.	2003-11	14569096
Ramipril-associated hepatotoxicity.	2003-11	14567716
Protection of organic trauma in sinoaortic-denervated rats treated with fosinopril.	2003-10	14730896
Introduction to monitoring. What is what you prescribed actually doing?	2003-10	14596082
Dual renin-angiotensin system blockade restores blood pressure-renin dependency in individuals with low renin concentrations.	2003-10	14508195
Long-term renal survival in HIV-associated nephropathy with angiotensin-converting enzyme inhibition.	2003-10	12969167
Precipitation of PTSD with metoprolol for hypertension.	2003-09-05	12954926
[Combination therapy with losartan and fosinopril for early diabetic nephropathy].	2003-09	13129736
Comparative metabolic effects of hydrochlorothiazide and indapamide in hypertensive diabetic patients receiving ACE inhibitor therapy.	2003-09	12925048
Acute visual loss after initiation of antihypertensive therapy: case report.	2003-08-19	12925427
Role of Angiotensin-converting enzyme and neutral endopeptidase in flow-dependent remodeling.	2003-07-16	15004434
Effects of fosinopril and valsartan on expressions of ICAM-1 and NO in human umbilical vein endothelial cells.	2003-06	12877808
Effect of xuezhikang, a cholestin extract, on reflecting postprandial triglyceridemia after a high-fat meal in patients with coronary heart disease.	2003-06	12801622
ANP but not BNP reflects early left diastolic dysfunction in type 1 diabetics with myocardial dysinnervation.	2003-05	12916000
Comparison of dipyridamole and fosinopril on renal progression in nephrectomized rats.	2003-04	15012738
A unique form of polycythemia associated with minimal change disease.	2003-01-30	15467313
A prospective, randomized, open labeled crossover trial of fosinopril and theophylline in post renal transplant erythrocytosis.	2003-01	12617335
[Efficacy of combined use of fosinopril and propranolol in acute myocardial infarction].	2003	12891269
[Tongue angioedema associated with angiotensin-converting enzyme inhibitor (diagnosis, differential diagnosis, treatment)].	2003	12829880
[Chronopharmacological approaches to the therapeutic prophylaxis of chronic cardiac insufficiency in type I diabetes mellitus].	2003	12741355
[Comparison of the antihypertensive activity of fosinopril and irbesartan].	2002-11	12522893
FOSIDIAL: a randomised placebo controlled trial of the effects of fosinopril on cardiovascular morbidity and mortality in haemodialysis patients. Study design and patients' baseline characteristics.	2002-10	12602460
[Effect of Erigeron breviscapus injection on ventricular and vascular remodeling in spontaneous hypertension rats].	2002-02	12585150
The effect and mechanism of forsinopril on ventricular hypertrophy of SHR and left ventricular pressure overloading rat.	2002	12658773
[Contrast of losartan, fosinopril and amlodipine on cardiomyocyte apoptosis and left ventricular remolding in hypertensive rats].	2001-10-28	12536482
[Effects of lorsartan, fosinopril on myocardial fibrosis, angiotensin II and cardiac remolding in hypertensive rats].	2001-04-28	12536639
Fosinopril, a phosphinic acid inhibitor of angiotensin I converting enzyme: in vitro and preclinical in vivo pharmacology.	1989-11	2481187

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Hypertension Initial dose: 10 mg orally once a day alone or in combination with a diuretic Maintenance dose: 20 to 40 mg orally once a day; some patients may have further response at 80 mg once a day Usual Adult Dose for Congestive Heart Failure Initial dose: 10 mg orally once a day Target dose range: 20 to 40 mg orally once a day Maximum dose: 40 mg orally once a day

Route of Administration: Oral

In Vitro Use Guide

Fosinopril up-regulated klotho mRNA in NRK-52E cells pretreated with Fos(10(-5) mol/L) for 12 h incubated with AngII

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:26:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:26:46 GMT 2025`
Record UNII	R43D2573WO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FOSINOPRIL

Official Name

English

C09AA09

Preferred Name

English

FOSINOPRIL [ORANGE BOOK]

Common Name

English

fosinopril [INN]

Common Name

English

Fosinopril [WHO-DD]

Common Name

English

FOSINOPRIL [VANDF]

Common Name

English

(4S)-4-Cyclohexyl-1-[2-[(R)-[(1S)-2-methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetyl]-L-proline

Systematic Name

English

L-Proline, 4-cyclohexyl-1-[2-[(R)-[(1S)-2-methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetyl]-, (4S)-

Systematic Name

English

FOSINOPRIL [MI]

Common Name

English

FOZITEC

Common Name

English

FOSENOPRIL

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175562