U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H34N2O7
Molecular Weight 498.5681
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOEXIPRIL

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=C(C[C@H]2C(O)=O)C=C(OC)C(OC)=C3

InChI

InChIKey=UWWDHYUMIORJTA-HSQYWUDLSA-N
InChI=1S/C27H34N2O7/c1-5-36-27(33)21(12-11-18-9-7-6-8-10-18)28-17(2)25(30)29-16-20-15-24(35-4)23(34-3)14-19(20)13-22(29)26(31)32/h6-10,14-15,17,21-22,28H,5,11-13,16H2,1-4H3,(H,31,32)/t17-,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H34N2O7
Molecular Weight 498.5681
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16620521 | https://www.ncbi.nlm.nih.gov/pubmed/26076923 | https://www.ncbi.nlm.nih.gov/pubmed/9257913 | https://www.ncbi.nlm.nih.gov/pubmed/9079232

Moexipril is a non-sulfhydryl containing the precursor of the active angiotensin-converting enzyme (ACE) inhibitor moexiprilat. Moexipril hydrochloride is a prodrug for Moexiprilat, which inhibits ACE in humans and animals. The mechanism through which Moexiprilat lowers blood pressure is believed to be primarily inhibition of ACE activity. ACE is a peptidyl dipeptidase that catalyzes the conversion of the inactive decapeptide angiotensin I to the vasoconstrictor substance angiotensin II. Angiotensin II is a potent peripheral vasoconstrictor that also stimulates aldosterone secretion by the adrenal cortex and provides negative feedback on renin secretion. ACE is identical to kininase II, an enzyme that degrades bradykinin, an endothelium-dependent vasodilator. Moexiprilat is about 1000 times as potent as Moexipril in inhibiting ACE and kininase II. Inhibition of ACE results in decreased angiotensin II formation, leading to decreased vasoconstriction, increased plasma renin activity and decreased aldosterone secretion. The latter results in diuresis and natriuresis and a small increase in serum potassium concentration.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Moexipril

Approved Use

Moexipril hydrochloride is indicated for treatment of patients with hypertension. It may be used alone or in combination with thiazide diuretics. In using moexipril hydrochloride, consideration should be given to the fact that another ACE inhibitor, captopril, has caused agranulocytosis, particularly in patients with renal impairment or collagen-vascular disease. Available data are insufficient to show that moexipril hydrochloride does not have a similar risk (see WARNINGS). In considering use of moexipril hydrochloride, it should be noted that in controlled trials ACE inhibitors have an effect on blood pressure that is less in black patients than in non-blacks. In addition, ACE inhibitors (for which adequate data are available) cause a higher rate of angioedema in black than in non-black patients (see WARNINGS , Angioedema ).

Launch Date

1995
Primary
Moexipril

Approved Use

Moexipril hydrochloride is indicated for treatment of patients with hypertension. It may be used alone or in combination with thiazide diuretics. In using moexipril hydrochloride, consideration should be given to the fact that another ACE inhibitor, captopril, has caused agranulocytosis, particularly in patients with renal impairment or collagen-vascular disease. Available data are insufficient to show that moexipril hydrochloride does not have a similar risk (see WARNINGS). In considering use of moexipril hydrochloride, it should be noted that in controlled trials ACE inhibitors have an effect on blood pressure that is less in black patients than in non-blacks. In addition, ACE inhibitors (for which adequate data are available) cause a higher rate of angioedema in black than in non-black patients (see WARNINGS , Angioedema ).

Launch Date

1995
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
16 ng/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
24 ng/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
97 ng/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
154 ng/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
98 ng × h/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
68 μg × h/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
160 ng × h/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
328 ng × h/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
30%
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
30%
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOEXIPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy, 55.4
n = 45
Health Status: unhealthy
Condition: hypertension
Age Group: 55.4
Sex: M+F
Population Size: 45
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as victim
PubMed

PubMed

TitleDatePubMed
Evidence for site-specific absorption of a novel ACE inhibitor.
1989 Sep
Tricenter assessment of the efficacy of the ACE inhibitor, moexipril, by ambulatory blood pressure monitoring.
1995 Mar
Evaluation of the antihypertensive efficacy and tolerability of moexipril, a new ACE inhibitor, compared to hydrochlorothiazide in elderly patients.
1996
Impact of antihypertensive therapy on the skeleton: effects of moexipril and hydrochlorothiazide on osteopenia in spontaneously hypertensive ovariectomized rats.
1997 Sep
Moexipril. A review of its use in the management of essential hypertension.
1998 Jun
Antihypertensive treatment in postmenopausal women: results from a prospective, randomized, double-blind, controlled study comparing an ACE inhibitor (moexipril) with a diuretic (hydrochlorothiazide).
1998 May
Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors.
1998 May-Jun
Increased arterial distensibility in postmenopausal hypertensive women with and without hormone replacement therapy after acute administration of the ACE inhibitor moexipril.
1998 Sep
Enalapril and moexipril protect from free radical-induced neuronal damage in vitro and reduce ischemic brain injury in mice and rats.
1999 May 28
Using ACE inhibitors appropriately.
2002 Aug 1
Systemic hypertension in postmenopausal women: a clinical approach.
2002 Dec
Reversal of left ventricular hypertrophy with the ACE inhibitor moexipril in patients with essential hypertension.
2002 Feb
Should perindopril be used to treat patients with heart failure?
2002 May 1
ACE Inhibition with moexipril: a review of potential effects beyond blood pressure control.
2003
Moexipril and quinapril inhibition of tissue angiotensin-converting enzyme activity in the rat: evidence for direct effects in heart, lung and kidney and stimulation of prostacyclin generation.
2003 Jan
Simultaneous determination of moexipril hydrochloride and hydrochlorothiazide in tablets by derivative spectrophotometric and high-performance liquid chromatographic methods.
2003 Oct 15
Pharmacological profile and clinical use of moexipril.
2003 Sep
[Hypertension in postmenopausal women: medical and social significance and results of therapy with moexipril.].
2004
Pharmacological and clinical profile of moexipril: a concise review.
2004 Aug
The influence of relative humidity and temperature on stability of moexipril hydrochloride in solid phase.
2004 Mar-Apr
[Assessment of antihypertensive efficacy of moexipril in metabolic syndrome].
2005
[Moexipril influence on quality of life in postmenopausal women with arterial hypertension].
2005
[The use of moexipril in postmenopausal women with hypertension and associated changes of bone mineral density].
2005
[Hemodynamic and anti-ischemic effects of moexipril in patients having postinfarction heart dysfunction and moderate left ventricular heart failure].
2005
MORE--MOexipril and REgression of left ventricle hypertrophy in combination therapy A multicentric open label clinical trial.
2005 Apr 20
Subchronic exposure to high-dose ACE-inhibitor moexipril induces catalase activity in rat liver.
2005 Dec
Regression of left ventricular hypertrophy with moexipril, an angiotensin-converting enzyme inhibitor, in hypertensive patients.
2005 Jan-Feb
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
[Dynamics of left ventricular longitudinal function in patients with arterial hypertension during therapy with angiotensin converting enzyme inhibitor moexipril].
2006
[Moexipril and cardiovascular diseases in women: is there a reason for optimism?].
2006
[Hypotensive, organoprotective, and metabolic effects of Angiotensin converting enzyme inhibitor moexipril in women with postmenopausal syndrome].
2006
[Comparative efficacy and safety of contemporary Angiotensin converting enzyme inhibitors moexipril and spirapril in women with postmenopausal metabolic syndrome].
2006
Monitoring the metabolism of moexipril to moexiprilat using high-performance liquid chromatography-electrospray ionization mass spectrometry.
2006 Apr
[Assessment of the effect of angiotensin converting enzyme inhibitor moexipril on the functional state of vascular wall in patients with I - III degree arterial hypertension].
2007
[Clinico-economical efficacy of angiotensin converting enzyme inhibitors in patients with arterial hypertension and ischemic heart disease].
2008
The Effect of the Dried-Bonito Broth on Blood Pressure, 8-Hydroxydeoxyguanosine (8-OHdG), an Oxidative Stress Marker, and Emotional States in Elderly Subjects.
2008 Nov
The prince and the pauper. A tale of anticancer targeted agents.
2008 Oct 23
[Preventive pharmacotherapy in arterial hypertension: problems of clinical assessment of drugs in women].
2009
Iatrogenic QT Abnormalities and Fatal Arrhythmias: Mechanisms and Clinical Significance.
2009 Aug
Stabilization of quinapril by incorporating hydrogen bonding interactions.
2009 Jul
Impact of statins and ACE inhibitors on mortality after COPD exacerbations.
2009 Jun 3
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Inhibition of central angiotensin-converting enzyme with enalapril protects the brain from ischemia/reperfusion injury in normotensive rat.
2010
Determination of antihypertensive drug moexipril hydrochloride based on the enhancement effect of sodium dodecyl sulfate at carbon paste electrode.
2010 Apr 15
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Adverse drug reaction monitoring with angiotensin converting enzyme inhibitors: A prospective, randomized, open-label, comparative study.
2010 Feb
Moexipril for treatment of primary biliary cirrhosis in patients with an incomplete response to ursodeoxycholic acid.
2010 Feb
Anti-hypertensive drugs have different effects on ventricular hypertrophy regression.
2010 Jul
Identification and determination of antihypertonics from the group of angiotensin-convertase inhibitors by densitometric method in comparition with HPLC method.
2010 Mar-Apr
Spectrophotometric method for simultaneous estimation of atenolol in combination with losartan potassium and hydrochlorothiazide in bulk and tablet formulation.
2010 Oct
Patents

Sample Use Guides

Unknown
Route of Administration: Intravenous
In Vitro Use Guide
After 24 h incubation in serum- and phenol red-free medium (DMEM), neonatal rat cardiac fibroblasts were stimulated with 17b-oestradiol (10^-7 ± 10^-9 M), oestrone (10^-7 ± 10^-9M), angiotensin II (10^-7 M) and moexiprilat (10^-7 M). Cells were harvested after 24 h and cellular proliferation was assessed by BrdU incorporation by use of a colorimetric immunoassay. Moexiprilat (10^-7 M) completely inhibited oestrone-induced cardiac fibroblast growth.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:46:27 GMT 2023
Edited
by admin
on Fri Dec 15 15:46:27 GMT 2023
Record UNII
WT87C52TJZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MOEXIPRIL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
MOEXIPRIL [MI]
Common Name English
3-ISOQUINOLINECARBOXYLIC ACID, 2-(2-((1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-, (3S-(2(R*(R*)),3R*))-
Common Name English
moexipril [INN]
Common Name English
(3S)-2-((2S)-N-((1S)-1-CARBOXY-3-PHENYLPROPYL)ALANYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-3-ISOQUINOLINECARBOXYLIC ACID, 2-ETHYL ESTER
Common Name English
(3S)-2-((2S)-2-(((1S)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-3-ISOQUINOLINECARBOXYLIC ACID
Systematic Name English
Moexipril [WHO-DD]
Common Name English
MOEXIPRIL [VANDF]
Common Name English
RS-10085
Code English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
NDF-RT N0000000181
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
LIVERTOX NBK547904
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
WHO-ATC C09AA13
Created by admin on Fri Dec 15 15:46:27 GMT 2023 , Edited by admin on Fri Dec 15 15:46:27 GMT 2023
WHO-VATC QC09BA13
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
WHO-ATC C09BA13
Created by admin on Fri Dec 15 15:46:27 GMT 2023 , Edited by admin on Fri Dec 15 15:46:27 GMT 2023
WHO-VATC QC09AA13
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
NDF-RT N0000175562
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
Code System Code Type Description
CAS
103775-10-6
Created by admin on Fri Dec 15 15:46:27 GMT 2023 , Edited by admin on Fri Dec 15 15:46:27 GMT 2023
PRIMARY
LACTMED
Moexipril
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY
INN
6266
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY
EVMPD
SUB09030MIG
Created by admin on Fri Dec 15 15:46:27 GMT 2023 , Edited by admin on Fri Dec 15 15:46:27 GMT 2023
PRIMARY
WIKIPEDIA
MOEXIPRIL
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID9023330
Created by admin on Fri Dec 15 15:46:27 GMT 2023 , Edited by admin on Fri Dec 15 15:46:27 GMT 2023
PRIMARY
SMS_ID
100000080331
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY
PUBCHEM
91270
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL1165
Created by admin on Fri Dec 15 15:46:27 GMT 2023 , Edited by admin on Fri Dec 15 15:46:27 GMT 2023
PRIMARY
DRUG CENTRAL
1827
Created by admin on Fri Dec 15 15:46:27 GMT 2023 , Edited by admin on Fri Dec 15 15:46:27 GMT 2023
PRIMARY
RXCUI
30131
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m7585
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C83967
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY
FDA UNII
WT87C52TJZ
Created by admin on Fri Dec 15 15:46:27 GMT 2023 , Edited by admin on Fri Dec 15 15:46:27 GMT 2023
PRIMARY
IUPHAR
6571
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY
DRUG BANK
DB00691
Created by admin on Fri Dec 15 15:46:27 GMT 2023 , Edited by admin on Fri Dec 15 15:46:27 GMT 2023
PRIMARY
MESH
C058302
Created by admin on Fri Dec 15 15:46:28 GMT 2023 , Edited by admin on Fri Dec 15 15:46:28 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
DERIVATIVE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
MINOR
PLASMA; URINE
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC