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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H34N2O7.ClH
Molecular Weight 535.029
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOEXIPRIL HYDROCHLORIDE

SMILES

Cl.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=JXRAXHBVZQZSIC-JKVLGAQCSA-N
InChI=1S/C27H34N2O7.ClH/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);1H/t17-,21-,22-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Moexiprilat is the pharmacologically active metabolite of Moexipril. Formation of Moexiprilat is caused by hydrolysis of a Moexipril’s ethyl ester group. Moexiprilat competitively inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the actions of the potent vasoconstrictor angiotensin II and leads to vasodilatation. This agent also prevents angiotensin II-induced aldosterone secretion by the adrenal cortex, thereby promoting diuresis and natriuresis. Moexiprilat showed an extended duration of action owing to a long terminal pharmacokinetic half-life and produced a persistent ACE inhibition.

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

7.9824958E11
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

7.9816321E11
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
Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update.
2002
Using ACE inhibitors appropriately.
2002 Aug 1
Systemic hypertension in postmenopausal women: a clinical approach.
2002 Dec
ACE Inhibition with moexipril: a review of potential effects beyond blood pressure control.
2003
[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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
[Angiotensin converting enzyme inhibitor moexipril in the treatment of arterial hypertension. Possibilities of moexipril in the treatment of postmenopausal women].
2006
[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
[Investigation of efficacy of cardiovascular drugs in women].
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
Moexipril and left ventricular hypertrophy.
2007
Metabolism of moexipril to moexiprilat: determination of in vitro metabolism using HPLC-ES-MS.
2007 Jan
[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
Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited.
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
Stabilization of quinapril by incorporating hydrogen bonding interactions.
2009 Jul
Impact of statins and ACE inhibitors on mortality after COPD exacerbations.
2009 Jun 3
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Moexipril for treatment of primary biliary cirrhosis in patients with an incomplete response to ursodeoxycholic acid.
2010 Feb
Patents

Sample Use Guides

Usual Adult Dose for Hypertension Initial dose: -Patients not receiving diuretic therapy: 7.5 mg orally once a day 1 hour before meals -Patients receiving diuretic therapy: 3.75 mg orally once a day 1 hour before meals Maintenance dose: 7.5 to 30 mg orally per day in 1 or 2 divided doses 1 hour before meals. Maximum dose: 60 mg/day
Route of Administration: Oral
In Vitro Use Guide
In vitro, moexiprilat (active diacid metabolite of moexipril) was a potent inhibitor of ACE in guinea pig serum as well as on purified ACE from rabbit lung with IC50 values of 2.6 and 4.9 nmol/l, respectively. Both, moexipril and moexiprilat inhibited the angiotensin I (ANG I)-induced contractions of rabbit aorta concentration-dependently.
Substance Class Chemical
Created
by admin
on Thu Jul 06 13:10:34 UTC 2023
Edited
by admin
on Thu Jul 06 13:10:34 UTC 2023
Record UNII
Q1UMG3UH45
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MOEXIPRIL HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
UNIVASC
Brand Name English
MOEXIPRIL HCL
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, monohydrochloride
Common Name English
MOEXIPRIL HYDROCHLORIDE [USP-RS]
Common Name English
UNIRETIC COMPONENT MOEXIPRIL HYDROCHLORIDE
Common Name English
SPM-925
Code English
SPM 925
Code English
MOEXIPRIL HYDROCHLORIDE [MI]
Common Name English
CI 925
Code English
RS-10085-197
Code English
MOEXIPRIL HYDROCHLORIDE COMPONENT OF UNIRETIC
Common Name English
MOEXIPRIL HYDROCHLORIDE [USAN]
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 HYDROCHLORIDE
Systematic Name English
MOEXIPRIL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
MOEXIPRIL HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
CI-925
Code English
3-ISOQUINOLINECARBOXYLIC ACID, 2-(2-((1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-, MONOHYDROCHLORIDE, (3S-(2(R*(R*)),3R*))-
Common Name English
MOEXIPRIL HYDROCHLORIDE [MART.]
Common Name English
MOEXIPRIL HYDROCHLORIDE [VANDF]
Common Name English
Moexipril hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
Code System Code Type Description
DRUG BANK
DBSALT000504
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
PUBCHEM
54889
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL1165
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
EVMPD
SUB03312MIG
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
RS_ITEM_NUM
1445426
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
NCI_THESAURUS
C29267
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
MERCK INDEX
M7585
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY Merck Index
DAILYMED
Q1UMG3UH45
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
RXCUI
236066
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY RxNorm
SMS_ID
100000091389
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
FDA UNII
Q1UMG3UH45
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
EPA CompTox
DTXSID7044267
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
CAS
82586-52-5
Created by admin on Thu Jul 06 13:10:34 UTC 2023 , Edited by admin on Thu Jul 06 13:10:34 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY