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

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H30N2O7
Molecular Weight 470.5159
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOEXIPRILAT

SMILES

C[C@@]([H])(C(=O)N1Cc2cc(c(cc2C[C@@]1([H])C(=O)O)OC)OC)N[C@@]([H])(CCc3ccccc3)C(=O)O

InChI

InChIKey=CMPAGYDKASJORH-YSSFQJQWSA-N
InChI=1S/C25H30N2O7/c1-15(26-19(24(29)30)10-9-16-7-5-4-6-8-16)23(28)27-14-18-13-22(34-3)21(33-2)12-17(18)11-20(27)25(31)32/h4-8,12-13,15,19-20,26H,9-11,14H2,1-3H3,(H,29,30)(H,31,32)/t15-,19-,20-/m0/s1

HIDE SMILES / InChI

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
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
Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update.
2002
Using ACE inhibitors appropriately.
2002 Aug 1
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
[Hemodynamic and anti-ischemic effects of moexipril in patients having postinfarction heart dysfunction and moderate left ventricular heart failure].
2005
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
[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
[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
[Preventive pharmacotherapy in arterial hypertension: problems of clinical assessment of drugs in women].
2009
Stabilization of quinapril by incorporating hydrogen bonding interactions.
2009 Jul
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
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
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

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.
Name Type Language
MOEXIPRILAT
INN   WHO-DD  
INN  
Official Name English
(3S)-2-((2S)-N-((1S)-1-CARBOXY-3-PHENYLPROPYL)ALANYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-3-ISOQUINOLINECARBOXYLIC ACID
Systematic Name English
MOEXIPRILAT [WHO-DD]
Common Name English
RS-10029
Code English
MOEXIPRILAT [INN]
Common Name English
3-ISOQUINOLINECARBOXYLIC ACID, 2-(2-((1-(CARBOXY)-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-, (3S-(2(R*(R*)),3R*))-
Common Name English
MOEXIPRIL RELATED COMPOUND A RS [USP]
Common Name English
(3S)-2-((2S)-2-(((1S)-1-(CARBOXY)-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-3-ISOQUINOLINECARBOXYLIC ACID
Systematic Name English
3-ISOQUINOLINECARBOXYLIC ACID, 2-((2S)-2-(((1S)-1-CARBOXY-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-, (3S)-
Systematic Name English
MOEXIPRIL RELATED COMPOUND A [USP]
Common Name English
MOEXIPRIL RELATED COMPOUND A
USP   USP-RS  
Common Name English
MOEXIPRIL RELATED COMPOUND A [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
NDF-RT N0000175562
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
Code System Code Type Description
MESH
C059506
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
EPA CompTox
103775-14-0
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
PUBCHEM
55331
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201405
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
USP_CATALOG
1445608
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY USP-RS
FDA UNII
H3753190JS
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
CAS
103775-14-0
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
NCI_THESAURUS
C66175
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
DRUG BANK
DB14210
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
EVMPD
SUB09031MIG
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
RXCUI
1546358
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY RxNorm
INN
6946
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY
IUPHAR
6572
Created by admin on Sat Jun 26 14:54:40 UTC 2021 , Edited by admin on Sat Jun 26 14:54:40 UTC 2021
PRIMARY