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

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H30N2O7
Molecular Weight 470.5149
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOEXIPRILAT

SMILES

COC1=CC2=C(CN([C@@H](C2)C(O)=O)C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(O)=O)C=C1OC

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

Molecular Formula C25H30N2O7
Molecular Weight 470.5149
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
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
Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update.
2002
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
Oestrogen action on the myocardium in vivo: specific and permissive for angiotensin-converting enzyme inhibition.
2002 May
Should perindopril be used to treat patients with heart failure?
2002 May 1
Pharmacological profile and clinical use of moexipril.
2003 Sep
[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
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
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
[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
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
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
Anti-hypertensive drugs have different effects on ventricular hypertrophy regression.
2010 Jul
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 Wed Jul 05 23:47:59 UTC 2023
Edited
by admin
on Wed Jul 05 23:47:59 UTC 2023
Record UNII
H3753190JS
Record Status Validated (UNII)
Record Version
  • Download
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
RS-10029
Code English
moexiprilat [INN]
Common Name English
MOEXIPRIL RELATED COMPOUND A [USP IMPURITY]
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
(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   USP-RS  
Common Name English
MOEXIPRIL RELATED COMPOUND A [USP-RS]
Common Name English
Moexiprilat [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
NDF-RT N0000175562
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
Code System Code Type Description
MESH
C059506
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID6057611
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
PUBCHEM
55331
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201405
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
DAILYMED
H3753190JS
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
RS_ITEM_NUM
1445608
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
FDA UNII
H3753190JS
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
CAS
103775-14-0
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
SMS_ID
100000080351
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
NCI_THESAURUS
C66175
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
DRUG BANK
DB14210
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
EVMPD
SUB09031MIG
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
RXCUI
1546358
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY RxNorm
INN
6946
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
IUPHAR
6572
Created by admin on Wed Jul 05 23:47:59 UTC 2023 , Edited by admin on Wed Jul 05 23:47:59 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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MINOR
FECAL; PLASMA; URINE
PRODRUG -> METABOLITE ACTIVE
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