MOEXIPRILAT

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 Search

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
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020312s033lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/14728069https://www.ncbi.nlm.nih.gov/pubmed/15286086
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 96 Target ID: CHEMBL1808 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020312s033lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/14728069	Inhibitor 8228		2.6 nM [IC50]
Angiotensin-converting enzyme 96 Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26076923	Inhibitor 8228		2.6 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 549 Sources: https://www.drugs.com/pro/moexipril.html	Primary		Approved 8360	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
Hypertension 549 Sources: https://www.drugs.com/pro/moexipril.html	Primary		Natural Metabolite	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

C_max

Value	Dose	Analyte	Population
16 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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 EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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 EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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 EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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

Value	Dose	Analyte	Population
98 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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 EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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 EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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 EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
10 h EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
30% EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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% EXPERIMENT https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1995.tb00304.x	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/11854821/	unhealthy, 55.4 n = 45 Health Status: unhealthy Condition: hypertension Age Group: 55.4 Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/11854821/	Sources: https://pubmed.ncbi.nlm.nih.gov/11854821/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CES1 22 CES2 28 PEPT1 48 PEPT2 32

Drug as victim

Target	Modality	Activity	Metabolite
CES2 28	substrate 3326 Sources: https://www.nature.com/articles/tpj201542	no
CES1 22	substrate 3326 Sources: https://www.nature.com/articles/tpj201542	yes
PEPT1 48	substrate 3326 Sources: https://www.tandfonline.com/doi/abs/10.1517/17425250903042292	yes	MOEXIPRIL 4
PEPT2 32	substrate 3326 Sources: https://www.tandfonline.com/doi/abs/10.1517/17425250903042292	yes	MOEXIPRIL 4

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L1IVG
ABI Chem	AC1Q5QO2
Alfa Chemistry	AP103775140	https://reagents.alfa-chemistry.com/product/moexipril-related-compound-a-cas-103775-14-0-948.html
Alfa Chemistry	103775-14-0	https://www.alfa-chemistry.com/cas_103775-14-0.htm
BOC Sciences	103775-14-0
BioSynth	J-001037	https://www.biosynth.com/en/products/all-products/products/J-001037.html
ChemTik	CTK8E8826
Chemieliva Pharmaceutical Co., Ltd	PBCM1057676
DC Chemicals	DC36859	http://www.dcchemicals.com//product_show-Moexiprilat.html
MuseChem	R044673	https://www.musechem.com/product/R044673.html
NovoSeek	55331
Smolecule	S535918	http://www.smolecule.com/products/s535918
Smolecule	S793772	https://www.smolecule.com/products/s793772
THE BioTek	bt-276722	https://www.thebiotek.com/product/inhibitors/bt-276722
Toronto Research Chemicals	M485320
Toronto Research Chemicals	M485360
Tractus	RT-013928
Wonderchem	WD04LWO
ZINC	ZINC000003789196	http://zinc15.docking.org/substances/ZINC000003789196
eMolecules	45917802

PubMed

Title	Date	PubMed
Impact of antihypertensive therapy on the skeleton: effects of moexipril and hydrochlorothiazide on osteopenia in spontaneously hypertensive ovariectomized rats.	1997 Sep	9379124
Moexipril. A review of its use in the management of essential hypertension.	1998 Jun	9617599
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	9643274
Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors.	1998 May-Jun	9620109
Increased arterial distensibility in postmenopausal hypertensive women with and without hormone replacement therapy after acute administration of the ACE inhibitor moexipril.	1998 Sep	9825188
Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update.	2002	11929321
Systemic hypertension in postmenopausal women: a clinical approach.	2002 Dec	12419176
Reversal of left ventricular hypertrophy with the ACE inhibitor moexipril in patients with essential hypertension.	2002 Feb	11918132
Oestrogen action on the myocardium in vivo: specific and permissive for angiotensin-converting enzyme inhibition.	2002 May	12011662
Should perindopril be used to treat patients with heart failure?	2002 May 1	12018799
Pharmacological profile and clinical use of moexipril.	2003 Sep	15030263
[Assessment of antihypertensive efficacy of moexipril in metabolic syndrome].	2005	16353045
[Moexipril influence on quality of life in postmenopausal women with arterial hypertension].	2005	16320692
[Hemodynamic and anti-ischemic effects of moexipril in patients having postinfarction heart dysfunction and moderate left ventricular heart failure].	2005	15759492
MORE--MOexipril and REgression of left ventricle hypertrophy in combination therapy A multicentric open label clinical trial.	2005 Apr 20	15823625
Subchronic exposure to high-dose ACE-inhibitor moexipril induces catalase activity in rat liver.	2005 Dec	16311918
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
[Angiotensin converting enzyme inhibitor moexipril in the treatment of arterial hypertension. Possibilities of moexipril in the treatment of postmenopausal women].	2006	17159885
[Dynamics of left ventricular longitudinal function in patients with arterial hypertension during therapy with angiotensin converting enzyme inhibitor moexipril].	2006	17047618
[Moexipril and cardiovascular diseases in women: is there a reason for optimism?].	2006	16883271
[Hypotensive, organoprotective, and metabolic effects of Angiotensin converting enzyme inhibitor moexipril in women with postmenopausal syndrome].	2006	16858353
[Investigation of efficacy of cardiovascular drugs in women].	2006	16710266
[Comparative efficacy and safety of contemporary Angiotensin converting enzyme inhibitors moexipril and spirapril in women with postmenopausal metabolic syndrome].	2006	16474309
Monitoring the metabolism of moexipril to moexiprilat using high-performance liquid chromatography-electrospray ionization mass spectrometry.	2006 Apr	16620521
[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	18260911
Moexipril and left ventricular hypertrophy.	2007	17583172
Metabolism of moexipril to moexiprilat: determination of in vitro metabolism using HPLC-ES-MS.	2007 Jan	17266629
[Clinico-economical efficacy of angiotensin converting enzyme inhibitors in patients with arterial hypertension and ischemic heart disease].	2008	18729835
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	19015752
Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited.	2008 Nov	18713951
[Preventive pharmacotherapy in arterial hypertension: problems of clinical assessment of drugs in women].	2009	19656111
Iatrogenic QT Abnormalities and Fatal Arrhythmias: Mechanisms and Clinical Significance.	2009 Aug	20676275
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
Determination of antihypertensive drug moexipril hydrochloride based on the enhancement effect of sodium dodecyl sulfate at carbon paste electrode.	2010 Apr 15	20188882
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Anti-hypertensive drugs have different effects on ventricular hypertrophy regression.	2010 Jul	20668631

Patents

Sample Use Guides

In Vivo Use Guide

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

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Name

Type

Language

MOEXIPRILAT

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

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