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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 97 Target ID: CHEMBL1808 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020312s033lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/14728069	Inhibitor 8297		2.6 nM [IC50]
Angiotensin-converting enzyme 97 Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26076923	Inhibitor 8297		2.6 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.drugs.com/pro/moexipril.html	Primary		Approved 8429	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
Hypertension 567 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 1995

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 49 PEPT2 32

Drug as victim

Target	Modality	Activity	Metabolite
CES2 28	substrate 3367 Sources: https://www.nature.com/articles/tpj201542	no
CES1 22	substrate 3367 Sources: https://www.nature.com/articles/tpj201542	yes
PEPT1 49	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.1517/17425250903042292	yes	MOEXIPRIL 4
PEPT2 32	substrate 3367 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
Evidence for site-specific absorption of a novel ACE inhibitor.	1989 Sep	2554270
Tricenter assessment of the efficacy of the ACE inhibitor, moexipril, by ambulatory blood pressure monitoring.	1995 Mar	7608310
Evaluation of the antihypertensive efficacy and tolerability of moexipril, a new ACE inhibitor, compared to hydrochlorothiazide in elderly patients.	1996	8803515
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
Using ACE inhibitors appropriately.	2002 Aug 1	12182524
Systemic hypertension in postmenopausal women: a clinical approach.	2002 Dec	12419176
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	12602539
Simultaneous determination of moexipril hydrochloride and hydrochlorothiazide in tablets by derivative spectrophotometric and high-performance liquid chromatographic methods.	2003 Oct 15	14550868
Pharmacological profile and clinical use of moexipril.	2003 Sep	15030263
[Hypertension in postmenopausal women: medical and social significance and results of therapy with moexipril.].	2004	15477782
Pharmacological and clinical profile of moexipril: a concise review.	2004 Aug	15286086
[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
Regression of left ventricular hypertrophy with moexipril, an angiotensin-converting enzyme inhibitor, in hypertensive patients.	2005 Jan-Feb	15662286
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
[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
The prince and the pauper. A tale of anticancer targeted agents.	2008 Oct 23	18947424
[Preventive pharmacotherapy in arterial hypertension: problems of clinical assessment of drugs in women].	2009	19656111
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
Inhibition of central angiotensin-converting enzyme with enalapril protects the brain from ischemia/reperfusion injury in normotensive rat.	2010	22615591
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
Identification and determination of antihypertonics from the group of angiotensin-convertase inhibitors by densitometric method in comparition with HPLC method.	2010 Mar-Apr	20369790
Spectrophotometric method for simultaneous estimation of atenolol in combination with losartan potassium and hydrochlorothiazide in bulk and tablet formulation.	2010 Oct	21180476

Patents

Sample Use Guides

In Vivo Use Guide

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 16:21:24 GMT 2023` Edited by `admin` on `Fri Dec 15 16:21:24 GMT 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