MOEXIPRILAT HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H30N2O7.ClH
Molecular Weight	506.976
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.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=ZVLZMESUJYRKKI-ZAFWUOJLSA-N

InChI=1S/C25H30N2O7.ClH/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);1H/t15-,19-,20-;/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	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 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 8146		2.6 nM [IC50]
Angiotensin-converting enzyme 96 Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26076923	Inhibitor 8146		2.6 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 546 Sources: https://www.drugs.com/pro/moexipril.html	Primary		Approved 8307	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 546 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 24 PEPT1 48 PEPT2 32

Drug as victim

Target	Modality	Activity	Metabolite
CES2 24	substrate 3264 Sources: https://www.nature.com/articles/tpj201542	no
CES1 22	substrate 3264 Sources: https://www.nature.com/articles/tpj201542	yes
PEPT1 48	substrate 3264 Sources: https://www.tandfonline.com/doi/abs/10.1517/17425250903042292	yes	MOEXIPRIL 4
PEPT2 32	substrate 3264 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
Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors.	1998 May-Jun	9620109
Enalapril and moexipril protect from free radical-induced neuronal damage in vitro and reduce ischemic brain injury in mice and rats.	1999 May 28	10408248
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
Oestrogen action on the myocardium in vivo: specific and permissive for angiotensin-converting enzyme inhibition.	2002 May	12011662
[Assessment of antihypertensive efficacy of moexipril in metabolic syndrome].	2005	16353045
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
[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
Iatrogenic QT Abnormalities and Fatal Arrhythmias: Mechanisms and Clinical Significance.	2009 Aug	20676275
Stabilization of quinapril by incorporating hydrogen bonding interactions.	2009 Jul	20502545
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
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 16 20:33:03 UTC 2022` Edited by `admin` on `Fri Dec 16 20:33:03 UTC 2022`
Record UNII	54BP281YEW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MOEXIPRILAT HYDROCHLORIDE

Common Name

English

Moexiprilat hydrochloride [WHO-DD]

Common Name

English

MOEXIPRIL DIACID HYDROCHLORIDE [MI]

Common Name

English

MOEXIPRIL DIACID HYDROCHLORIDE

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 HYDROCHLORIDE

Systematic Name

English

MOEXIPRILAT HCL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C247