CAS 103775-10-6|Moexipril HCl|Moexiprilum [INN-Latin]|Univasc|(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid|...

General Information

Structure

Molecular Formula

C₂₇H₃₄N₂O₇

Molecular Mass

498.56806

Exact Mass

498.23660144

Charge

InChI

InChI=1S/C27H34N2O7/c1-5-36-27(33)21(12-11-18-9-7-6-8-10-18)28-17(2)25(30)29-16-20-15-24(35-4)23(34-3)14-19(20)13-22(29)26(31)32/h6-10,14-15,17,21-22,28H,5,11-13,16H2,1-4H3,(H,31,32)/t17-,21-,22-/m0/s1

InChIKey

UWWDHYUMIORJTA-HSQYWUDLSA-N

Canonic Smiles

CCOC(=O)[C@@H](N[C@H](C(=O)N1Cc2cc(OC)c(cc2C[C@H]1C(=O)O)OC)C)CCc1ccccc1

Isomeric Smiles

O=C(N1[C@@H](Cc2c(C1)cc(OC)c(OC)c2)C(=O)O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)OCC)C

Calculated Properties

JChem

Acid pKa

3.462318

H Acceptors

H Donor

LogD (pH = 5.5)

1.1609751

LogD (pH = 7.4)

-0.08144003

Log P

1.5021217

Molar Refractivity

132.8822

Polarizability

52.210068

Polar Surface Area

114.4

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

1.52

LOG S

-4.93

Solubility (Water)

5.85e-03 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

Moexiprilum [INN-Latin]Moexipril hydrochlorideMoexipril HClMoexipril

IUPAC name

(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

IUPAC Traditional name

moexipril

Brand Name

Univasc

Names and Identifiers

Registration numbers

PubChem CID

91270

PubChem SID

46508441160964036

CAS Number

103775-10-6

Registration numbers

Properties

Physical Property

Solubility

Soluble (about 10% weight-to-volume) in distilled water at room temperature as HCl salt.

Hydrophobicity(logP)

2.7

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00691

Drug Groups

approved

Description

Moexipril is a non-sulfhydryl containing precursor of the active angiotensin-converting enzyme (ACE) inhibitor moexiprilat. It is used to treat high blood pressure (hypertension). It works by relaxing blood vessels, causing them to widen. Lowering high blood pressure helps prevent strokes, heart attacks and kidney problems.

Indication

For the treatment of hypertension.

Pharmacology

Toxicity

Human overdoses of moexipril have not been reported. In case reports of overdoses with other ACE inhibitors, hypotension has been the principal adverse effect noted. Single oral doses of 2 g/kg moexipril were associated with significant lethality in mice. Rats, however, tolerated single oral doses of up to 3 g/kg. Common adverse effects include cough, dizziness, diarrhea, flu syndrome, fatigue, pharyngitis, flushing, rash, and myalgia

Affected Organisms

Humans and other mammals

Biotransformation

Rapidly converted to moexiprilat, the active metabolite. Conversion to the active metabolite is thought to require carboxyesterases and is likely to occur in organs or tissues, other than the gastrointestinal tract, in which carboxyesterases occur. The liver is thought to be one site of conversion, but not the primary site.

Absorption

Moexipril is incompletely absorbed, with bioavailability as moexiprilat of about 13% compared to intravenous (I.V.) moexipril (both measuring the metabolite moexiprilat), and is markedly affected by food, which reduces C_max and AUC by about 70% and 40%, respectively, after the ingestion of a low-fat breakfast or by 80% and 50%, respectively, after the ingestion of a high-fat breakfast.

Half Life

Moexipril elimination half-life is approximately 1 hour. Moexiprilat elimination half-life is 2 to 9 hours.

Protein Binding

Moexiprilat is approxomately 50% protein bound.

Elimination

Moexiprilat undergoes renal elimination.

Distribution

* 183 L

Clearance

* 441 mL/min

References

• Asmar R, Sayegh F, Tracz W, Hlawaty M, Olszowska M, Jourde M, Vincent M, Goujoun B, Maldonado J: Reversal of left ventricular hypertrophy with the ACE inhibitor moexipril in patients with essential hypertension. Acta Cardiol. 2002 Feb;57(1):31-2. [Pubmed]

• Blacher J, Raison J, Amah G, Schiemann AL, Stimpel M, Safar ME: Increased arterial distensibility in postmenopausal hypertensive women with and without hormone replacement therapy after acute administration of the ACE inhibitor moexipril. Cardiovasc Drugs Ther. 1998 Sep;12(4):409-14. [Pubmed]

• Brogden RN, Wiseman LR: Moexipril. A review of its use in the management of essential hypertension. Drugs. 1998 Jun;55(6):845-60. [Pubmed]

• Cawello W, Boekens H, Waitzinger J, Miller U: Moexipril shows a long duration of action related to an extended pharmacokinetic half-life and prolonged ACE inhibition. Int J Clin Pharmacol Ther. 2002 Jan;40(1):9-17. [Pubmed]

• Chrysant SG, Chrysant GS: Pharmacological and clinical profile of moexipril: a concise review. J Clin Pharmacol. 2004 Aug;44(8):827-36. [Pubmed]

• Chrysant SG, Chrysant GS: Pharmacological profile and clinical use of moexipril. Expert Rev Cardiovasc Ther. 2003 Sep;1(3):345-52. [Pubmed]

• Chrysant GS, Nguyen PK: Moexipril and left ventricular hypertrophy. Vasc Health Risk Manag. 2007;3(1):23-30. [Pubmed]

• Grass GM, Morehead WT: Evidence for site-specific absorption of a novel ACE inhibitor. Pharm Res. 1989 Sep;6(9):759-65. [Pubmed]

• Kalasz H, Petroianu G, Tekes K, Klebovich I, Ludanyi K, Gulyas Z: Metabolism of moexipril to moexiprilat: determination of in vitro metabolism using HPLC-ES-MS. Med Chem. 2007 Jan;3(1):101-6. [Pubmed]

• Persson B, Stimpel M: Evaluation of the antihypertensive efficacy and tolerability of moexipril, a new ACE inhibitor, compared to hydrochlorothiazide in elderly patients. Eur J Clin Pharmacol. 1996;50(4):259-64. [Pubmed]

• Spinar J, Vitovec J: MORE--MOexipril and REgression of left ventricle hypertrophy in combination therapy A multicentric open label clinical trial. Int J Cardiol. 2005 Apr 20;100(2):199-206. [Pubmed]

• Stimpel M, Koch B, Oparil S: Antihypertensive treatment in postmenopausal women: results from a prospective, randomized, double-blind, controlled study comparing an ACE inhibitor (moexipril) with a diuretic (hydrochlorothiazide). Cardiology. 1998 May;89(4):271-6. [Pubmed]

• White CM: Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors. Pharmacotherapy. 1998 May-Jun;18(3):588-99. [Pubmed]

• White WB, Whelton A, Fox AA, Stimpel M, Kaihlanen PM: Tricenter assessment of the efficacy of the ACE inhibitor, moexipril, by ambulatory blood pressure monitoring. J Clin Pharmacol. 1995 Mar;35(3):233-8. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Grass GM, Morehead WT: Evidence for site-specific absorption of a novel ACE inhibitor. Pharm Res. 1989 Sep;6(9):759-65. Pubmed

• Chrysant SG, Chrysant GS: Pharmacological profile and clinical use of moexipril. Expert Rev Cardiovasc Ther. 2003 Sep;1(3):345-52. Pubmed

• White CM: Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors. Pharmacotherapy. 1998 May-Jun;18(3):588-99. Pubmed

• Chrysant SG, Chrysant GS: Pharmacological and clinical profile of moexipril: a concise review. J Clin Pharmacol. 2004 Aug;44(8):827-36. Pubmed

• Brogden RN, Wiseman LR: Moexipril. A review of its use in the management of essential hypertension. Drugs. 1998 Jun;55(6):845-60. Pubmed

• Chrysant GS, Nguyen PK: Moexipril and left ventricular hypertrophy. Vasc Health Risk Manag. 2007;3(1):23-30. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• Synonyms

• IUPAC name

• IUPAC Traditional name

• Brand Name

Registration numbers

• PubChem CID

• PubChem SID

• CAS Number

• Physical Property

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Synonyms

Moexiprilum [INN-Latin]Moexipril hydrochlorideMoexipril HClMoexipril

IUPAC name

(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

IUPAC Traditional name

moexipril

PubChem SID

46508441160964036

CAS Number

103775-10-6

Physical Property

Solubility

Soluble (about 10% weight-to-volume) in distilled water at room temperature as HCl salt.

Hydrophobicity(logP)

2.7

DrugBank

DB00691

Drug Groups

approved

Description

Indication

For the treatment of hypertension.

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

Half Life

Moexipril elimination half-life is approximately 1 hour. Moexiprilat elimination half-life is 2 to 9 hours.

Protein Binding

Moexiprilat is approxomately 50% protein bound.

Elimination

Moexiprilat undergoes renal elimination.

Distribution

* 183 L

Clearance

* 441 mL/min

References

• Brogden RN, Wiseman LR: Moexipril. A review of its use in the management of essential hypertension. Drugs. 1998 Jun;55(6):845-60. [Pubmed]

• Chrysant SG, Chrysant GS: Pharmacological and clinical profile of moexipril: a concise review. J Clin Pharmacol. 2004 Aug;44(8):827-36. [Pubmed]

• Chrysant SG, Chrysant GS: Pharmacological profile and clinical use of moexipril. Expert Rev Cardiovasc Ther. 2003 Sep;1(3):345-52. [Pubmed]

• Chrysant GS, Nguyen PK: Moexipril and left ventricular hypertrophy. Vasc Health Risk Manag. 2007;3(1):23-30. [Pubmed]

• Grass GM, Morehead WT: Evidence for site-specific absorption of a novel ACE inhibitor. Pharm Res. 1989 Sep;6(9):759-65. [Pubmed]

• White CM: Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors. Pharmacotherapy. 1998 May-Jun;18(3):588-99. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

From Data Sources

• Grass GM, Morehead WT: Evidence for site-specific absorption of a novel ACE inhibitor. Pharm Res. 1989 Sep;6(9):759-65. Pubmed

• Chrysant SG, Chrysant GS: Pharmacological profile and clinical use of moexipril. Expert Rev Cardiovasc Ther. 2003 Sep;1(3):345-52. Pubmed

• White CM: Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors. Pharmacotherapy. 1998 May-Jun;18(3):588-99. Pubmed

• Chrysant SG, Chrysant GS: Pharmacological and clinical profile of moexipril: a concise review. J Clin Pharmacol. 2004 Aug;44(8):827-36. Pubmed

• Brogden RN, Wiseman LR: Moexipril. A review of its use in the management of essential hypertension. Drugs. 1998 Jun;55(6):845-60. Pubmed

• Chrysant GS, Nguyen PK: Moexipril and left ventricular hypertrophy. Vasc Health Risk Manag. 2007;3(1):23-30. Pubmed

Molecule

ID:573