Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H34N2O7 |
| Molecular Weight | 498.5681 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=C(C[C@H]2C(O)=O)C=C(OC)C(OC)=C3
InChI
InChIKey=UWWDHYUMIORJTA-HSQYWUDLSA-N
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
| Molecular Formula | C27H34N2O7 |
| Molecular Weight | 498.5681 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: 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/14728069Curator'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
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 2.6 nM [IC50] | |||
Target ID: CHEMBL1808 |
2.6 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Moexipril Approved UseMoexipril 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 Date1995 |
|||
| Primary | Moexipril Approved UseMoexipril 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 Date1995 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evidence for site-specific absorption of a novel ACE inhibitor. | 1989 Sep |
|
| 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 |
|
| Increased arterial distensibility in postmenopausal hypertensive women with and without hormone replacement therapy after acute administration of the ACE inhibitor moexipril. | 1998 Sep |
|
| Enalapril and moexipril protect from free radical-induced neuronal damage in vitro and reduce ischemic brain injury in mice and rats. | 1999 May 28 |
|
| Chemical reactivity in solid-state pharmaceuticals: formulation implications. | 2001 May 16 |
|
| Using ACE inhibitors appropriately. | 2002 Aug 1 |
|
| Systemic hypertension in postmenopausal women: a clinical approach. | 2002 Dec |
|
| Moexipril shows a long duration of action related to an extended pharmacokinetic half-life and prolonged ACE inhibition. | 2002 Jan |
|
| Oestrogen action on the myocardium in vivo: specific and permissive for angiotensin-converting enzyme inhibition. | 2002 May |
|
| 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 |
|
| Simultaneous determination of moexipril hydrochloride and hydrochlorothiazide in tablets by derivative spectrophotometric and high-performance liquid chromatographic methods. | 2003 Oct 15 |
|
| Pharmacological profile and clinical use of moexipril. | 2003 Sep |
|
| [Hypertension in postmenopausal women: medical and social significance and results of therapy with moexipril.]. | 2004 |
|
| Pharmacological and clinical profile of moexipril: a concise review. | 2004 Aug |
|
| The influence of relative humidity and temperature on stability of moexipril hydrochloride in solid phase. | 2004 Mar-Apr |
|
| [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 |
|
| 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 |
|
| [Hypotensive, organoprotective, and metabolic effects of Angiotensin converting enzyme inhibitor moexipril in women with postmenopausal syndrome]. | 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 |
|
| 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 prince and the pauper. A tale of anticancer targeted agents. | 2008 Oct 23 |
|
| [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 |
|
| Impact of statins and ACE inhibitors on mortality after COPD exacerbations. | 2009 Jun 3 |
|
| 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 |
|
| Spectrophotometric method for simultaneous estimation of atenolol in combination with losartan potassium and hydrochlorothiazide in bulk and tablet formulation. | 2010 Oct |
Patents
Sample Use Guides
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
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on
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| Record UNII |
WT87C52TJZ
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Validated (UNII)
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NCI_THESAURUS |
C247
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NDF-RT |
N0000000181
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LIVERTOX |
NBK547904
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WHO-ATC |
C09AA13
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WHO-VATC |
QC09BA13
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WHO-ATC |
C09BA13
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WHO-VATC |
QC09AA13
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NDF-RT |
N0000175562
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103775-10-6
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Moexipril
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6266
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SUB09030MIG
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MOEXIPRIL
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DTXSID9023330
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100000080331
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91270
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CHEMBL1165
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1827
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30131
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m7585
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C83967
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WT87C52TJZ
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6571
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DB00691
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C058302
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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DERIVATIVE -> PARENT |
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TARGET -> INHIBITOR |
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Volume of Distribution | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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