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
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
| 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 |
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 Date7.9824958E11 |
|||
| 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 Date7.9816321E11 |
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 |
|
| Moexipril. A review of its use in the management of essential hypertension. | 1998 Jun |
|
| Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors. | 1998 May-Jun |
|
| Moexipril shows a long duration of action related to an extended pharmacokinetic half-life and prolonged ACE inhibition. | 2002 Jan |
|
| ACE Inhibition with moexipril: a review of potential effects beyond blood pressure control. | 2003 |
|
| 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 |
|
| [Angiotensin converting enzyme inhibitor moexipril in the treatment of arterial hypertension. Possibilities of moexipril in the treatment of postmenopausal women]. | 2006 |
|
| [Investigation of efficacy of cardiovascular drugs in women]. | 2006 |
|
| Moexipril and left ventricular hypertrophy. | 2007 |
|
| Metabolism of moexipril to moexiprilat: determination of in vitro metabolism using HPLC-ES-MS. | 2007 Jan |
|
| Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. | 2008 Nov |
|
| 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 |
|
| Inhibition of central angiotensin-converting enzyme with enalapril protects the brain from ischemia/reperfusion injury in normotensive rat. | 2010 |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
| Moexipril for treatment of primary biliary cirrhosis in patients with an incomplete response to ursodeoxycholic acid. | 2010 Feb |
|
| 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
by
admin
on
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| Record UNII |
H3753190JS
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C247
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NDF-RT |
N0000175562
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C059506
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DTXSID6057611
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55331
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CHEMBL1201405
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H3753190JS
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1445608
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H3753190JS
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103775-14-0
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C66175
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DB14210
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SUB09031MIG
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1546358
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6946
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6572
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SALT/SOLVATE -> PARENT |
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METABOLITE -> PARENT |
MINOR
FECAL; PLASMA; URINE
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
