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.accessdata.fda.gov/drugsatfda_docs/label/2011/020312s033lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/14728069https://www.ncbi.nlm.nih.gov/pubmed/15286086Curator'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.accessdata.fda.gov/drugsatfda_docs/label/2011/020312s033lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/14728069https://www.ncbi.nlm.nih.gov/pubmed/15286086
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
Moexiprilat is the pharmacologically active metabolite of Moexipril. Formation of Moexiprilat is caused by hydrolysis of a Moexipril’s ethyl ester group. Moexiprilat competitively inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the actions of the potent vasoconstrictor angiotensin II and leads to vasodilatation. This agent also prevents angiotensin II-induced aldosterone secretion by the adrenal cortex, thereby promoting diuresis and natriuresis. Moexiprilat showed an extended duration of action owing to a long terminal pharmacokinetic half-life and produced a persistent ACE inhibition.
Originator
Sources: http://adisinsight.springer.com/drugs/800002317https://www.ncbi.nlm.nih.gov/pubmed/3020249
Curator's Comment: # Pfizer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
2.6 nM [IC50] | |||
Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26076923 |
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 |
---|---|---|
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 |
|
Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors. | 1998 May-Jun |
|
Increased arterial distensibility in postmenopausal hypertensive women with and without hormone replacement therapy after acute administration of the ACE inhibitor moexipril. | 1998 Sep |
|
Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. | 2002 |
|
Systemic hypertension in postmenopausal women: a clinical approach. | 2002 Dec |
|
Reversal of left ventricular hypertrophy with the ACE inhibitor moexipril in patients with essential hypertension. | 2002 Feb |
|
Oestrogen action on the myocardium in vivo: specific and permissive for angiotensin-converting enzyme inhibition. | 2002 May |
|
Should perindopril be used to treat patients with heart failure? | 2002 May 1 |
|
Pharmacological profile and clinical use of moexipril. | 2003 Sep |
|
[Assessment of antihypertensive efficacy of moexipril in metabolic syndrome]. | 2005 |
|
[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 |
|
MORE--MOexipril and REgression of left ventricle hypertrophy in combination therapy A multicentric open label clinical trial. | 2005 Apr 20 |
|
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 |
|
[Moexipril and cardiovascular diseases in women: is there a reason for optimism?]. | 2006 |
|
[Hypotensive, organoprotective, and metabolic effects of Angiotensin converting enzyme inhibitor moexipril in women with postmenopausal syndrome]. | 2006 |
|
[Investigation of efficacy of cardiovascular drugs in women]. | 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 |
|
[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 |
|
Moexipril and left ventricular hypertrophy. | 2007 |
|
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 Effect of the Dried-Bonito Broth on Blood Pressure, 8-Hydroxydeoxyguanosine (8-OHdG), an Oxidative Stress Marker, and Emotional States in Elderly Subjects. | 2008 Nov |
|
Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. | 2008 Nov |
|
[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 |
|
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 |
|
Anti-hypertensive drugs have different effects on ventricular hypertrophy regression. | 2010 Jul |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/moexipril.html
Usual Adult Dose for Hypertension
Initial dose:
-Patients not receiving diuretic therapy: 7.5 mg orally once a day 1 hour before meals
-Patients receiving diuretic therapy: 3.75 mg orally once a day 1 hour before meals
Maintenance dose: 7.5 to 30 mg orally per day in 1 or 2 divided doses 1 hour before meals.
Maximum dose: 60 mg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9079232
In vitro, moexiprilat (active diacid metabolite of moexipril) was a potent inhibitor of ACE in guinea pig serum as well as on purified ACE from rabbit lung with IC50 values of 2.6 and 4.9 nmol/l, respectively. Both, moexipril and moexiprilat inhibited the angiotensin I (ANG I)-induced contractions of rabbit aorta concentration-dependently.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:47:59 UTC 2023
by
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Record UNII |
H3753190JS
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Record Status |
Validated (UNII)
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Record Version |
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C247
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N0000175562
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METABOLITE -> PARENT |
MINOR
FECAL; PLASMA; URINE
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |