Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H30N2O5 |
Molecular Weight | 438.5161 |
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=CC=C3
InChI
InChIKey=JSDRRTOADPPCHY-HSQYWUDLSA-N
InChI=1S/C25H30N2O5/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30)/t17-,21-,22-/m0/s1
Molecular Formula | C25H30N2O5 |
Molecular Weight | 438.5161 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT00651287 | https://www.ncbi.nlm.nih.gov/pubmed/25922179 | https://www.ncbi.nlm.nih.gov/pubmed/1691409
Curator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT00651287 | https://www.ncbi.nlm.nih.gov/pubmed/25922179 | https://www.ncbi.nlm.nih.gov/pubmed/1691409
Quinapril is the hydrochloride salt of quinapril, the ethyl ester of a non-sulfhydryl, angiotensin-converting enzyme (ACE) inhibitor, quinaprilat. Quinapril hydrochloride is a white to off-white amorphous powder that is freely soluble in aqueous solvents. Quinapril is indicated for the treatment of high blood pressure (hypertension) and as adjunctive therapy in the management of heart failure. It may be used for the treatment of hypertension by itself or in combination with thiazide diuretics, and with diuretics and digoxin for heart failure.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3020249 |
2.8 nM [IC50] | ||
Target ID: CHEMBL4074 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25922179 |
110.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ACCURETIC Approved UseINDICATIONS AND USA. Hypertension: ACCURETIC is indicated for the treatment of hypertension, to lower blood
pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular
events, primarily strokes and myocardial infarctions. These benefits have been seen in
controlled trials of antihypertensive drugs from a wide variety of pharmacologic classes
including the class to which this drug principally belongs. There are no controlled trials
demonstrating risk reduction with ACCURETIC.
Control of high blood pressure should be part of comprehensive cardiovascular risk
management, including, as appropriate, lipid control, diabetes management, antithrombotic
therapy, smoking cessation, exercise, and limited sodium intake. Many patients will require
more than one drug to achieve blood pressure goals. For specific advice on goals and
management, see published guidelines, such as those of the National High Blood Pressure
Education Program’s Joint National Committee on Prevention, Detection, Evaluation, and
Treatment of High Blood Pressure (JNC).
Numerous antihypertensive drugs, from a variety of pharmacologic classes and with
different mechanisms of action, have been shown in randomized controlled trials to reduce
cardiovascular morbidity and mortality, and it can be concluded that it is blood pressure
reduction, and not some other pharmacologic property of the drugs, that is largely
responsible for those benefits. The largest and most consistent cardiovascular outcome
benefit has been a reduction in the risk of stroke, but reductions in myocardial infarction
and cardiovascular mortality also have been seen regularly.
6
Reference ID: 3818285
Elevated systolic or diastolic pressure causes increased cardiovascular risk, and the
absolute risk increase per mmHg is greater at higher blood pressures, so that even modest
reductions of severe hypertension can provide substantial benefit. Relative risk reduction
from blood pressure reduction is similar across populations with varying absolute risk, so
the absolute benefit is greater in patients who are at higher risk independent of their
hypertension (for example, patients with diabetes or hyperlipidemia), and such patients
would be expected to benefit from more aggressive treatment to a lower blood pressure
goal.
Some antihypertensive drugs have smaller blood pressure effects (as monotherapy) in black
patients, and many antihypertensive drugs have additional approved indications and effects
(e.g., on angina, heart failure, or diabetic kidney disease). These considerations may guide
selection of therapy.
This fixed combination is not indicated for the initial therapy of hypertension (see
DOSAGE AND ADMINISTRATION).
In using ACCURETIC, consideration should be given to the fact that another angiotensinconverting
enzyme inhibitor, captopril, has caused agranulocytosis, particularly in patients
with renal impairment or collagen-vascular disease. Available data are insufficient to show
that quinapril does not have a similar risk (see WARNINGS:
Neutropenia/Agranulocytosis).
Angioedema in Black Patients: Black patients receiving ACE inhibitor monotherapy have
been reported to have a higher incidence of angioedema compared to non-blacks. It should
also be noted that in controlled clinical trials, ACE inhibitors have an effect on blood
pressure that is less in black patients than in non-blacks. Launch Date9.4625281E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1526 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739020/ |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
QUINAPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
345 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739020/ |
2.5 mg single, intravenous dose: 2.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
QUINAPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1706 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8198942/ |
10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUINAPRILAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2670 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739020/ |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
QUINAPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
580 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739020/ |
2.5 mg single, intravenous dose: 2.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
QUINAPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8198942/ |
10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
QUINAPRILAT plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739020/ |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
QUINAPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8739020/ |
2.5 mg single, intravenous dose: 2.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
QUINAPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 11 |
unhealthy, adult n = 1563 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 1563 Sources: Page: 11 |
Disc. AE: Headache, Dizziness... AEs leading to discontinuation/dose reduction: Headache (0.7%) Sources: Page: 11Dizziness (0.8%) Fatigue (0.3%) Coughing (0.5%) Nausea and vomiting (0.3%) Abdominal pain (0.2%) |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 12 |
unhealthy, adult n = 585 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 585 Sources: Page: 12 |
Disc. AE: Dizziness, Coughing... AEs leading to discontinuation/dose reduction: Dizziness (0.7%) Sources: Page: 12Coughing (0.3%) Fatigue (0.2%) Nausea and vomiting (0.2%) Hypotension (0.5%) Dyspnea (0.2%) Rash (0.2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abdominal pain | 0.2% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 11 |
unhealthy, adult n = 1563 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 1563 Sources: Page: 11 |
Fatigue | 0.3% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 11 |
unhealthy, adult n = 1563 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 1563 Sources: Page: 11 |
Nausea and vomiting | 0.3% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 11 |
unhealthy, adult n = 1563 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 1563 Sources: Page: 11 |
Coughing | 0.5% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 11 |
unhealthy, adult n = 1563 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 1563 Sources: Page: 11 |
Headache | 0.7% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 11 |
unhealthy, adult n = 1563 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 1563 Sources: Page: 11 |
Dizziness | 0.8% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 11 |
unhealthy, adult n = 1563 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 1563 Sources: Page: 11 |
Dyspnea | 0.2% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 12 |
unhealthy, adult n = 585 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 585 Sources: Page: 12 |
Fatigue | 0.2% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 12 |
unhealthy, adult n = 585 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 585 Sources: Page: 12 |
Nausea and vomiting | 0.2% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 12 |
unhealthy, adult n = 585 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 585 Sources: Page: 12 |
Rash | 0.2% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 12 |
unhealthy, adult n = 585 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 585 Sources: Page: 12 |
Coughing | 0.3% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 12 |
unhealthy, adult n = 585 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 585 Sources: Page: 12 |
Hypotension | 0.5% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 12 |
unhealthy, adult n = 585 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 585 Sources: Page: 12 |
Dizziness | 0.7% Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: 12 |
unhealthy, adult n = 585 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: M+F Population Size: 585 Sources: Page: 12 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 6.2 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Preservation of cardiac function and energy reserve by the angiotensin-converting enzyme inhibitor quinapril during postmyocardial infarction remodeling in the rat. | 2001 |
|
Activation of NF-kappaB in tubular epithelial cells of rats with intense proteinuria: role of angiotensin II and endothelin-1. | 2001 Apr |
|
[Hypertensive patients with signs of coronary heart disease. An ACE inhibitor improves endothelial function]. | 2001 Aug 23 |
|
Comparison of endothelial pleiotropic actions of angiotensin converting enzyme inhibitors and statins. | 2001 Dec |
|
ACE inhibitors for hypertension. | 2001 Jan 26 |
|
Angiotensin converting enzyme inhibitors and restenosis: let's stop teasing ourselves. | 2001 Jul |
|
Low-dose alpha/beta blockade in the treatment of essential hypertension. | 2001 Jun |
|
Effect of quinapril versus nitrendipine on endothelial dysfunction in patients with systemic hypertension. | 2001 Jun 15 |
|
Quinapril and its metabolite quinaprilat in human milk. | 2001 May |
|
Chemical reactivity in solid-state pharmaceuticals: formulation implications. | 2001 May 16 |
|
Chronic effects of ACE-inhibition (quinapril) and angiotensin-II-type-1 receptor blockade (losartan) on atrial natriuretic peptide in brain nuclei of rats with experimental myocardial infarction. | 2001 May-Jun |
|
Vitamin C and quinapril abrogate LVH and endothelial dysfunction in aortic-banded guinea pigs. | 2001 Oct |
|
[Effects of ACE inhibitors on angiographic restenosis after coronary stenting (PARIS): double-blind randomized trial]. | 2001 Sep |
|
Hyperkalemia, renal failure, and converting-enzyme inhibition: an overrated connection. | 2001 Sep |
|
[Some new data concerning effectiveness of amlodipine, atorvastatine and quinaprile for heart diseases]. | 2002 |
|
[Clinical sequelae of tissue angiotensin converting enzyme inhibition: practicability of use in ischemic heart disease]. | 2002 |
|
Angiotensin II induced inflammation in the kidney and in the heart of double transgenic rats. | 2002 |
|
Quinapril: a further update of its pharmacology and therapeutic use in cardiovascular disorders. | 2002 |
|
Rapid increase in cardiac adrenomedullin gene expression caused by acute pressure overload: effect of the renin-angiotensin system on gene expression. | 2002 Apr |
|
Quinapril prevents restenosis after coronary stenting in patients with angiotensin-converting enzyme D allele. | 2002 Apr |
|
Inhibition of left ventricular fibrosis by tranilast in rats with renovascular hypertension. | 2002 Apr |
|
Time-effect profile of antihypertensive agents assessed with trough/peak ratio, smoothness index and dose omission: an ambulatory blood pressure monitoring study with trandolapril vs. quinapril. | 2002 Dec |
|
Effects of quinapril on myocardial function, ventricular remodeling and cardiac cytokine expression in congestive heart failure in the rat. | 2002 Jan |
|
Effects of losartan and its combination with quinapril on the cardiac sympathetic nervous system and neurohormonal status in essential hypertension. | 2002 Jan |
|
Oxidative stress and nitric oxide synthase in rat diabetic nephropathy: effects of ACEI and ARB. | 2002 Jan |
|
Psychological characteristics and responses to antihypertensive drug therapy. | 2002 Jan-Feb |
|
Subacute and chronic effects of quinapril on cardiac cytokine expression, remodeling, and function after myocardial infarction in the rat. | 2002 Jun |
|
Blockade of endothelial enzymes: new therapeutic targets. | 2002 Mar |
|
Pretreatment with angiotensin-converting enzyme inhibitors attenuates ischemia-reperfusion injury. | 2002 May |
|
Bradykinin as a major endogenous regulator of endothelial function. | 2002 May-Jun |
|
Quinapril treatment restores the vasodilator action of insulin in fructose-hypertensive rats. | 2002 May-Jun |
|
Ischemia Management with Accupril post bypass Graft via Inhibition of angiotensin coNverting enzyme (IMAGINE): a multicentre randomized trial - design and rationale. | 2002 Nov |
|
[Angiotensin-converting enzyme, quinapril, in treating chronic cardiac failure]. | 2003 |
|
Role of PKC in autocrine regulation of rat ventricular K+ currents by angiotensin and endothelin. | 2003 Apr |
|
Pharmacokinetics of quinapril in children: assessment during substitution for chronic angiotensin-converting enzyme inhibitor treatment. | 2003 Feb |
|
Effect of combination therapy with dipyridamole and quinapril in diabetic nephropathy. | 2003 Feb |
|
Comparative effects of angiotensin II receptor blockade (candesartan) with angiotensin-converting enzyme inhibitor (quinapril) in rats with dilated cardiomyopathy. | 2003 Jan |
|
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 |
|
Effects of angiotensin-converting enzyme inhibition and calcium channel blockade on cardiac apoptosis in rats with 2K1C (two-kidney/one-clip) renovascular hypertension. | 2003 Jan |
|
Attenuation of heart failure due to coronary stenosis by ACE inhibitor and angiotensin receptor blocker. | 2003 Jul |
|
Improvement of endothelial dysfunction by angiotensin II blockade accompanied by induction of vascular hepatocyte growth factor system in diabetic spontaneously hypertensive rats. | 2003 Mar |
|
Square wave voltammetric determination of the angiotensin-converting enzyme inhibitors cilazapril, quinapril and ramipril in pharmaceutical formulations. | 2003 May |
|
Usefulness of quinapril and irbesartan to improve the anti-inflammatory response of atorvastatin and aspirin in patients with coronary heart disease. | 2003 May 1 |
|
In vitro study on binding interaction of quinapril with bovine serum albumin (BSA) using multi-spectroscopic and molecular docking methods. | 2017 Aug |
|
Genetic variants associated with angiotensin-converting enzyme inhibitor-induced cough: a genome-wide association study in a Swedish population. | 2017 Feb |
Sample Use Guides
The recommended initial dosage of ACCUPRIL in patients not on diuretics is 10 or 20 mg once daily. Dosage should be adjusted according to blood pressure response measured at peak (2–6 hours after dosing) and trough (predosing). Generally, dosage adjustments should be made at intervals of at least 2 weeks. Most patients have required dosages of 20, 40, or 80 mg/day, given as a single dose or in two equally divided doses.
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:14:24 UTC 2023
by
admin
on
Wed Jul 05 23:14:24 UTC 2023
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Record UNII |
RJ84Y44811
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Record Status |
Validated (UNII)
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Record Version |
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-
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Official Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Code | English |
Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175562
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NDF-RT |
N0000000181
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WHO-VATC |
QC09BA06
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WHO-ATC |
C09BA06
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NCI_THESAURUS |
C247
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WHO-VATC |
QC09AA06
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WHO-ATC |
C09AA06
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LIVERTOX |
NBK548451
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Code System | Code | Type | Description | ||
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Quinapril
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35208
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6350
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2340
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SUB10201MIG
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DB00881
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CHEMBL1592
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QUINAPRIL
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54892
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M9437
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5780
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8713
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C62074
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100000081087
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RJ84Y44811
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RJ84Y44811
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85441-61-8
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DTXSID4023547
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C041125
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR |
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
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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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Elimination PHARMACOKINETIC |
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