Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H28N2O5 |
Molecular Weight | 424.4895 |
Optical Activity | ( - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCC3=CC=CC=C3N(CC(O)=O)C2=O
InChI
InChIKey=XPCFTKFZXHTYIP-PMACEKPBSA-N
InChI=1S/C24H28N2O5/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28)/t19-,20-/m0/s1
Molecular Formula | C24H28N2O5 |
Molecular Weight | 424.4895 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdfhttps://www.google.com/patents/WO2006084761A1 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdf | http://usp35.infostar.com.cn/uspnf/pub/data/v35300/usp35nf30s0_m7495.htmlCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/benazepril.html | DOI: 10.1111/j.1527-3466.1990.tb00432.x
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdfhttps://www.google.com/patents/WO2006084761A1 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdf | http://usp35.infostar.com.cn/uspnf/pub/data/v35300/usp35nf30s0_m7495.html
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/benazepril.html | DOI: 10.1111/j.1527-3466.1990.tb00432.x
BENAZEPRIL, (±)- is an impurity referred to as Related Compound B, which is a diastereomer of benazepril, an ACE inhibitor, under the brand name Lotensin used primarily in treatment of hypertension, congestive heart failure, and heart attacks, and also in preventing the renal and retinal complications of diabetes. BENAZEPRIL, (±)- is used as USP Reference Standard.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1808 |
14.0 nM [IC50] | ||
Target ID: CHEMBL1808 |
0.1 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LOTENSIN Approved UseAmlodipine besylate and benazepril hydrochloride capsules is a combination capsule of amlodipine, a dihydropyridine calcium channel blocker (DHP CCB) and benazepril, an angiotensin converting enzyme (ACE) inhibitor. Amlodipine besylate and benazepril hydrochloride capsules are indicated for the treatment of hypertension in patients not adequately controlled on monotherapy with either agent (1) 1.1 Hypertension Amlodipine besylate and benazepril hydrochloride capsules are indicated for the treatment of hypertension in patients not adequately controlled on monotherapy with either agent. Launch Date1991 |
|||
Primary | BENAZEPRIL HYDROCHLORIDE Approved UseBenazepril hydrochloride tablets are indicated for the treatment of hypertension. They
may be used alone or in combination with thiazide diuretics. Launch Date1991 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
437 pmol/g EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2344861 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENAZEPRIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
334 pmol × h/g EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2344861 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENAZEPRIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2344861 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENAZEPRIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Other AEs: Headache, Back pain... Other AEs: Headache (8.6%) Sources: Back pain (2.6%) Diarrhoea (0.9%) Upper respiratory tract infection (3.4%) Peripheral oedema (1.7%) Sinusitis (1.7%) Fatigue (0.9%) Cough (1.7%) Arthralgia (0.9%) |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Fatigue... Other AEs: Headache (9%) Sources: Fatigue (2%) Nausea (2%) Dizziness (2%) Cough increased (2%) |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Fatigue... Other AEs: Headache (3%) Sources: Fatigue (2%) Nausea (1%) Dizziness (3%) Dizziness postural (1%) Cough increased (2%) |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Fatigue... Other AEs: Headache (3%) Sources: Fatigue (2%) Nausea (1%) Dizziness (2%) Dizziness postural (1%) Cough increased (1%) |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Dizziness... Other AEs: Headache (6%) Sources: Dizziness (2%) Dizziness postural (2%) |
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Fatigue... Other AEs: Headache (2%) Sources: Fatigue (5%) Nausea (1%) Cough increased (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Arthralgia | 0.9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Diarrhoea | 0.9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Fatigue | 0.9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Cough | 1.7% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Peripheral oedema | 1.7% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Sinusitis | 1.7% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Back pain | 2.6% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Upper respiratory tract infection | 3.4% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Headache | 8.6% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Cough increased | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
Dizziness | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
Fatigue | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
Nausea | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
Headache | 9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
Dizziness postural | 1% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
Nausea | 1% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
Cough increased | 2% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
Fatigue | 2% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
Dizziness | 3% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
Headache | 3% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
Cough increased | 1% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
Dizziness postural | 1% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
Nausea | 1% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
Dizziness | 2% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
Fatigue | 2% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
Headache | 3% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
Dizziness postural | 2% | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy |
Dizziness | 2% | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy |
Headache | 6% | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy |
Cough increased | 1% | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
Nausea | 1% | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
Headache | 2% | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
Fatigue | 5% | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
PubMed
Title | Date | PubMed |
---|---|---|
Sympathomoderating influence of benazepril in essential hypertension. | 1992 Apr |
|
Benazepril versus felodipine as supplement to bendroflumethiazide: evaluation by office and ambulatory blood pressure. | 1998 Apr |
|
Antiatherogenic effect of angiotensin converting enzyme inhibitor (benazepril) and angiotensin II receptor antagonist (valsartan) in the cholesterol-fed rabbits. | 1999 Apr |
|
Low Dose Combination Therapy vs. High Dose Monotherapy in the Management of Hypertension. | 1999 Nov |
|
Renal protective effects of blocking the intrarenal renin-angiotensin system. | 1999 Sep |
|
Safety of the combination of valsartan and benazepril in patients with chronic renal disease. European Group for the Investigation of Valsartan in Chronic Renal Disease. | 2000 Jan |
|
Effect of combination of valsartan with benazepril on blood pressure and left ventricular hypertrophy in SHR. | 2000 Nov |
|
Renin-angiotensin system plays an important role in the regulation of water transport in the peritoneum. | 2001 |
|
Angiotensin-converting enzyme inhibition potentiates angiotensin II type 1 receptor effects on renal bradykinin and cGMP. | 2001 Aug |
|
Efficacy and safety of a therapeutic interchange from high-dose calcium channel blockers to a fixed-dose combination of amlodipine/benazepril in patients with moderate-to-severe hypertension. | 2001 Aug |
|
Significance of ACE genotypes and medical treatments in childhood focal glomerulosclerosis. | 2001 Aug |
|
Amlodipine/benazepril: fixed dose combination therapy for hypertension. | 2001 Jan |
|
Cilnidipine is as effective as benazepril for control of blood pressure and proteinuria in hypertensive patients with benign nephrosclerosis. | 2001 Jul |
|
Valsartan alone or with a diuretic or ACE inhibitor as treatment for African American hypertensives: relation to salt intake. | 2001 Jul |
|
Once-daily treatment of patients with hypertension: a placebo-controlled study of amlodipine and benazepril vs amlodipine or benazepril alone. | 2001 Jul |
|
The quantitative determination of several inhibitors of the angiotensin-converting enzyme by CE. | 2001 Jul |
|
Comparison of the effects of an ACE inhibitor and alphabeta blocker on the progression of renal failure with left ventricular hypertrophy: preliminary report. | 2001 Mar |
|
Effects of the angiotensin converting enzyme inhibitor benazepril in cats with induced renal insufficiency. | 2001 Mar |
|
Spectrophotometric determination of benazepril hydrochloride and hydrochlorothiazide in binary mixture using second derivative, second derivative of the ratio spectra and chemometric methods. | 2001 May |
|
Prescribing patterns and cost of antihypertensive drugs in an internal medicine clinic. | 2001 May-Jun |
|
Combination of hydrochlorothiazide or benazepril with valsartan in hypertensive patients unresponsive to valsartan alone. | 2001 Nov |
|
Treatment of IgA nephropathy with angiotensin converting enzyme inhibitors: design of a prospective randomized multicenter trial. | 2001 Nov-Dec |
|
Pilot study to evaluate a water displacement technique to compare effects of diuretics and ACE inhibitors to alleviate lower extremity edema due to dihydropyridine calcium antagonists. | 2001 Sep |
|
Valsartan/hydrochlorothiazide: a review of its pharmacology, therapeutic efficacy and place in the management of hypertension. | 2002 |
|
Using ACE inhibitors appropriately. | 2002 Aug 1 |
|
Kinetics of the acidic and enzymatic hydrolysis of benazepril HCl studied by LC. | 2002 Jan 1 |
|
Potentiometric and thermal studies of a coated-wire benazepril-selective electrode. | 2002 Jan 1 |
|
[The effects of angiotensin-converting enzyme inhibitor on IgA nephropathy and the influencing factors]. | 2002 Jun |
|
Comparison of benazepril-amlodipine and captopril-thiazide combinations in the management of mild-to-moderate hypertension. | 2002 Jun |
|
Combination therapy of amlodipine/benazepril versus monotherapy of amlodipine in a practice-based setting. | 2002 Jun |
|
Self-measured systolic blood pressure in the morning is a strong indicator of decline of renal function in hypertensive patients with non-diabetic chronic renal insufficiency. | 2002 May |
|
The effects of antihypertensive agents on the survival rate of polycystic kidney disease in Han:SPRD rats. | 2002 Nov |
|
Rhabdomyolysis with concurrent atorvastatin and diltiazem. | 2002 Oct |
|
Pregnancy with prolonged fetal exposure to an angiotensin-converting enzyme inhibitor. | 2002 Oct-Nov |
|
Fentanyl-associated syndrome of inappropriate antidiuretic hormone secretion. | 2002 Sep |
|
Effects of valsartan with or without benazepril on blood pressure, angiotensin II, and endoxin in patients with essential hypertension. | 2003 Apr |
|
Additive effect of ACE inhibition and angiotensin II receptor blockade in type I diabetic patients with diabetic nephropathy. | 2003 Apr |
|
[Effect of the compound of traditional Chinese drugs on gene expression of renal endothelin and its receptor of experimental diabetic nephropathy]. | 2003 Feb |
|
Quantitative determination of benazepril and benazeprilat in human plasma by gas chromatography-mass spectrometry using automated 96-well disk plate solid-phase extraction for sample preparation. | 2003 Jan 5 |
|
Rationale for combination therapy as initial treatment for hypertension. | 2003 Jul-Aug |
|
Combination is better than monotherapy with ACE inhibitor or angiotensin receptor antagonist at recommended doses. | 2003 Mar |
|
Correlation of Angiotensin-converting enzyme gene polymorphism with effect of antihypertensive therapy by Angiotensin-converting enzyme inhibitor. | 2003 Mar |
|
Effects of combined ACE inhibitor and angiotensin II antagonist treatment in human chronic nephropathies. | 2003 Mar |
|
Effect of benazepril addition to amlodipine on ankle oedema and subcutaneous tissue pressure in hypertensive patients. | 2003 Mar |
|
Systemic contact dermatitis due to captopril without cross-sensitivity to fosinopril, quinapril and benazepril. | 2004 |
|
Effects of co-administration of urokinase and benazepril on severe IgA nephropathy. | 2004 Apr |
|
Hypertensive patients from two rural Chinese counties respond differently to benazepril: the Anhui Hypertension Health Care Study. | 2004 Feb |
Patents
Sample Use Guides
The recommended initial dose for patients not receiving a diuretic is 10 mg once a day. The usual maintenance dosage range is 20-40 mg per day administered as a single dose or in two equally divided doses. A dose of 80 mg gives an increased response, but experience with this dose is limited.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3140614
Curator's Comment: In the isolated rabbit aorta the vasocontraction induced by PGF2 alpha was competitively antagonized at 10(-5)-10(-4) mol/l, while vascular responses induced by PGE1, PGE2 or PGI2 was inhibited at 3 x 10(-4) mol/l of benazepril. https://www.ncbi.nlm.nih.gov/pubmed/2080946
Benazepril inhibited both adrenaline-stimulated aortic PGI2 synthesis (25 pg mg -1 min-1) and carbachol-stimulated urinary bladder PGI2 synthesis (20 pg mg -1 min-1) in dose-dependent manners. IC50 (concentrations of antagonist at which agonist-stimulated PGI2 synthesis was inhibited by 50%) was 8 x 10-5.
Substance Class |
Chemical
Created
by
admin
on
Edited
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by
admin
on
Mon Mar 31 18:29:36 GMT 2025
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Record UNII |
UDM7Q7QWP8
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175562
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EMA VETERINARY ASSESSMENT REPORTS |
FORTEKOR PLUS [AUHTORIZED]
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NDF-RT |
N0000000181
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WHO-ATC |
C09AA07
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NCI_THESAURUS |
C247
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WHO-VATC |
QC09AA07
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WHO-ATC |
C09BA07
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WHO-VATC |
QC09BA07
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LIVERTOX |
NBK548659
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6129
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BENAZEPRIL
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18867
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Benazepril
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C044946
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m2303
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C61645
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
Impurity C: not more than 1.5 times the area of the principal peak in the chromatogram obtained with reference solution (c) (0.3 per cent)
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ACTIVE MOIETY |
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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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