Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H45NO7P.Na |
Molecular Weight | 585.6443 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCC(=O)O[C@@H](O[P@](=O)(CCCCC1=CC=CC=C1)CC(=O)N2C[C@@H](C[C@H]2C([O-])=O)C3CCCCC3)C(C)C
InChI
InChIKey=TVTJZMHAIQQZTL-WATAJHSMSA-M
InChI=1S/C30H46NO7P.Na/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24;/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35);/q;+1/p-1/t25-,26+,30+,39-;/m1./s1
Molecular Formula | C30H45NO7P |
Molecular Weight | 562.6546 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00492Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/fosinopril.html
Sources: http://www.drugbank.ca/drugs/DB00492
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/fosinopril.html
Fosinopril is a phosphinic acid-containing ester prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly hydrolyzed to fosinoprilat, its principle active metabolite. Fosinoprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Fosinopril may be used to treat mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.
CNS Activity
Sources: https://www.drugs.com/ppa/fosinopril-sodium.html
Curator's Comment: Fosinopril does not cross the blood-brain barrier.
Originator
Sources: http://adisinsight.springer.com/drugs/800003012
Curator's Comment: # Bristol-Myers Squibb
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1808 Sources: http://www.drugbank.ca/drugs/DB00492 |
1.0 nM [IC50] | ||
Target ID: P12822 Gene ID: 1.00009272E8 Gene Symbol: ACE Target Organism: Oryctolagus cuniculus (Rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2481187 |
11.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FOSINOPRIL SODIUM Approved UseFosinopril sodium tablets are indicated for the treatment of hypertension. They may be used alone or in combination with thiazide diuretics.
Fosinopril sodium tablets are indicated in the management of heart failure as adjunctive therapy when added to conventional therapy including diuretics with or without digitalis Launch Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1556 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/ |
7.5 mg single, intravenous dose: 7.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FOSINOPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
112 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
533 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
711 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
40 mg 2 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1018 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1217 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
80 mg 2 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
131 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5598 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
640 mg single, oral dose: 640 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3302 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/ |
7.5 mg single, intravenous dose: 7.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FOSINOPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
920 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
40 mg 2 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
80 mg 2 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
58.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1646240/ |
640 mg single, oral dose: 640 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT serum | 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/2967089/ |
7.5 mg single, intravenous dose: 7.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FOSINOPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/ |
7.5 mg single, intravenous dose: 7.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FOSINOPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
8% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2967089/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FOSINOPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy, 28 - 68years n = 12 Health Status: unhealthy Condition: essential hypertension Age Group: 28 - 68years Sex: M+F Population Size: 12 Sources: |
|
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: Page: 16 |
unhealthy, >65 years n = 688 Health Status: unhealthy Condition: hypertension Age Group: >65 years Sex: unknown Population Size: 688 Sources: Page: 16 |
Disc. AE: Headache, Transaminases increased... AEs leading to discontinuation/dose reduction: Headache (0.4 - 0.9) Sources: Page: 16Transaminases increased (0.4 - 0.9) Fatigue (0.4 - 0.9) Cough (0.4 - 0.9) |
40 mg 1 times / day steady, oral MTD Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: hypertension Age Group: adult Sex: unknown Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Cough | 0.4 - 0.9 Disc. AE |
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: Page: 16 |
unhealthy, >65 years n = 688 Health Status: unhealthy Condition: hypertension Age Group: >65 years Sex: unknown Population Size: 688 Sources: Page: 16 |
Fatigue | 0.4 - 0.9 Disc. AE |
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: Page: 16 |
unhealthy, >65 years n = 688 Health Status: unhealthy Condition: hypertension Age Group: >65 years Sex: unknown Population Size: 688 Sources: Page: 16 |
Headache | 0.4 - 0.9 Disc. AE |
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: Page: 16 |
unhealthy, >65 years n = 688 Health Status: unhealthy Condition: hypertension Age Group: >65 years Sex: unknown Population Size: 688 Sources: Page: 16 |
Transaminases increased | 0.4 - 0.9 Disc. AE |
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: Page: 16 |
unhealthy, >65 years n = 688 Health Status: unhealthy Condition: hypertension Age Group: >65 years Sex: unknown Population Size: 688 Sources: Page: 16 |
PubMed
Title | Date | PubMed |
---|---|---|
[Effects of lorsartan, fosinopril on myocardial fibrosis, angiotensin II and cardiac remolding in hypertensive rats]. | 2001 Apr 28 |
|
[Contrast of losartan, fosinopril and amlodipine on cardiomyocyte apoptosis and left ventricular remolding in hypertensive rats]. | 2001 Oct 28 |
|
The effect and mechanism of forsinopril on ventricular hypertrophy of SHR and left ventricular pressure overloading rat. | 2002 |
|
[FLAG--a program of achievability of target blood pressure levels during treatment of patients with hypertension with fosinopril]. | 2002 |
|
[Changes of distensibility of the aorta in elderly patients during long-term therapy with various classes of hypotensive drugs (magnetic resonance tomography data)]. | 2002 |
|
Regression of ventricular and vascular hypertrophy: are there differences between structurally different angiotensin-converting enzyme inhibitors? | 2002 Dec |
|
[Effect of Erigeron breviscapus injection on ventricular and vascular remodeling in spontaneous hypertension rats]. | 2002 Feb |
|
[Comparison of the antihypertensive activity of fosinopril and irbesartan]. | 2002 Nov |
|
FOSIDIAL: a randomised placebo controlled trial of the effects of fosinopril on cardiovascular morbidity and mortality in haemodialysis patients. Study design and patients' baseline characteristics. | 2002 Oct |
|
[Efficacy of combined use of fosinopril and propranolol in acute myocardial infarction]. | 2003 |
|
[Chronopharmacological approaches to the therapeutic prophylaxis of chronic cardiac insufficiency in type I diabetes mellitus]. | 2003 |
|
Comparison of dipyridamole and fosinopril on renal progression in nephrectomized rats. | 2003 Apr |
|
Acute visual loss after initiation of antihypertensive therapy: case report. | 2003 Aug 19 |
|
A prospective, randomized, open labeled crossover trial of fosinopril and theophylline in post renal transplant erythrocytosis. | 2003 Jan |
|
Effect of xuezhikang, a cholestin extract, on reflecting postprandial triglyceridemia after a high-fat meal in patients with coronary heart disease. | 2003 Jun |
|
ANP but not BNP reflects early left diastolic dysfunction in type 1 diabetics with myocardial dysinnervation. | 2003 May |
|
Effect of dual angiotensin converting enzyme/neutral endopeptidase inhibition, angiotensin converting enzyme inhibition, or AT1 antagonism on coronary microvasculature in spontaneously hypertensive rats. | 2003 Nov |
|
Angiotensin-converting enzyme inhibition but not angiotensin II receptor blockade regulates matrix metalloproteinase activity in patients with glomerulonephritis. | 2003 Nov |
|
Ramipril-associated hepatotoxicity. | 2003 Nov |
|
Protection of organic trauma in sinoaortic-denervated rats treated with fosinopril. | 2003 Oct |
|
Introduction to monitoring. What is what you prescribed actually doing? | 2003 Oct |
|
Dual renin-angiotensin system blockade restores blood pressure-renin dependency in individuals with low renin concentrations. | 2003 Oct |
|
Long-term renal survival in HIV-associated nephropathy with angiotensin-converting enzyme inhibition. | 2003 Oct |
|
[Combination therapy with losartan and fosinopril for early diabetic nephropathy]. | 2003 Sep |
|
Comparative metabolic effects of hydrochlorothiazide and indapamide in hypertensive diabetic patients receiving ACE inhibitor therapy. | 2003 Sep |
|
Precipitation of PTSD with metoprolol for hypertension. | 2003 Sep-Oct |
|
[Effect of fosinopril on the rate of neurohumoral and proinflammatory activation in patients with heart failure]. | 2004 |
|
[Effects of carvedilol, atenolol and their combination with fosinopril on cardiac rhythm variability, clinicofunctional status and quality of life in patients with postinfarction left ventricular dysfunction]. | 2004 |
|
Systemic contact dermatitis due to captopril without cross-sensitivity to fosinopril, quinapril and benazepril. | 2004 |
|
American Heart Association scientific sessions. | 2004 Apr |
|
Clinical trials update from the European Society of Cardiology Heart Failure meeting: SHAPE, BRING-UP 2 VAS, COLA II, FOSIDIAL, BETACAR, CASINO and meta-analysis of cardiac resynchronisation therapy. | 2004 Aug |
|
Studies on the glycemic and lipidemic effect of monopril and losartan in normal and diabetic rats. | 2004 Aug |
|
Heart failure and first dose hypotension after angiotensin converting enzyme inhibitors. | 2004 Dec |
|
Different effects of antihypertensive regimens based on fosinopril or hydrochlorothiazide with or without lipid lowering by pravastatin on progression of asymptomatic carotid atherosclerosis: principal results of PHYLLIS--a randomized double-blind trial. | 2004 Dec |
|
[Changes of collagen expression of pulmonary arteries and heart ventricles and intervention of fosinopril and losartan in rats with heart failure]. | 2004 Dec 2 |
|
Cardiorenal protective effects of vasopeptidase inhibition with omapatrilat in hypertensive transgenic (mREN-2)27 rats. | 2004 Jan |
|
Fosinopril and amlodipine in the treatment of isolated systolic hypertension. | 2004 Jan-Feb |
|
Comparative effects of fosinopril and irbesartan on hematopoiesis in essential hypertensives. | 2004 Jul |
|
Mortality rates in elderly patients who take different angiotensin-converting enzyme inhibitors after acute myocardial infarction: a class effect? | 2004 Jul 20 |
|
Normalization of renal aquaporin-2 water channel expression by fosinopril, valsartan, and combination therapy in congestive heart failure: a new mechanism of action. | 2004 Mar |
|
Role of Angiotensin-converting enzyme and neutral endopeptidase in flow-dependent remodeling. | 2004 Mar-Apr |
|
Framingham score and microalbuminuria: combined future targets for primary prevention? | 2004 Nov |
|
Effects of fosinopril and pravastatin on cardiovascular events in subjects with microalbuminuria. | 2004 Nov 2 |
|
A unique form of polycythemia associated with minimal change disease. | 2004 Nov-Dec |
|
Lumbar incisional hernias: diagnostic and management dilemma. | 2004 Oct-Dec |
|
Possible induction of diabetes by treatment of hypertension with indapamide (with four case reports). | 2004 Sep |
|
Therapeutic approaches in the prevention of cardiovascular disease in metabolic syndrome and in patients with type 2 diabetes. | 2004 Sep |
|
Is the extrapolated adult dose of fosinopril safe and effective in treating hypertensive children? | 2004 Sep |
|
Lithium toxicity after switch from fosinopril to lisinopril. | 2005 Mar |
|
Effects of fosinopril and pravastatin on carotid intima-media thickness in subjects with increased albuminuria. | 2005 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/fosinopril.html
Usual Adult Dose for Hypertension
Initial dose: 10 mg orally once a day alone or in combination with a diuretic
Maintenance dose: 20 to 40 mg orally once a day; some patients may have further response at 80 mg once a day
Usual Adult Dose for Congestive Heart Failure
Initial dose: 10 mg orally once a day
Target dose range: 20 to 40 mg orally once a day
Maximum dose: 40 mg orally once a day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21038689
Fosinopril up-regulated klotho mRNA in NRK-52E cells pretreated with Fos(10(-5) mol/L) for 12 h incubated with AngII
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:24:04 GMT 2023
by
admin
on
Fri Dec 15 15:24:04 GMT 2023
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Record UNII |
NW2RTH6T2N
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C247
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CHEMBL3039598
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NW2RTH6T2N
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m5553
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NW2RTH6T2N
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227278
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DBSALT000193
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
sum of impurities B, E and H: not more than 10 times the area of the principal peak in the chromatogram obtained with reference solution (b) (1.0 per cent.)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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IMPURITY -> PARENT |
sum of impurities B, E and H: not more than 10 times the area of the principal peak in the chromatogram obtained with reference solution (b) (1.0 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
sum of impurities B, E and H: not more than 10 times the area of the principal peak in the chromatogram obtained with reference solution (b) (1.0 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
if present
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |