Details
Stereochemistry | RACEMIC |
Molecular Formula | C33H34N6O6 |
Molecular Weight | 610.6597 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC1=NC2=C(N1CC3=CC=C(C=C3)C4=C(C=CC=C4)C5=NN=NN5)C(=CC=C2)C(=O)OC(C)OC(=O)OC6CCCCC6
InChI
InChIKey=GHOSNRCGJFBJIB-UHFFFAOYSA-N
InChI=1S/C33H34N6O6/c1-3-42-32-34-28-15-9-14-27(31(40)43-21(2)44-33(41)45-24-10-5-4-6-11-24)29(28)39(32)20-22-16-18-23(19-17-22)25-12-7-8-13-26(25)30-35-37-38-36-30/h7-9,12-19,21,24H,3-6,10-11,20H2,1-2H3,(H,35,36,37,38)
Molecular Formula | C33H34N6O6 |
Molecular Weight | 610.6597 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.japsonline.com/admin/php/uploads/290_pdf.pdf
Curator's Comment: description was created based on several sources, including
http://www.japsonline.com/admin/php/uploads/290_pdf.pdf
Candesartan is classified as an angiotensin II receptor type 1 antagonist. Candesartan is an orally active lipophilic drug and possesses rapid oral absorption. It causes a reduction in blood pressure and is used in the treatment of hypertension. It is also used in the treatment of congestive heart failure and given as prophylaxis to reduce the severity and duration of migraine. Candesartan cilexetil, a prodrug of Candesartan, is available in the market under the trade names Atacand, Amias. Candesartan cilexetil is rapidly converted to candesartan, its active metabolite, during absorption from the gastrointestinal tract. Candesartan confers blood pressure lowering effects by antagonizing the hypertensive effects of angiotensin II via the RAAS (renin–angiotensin–aldosterone system). RAAS is a homeostatic mechanism for regulating hemodynamics, water, and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from granular cells of the juxtaglomerular apparatus in the kidneys. Renin cleaves circulating angiotensinogen to angiotensin I, which is cleaved by angiotensin converting enzyme (ACE) to angiotensin II. Angiotensin II increases blood pressure by increasing total peripheral resistance, increasing sodium and water reabsorption in the kidneys via aldosterone secretion, and altering the cardiovascular structure. Angiotensin II binds to two receptors: type-1 angiotensin II receptor (AT1) and type-2 angiotensin II receptor (AT2). Candesartan selectively blocks the binding of angiotensin II to AT1 in many tissues including vascular smooth muscle and the adrenal glands. This inhibits the AT1-mediated vasoconstrictive and aldosterone-secreting effects of angiotensin II and results in an overall decrease in blood pressure. Candesartan is greater than 10,000 times more selective for AT1 than AT2.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8205603
Curator's Comment: TCV-116 # Takeda, Osaka, Japan
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL227 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ATACAND Approved UseCandesartan Cilexetil Tablets are an angiotensin II receptor blocker (ARB) indicated for: •Treatment of hypertension in adults and children 1 to < 17 years of age (1.1). •Treatment of heart failure (NYHA class II-IV); candesartan cilexetil tablets reduces cardiovascular death and heart failure hospitalization (1.2). 1.1 Hypertension Candesartan cilexetil tablets are indicated for the treatment of hypertension in adults and children 1 to < 17 years of age. It may be used alone or in combination with other antihypertensive agents. 1.2 Heart Failure Candesartan cilexetil tablets is indicated for the treatment of heart failure (NYHA class II-IV) in adults with left ventricular systolic dysfunction (ejection fraction ≤ 40%) to reduce cardiovascular death and to reduce heart failure hospitalizations [see CLINICAL STUDIES (14.2) Launch Date1998 |
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Primary | ATACAND Approved UseCandesartan Cilexetil Tablets are an angiotensin II receptor blocker (ARB) indicated for: •Treatment of hypertension in adults and children 1 to < 17 years of age (1.1). •Treatment of heart failure (NYHA class II-IV); candesartan cilexetil tablets reduces cardiovascular death and heart failure hospitalization (1.2). 1.1 Hypertension Candesartan cilexetil tablets are indicated for the treatment of hypertension in adults and children 1 to < 17 years of age. It may be used alone or in combination with other antihypertensive agents. 1.2 Heart Failure Candesartan cilexetil tablets is indicated for the treatment of heart failure (NYHA class II-IV) in adults with left ventricular systolic dysfunction (ejection fraction ≤ 40%) to reduce cardiovascular death and to reduce heart failure hospitalizations [see CLINICAL STUDIES (14.2) Launch Date1998 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
92 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
61 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
79 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
55 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1152 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
509 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1359 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
485 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757 |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
CANDESARTAN CILEXETIL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
unknown, unknown |
CANDESARTAN CILEXETIL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
16 mg 1 times / day steady, oral Recommended Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Co-administed with:: amlodipine(10 mg/day) Sources: |
unhealthy, 41 years n = 1 Health Status: unhealthy Age Group: 41 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hepatitis... AEs leading to discontinuation/dose reduction: Hepatitis (acute, 1 patient) Sources: |
32 mg 1 times / day steady, oral Highest studied dose Dose: 32 mg, 1 times / day Route: oral Route: steady Dose: 32 mg, 1 times / day Sources: |
unhealthy, 59 years n = 6 Health Status: unhealthy Condition: Type 2 Diabetes Age Group: 59 years Population Size: 6 Sources: |
|
23 mg 1 times / day steady, oral (mean) Recommended Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: |
unhealthy, 67 years n = 207 Health Status: unhealthy Condition: heart failure Age Group: 67 years Sex: M+F Population Size: 207 Sources: |
Disc. AE: Hypotension, Hyperkalemia... AEs leading to discontinuation/dose reduction: Hypotension (4.1%) Sources: Hyperkalemia (2.4%) |
16 mg 1 times / day steady, oral Recommended Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Disorder fetal... Other AEs: Disorder fetal Sources: |
2 mg 1 times / day steady, oral Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: |
unhealthy n = 2350 Health Status: unhealthy Population Size: 2350 Sources: |
Disc. AE: Headache, Dizziness... AEs leading to discontinuation/dose reduction: Headache (0.6%) Sources: Dizziness (0.3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hepatitis | acute, 1 patient Disc. AE |
16 mg 1 times / day steady, oral Recommended Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Co-administed with:: amlodipine(10 mg/day) Sources: |
unhealthy, 41 years n = 1 Health Status: unhealthy Age Group: 41 years Sex: F Population Size: 1 Sources: |
Hyperkalemia | 2.4% Disc. AE |
23 mg 1 times / day steady, oral (mean) Recommended Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: |
unhealthy, 67 years n = 207 Health Status: unhealthy Condition: heart failure Age Group: 67 years Sex: M+F Population Size: 207 Sources: |
Hypotension | 4.1% Disc. AE |
23 mg 1 times / day steady, oral (mean) Recommended Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: |
unhealthy, 67 years n = 207 Health Status: unhealthy Condition: heart failure Age Group: 67 years Sex: M+F Population Size: 207 Sources: |
Disorder fetal | 16 mg 1 times / day steady, oral Recommended Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Dizziness | 0.3% Disc. AE |
2 mg 1 times / day steady, oral Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: |
unhealthy n = 2350 Health Status: unhealthy Population Size: 2350 Sources: |
Headache | 0.6% Disc. AE |
2 mg 1 times / day steady, oral Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: |
unhealthy n = 2350 Health Status: unhealthy Population Size: 2350 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Distinction between surmountable and insurmountable selective AT1 receptor antagonists by use of CHO-K1 cells expressing human angiotensin II AT1 receptors. | 1999 Feb |
|
Binding of the antagonist [3H]candesartan to angiotensin II AT1 receptor-transfected [correction of tranfected] Chinese hamster ovary cells. | 1999 Feb 19 |
|
Effect of beta(2)-adrenoceptor activation and angiotensin II on tumour necrosis factor and interleukin 6 gene transcription in the rat renal resident macrophage cells. | 1999 Oct |
|
The mechanism of action of angiotensin II is dependent on direct activation of vascular smooth muscle carbonic anhydrase I. | 2000 |
|
[Angiotensin I receptor blockers for heart failure]. | 2001 |
|
The comparative pharmacology of angiotensin II receptor antagonists. | 2001 |
|
The effect duration of candesartan cilexetil once daily, in comparison with enalapril once daily, in patients with mild to moderate hypertension. | 2001 |
|
Efficacy and tolerability of angiotensin II type 1 receptor antagonists in dialysis patients using AN69 dialysis membranes. | 2001 |
|
Effects of blockade of the renin-angiotensin system on tissue factor and plasminogen activator inhibitor-1 synthesis in human cultured monocytes. | 2001 Apr |
|
Inhibition of platelet activation in stroke-prone spontaneously hypertensive rats: comparison of losartan, candesartan, and valsartan. | 2001 Apr |
|
Temporary treatment of prepubescent rats with angiotensin inhibitors suppresses the development of hypertensive nephrosclerosis. | 2001 Apr |
|
Angiotensin blockade inhibits increased JNKs, AP-1 and NF- kappa B DNA-binding activities in myocardial infarcted rats. | 2001 Apr |
|
Protective effect of agiotensin II type I receptor antagonist, CV-11974, on ischemia and reperfusion injury of the liver. | 2001 Apr 27 |
|
Role of nNOS in regulation of renal function in angiotensin II-induced hypertension. | 2001 Aug |
|
Candesartan cilexetil reduces graft arteriosclerosis in aortic transplantation model in rat. | 2001 Feb |
|
[Clinical study of the month. The CALM study assessing the combination of an angiotensin-converting enzyme inhibitor and an angiotensin II receptor antagonist in the treatment of diabetic nephropathy]. | 2001 Feb |
|
Cyclic stretch and hypertension induce retinal expression of vascular endothelial growth factor and vascular endothelial growth factor receptor-2: potential mechanisms for exacerbation of diabetic retinopathy by hypertension. | 2001 Feb |
|
Mechanisms underlying renoprotection during renin-angiotensin system blockade. | 2001 Feb |
|
Alterations of the renin-angiotensin system at the RVLM of transgenic rats with low brain angiotensinogen. | 2001 Feb |
|
Myocardial ischemia activates the JAK-STAT pathway through angiotensin II signaling in in vivo myocardium of rats. | 2001 Feb |
|
A two-state receptor model for the interaction between angiotensin II type 1 receptors and non-peptide antagonists. | 2001 Feb 1 |
|
Role of local renin-angiotensin system in warm ischemia and reperfusion injury of the liver. | 2001 Feb-Mar |
|
New competition in the realm of renin-angiotensin axis inhibition; the angiotensin II receptor antagonists in congestive heart failure. | 2001 Jan |
|
Antihypertensive efficacy of candesartan in comparison to losartan: the CLAIM study. | 2001 Jan-Feb |
|
Cardioprotection with angiotensin converting enzyme inhibitor and angiotensin II type 1 receptor antagonist is not abolished by nitric oxide synthase inhibitor in ischemia-reperfused rabbit hearts. | 2001 Jul |
|
The angiotensin II receptor antagonist candesartan cilexetil (TCV-116) ameliorates retinal disorders in rats. | 2001 Jul |
|
Activation of angiotensin II subtype 2 receptor induces catecholamine release in an extracellular Ca(2+)-dependent manner through a decrease of cyclic guanosine 3',5'-monophosphate production in cultured porcine adrenal medullary chromaffin Cells. | 2001 Jul |
|
Angiotensin receptor blockers for chronic heart failure and acute myocardial infarction. | 2001 Jul |
|
Angiotensin II activates the GFAT promoter in mesangial cells. | 2001 Jul |
|
Efficacy of candesartan cilexetil as add-on therapy in hypertensive patients uncontrolled on background therapy: a clinical experience trial. ACTION Study Investigators. | 2001 Jun |
|
Coronary hemodynamic and ventricular responses to angiotensin type 1 receptor inhibition in SHR: interaction with angiotensin type 2 receptors. | 2001 Jun |
|
Mildly oxidized low-density lipoprotein acts synergistically with angiotensin II in inducing vascular smooth muscle cell proliferation. | 2001 Jun |
|
Effects of TCV-116 on expression of NOS and adrenomedullin in failing heart of Dahl salt-sensitive rats. | 2001 Jun |
|
Antihypertensive effects of losartan and candesartan. | 2001 Mar |
|
Lithium intoxication after administration of AT1 blockers. | 2001 Mar |
|
Can angiotensin II receptor blockers be used in patients who have developed a cough or angioedema as a result of taking an ACE inhibitor? | 2001 Mar |
|
Perceived benefit after participating in positive or negative/neutral heart failure trials: the patients' perspective. | 2001 Mar |
|
Effects of converting enzyme inhibitors on renal P-450 metabolism of arachidonic acid. | 2001 Mar |
|
Combination treatment effective option for hypertensive, diabetic patients with microalbuminuria. | 2001 Mar 20 |
|
An angiotensin II type 1 receptor blocker, candesartan, increases myocardial apoptosis in rats with acute ischemia-reperfusion. | 2001 May |
|
A candesartan cilexetil/hydrochlorothiazide combination tablet provides effective blood pressure control in hypertensive patients inadequately controlled on monotherapy. | 2001 May |
|
Role of cardiac ATP-sensitive K+ channels induced by angiotensin II type 1 receptor antagonist on metabolism, contraction and relaxation in ischemia-reperfused rabbit heart. | 2001 May |
|
[Change from ACE inhibitor, Ca-antagonist or beta-blocker to candesartan cilexetil: better efficacy and tolerance. SWITCH study (German study segment)]. | 2001 May 11 |
|
Reversible renal impairment induced by treatment with the angiotensin II receptor antagonist candesartan in a patient with bilateral renal artery stenosis. | 2001 May 17 |
|
Angiotensin-II-receptor inhibitors in pregnancy. | 2001 May 19 |
|
Effects of angiotensin II type 1 receptor antagonist (candesartan) in preventing fatal ventricular arrhythmias in dogs during acute myocardial ischemia and reperfusion. | 2001 Nov |
|
Reliability, validity, and responsiveness of the six-minute walk test in patients with heart failure. | 2001 Oct |
|
pK(a) determination of angiotensin II receptor antagonists (ARA II) by spectrofluorimetry. | 2001 Oct |
|
ERK and p38 MAPK, but not NF-kappaB, are critically involved in reactive oxygen species-mediated induction of IL-6 by angiotensin II in cardiac fibroblasts. | 2001 Oct 12 |
|
Peripheral administration of an angiotensin II AT(1) receptor antagonist decreases the hypothalamic-pituitary-adrenal response to isolation Stress. | 2001 Sep |
Patents
Sample Use Guides
Adult Hypertension:
2 DOSAGE AND ADMINISTRATION
2.1 Adult Hypertension
The usual recommended starting dose of ATACAND (candesartan cilexetil) is 16 mg once daily when it is used as monotherapy in patients who are not volume depleted. ATACAND can be administered once or twice daily with total daily doses ranging from 8 mg to 32 mg.
Pediatric Hypertension 1 to < 17 Years of Age:
Children 1 to < 6 years of age: The dose range is 0.05 to 0.4 mg/kg per day. The recommended starting dose is 0.20 mg/kg (oral suspension).
Children 6 to < 17 years of age: For those less than 50 kg, the dose range is 2 to 16 mg per day. The recommended starting dose is 4 to 8 mg.
For those greater than 50 kg, the dose range is 4 to 32 mg per day. The recommended starting dose is 8 to 16 mg.
Adult Heart Failure:
The recommended initial dose for treating heart failure is 4 mg once daily. The target dose is 32 mg once daily, which is achieved by doubling the dose at approximately 2-week intervals, as tolerated by the patient.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25420481
Primary cultures of human retinal endothelial cells (EC) were candesartan treatment (1μg/ml).
Substance Class |
Chemical
Created
by
admin
on
Edited
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on
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Record UNII |
R85M2X0D68
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Record Status |
Validated (UNII)
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C66930
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
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METABOLITE ACTIVE -> PRODRUG |
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IMPURITY -> PARENT |
For the calculation of content, multiply the peak area by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
for the calculation of content, multiply the peak area by 0.7.
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 |
For the calculation of content, multiply the peak area by 1.6
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |