Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H17ClN2 |
Molecular Weight | 344.837 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=C(C=CC=C1)C(N2C=CN=C2)(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=VNFPBHJOKIVQEB-UHFFFAOYSA-N
InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
Molecular Formula | C22H17ClN2 |
Molecular Weight | 344.837 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018052Orig1s032lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018052Orig1s032lbl.pdf
Clotrimazole is an anti-fungal medicine indicated for the treatment of vaginal yeast infections and tinea. It can be used either in combination with other drugs (betamethasone dipropionate) or alone, in form of topical or vaginal cream. The drug exerts its action by inhibiting lanosterol demethylase thereby affecting the growth of fungi.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1780 |
19.7 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | GYNE-LOTRIMIN Approved UseTo treat vaginal yeast infections. Launch Date1.96473602E11 |
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Curative | LOTRISONE Approved UseLOTRISONE cream contains a combination of clotrimazole, an azole antifungal, and betamethasone dipropionate, a corticosteroid, and is indicated for the topical treatment of symptomatic inflammatory tinea pedis, tinea cruris, and tinea corporis due to Epidermophyton floccosum, Trichophyton mentagrophytes, and Trichophyton rubrum in patients 17 years and older. Launch Date4.58265592E11 |
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Curative | LOTRISONE Approved UseLOTRISONE cream contains a combination of clotrimazole, an azole antifungal, and betamethasone dipropionate, a corticosteroid, and is indicated for the topical treatment of symptomatic inflammatory tinea pedis, tinea cruris, and tinea corporis due to Epidermophyton floccosum, Trichophyton mentagrophytes, and Trichophyton rubrum in patients 17 years and older. Launch Date4.58265592E11 |
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Curative | LOTRISONE Approved UseLOTRISONE cream contains a combination of clotrimazole, an azole antifungal, and betamethasone dipropionate, a corticosteroid, and is indicated for the topical treatment of symptomatic inflammatory tinea pedis, tinea cruris, and tinea corporis due to Epidermophyton floccosum, Trichophyton mentagrophytes, and Trichophyton rubrum in patients 17 years and older. Launch Date4.58265592E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.3 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7882513 |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
CLOTRIMAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.59 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7882513 |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
CLOTRIMAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.99 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7882513 |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
CLOTRIMAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
10 mg 5 times / day multiple, oral Recommended Dose: 10 mg, 5 times / day Route: oral Route: multiple Dose: 10 mg, 5 times / day Sources: |
unhealthy, 33 years (range: 22 - 43 years) n = 20 Health Status: unhealthy Condition: Oral Candidiasis Age Group: 33 years (range: 22 - 43 years) Sex: M+F Population Size: 20 Sources: |
Disc. AE: Nausea, Taste abnormality... AEs leading to discontinuation/dose reduction: Nausea (2 patients) Sources: Taste abnormality (2 patients) |
500 mg single, vaginal Highest studied dose Dose: 500 mg Route: vaginal Route: single Dose: 500 mg Co-administed with:: lactic acid Sources: |
unhealthy, adult n = 89 Health Status: unhealthy Age Group: adult Sex: F Population Size: 89 Sources: |
Disc. AE: Vulvovaginal burning sensation... AEs leading to discontinuation/dose reduction: Vulvovaginal burning sensation (1 patient) Sources: |
500 mg single, vaginal Highest studied dose Dose: 500 mg Route: vaginal Route: single Dose: 500 mg Co-administed with:: lactic acid Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: |
Disc. AE: Vulvovaginal pruritus... AEs leading to discontinuation/dose reduction: Vulvovaginal pruritus (1 patient) Sources: |
50 mg 1 times / day multiple, vaginal Dose: 50 mg, 1 times / day Route: vaginal Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 323 Health Status: unhealthy Age Group: adult Sex: F Population Size: 323 Sources: Page: p. 5 |
Disc. AE: Vaginal irritation, Spotting vaginal... AEs leading to discontinuation/dose reduction: Vaginal irritation (1 patient) Sources: Page: p. 5Spotting vaginal (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 2 patients Disc. AE |
10 mg 5 times / day multiple, oral Recommended Dose: 10 mg, 5 times / day Route: oral Route: multiple Dose: 10 mg, 5 times / day Sources: |
unhealthy, 33 years (range: 22 - 43 years) n = 20 Health Status: unhealthy Condition: Oral Candidiasis Age Group: 33 years (range: 22 - 43 years) Sex: M+F Population Size: 20 Sources: |
Taste abnormality | 2 patients Disc. AE |
10 mg 5 times / day multiple, oral Recommended Dose: 10 mg, 5 times / day Route: oral Route: multiple Dose: 10 mg, 5 times / day Sources: |
unhealthy, 33 years (range: 22 - 43 years) n = 20 Health Status: unhealthy Condition: Oral Candidiasis Age Group: 33 years (range: 22 - 43 years) Sex: M+F Population Size: 20 Sources: |
Vulvovaginal burning sensation | 1 patient Disc. AE |
500 mg single, vaginal Highest studied dose Dose: 500 mg Route: vaginal Route: single Dose: 500 mg Co-administed with:: lactic acid Sources: |
unhealthy, adult n = 89 Health Status: unhealthy Age Group: adult Sex: F Population Size: 89 Sources: |
Vulvovaginal pruritus | 1 patient Disc. AE |
500 mg single, vaginal Highest studied dose Dose: 500 mg Route: vaginal Route: single Dose: 500 mg Co-administed with:: lactic acid Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: |
Spotting vaginal | 1 patient Disc. AE |
50 mg 1 times / day multiple, vaginal Dose: 50 mg, 1 times / day Route: vaginal Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 323 Health Status: unhealthy Age Group: adult Sex: F Population Size: 323 Sources: Page: p. 5 |
Vaginal irritation | 1 patient Disc. AE |
50 mg 1 times / day multiple, vaginal Dose: 50 mg, 1 times / day Route: vaginal Route: multiple Dose: 50 mg, 1 times / day Sources: Page: p. 5 |
unhealthy, adult n = 323 Health Status: unhealthy Age Group: adult Sex: F Population Size: 323 Sources: Page: p. 5 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://dmd.aspetjournals.org/content/29/6/837.short Page: - |
no | |||
Sources: https://dmd.aspetjournals.org/content/29/6/837.short Page: - |
yes [IC50 0.00315 uM] | |||
Sources: https://dmd.aspetjournals.org/content/29/6/837.short Page: - |
yes [IC50 0.00822 uM] | |||
Sources: https://dmd.aspetjournals.org/content/29/6/837.short Page: - |
yes [IC50 0.1 uM] | |||
Sources: https://dmd.aspetjournals.org/content/29/6/837.short Page: - |
yes [IC50 0.745 uM] | |||
Sources: https://dmd.aspetjournals.org/content/29/6/837.short Page: - |
yes [IC50 2.3 uM] | |||
Page: - |
yes [IC50 >10 uM] | |||
Page: - |
yes [IC50 >10 uM] | |||
Page: - |
yes [IC50 >10 uM] | |||
Page: - |
yes [IC50 >10 uM] | |||
Page: - |
yes [IC50 >10 uM] | |||
Page: - |
yes [IC50 >10 uM] | |||
Page: - |
yes [IC50 >10 uM] | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
PubMed
Title | Date | PubMed |
---|---|---|
Swelling-induced K(+) fluxes in vascular smooth muscle cells are mediated by charybdotoxin-sensitive K(+) channels. | 2001 |
|
[Vulvovaginal candidiasis in childhood--diagnostic and therapeutic results]. | 2001 |
|
Topical treatment for vaginal candidiasis (thrush) in pregnancy. | 2001 |
|
Tinea incognito caused by trichophyton mentagrophytes -- a case report. | 2001 Dec |
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Effects of clotrimazole on transport mediated by multidrug resistance associated protein 1 (MRP1) in human erythrocytes and tumour cells. | 2001 Dec |
|
Regulation of K(+) current in human airway epithelial cells by exogenous and autocrine adenosine. | 2001 Dec |
|
Toward a novel metal-based chemotherapy against tropical diseases. 6. Synthesis and characterization of new copper(II) and gold(I) clotrimazole and ketoconazole complexes and evaluation of their activity against Trypanosoma cruzi. | 2001 Dec 31 |
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Outcome of 22 cases of perforated tympanic membrane caused by otomycosis. | 2001 Nov |
|
Otomycosis in Nigeria: treatment with mercurochrome. | 2001 Nov |
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Intracellular signalling involved in activation of the volume-sensitive K+ current in Ehrlich ascites tumour cells. | 2001 Oct |
|
[How I treat ... sickle cell anemia: current therapies]. | 2001 Oct |
|
Sertaconazole: in-vitro antifungal activity against vaginal and other superficial yeast isolates. | 2001 Oct |
|
In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens. | 2001 Oct |
|
Novel effects of minocycline on Ca(2+)-dependent Cl(-) secretion in human airway epithelial Calu-3 cells. | 2001 Oct 15 |
|
Angiotensin II type AT(2) receptor mRNA expression and renal vasodilatation are increased in renal failure. | 2001 Sep |
|
Orphan nuclear receptor binding site in the human inducible nitric oxide synthase promoter mediates responsiveness to steroid and xenobiotic ligands. | 2002 |
|
Interventions for treating oral candidiasis for patients with cancer receiving treatment. | 2002 |
|
Clinical comparison of the efficacy and tolerability of once daily Canesten with twice daily Nizoral (clotrimazole 1% cream vs. ketoconazole 2% cream) during a 28-day topical treatment of interdigital tinea pedis. | 2002 Apr |
|
Do azoles and chloroquine share similar mechanisms of antimalarial action? | 2002 Apr |
|
Crystallization and preliminary crystallographic analysis of a novel cytochrome P450 from Mycobacterium tuberculosis. | 2002 Apr |
|
Cytochrome P450 3A conjugation to ubiquitin in a process distinct from classical ubiquitination pathway. | 2002 Apr |
|
Fluconazole to prevent yeast infections in bone marrow transplantation patients: a randomized trial of high versus reduced dose, and determination of the value of maintenance therapy. | 2002 Apr 1 |
|
Dehydration response of sickle cells to sickling-induced Ca(++) permeabilization. | 2002 Apr 1 |
|
Translation initiation and its deregulation during tumorigenesis. | 2002 Apr 8 |
|
Clotrimazole-triiodide ion association as an ion exchanger for a triiodide ion-selective electrode. | 2002 Feb |
|
Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts. | 2002 Feb |
|
Activation of ion secretion via proteinase-activated receptor-2 in human colon. | 2002 Feb |
|
Characterization of basolateral K+ channels underlying anion secretion in the human airway cell line Calu-3. | 2002 Feb 1 |
|
Modulation of mouse Paneth cell alpha-defensin secretion by mIKCa1, a Ca2+-activated, intermediate conductance potassium channel. | 2002 Feb 1 |
|
Arginine supplementation of sickle transgenic mice reduces red cell density and Gardos channel activity. | 2002 Feb 15 |
|
Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. | 2002 Feb 28 |
|
Topical antifungal drug products for over-the-counter human use; amendment of final monograph. Final rule. | 2002 Feb 8 |
|
Clotrimazole binds to heme and enhances heme-dependent hemolysis: proposed antimalarial mechanism of clotrimazole. | 2002 Feb 8 |
|
Comparison of two methods for antifungal susceptibility testing of Trichophyton rubrum. | 2002 Jan |
|
Development of a topical suspension containing three active ingredients. | 2002 Jan |
|
Perianal ulcerations from topical steroid use. | 2002 Jan |
|
A pilot study evaluating the safety and microbiologic efficacy of an economically viable antimicrobial lozenge in patients with head and neck cancer receiving radiation therapy. | 2002 Jan |
|
Adenovirus vector-mediated reporter system for in vivo analyses of human CYP3A4 gene activation. | 2002 Jan |
|
Spectrofluorimetric determination of vigabatrin and gabapentin in urine and dosage forms through derivatization with fluorescamine. | 2002 Jan 1 |
|
Differential pulse polarographic determination of clotrimazole after derivatization with Procion Red HE-3B. | 2002 Jan 1 |
|
Topical antibiotic, antifungal, and antiseptic solutions decrease ciliary activity in nasal respiratory cells. | 2002 Jan-Feb |
|
Clotrimazole/betamethasone diproprionate: a review of costs and complications in the treatment of common cutaneous fungal infections. | 2002 Jan-Feb |
|
K+ currents generated by NMDA receptor activation in rat hippocampal pyramidal neurons. | 2002 Jun |
|
The flavonol quercetin activates basolateral K(+) channels in rat distal colon epithelium. | 2002 Mar |
|
Effect of antifungal azoles on the heme detoxification system of malarial parasite. | 2002 Mar |
|
Inhibition of cytochromes P450 by antifungal imidazole derivatives. | 2002 Mar |
|
Regulation of a calcium-sensitive K+ channel (cIK1) by protein kinase C. | 2002 May 1 |
|
Use of intermittent bladder infusion with clotrimazole for treatment of candiduria in a dog. | 2002 May 15 |
|
Inhibition of vascular smooth muscle cell migration by cytochrome p450 epoxygenase-derived eicosanoids. | 2002 May 17 |
|
Involvement of nitric oxide and potassium channels in the bradykinin-induced vasodilatation in the rat kidney perfused ex situ. | 2002 May 30 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018052Orig1s032lbl.pdf
Vaginal 1% cream: insert an applicator full of cream into the vagina at bedtime for 7 days. External 1% cream for vaginal yeast infections: apply to the skin outside the vagina 2 times daily for up to 7 days. Topical 1% cream: apply a thin layer to the affected area twice daily for 2 weeks (tinea pedis) or 1 week (tinea cruris and tinea corporis).
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22455297
In vitro antifungal activity indicated Clotrimazole (MIC 16 and 8 microg/ml) effective against 68 (70%) of Candida SPP.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:05:12 UTC 2023
by
admin
on
Fri Dec 15 15:05:12 UTC 2023
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Record UNII |
G07GZ97H65
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 524.1044G
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FDA ORPHAN DRUG |
204005
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WHO-VATC |
QJ02AB90
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WHO-VATC |
QG01AF02
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NDF-RT |
N0000008217
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WHO-ESSENTIAL MEDICINES LIST |
6.3
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CFR |
21 CFR 524.450
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FDA ORPHAN DRUG |
216705
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WHO-VATC |
QA01AB18
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FDA ORPHAN DRUG |
88094
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WHO-VATC |
QD01AC01
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LIVERTOX |
NBK548320
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WHO-ATC |
D01AC01
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NDF-RT |
N0000175487
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WHO-ATC |
G01AF02
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NCI_THESAURUS |
C514
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WHO-ATC |
A01AB18
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CFR |
21 CFR 333.210
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CFR |
21 CFR 524.1044H
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FDA ORPHAN DRUG |
520516
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D003022
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2330
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CLOTRIMAZOLE
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245-764-8
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2912
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m3671
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DTXSID7029871
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SUB06777MIG
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G07GZ97H65
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3266
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2623
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257473
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100000092074
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DB00257
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3764
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clotrimazole
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CHEMBL104
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2812
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C381
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23593-75-1
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Clotrimazole
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1141002
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719
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G07GZ97H65
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METABOLIC ENZYME -> INDUCER | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
FECAL; PLASMA; URINE
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METABOLITE -> PARENT |
MINOR
FECAL; PLASMA; URINE
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METABOLITE -> PARENT |
MAJOR
FECAL; PLASMA; URINE
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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 |
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)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |