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=CC=CC=C1C(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 Date1976 |
|||
| 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 Date1984 |
|||
| 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 Date1984 |
|||
| 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 Date1984 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.4 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 |
|
4.98 ng/mL |
10 mg single, buccal dose: 10 mg route of administration: Buccal experiment type: SINGLE co-administered: |
CLOTRIMAZOLE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
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 |
|
4.25 h |
500 mg single, vaginal dose: 500 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
CLOTRIMAZOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE food status: UNKNOWN |
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) Health Status: unhealthy Age Group: 33 years (range: 22 - 43 years) Sex: M+F 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 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: |
500 mg single, vaginal Highest studied dose Dose: 500 mg Route: vaginal Route: single Dose: 500 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: |
Disc. AE: Vulvovaginal burning sensation... AEs leading to discontinuation/dose reduction: Vulvovaginal burning sensation (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: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: |
Disc. AE: Vaginal irritation, Spotting vaginal... AEs leading to discontinuation/dose reduction: Vaginal irritation (1 patient) Sources: Spotting 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) Health Status: unhealthy Age Group: 33 years (range: 22 - 43 years) Sex: M+F 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) Health Status: unhealthy Age Group: 33 years (range: 22 - 43 years) Sex: M+F Sources: |
| Vulvovaginal pruritus | 1 patient Disc. AE |
500 mg single, vaginal Highest studied dose Dose: 500 mg Route: vaginal Route: single Dose: 500 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F 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 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: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: |
| 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: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: |
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 |
|---|---|---|
| K+ currents generated by NMDA receptor activation in rat hippocampal pyramidal neurons. | 2002-06 |
|
| Involvement of nitric oxide and potassium channels in the bradykinin-induced vasodilatation in the rat kidney perfused ex situ. | 2002-05-30 |
|
| Inhibition of vascular smooth muscle cell migration by cytochrome p450 epoxygenase-derived eicosanoids. | 2002-05-17 |
|
| Use of intermittent bladder infusion with clotrimazole for treatment of candiduria in a dog. | 2002-05-15 |
|
| Regulation of a calcium-sensitive K+ channel (cIK1) by protein kinase C. | 2002-05-01 |
|
| Translation initiation and its deregulation during tumorigenesis. | 2002-04-08 |
|
| 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. | 2002-04-01 |
|
| Dehydration response of sickle cells to sickling-induced Ca(++) permeabilization. | 2002-04-01 |
|
| 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. | 2002-04 |
|
| Do azoles and chloroquine share similar mechanisms of antimalarial action? | 2002-04 |
|
| Crystallization and preliminary crystallographic analysis of a novel cytochrome P450 from Mycobacterium tuberculosis. | 2002-04 |
|
| Cytochrome P450 3A conjugation to ubiquitin in a process distinct from classical ubiquitination pathway. | 2002-04 |
|
| Topical antibiotic, antifungal, and antiseptic solutions decrease ciliary activity in nasal respiratory cells. | 2002-03-16 |
|
| The flavonol quercetin activates basolateral K(+) channels in rat distal colon epithelium. | 2002-03 |
|
| Effect of antifungal azoles on the heme detoxification system of malarial parasite. | 2002-03 |
|
| Inhibition of cytochromes P450 by antifungal imidazole derivatives. | 2002-03 |
|
| Clotrimazole/betamethasone diproprionate: a review of costs and complications in the treatment of common cutaneous fungal infections. | 2002-02-28 |
|
| Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. | 2002-02-28 |
|
| Arginine supplementation of sickle transgenic mice reduces red cell density and Gardos channel activity. | 2002-02-15 |
|
| Topical antifungal drug products for over-the-counter human use; amendment of final monograph. Final rule. | 2002-02-08 |
|
| Clotrimazole binds to heme and enhances heme-dependent hemolysis: proposed antimalarial mechanism of clotrimazole. | 2002-02-08 |
|
| Characterization of basolateral K+ channels underlying anion secretion in the human airway cell line Calu-3. | 2002-02-01 |
|
| Modulation of mouse Paneth cell alpha-defensin secretion by mIKCa1, a Ca2+-activated, intermediate conductance potassium channel. | 2002-02-01 |
|
| Clotrimazole-triiodide ion association as an ion exchanger for a triiodide ion-selective electrode. | 2002-02 |
|
| Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts. | 2002-02 |
|
| Activation of ion secretion via proteinase-activated receptor-2 in human colon. | 2002-02 |
|
| Spectrofluorimetric determination of vigabatrin and gabapentin in urine and dosage forms through derivatization with fluorescamine. | 2002-01-01 |
|
| Differential pulse polarographic determination of clotrimazole after derivatization with Procion Red HE-3B. | 2002-01-01 |
|
| Comparison of two methods for antifungal susceptibility testing of Trichophyton rubrum. | 2002-01 |
|
| Development of a topical suspension containing three active ingredients. | 2002-01 |
|
| Perianal ulcerations from topical steroid use. | 2002-01 |
|
| 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. | 2002-01 |
|
| Adenovirus vector-mediated reporter system for in vivo analyses of human CYP3A4 gene activation. | 2002-01 |
|
| 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 |
|
| 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. | 2001-12-31 |
|
| Tinea incognito caused by trichophyton mentagrophytes -- a case report. | 2001-12 |
|
| Effects of clotrimazole on transport mediated by multidrug resistance associated protein 1 (MRP1) in human erythrocytes and tumour cells. | 2001-12 |
|
| Regulation of K(+) current in human airway epithelial cells by exogenous and autocrine adenosine. | 2001-12 |
|
| Outcome of 22 cases of perforated tympanic membrane caused by otomycosis. | 2001-11 |
|
| Otomycosis in Nigeria: treatment with mercurochrome. | 2001-11 |
|
| Novel effects of minocycline on Ca(2+)-dependent Cl(-) secretion in human airway epithelial Calu-3 cells. | 2001-10-15 |
|
| Intracellular signalling involved in activation of the volume-sensitive K+ current in Ehrlich ascites tumour cells. | 2001-10 |
|
| [How I treat ... sickle cell anemia: current therapies]. | 2001-10 |
|
| Sertaconazole: in-vitro antifungal activity against vaginal and other superficial yeast isolates. | 2001-10 |
|
| In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens. | 2001-10 |
|
| Angiotensin II type AT(2) receptor mRNA expression and renal vasodilatation are increased in renal failure. | 2001-09 |
|
| 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 |
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
Mon Mar 31 17:45:54 GMT 2025
by
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| Record UNII |
G07GZ97H65
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| Record Status |
Validated (UNII)
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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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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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| Related Record | Type | Details | ||
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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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| 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 |
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
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |