Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H14Cl4N2O.HNO3 |
Molecular Weight | 479.141 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[N+]([O-])=O.ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1
InChI
InChIKey=MCCACAIVAXEFAL-UHFFFAOYSA-N
InChI=1S/C18H14Cl4N2O.HNO3/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22;2-1(3)4/h1-8,11,18H,9-10H2;(H,2,3,4)
Molecular Formula | HNO3 |
Molecular Weight | 63.0128 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C18H14Cl4N2O |
Molecular Weight | 416.129 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Miconazole is a synthetic imidazole derivative, a topical antifungal agent for use in the local treatment of vaginal, and skin and nail infections due to yeasts and dermatophytes. It is particularly active against Candida spp., Trichophyton spp., Epidermophyton spp., Microsporum spp. and Pityrosporon orbiculare (Malassezia furfur), but also possesses some activity against Gram-positive bacteria. It binds to the heme moiety of the fungal cytochrome P-450 dependent enzyme lanosterol 14-alpha-demethlyase. Inhibits 14-alpha-demethlyase, blocks formation of ergosterol and leads to the buildup of toxic methylated 14-a-sterols. Miconazole also affects the synthesis of triglycerides and fatty acids and inhibits oxidative and peroxidative enzymes, increasing the amount of active oxygen species within the cell.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1780 |
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Target ID: CHEMBL3286061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28930429 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | ORAVIG Approved UseORAVIG is an azole antifungal indicated for the local treatment of oropharyngeal candidiasis in adults Launch Date1973 |
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Curative | MONISTAT 1 COMBINATION PACK Approved UseUsed to treats vaginal yeast infections, relieves external itching and irritation due to a vaginal yeast infection Launch Date2001 |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
39.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MICONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
136.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MICONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MICONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg single, vaginal Recommended Dose: 1200 mg Route: vaginal Route: single Dose: 1200 mg Sources: |
unhealthy, 18 - 60 years n = 50 Health Status: unhealthy Condition: vaginal candidosis Age Group: 18 - 60 years Sex: F Population Size: 50 Sources: |
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200 mg 1 times / day multiple, intravenous Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Co-administed with:: amphotericin B Sources: itraconazole |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: |
Disc. AE: Fibrillation ventricular... AEs leading to discontinuation/dose reduction: Fibrillation ventricular (grade 5, 11.1%) Sources: |
800 mg single, intravenous Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Co-administed with:: amphotericin B Sources: itraconazole |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: |
Disc. AE: Bradyarrhythmia... AEs leading to discontinuation/dose reduction: Bradyarrhythmia (5.2%) Sources: |
0.25 % 7 times / day steady, topical Recommended Dose: 0.25 %, 7 times / day Route: topical Route: steady Dose: 0.25 %, 7 times / day Sources: |
unhealthy, newborns n = 330 Health Status: unhealthy Condition: Diaper dermatitis complicated by candidiasis Age Group: newborns Sex: M+F Population Size: 330 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fibrillation ventricular | grade 5, 11.1% Disc. AE |
200 mg 1 times / day multiple, intravenous Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Co-administed with:: amphotericin B Sources: itraconazole |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: |
Bradyarrhythmia | 5.2% Disc. AE |
800 mg single, intravenous Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Co-administed with:: amphotericin B Sources: itraconazole |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
yes [IC50 0.175 uM] | |||
Page: - |
yes [Ki 0.01 uM] | |||
Page: - |
yes [Ki 0.028 uM] | |||
Page: - |
yes [Ki 0.05 uM] | |||
Page: - |
yes [Ki 0.7 uM] | |||
Page: - |
yes [Ki 1.2 uM] | |||
Page: - |
yes [Ki 2.2 uM] | |||
Page: - |
yes [Ki 3.2 uM] | |||
Page: - |
yes [Ki 7.3 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/ Page: - |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
PubMed
Title | Date | PubMed |
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Antituberculosis activity of certain antifungal and antihelmintic drugs. | 1999 |
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Triorganotin compounds as antimicrobial agents. | 1999 Apr 30 |
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Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis. | 2000 Nov 15 |
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In vitro antifungal activity of a novel lipopeptide antifungal agent, FK463, against various fungal pathogens. | 2000 Oct |
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The importance of reassessment to chronic wound care. | 2001 Aug |
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Comparison of the chiral resolution of econazole, miconazole, and sulconazole by HPLC using normal-phase amylose CSPs. | 2001 Aug |
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Anti-mycotics suppress interleukin-4 and interleukin-5 production in anti-CD3 plus anti-CD28-stimulated T cells from patients with atopic dermatitis. | 2001 Dec |
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Chronic sino-naso-orbital fungal infection due to Pseudallescheria boydii in a nonimmunocompromised host--a case report. | 2001 Jul |
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Systemic antifungal agents. | 2001 Jul |
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Miconazole-warfarin interaction: increased INR. | 2001 Jul 10 |
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A neuronal isoform of nitric oxide synthase expressed in pancreatic beta-cells controls insulin secretion. | 2001 Jun |
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Characterization of endothelium-derived hyperpolarizing factor in the human forearm microcirculation. | 2001 Jun |
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EDHF mediates flow-induced dilation in skeletal muscle arterioles of female eNOS-KO mice. | 2001 Jun |
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Gender-specific compensation for the lack of NO in the mediation of flow-induced arteriolar dilation. | 2001 Jun |
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Lipid-based antifungal agents: current status. | 2001 Mar |
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Diaper dermatitis: a therapeutic dilemma. Results of a double-blind placebo controlled trial of miconazole nitrate 0.25%. | 2001 Mar-Apr |
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Contact imidazole activity against resistant bacteria and fungi. | 2001 May |
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HWY-289, a novel semi-synthetic protoberberine derivative with multiple target sites in Candida albicans. | 2001 May |
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Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions. | 2001 May 15 |
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Effects of azoles on human acute myelogenous leukemia blasts and T lymphocytes derived from acute leukemia patients with chemotherapy-induced cytopenia. | 2001 Nov |
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Anandamide-induced relaxation of sheep coronary arteries: the role of the vascular endothelium, arachidonic acid metabolites and potassium channels. | 2001 Nov |
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Initial and sustained phases of myogenic response of rat mesenteric small arteries. | 2001 Nov |
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Chronic estrogen depletion alters adenosine diphosphate-induced pial arteriolar dilation in female rats. | 2001 Nov |
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Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria. | 2001 Oct |
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Signaling pathway and chronotropic action of parathyroid hormone in isolated perfused rat heart. | 2001 Oct |
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[Vaginal candidiasis: etiology and sensitivity profile to antifungal agents in clinical use]. | 2001 Oct-Dec |
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Involvement of cytochrome P450 metabolites in the vascular action of angiotensin II on the afferent arterioles. | 2001 Sep |
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The role of endothelium-derived hyperpolarizing factor in the regulation of the uterine circulation in pregnant rats. | 2001 Sep |
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Reversal effects of antifungal drugs on multidrug resistance in MDR1-overexpressing HeLa cells. | 2001 Sep |
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7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures. | 2001 Sep |
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Distribution and susceptibility of Candida species isolated in the Medical University of Debrecen. | 2002 |
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Crystallization and preliminary crystallographic analysis of a novel cytochrome P450 from Mycobacterium tuberculosis. | 2002 Apr |
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N-methyl-D-aspartate-induced vasodilation is mediated by endothelium-independent nitric oxide release in piglets. | 2002 Apr |
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Antitumor effects of miconazole on human colon carcinoma xenografts in nude mice through induction of apoptosis and G0/G1 cell cycle arrest. | 2002 Apr 1 |
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[Efficacy and tolerance of 200 mg of fenticonazole versus 400 mg of miconazole in the intravaginal treatment of mycotic vulvovaginitis]. | 2002 Feb |
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Funicone-related compounds, potentiators of antifungal miconazole activity, produced by Talaromycesflavus FKI-0076. | 2002 Feb |
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Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts. | 2002 Feb |
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Inhibition of sarcoplasmic reticulum Ca2+-ATPase by miconazole. | 2002 Jul |
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Interaction between warfarin and topical miconazole cream. | 2002 Jul 13 |
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The opposite effects of cyclic AMP-protein kinase a signal transduction pathway on renal cortical and medullary Na+,K+-ATPase activity. | 2002 Jun |
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Overanticoagulation associated with combined use of antifungal agents and coumarin anticoagulants. | 2002 Jun |
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7-Benzyloxyquinoline oxidation by P450eryF A245T: finding of a new fluorescent substrate probe. | 2002 Jun |
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Antifungal prophylaxis for severely neutropenic chemotherapy recipients: a meta analysis of randomized-controlled clinical trials. | 2002 Jun 15 |
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Rapid viability assessment of yeast cells using vital staining with 2-NBDG, a fluorescent derivative of glucose. | 2002 Jun 5 |
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Effect of direct infusion of antifungal agent on invasive pulmonary aspergillosis in a patient with acute leukemia. | 2002 Mar |
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Comparison of dermatopharmacokinetic vs. clinicial efficacy methods for bioequivalence assessment of miconazole nitrate vaginal cream, 2% in humans. | 2002 Mar |
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Effect of antifungal azoles on the heme detoxification system of malarial parasite. | 2002 Mar |
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Inhibition of cytochromes P450 by antifungal imidazole derivatives. | 2002 Mar |
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ABC transporters Cdr1p, Cdr2p and Cdr3p of a human pathogen Candida albicans are general phospholipid translocators. | 2002 Mar 15 |
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Pityriasis versicolor rubra. | 2002 Mar-Apr |
Sample Use Guides
Application of one ORAVIG 50 mg buccal tablet to the gum region once daily for 14 consecutive days.
External miconazole nitrate vulvar cream (2%): twice daily, for up to 7 days as needed.
Miconazole nitrate vaginal insert (1200mg): with the applicator place the vaginal insert into the vagina.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15825399
The antifungal drug, miconazole nitrate, inhibits the growth of several species of Candida. Candida albicans, one of the pathogenic species, was totally inhibited at a concentration of approximately 10 mug/ml.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:10:10 GMT 2023
by
admin
on
Fri Dec 15 15:10:10 GMT 2023
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Record UNII |
VW4H1CYW1K
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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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EMA VETERINARY ASSESSMENT REPORTS |
EASOTIC (AUTHORISED)
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NCI_THESAURUS |
C514
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CFR |
21 CFR 333.210
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CHEMBL91
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169434
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68553
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42790
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SUB03285MIG
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m7527
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C29257
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DBSALT001242
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MICONAZOLE NITRATE
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PRIMARY | Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water and ether R; soluble in 140 parts of ethanol (~750 g/l) TS. Category: Antifungal drug. Storage: Miconazole nitrate should be kept in a well-closed container, protected from light. Additional information: Miconazole nitrate melts at about 182?C with decomposition. Definition: Miconazole nitrate contains not less than 98.5% and not more than 101.5% of C18H14Cl4N2O,HNO3, calculated with reference to the dried substance. | ||
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100000091859
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ENANTIOMER -> RACEMATE |
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PARENT -> SALT/SOLVATE |
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ENANTIOMER -> RACEMATE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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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)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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