MICONAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H14Cl4N2O
Molecular Weight	416.129
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1

InChI

InChIKey=BYBLEWFAAKGYCD-UHFFFAOYSA-N

InChI=1S/C18H14Cl4N2O/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/h1-8,11,18H,9-10H2

HIDE SMILES / InChI

Molecular Formula	C18H14Cl4N2O
Molecular Weight	416.129
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 28	Inhibitor 8,297
Sphingosine-1-phosphate lyase 1 4	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Oropharyngeal candidiasis 4	Curative	Approved 8,429	ORAVIG
Vulvovaginal candidiasis 9	Curative	Approved 8,429	MONISTAT 1 COMBINATION PACK
Multiple sclerosis 104	Primary	Preclinical	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
39.1 μg/mL	100 mg single, oral		MICONAZOLE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
136.1 μg × h/mL	100 mg single, oral		MICONAZOLE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.5 h	100 mg single, oral		MICONAZOLE plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587	inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2A6 707 CYP2B6 810 CYP2C19 1,478 CYP2E1 882 CYP3A4/5 278	P-gp 1,537

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP3A4 1,925	inhibitor 3,277	yes [IC50 0.175 uM]
CYP2C19 1,553	inhibitor 3,277	yes [Ki 0.01 uM]
CYP3A4/5 335	inhibitor 3,277	yes [Ki 0.028 uM]
CYP2B6 1,001	inhibitor 3,277	yes [Ki 0.05 uM]
CYP2D6 1,891	inhibitor 3,277	yes [Ki 0.7 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1,537	substrate 3,367	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY542733	https://www.001chemical.com/chem/22832-87-7
001 Chemical	NO20569	https://www.001chemical.com/chem/22916-47-8
3B Scientific (Wuhan) Corp	3B3-027676	http://www.3bsc.com/index/pro_info.php?id=48932
AA Blocks	AA002LEB	http://www.aablocks.com/goods/Goods/detail?id=AA002LEB
Aaron Chemicals	AR002M63	http://www.aaronchem.com/22916-47-8

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PubMed

Show entries

Title	Date	PubMed
Antifungal activity of a new triazole, voriconazole (UK-109496), against clinical isolates of Aspergillus spp.	2000 Jun	11810544
Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis.	2000 Nov 15	11064188
Systemic Candida infection in University hospital 1997-1999: the distribution of Candida biotypes and antifungal susceptibility patterns.	2001	11307597
Comparison of the chiral resolution of econazole, miconazole, and sulconazole by HPLC using normal-phase amylose CSPs.	2001 Aug	11569882
Increase of Candida cell virulence by anticancer drugs and irradiation.	2001 Aug	11442850

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Patents

Sample Use Guides

In Vivo Use Guide

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

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.