Details of the Drug

General Information of Drug (ID: DMNYPGS)

Drug Name

Tioconazole

Synonyms

Fungibacid; GyneCure; Tioconazol; Tioconazolum; Trosyd; Trosyl; Vagistat; Zoniden; Trosyd AF; Trosyd J; Monistat 1; UK 20349; Gyno-trosyd; Tioconazol [INN-Spanish]; Tioconazolum [INN-Latin]; Tz-3; UK 20,349; UK-20349; Vagistat-1; Vagistat-1 (TN); Tioconazole (JAN/USP/INN); Tioconazole [USAN:BAN:INN:JAN]; (+-)-1-(2,4-Dichloro-beta-((2-chloro-3-ethenyl)oxy)phenethyl)imidazole; (+-)-1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole; 1-(2,4-Dichloro-(beta-(2-chloro-3-thenyl)oxy)phenethyl)imidazole; 1-(2,4-Dichloro-beta-((2-chloro-3-thenyl)-oxy)phenethyl)imidazole; 1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole

Indication

Disease Entry	ICD 11	Status	REF
Onychomycosis	EE12.1	Approved	[1], [2]

Therapeutic Class

Antifungal Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

387.7

Topological Polar Surface Area (xlogp)

5.3

Rotatable Bond Count (rotbonds)

6

Hydrogen Bond Donor Count (hbonddonor)

0

Hydrogen Bond Acceptor Count (hbondacc)

3

Chemical Identifiers

Formula: C16H13Cl3N2OS
IUPAC Name: 1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
Canonical SMILES: C1=CC(=C(C=C1Cl)Cl)C(CN2C=CN=C2)OCC3=C(SC=C3)Cl
InChI: InChI=1S/C16H13Cl3N2OS/c17-12-1-2-13(14(18)7-12)15(8-21-5-4-20-10-21)22-9-11-3-6-23-16(11)19/h1-7,10,15H,8-9H2
InChIKey: QXHHHPZILQDDPS-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5482
ChEBI ID: CHEBI:77898
CAS Number: 65899-73-2
DrugBank ID: DB01007
TTD ID: D0CA6J
ACDINA ID: D01488

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Candida Cytochrome P450 51 (Candi ERG11)	TTTSOUD	CP51_CANAL	Inhibitor	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Butylhydroxyanisole	E00308	24667	Antimicrobial preservative; Antioxidant
Magnesium aluminum silicate	E00462	3084116	Adsorbent; Binding agent; Disintegrant; Suspending agent; Viscosity-controlling agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Tioconazole 6.5% ointment	6.50%	Ointment	Vaginal

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References

1	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 075915.
2	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3	Biological spectra analysis: Linking biological activity profiles to molecular structure. Proc Natl Acad Sci U S A. 2005 Jan 11;102(2):261-6.
4	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
5	A new, broad-spectrum azole antifungal: posaconazole--mechanisms of action and resistance, spectrum of activity. Mycoses. 2006;49 Suppl 1:2-6.
6	Clinical pharmacokinetics and pharmacodynamics of solifenacin. Clin Pharmacokinet. 2009;48(5):281-302.
7	Antifungal agents: mechanisms of action. Trends Microbiol. 2003 Jun;11(6):272-9.
8	Mode of action of anti-Candida drugs: focus on terconazole and other ergosterol biosynthesis inhibitors. Am J Obstet Gynecol. 1991 Oct;165(4 Pt 2):1193-9.
9	Investigation of the role of cytochrome P450 2B4 active site residues in substrate metabolism based on crystal structures of the ligand-bound enzyme. Arch Biochem Biophys. 2006 Nov 1;455(1):61-7.
10	Differential azole antifungal efficacies contrasted using a Saccharomyces cerevisiae strain humanized for sterol 14 alpha-demethylase at the homolo... Antimicrob Agents Chemother. 2008 Oct;52(10):3597-603.