Butoconazole

Butoconazole
Clinical data

Trade names	Gynazole-1, Mycelex-3
AHFS/Drugs.com	Monograph
MedlinePlus	a682012
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Vaginal cream
ATC code	G01AF15 (WHO)
Legal status
Legal status	US: OTC
Identifiers
IUPAC name 1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole
CAS Number	67085-13-6^Y
PubChem (CID)	47472
DrugBank	DB00639^Y
ChemSpider	43192^Y
UNII	0Q771797PH^Y
KEGG	D00880^N
ChEBI	CHEBI:3240^Y
ChEMBL	CHEMBL1295^Y
Chemical and physical data
Formula	C₁₉H₁₇Cl₃N₂S
Molar mass	411.776 g/mol
3D model (Jmol)	Interactive image
SMILES Clc1ccc(cc1)CCC(Sc2c(Cl)cccc2Cl)Cn3ccnc3
InChI InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2^Y Key:SWLMUYACZKCSHZ-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Butoconazole (trade names Gynazole-1, Mycelex-3) is an imidazole antifungal used in gynecology. It is administered as a vaginal cream.^[1]^[2]

Synthesis

Butoconazole synthesis:^[3] Keith A. M. Walker U.S. Patent 4,078,071 (1978 to Syntex)

Reaction of epichlorohydrin with 4-chlorophenylbenzylmganeium chloride leads to 1-chloro-4-(4-chlorophenyl)butan-2-ol (3). Displacement with sodium imidazole, conversion of the secondary alcohol to the chloride (SOCl2), and displacement with 2,6-dichlorobenzenethiol concludes the synthesis of the antifungal butoconazole.

References

↑ Seidman, L. S.; Skokos, C. K. (2005). "An evaluation of butoconazole nitrate 2% site release vaginal cream (Gynazole-1) compared to fluconazole 150 mg tablets (Diflucan) in the time to relief of symptoms in patients with vulvovaginal candidiasis". Infectious diseases in obstetrics and gynecology. 13 (4): 197–206. doi:10.1080/10647440500240615 (inactive 2016-05-14). PMC 1784583. PMID 16338779.
↑ Butoconazole Monograph
↑ Walker, Keith A. M.; Braemer, Allen C.; Hitt, Sharon; Jones, Richard E.; Matthews, Thomas R. (1978). "1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-1H-imidazole nitrate, a new potent antifungal agent". Journal of Medicinal Chemistry. 21 (8): 840. doi:10.1021/jm00206a028. PMID 357722.

Gynecological anti-infectives and antiseptics (G01)

Antibiotics

Arsenic compounds

Acetarsol

Quinoline derivatives

Organic acids

Sulfonamides

Sulfatolamide

Antifungals

Imidazoles	Metronidazole Clotrimazole Miconazole Econazole Ornidazole Isoconazole Tioconazole Ketoconazole Fenticonazole Azanidazole Propenidazole Butoconazole Omoconazole Oxiconazole Flutrimazole

Triazoles	Terconazole

Polyenes	Nystatin Natamycin Amphotericin B

Other	Ciclopirox Methylrosaniline

Other

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ clotrimazole^# croconazole^‡ econazole fenticonazole^‡ flutrimazole isoconazole^‡ ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole

Triazoles	Topical: efinaconazole fluconazole^# fosfluconazole terconazole Systemic: fluconazole^# hexaconazole^‡ isavuconazole itraconazole posaconazole voriconazole Unknown: albaconazole^‡ ravuconazole^†

Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine

Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	flucytosine^#

Mitotic inhibitors	griseofulvin^#

Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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