Butoconazole

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Butoconazole
Butoconazole.svg
Names
Trade namesGynazole-1, Femstat-3, others
  • (RS)-1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole
Clinical data
Drug classAntifungal[1]
Main usesVaginal yeast infections[1]
Side effectsBurning, itchiness, abdominal pain[1]
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
Routes of
use
Vaginal cream
External links
AHFS/Drugs.comMonograph
US NLMButoconazole
MedlinePlusa682012
Legal
License data
Legal status
  • US: OTC / Rx-only
Chemical and physical data
FormulaC19H17Cl3N2S
Molar mass411.77 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1)CCC(Sc2c(Cl)cccc2Cl)Cn3ccnc3
  • 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 checkY
  • Key:SWLMUYACZKCSHZ-UHFFFAOYSA-N checkY

Butoconazole, sold under the brand name Gynazole-1 among others, is antifungal used to treat vaginal yeast infections.[1] It is used inside the vagina.[1]

Common side effects include burning, itchiness, and abdominal pain.[1] Its use may weaken condoms in the 3 days following application.[1] It may be used in pregnancy.[1] It is an imidazole.[1]

Butoconazole was first made in 1978 and approved for medical use in the United States in 1995.[2][1] It is available over the counter.[1] In the United States a dose costs about 105 USD as of 2022.[3]

Medical uses

Dosage

It is generally used once a day for one to three days.[1] For complicated cases up to 14 days may be used.[1]

Synthesis

Butoconazole synthesis:[4][5]

Reaction of epichlorohydrin with 4-Chlorobenzyl magnesium bromide 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

  1. 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 "Butoconazole Monograph for Professionals". Drugs.com. Archived from the original on 3 January 2022. Retrieved 12 January 2022.
  2. Grayson, M. Lindsay; Crowe, Suzanne M.; McCarthy, James S.; Mills, John; Mouton, Johan W.; Norrby, S. Ragnar; Paterson, David L.; Pfaller, Michael A. (29 October 2010). Kucers' The Use of Antibiotics Sixth Edition: A Clinical Review of Antibacterial, Antifungal and Antiviral Drugs. CRC Press. p. 1893. ISBN 978-1-4441-4752-0. Archived from the original on 12 January 2022. Retrieved 12 January 2022.
  3. "Gynazole-1 Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 29 October 2016. Retrieved 12 January 2022.
  4. Walker KA, Braemer AC, Hitt S, Jones RE, Matthews TR (August 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): 840–3. doi:10.1021/jm00206a028. PMID 357722.
  5. US 4078071, Walker KA, "Derivatives of substituted N-alkyl imidazoles", issued 7 March 1978, assigned to Syntex 

External links

External sites:
Identifiers: