Butoconazole

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Butoconazole
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
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:
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