Butoconazole nitrate

Names

[ Name ]:
Butoconazole nitrate

[Synonym ]:
(2S)-1-[2-(2,6-Dichlorophenylthio)-4-(4-chlorophenyl)butyl]-1H-imidazole nitrate
Butoconazole Nitrate
MFCD00058159
1-{4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl}-1H-imidazole nitrate
UNII:4805237NP5
1-{4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl}-1H-imidazole nitrate (1:1)
1H-Imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, nitrate
1-{4-(4-chlorophényl)-2-[(2,6-dichlorophényl)sulfanyl]butyl}-1H-imidazole nitrate
1H-Imidazole, 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-, nitrate (1:1)
(2R)-1-[2-(2,6-Dichlorophenylthio)-4-(4-chlorophenyl)butyl]-1H-imidazole nitrate

Biological Activity

[Description]:

Butoconazole nitrate is an anti-fungal agent.Target: Antifungalbutoconazole 1-BSR is an effective and safe alternative to longer-term therapy with miconazole nitrate (seven days) for vulvovaginal candidiasis [1]. A sustained-release (SR) bioadhesive vaginal cream (2% butoconazole nitrate) has incorporated VagiSite technology, a topical drug delivery system that allows SR of the drug [2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

[References]

[1]. Brown, D., M.R. Henzl, and R.H. Kaufman, Butoconazole nitrate 2% for vulvovaginal candidiasis. New, single-dose vaginal cream formulation vs. seven-day treatment with miconazole nitrate. Gynazole 1 Study Group. J Reprod Med, 1999. 44(11): p. 933-8.

[2]. Heng, L.Z., Y. Chen, and T.C. Tan, Treatment of recurrent vulvo-vaginal candidiasis with sustained-released butoconazole pessary. Singapore Med J, 2012. 53(12): p. e269-71.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
566.9ºC at 760 mmHg

[ Melting Point ]:
159ºC (dec.)

[ Molecular Formula ]:
C₁₉H₁₈Cl₃N₃O₃S

[ Molecular Weight ]:
474.789

[ Flash Point ]:
296.7ºC

[ Exact Mass ]:
473.013458

[ PSA ]:
109.17000

[ LogP ]:
6.81250

[ Storage condition ]:
-20?C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI4399500

CHEMICAL NAME :: 1H-Imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)but yl)-, (+-)-, mononitrate

CAS REGISTRY NUMBER :: 64872-77-1

LAST UPDATED :: 199109

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C19-H17-Cl3-N2-S.H-N-O3

MOLECULAR WEIGHT :: 474.81

WISWESSER LINE NOTATION :: T5N CNJ A1Y2R DG&SR BG FG &..H..N-O3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1720 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 21,840,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 940 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 21,840,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 21,840,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 21,840,1978

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933290090

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Effects of terconazole and other azole antifungal agents on the sterol and carbohydrate composition of Candida albicans.

Diagn. Microbiol. Infect. Dis. 13(1) , 31-5, (1990)

The effects of terconazole, a triazole antifungal, on the sterol and carbohydrate composition of Candida albicans was compared with that of three imidazoles: clotrimazole, miconazole, and butoconazole...

Effect of butoconazole nitrate cream and wax insert on the barrier property of contraceptive devices.

Am. J. Obstet. Gynecol. 158(4) , 1011-3, (1988)

A new method was developed to assess the quality of the barrier property of several types of commonly used contraceptive devices (diaphragm, cervical cap, and condom). Our data showed that butoconazol...

Patient acceptance of prefilled disposable vaginal applicator.

Am. J. Obstet. Gynecol. 158(4) , 1006-8, (1988)

Patient acceptance of a new, compact, prefilled disposable vaginal applicator was tested in an open study in which 2% butoconazole cream was used for the treatment of vulvovaginal candidiasis. Twenty ...