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86386-73-4

86386-73-4 structure
86386-73-4 structure
  • Name: Fluconazole
  • Chemical Name: fluconazole
  • CAS Number: 86386-73-4
  • Molecular Formula: C13H12F2N6O
  • Molecular Weight: 306.271
  • Catalog: API Synthetic anti-infective drugs Antifungal drugs
  • Create Date: 2018-02-04 08:00:00
  • Modify Date: 2024-01-01 17:51:35
  • Fluconazole is a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections.Target: AntifungalFluconazole is a triazole antifungal intended for oral treatment of superficial and systemic mycoses. In tests done in standard mycological media, the compound had minimal inhibitory concentrations against pathogenic Candida species that were usually in excess of 100 mg/l. Fluconazole inhibited branching and hyphal development in C. albicans at concentrations as low as 10(-6) M (0.3 mg/l), but miconazole and ketoconazole were still active in these tests at concentrations 100 times lower than this [1]. Oral fluconazole was not associated with a significantly increased risk of birth defects overall or of 14 of the 15 specific birth defects of previous concern. Fluconazole exposure may confer an increased risk of tetralogy of Fallot [2]. Fluconazole is predicted to be ineffective against Cryptococcus gattii in the koala as a sole therapeutic agent administered at 10 mg/kg p.o. every 12 h [3].Clinical indications: Balanitis; Candida infection; Cryptococcus infection; Cryptococcus neoformans meningitis; Dermatomycosis; Female genital tract infection; Fungal infection; Fungal respiratory tract infection; Fungal urinary tract infection; Prophylaxis; Tinea capitis; Tinea corporis; Tinea cruris; Tinea pedis .Toxicity: Symptoms of overdose include hallucinations and paranoid behavior.

Name fluconazole
Synonyms 2-(2,4-Difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)-2-propanol
triflucan
Flunazol
Apo Fluconazole
FluMycon
α-(2,4-Difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol
Zonal
2-(2,4-Difluorphenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-ol
Apo-Fluconazole
2,4-Difluoro-a,a-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl Alcohol
Diflucan
Zoltec
Difluean
1H-1,2,4-Triazole-1-ethanol, α-(2,4-difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-
2-(2,4-Difluorphenyl)-1,3-di-1H-1,2,4-triazol-1-ylpropan-2-ol
a-(2,4-Difluorophenyl)-a-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol
2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-ol
Fluconazole
EINECS 200-659-6
1H-1,2,4-triazole-1-ethanol, a-(2,4-difluorophenyl)-a-(1H-1,2,4-triazol-1-ylmethyl)-
Diflazon
MFCD00274549
Flusol
Elazor
Flucostat
Fluconal
2-(2,4-DIFLUOROPHENYL)-1,3-BIS-(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL
Description Fluconazole is a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections.Target: AntifungalFluconazole is a triazole antifungal intended for oral treatment of superficial and systemic mycoses. In tests done in standard mycological media, the compound had minimal inhibitory concentrations against pathogenic Candida species that were usually in excess of 100 mg/l. Fluconazole inhibited branching and hyphal development in C. albicans at concentrations as low as 10(-6) M (0.3 mg/l), but miconazole and ketoconazole were still active in these tests at concentrations 100 times lower than this [1]. Oral fluconazole was not associated with a significantly increased risk of birth defects overall or of 14 of the 15 specific birth defects of previous concern. Fluconazole exposure may confer an increased risk of tetralogy of Fallot [2]. Fluconazole is predicted to be ineffective against Cryptococcus gattii in the koala as a sole therapeutic agent administered at 10 mg/kg p.o. every 12 h [3].Clinical indications: Balanitis; Candida infection; Cryptococcus infection; Cryptococcus neoformans meningitis; Dermatomycosis; Female genital tract infection; Fungal infection; Fungal respiratory tract infection; Fungal urinary tract infection; Prophylaxis; Tinea capitis; Tinea corporis; Tinea cruris; Tinea pedis .Toxicity: Symptoms of overdose include hallucinations and paranoid behavior.
Related Catalog
References

[1]. Odds, F.C., S.L. Cheesman, and A.B. Abbott, Antifungal effects of fluconazole (UK 49858), a new triazole antifungal, in vitro. J Antimicrob Chemother, 1986. 18(4): p. 473-8.

[2]. Molgaard-Nielsen, D., B. Pasternak, and A. Hviid, Use of oral fluconazole during pregnancy and the risk of birth defects. N Engl J Med, 2013. 369(9): p. 830-9.

[3]. Black, L.A., et al., Pharmacokinetics of fluconazole following intravenous and oral administration to koalas (Phascolarctos cinereus). J Vet Pharmacol Ther, 2013.

Density 1.5±0.1 g/cm3
Boiling Point 579.8±60.0 °C at 760 mmHg
Melting Point 138-140°C
Molecular Formula C13H12F2N6O
Molecular Weight 306.271
Flash Point 304.4±32.9 °C
Exact Mass 306.104065
PSA 81.65000
LogP 0.50
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.663
Storage condition −20°C
Water Solubility DMSO: 5 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XZ4810000
CHEMICAL NAME :
1H-1,2,4-Triazole-1-ethanol, alpha-(2,4-difluorophenyl)-alpha-(1H-1,2,4-triazol-1- ylmethyl)-
CAS REGISTRY NUMBER :
86386-73-4
LAST UPDATED :
199609
DATA ITEMS CITED :
13
MOLECULAR FORMULA :
C13-H12-F2-N6-O
MOLECULAR WEIGHT :
306.31

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1456 mg/kg/26W-I
TOXIC EFFECTS :
Skin and Appendages - hair
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 123,354,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1040 mg/kg/26W-I
TOXIC EFFECTS :
Skin and Appendages - hair
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 123,354,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
60 mg/kg/3W-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - changes in potassium Nutritional and Gross Metabolic - other changes
REFERENCE :
PGMJAO Postgraduate Medical Journal. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1925- Volume(issue)/page/year: 67,1084,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1271 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,983,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>941 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,983,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,983,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 29,161,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1408 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,983,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1273 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,983,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,983,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 29,161,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,983,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,983,1990
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn: Harmful;
Risk Phrases R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
RTECS XZ4810000
HS Code 2933990090

~66%

86386-73-4 structure

86386-73-4

Literature: Zhang, Yi-Yi; Mi, Jia-Li; Zhou, Cheng-He; Zhou, Xiang-Dong European Journal of Medicinal Chemistry, 2011 , vol. 46, # 9 p. 4391 - 4402

~96%

86386-73-4 structure

86386-73-4

Literature: CENTRO GENESIS PARA LA INVESTIGACION, S.L. Patent: EP967210 A1, 1999 ;

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86386-73-4 structure

86386-73-4

Literature: US5484936 A1, ;

~26%

Detail
Literature: Pfizer Inc. Patent: US4404216 A1, 1983 ;

~67%

86386-73-4 structure

86386-73-4

Literature: Chen, Same-Ting; Fang, Jim-Min Journal of the Chinese Chemical Society, 2003 , vol. 50, # 4 p. 927 - 930

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86386-73-4 structure

86386-73-4

Literature: Journal of the Chinese Chemical Society, , vol. 50, # 4 p. 927 - 930

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86386-73-4 structure

86386-73-4

Literature: European Journal of Medicinal Chemistry, , vol. 46, # 9 p. 4391 - 4402

~%

86386-73-4 structure

86386-73-4

Literature: European Journal of Medicinal Chemistry, , vol. 46, # 9 p. 4391 - 4402

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86386-73-4 structure

86386-73-4

Literature: Journal of Heterocyclic Chemistry, , vol. 30, # 5 p. 1405 - 1412
HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%