Fluconazole

Names

[ Name ]:
Fluconazole

[Synonym ]:
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

Biological Activity

[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]:

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ 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

MSDS

Click to get detail MSDS

Toxicological Information

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

Safety Information

[ Symbol ]:

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ 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%

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Prophylactic oral/topical non-absorbed antifungal agents to prevent invasive fungal infection in very low birth weight infants.

Cochrane Database Syst. Rev. 3 , CD003478, (2013)

Invasive fungal infection is an important cause of mortality and morbidity in very preterm or very low birth weight infants. Uncertainty exists about the effect of prophylactic oral/topical non-absorb...

Related Compounds

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