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Fluconazole

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Name

Fluconazole

EINECS 200-659-6
CAS No. 86386-73-4 Density 1.49 g/cm3
PSA 81.65000 LogP 0.73580
Solubility DMSO: 5 mg/mL Melting Point 138-140 ºC
Formula C13H12F2N6O Boiling Point 579.8 ºC at 760 mmHg
Molecular Weight 306.275 Flash Point 304.4 ºC
Transport Information N/A Appearance white or off white crystalline powder
Safety 26-36/37/39-24/25 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 86386-73-4 (Fluconazole) Hazard Symbols HarmfulXn
Synonyms

Flucostat;Fluconazolum [Latin];Biozolene;FLU;Zemyc;Forcan;FCZ;Diflucan;Flusol;Flukezol;Pritenzol;2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol;Biocanol;Fluzone;Cryptal;UK 49858;Syscan;Alflucoz;1H-1,2,4-Triazole-1-ethanol,R-(2,4-difluorophenyl)- R-(1H-1,2,4-triazol-1-ylmethyl)-;FLZ;Diflucan (TN);Flucazol;FLC;Canzol;Oxifugol;Fluconazole (JAN/USAN);Fungata;Mutum;FLCZ;Baten;alpha-(2,4-Difluorophenyl)-alpha-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol;Fluconazol [Spanish];Triflucan;Afungil;Zonal;Elazor;

Article Data 22

Fluconazole Synthetic route

101-05-3

anilazine

86386-73-4

fluconazole

Conditions
ConditionsYield
With formic acid; sodium chloride In dichloromethane; water97.4%
With formic acid; sodium chloride In dichloromethane; water96.7%
95.4%
1435-44-5

1-chloro-2,4-difluorobenzene

1,3-bis(1H-1,2,4-triazol-1-yl)propanone

86386-73-4

fluconazole

Conditions
ConditionsYield
Stage #1: 1-chloro-2,4-difluorobenzene With iodine; magnesium; lithium chloride In 2-methyltetrahydrofuran at 40 - 50℃; for 3h;
Stage #2: 1,3-bis(1H-1,2,4-triazol-1-yl)propanone In 2-methyltetrahydrofuran at 20 - 40℃; for 2h;
96.1%

Fluconazole Consensus Reports

"The efficacy of Fluconazole (CAS NO.86386-73-4) in the treatment of onchomycosis (fungal infection of the nails) has not been demonstrated." I was treated with Apo-Fluconazole for onychomycosis, and it would seem that it works fine. Although I don't have any medical experience, I was wondering if someone would comment on this statement for me. Schnarr 01:48, 20 April 2006 (UTC)
I had phimosis and my doctor prscribed it as one of the medicines... I am wondering if dealing with a possible fungal infection can stop the preputial ring from forming... please give me some feedback if you have had this problem and how it was solved.. Brian (brianmatambo@gmail.com)

Fluconazole Specification

1. Introduction of Fluconazole

Fluconazole, with the IUPAC name of 2-(2,4-Difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol, is one kind of  white or type white crystalline powder. This chemical belongs to the Classification Code which include Anti-Infective Agents; Antifungal ; Antifungal agents; Drug / Therapeutic Agent; Human Data.

2. Properties of Fluconazole

Fluconazole has the following property datas: (1)Melting point: 138-140°C; (2)Index of Refraction: 1.663; (3)Molar Refractivity: 76.06 cm3; (4)Molar Volume: 205.2 cm3; (5)Surface Tension: 55.4 dyne/cm; (6)Density: 1.49 g/cm3; (7)Flash Point: 304.4 °C; (8)Enthalpy of Vaporization: 91.24 kJ/mol; (9)Boiling Point: 579.8 °C at 760 mmHg; (10)Vapour Pressure: 2.78E-14 mmHg at 25°C.

3. Structure Descriptors of Fluconazole

You could convert the following datas into the molecular structure:
InChI: InChI=1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2 
InChIKey: InChIKey=RFHAOTPXVQNOHP-UHFFFAOYSA-N 
Smiles: c1c(cc(c(C(Cn2ncnc2)(O)Cn2cncn2)c1)F)F

4. Toxicity of Fluconazole

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 100mg/kg (100mg/kg)   Drugs in Japan Vol. -, Pg. 983, 1990.
dog LD50 oral > 300mg/kg (300mg/kg)   Drugs in Japan Vol. -, Pg. 983, 1990.
man TDLo oral 60mg/kg/3W-I (60mg/kg)   Postgraduate Medical Journal. Vol. 67, Pg. 1084, 1991.
man TDLo oral 60mg/kg/3W-I (60mg/kg)   Postgraduate Medical Journal. Vol. 67, Pg. 1084, 1991.
man TDLo oral 1040mg/kg/26W (1040mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Annals of Internal Medicine. Vol. 123, Pg. 354, 1995.
mouse LD50 intraperitoneal 1273mg/kg (1273mg/kg)   Drugs in Japan Vol. -, Pg. 983, 1990.
mouse LD50 intravenous > 200mg/kg (200mg/kg)   Drugs in Japan Vol. -, Pg. 983, 1990.
mouse LD50 oral 1408mg/kg (1408mg/kg)   Drugs in Japan Vol. -, Pg. 983, 1990.
mouse LD50 unreported > 1gm/kg (1000mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 29, Pg. 161, 1986.
rat LD50 intraperitoneal > 941mg/kg (941mg/kg)   Drugs in Japan Vol. -, Pg. 983, 1990.
rat LD50 intravenous > 200mg/kg (200mg/kg)   Drugs in Japan Vol. -, Pg. 983, 1990.
rat LD50 oral 1271mg/kg (1271mg/kg)   Drugs in Japan Vol. -, Pg. 983, 1990.
rat LD50 unreported > 1gm/kg (1000mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 29, Pg. 161, 1986.
women TDLo multiple routes 426mg/kg/37D- (426mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Annals of Internal Medicine. Vol. 131, Pg. 797, 1999.
women TDLo oral 1456mg/kg/26W (1456mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Annals of Internal Medicine. Vol. 123, Pg. 354, 1995.

5. Safety Information of Fluconazole

Hazard Codes: HarmfulXn,Xi
Risk Statements: 36/37/38-20/21/22
R36/37/38: Irritating to eyes, respiratory system and skin. 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S24/25: Avoid contact with skin and eyes.
RTECS: XZ4810000
 Fluconazole (CAS NO.86386-73-4) is contraindicated in patients with:
Pregnancy
Known hypersensitivity to fluconazole or other azole antifungals
Concomitant use of cisapride, due to risk of serious cardiac arrhythmias (relative contraindication).

6. Use of Fluconazole

Fluconazole (CAS NO.86386-73-4) is used in the treatment and prophylaxis of fungal infections where other antifungals are not worked or not tolerated (e.g. due to adverse effects), including:
1)Candidiasis caused by susceptible strains of Candida
2)Tinea corporis, tinea cruris or tinea pedis
3)Onychomycosis
4)Cryptococcal meningitis
 Fluconazole can be used first-line for the following indications:
Histoplasmosis
Coccidioidomycosis
Cryptococcosis
Prophylaxis of candidiasis in immunocompromised people

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