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Anti-fungal infection drug Chemical Properties Uses Production method

CAS No.86386-73-4
Chemical Name:Fluconazole
Molecular Formula:C13H12F2N6O
Formula Weight:306.27
MOL File:86386-73-4.mol
Fluconazole Property
Melting point : 138-140°C
storage temp. : −20°C
solubility : DMSO: 5 mg/mL
form : solid
CAS DataBase Reference: 86386-73-4(CAS DataBase Reference)
Hazard Codes : Xn,Xi,T,F
Risk Statements : 22-36/37/38-20/21/22-39/23/24/25-23/24/25-11
Safety Statements : 26-36-36/37/39-24/25-45-36/37-16-7
RTECS : XZ4810000
Hazardous Substances Data: 86386-73-4(Hazardous Substances Data)

Fluconazole Chemical Properties,Usage,Production

Anti-fungal infection drug
Fluconazole is a novel kind triazole drug of anti-fungal infection which was first successfully developed by the American Pfizer with broad-spectrum anti-fungal effect. It belongs to a kind of systemic anti-fungal products and has high selectivity on the inhibitory effect of the fungal cytochrome P450-dependent enzyme. It is also a kind of potent and specific inhibitor for the fungi alcohol synthesis. Clinically it is mainly used for the treatment of vaginal candidiasis, thrush, atrophic oral candidiasis, fungal meningitis, pulmonary fungal infections, abdominal infections, urinary tract infections and skin fungi infection.
The main indication for fluconazole as follows:
1, systemic candidiasis: including candidemia, disseminated candidiasis and other forms of invasive Candida infections such as the peritoneum, endocardium, lungs and urinary tract infections. It can also be applied to patients of malignant tumors, special-care patients, patients who received radiotherapy, chemotherapy or immunosuppressive therapy as well as patients who are susceptible to other factors such as infection of Candida. It can also be used for prevention of the occurrence of candida infection for bone marrow transplant patients upon receiving cytotoxic drugs treatment or radiation treatment.
2, cryptococcosis: including cryptococcal meningitis and the cryptococcal infection in other parts (such as lung, skin). It can be applied to the patient of normal immune function, AIDS patients as well as patient of suppressed immune function due to organ transplant and other reasons. AIDS patients can administer this kind of drug for maintenance therapy and prevention of the relapse of cryptococcal disease.
3, mucosal candidiasis: including oropharyngeal, esophageal, non-invasive bronchial mucosal candidiasis, pulmonary candidiasis, Candida urine disease, mucocutaneous and chronic atrophic oral candidiasis. It can be applied to patients of both normal immune function and with impaired immune function.
4, fluconazole can be used as substitute of itraconazole for the treatment of blastomycosis and histoplasmosis.
5, it can be used for the treatment of acute or recurrent vaginal candidiasis.
6, for leukemia patients or patients of other malignant tumor who is susceptible to fungal infection upon undergoing chemotherapy or radiotherapy can apply it as means of preventive treatment.
7, it can be used for the treatment coccidioidomycosis.
8, it can be used for treatment of fungal skin disease including fungal skin infections such as body ringworm, tinea pedis, tinea versicolor, tinea capitis, onychomycosis and nail ringworm.
9, fluconazole can also be used for the treatment of skin chromomycosis.
In August 2002, the voriconazole (Pfizer) which enters in the United States is the further structural modified derivative of fluconazole with its antibacterial activity against pathogenic yeast being higher than fluconazole. Some case reports have demonstrated that the drug can successfully cure some rare fungal disease.
Chemical Properties
It appears as white to yellow-white crystalline powder and is slightly smelly with bitter taste. It is easily soluble in glacial acetic acid, methanol or ethanol, hardly soluble in water and almost insoluble in ether with the melting point being 137 ~ 141.6 ℃, or melting point being 138 ~ 140 ℃ (derived from ethyl acetate - hexane).
The above information is edited by the chemicalbook of Dai Xiongfeng.
This product belongs to fluorinated triazole antifungal drug with the antifungal spectrum being similar as ketoconazole but antifungal activity being higher than ketoconazole. Its mechanism of action is through inhibition of essential component of the fungal cell membrane, the ergosterol biosynthesis enzyme, blocking the ergosterol synthesis and breaking the integrity of the fungal cell wall, further inhibiting their growth and reproduction. The product has potent antifungal activity against Candida albicans, Microsporum canis, Cryptococcus neoformans, histoplasma capsulatum and epidermophyton.
Production method
Method 1: From reaction between the formamide, hydrazine hydrate and 85% formic acid, we can obtain 1H-1, 2, 4- triazole. From phenylenediamine, we can obtain difluorobenzene, which is further subject to bromination to generate 2, 4-difluoro-bromobenzene. Magnesium was dissolved in anhydrous diethyl ether and added drop wise of the diethyl ether solution of 2, 4-difluoro-bromobenzene under ultrasonic irradiation, followed by adding drop wise of the diethyl ether solution of 1, 3-dichloroacetone under ice-cooling condition. Stir at room temperature overnight. Add glacial acetic acid and water. The separated organic layer was dried and concentrated. Concentrate, triazole, potassium carbonate and PEG600 were dissolved in anhydrous ethyl acetate and were subject to reflux. Then filter, wash with water to neutralization and dryness. The solvent was distilled off and was further subject to cyclohexane-ethyl acetate (1: 1) recrystallization to obtain the fluconazole with the overall yield being 33.6% and the m.p. being 138.5-140 ℃.
The last step can also be carried out in propionitrile. 1, 3-dihalo (x = Br or Cl) -2- (2, 4- difluorophenyl) -2-propanol and 1H-1, 2, 4-triazol-propionitrile were put into propionitrile and subject to reflux under the catalysis of sodium hydroxide and PEG 600 phase transfer catalysis and obtain the fluconazole crude product. The crude product was dissolved in fatty alcohols (such as propanol, isopropanol or butanol, etc.), dissolved upon heating with a small amount of active carbon for decoloring and then cooled to give crystals which is the refined product of fluconazole with the melting point being 139 ~ 140 ℃.
Method 2:2: 2, 4-difluorophenyl methyl is reacted with the Grignard reagent of 1-chloromethyl-1, 2, 4-triazole, and hydrolyzed to obtain fluconazole.
Method 3: difluorophenyl is subject to bromination to generate 1-bromo-2, 4-difluorobenzene, and then further converted to Grignard reagent. The resulting Grignard reagent above is reacted with 1, 3-bis (1H-1, 2, 4- triazole group) acetone, followed by hydrolysis to give fluconazole.
Chemical Properties
White to Off-White Solid
Labelled Fluconazole (F421000). Used as an antifungal.
For the treatment of fungal infections.
Biological Activity
Triazole antifungal agent. Effective against Candida strains in vitro and in vivo .
Fluconazole Preparation Products And Raw materials
Raw materials
METHYL 2,4-DIFLUOROBENZOATE Grignard reagent 1,2,4-Triazole Etanol 1-Bromo-2,4-difluorobenzene Methanesulfonic acid 1,3-Dichloroacetone Cyclohexane Toluene Potassium carbonate tert-Butanol Diethyl ether m-Phenylenediamine Isopropanol 2,4 DIFLUOROBENZENE 1,3-Difluorobenzene
Preparation Products
Fluconazole Suppliers      Global( 258)Suppliers     
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Hubei HongxinRuiYu Fine Chemical Co., Ltd. 15671591110027-655266692545103399@qq.comCHINA 175 58
Qufu Haida Tiancheng Biochemical Co., Ltd. +86 (537) 456-7186 / +86 15998733238 qfhdtc@126.comCHINA 52 55
Wuhan Biocar Bio-Pharm Co., Ltd. 027-8700270586-027-87050469jason@biocar.cnCHINA 1030 50
Shenzhen Simeiquan Biotechnology Co. Ltd 18126413629 0755-23311925 QQ23553270530755-23311925abel@ycgmp.comCHINA 4923 58
Taian Jiaye Biotechnology Co.Ltd ----2885318166@yuanchengtech.comCHINA 243 55
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86386-73-4(Fluconazole)Related Search:
2-AMINO-1-(2-FLUORO-PHENYL)-ETHANOL 1,3-PROPANEDIAMINE-1,1,3,3-D4 2-amino-1-(2,4-difluorophenyl)ethanol Benzeneethanamine, 2,4-difluoro- (9CI) 1H-1,2,4-Triazole-1-propanamine 1-(2-Fluorophenyl)ethanol 2-FLUOROCUMENE (R)-1-(2-FLUOROPHENYL)ETHANOL Fluconazole Flusilazole Benzyl alcohol Benzyl Benzoyl peroxide Benzyl chloride Benzyl acetate beta-Methylphenethyl alcohol 1,1,1,3,3,3-Hexafluoro-2-propanol FLUQUINCONAZOLE
FLUCONAZOLE FLUCONAZOLE-D4 FLUCONAZOLE-D4 (BISMETHYLENE-D4) diflucan Antibiotics Antibiotics A to Z Antibiotics A-F BioChemical 2,4-DIFLUORO-ALPHA, ALPHA-1-BIS(1H-1,2,4-TRIAZOL-1-YLMETHYL)BENZYL ALCOHOL 2,4-DIFLUORO-,1-BIS(1H-1,2,4-TRIAZOL-1-YLMETHYL)BENZYL ALCOHOL A-(2,4-DIFLUOROPHENYL)-A-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-1H-1,2,4-TRIAZOL-1-ETHANOL 86386-73-4 alpha-(2,4-difluorophenyl)-alpha-(1h-1,2,4-triazol-1-ylmethyl)-1h-1,2,4-triazole-1-ethanol AKOS 92106 1h-1,2,4-triazole-1-ethanol,alpha-(2,4-difluorophenyl)-alpha-(1h-1,2,4-triazol -1-ylmethyl)- 2-(2,4-difluorophenyl)-1,3-bis(1h-1,2,4-triazol-1-yl)-2-propanol alpha-(2,4-difluorophenyl)-alpha-(1h-1,2,4-triazol-1-ylmethyl)-1h-1,2,4-tria uk49858 zole-1-ethanol triflucan FLUCONAZOLE MM(CRM STANDARD) FLUCONAZOLE(REAGENT / STANDARD GRADE) C13H12F2N6O a-(2,4-Difluorophenyl)-a-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol-d4 Biozolene-d4 Diflucan-d4 Elazor-d4 Triflucan-d4 UK-49858-d4 86368-73-4 2-(2,4-difluorophenyl)-1,3-bis(1h-1,2,4-triazol-1-yl)propan-2-ol FLUCONAZOLE(PATENT-NO-SUPPLY) Fluconazol C13H12F2N60 Active Pharmaceutical Ingredients α-(2,4-Difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazol-1-ethanol α-(2,4-Difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol-d4 C13H8D4F2N6O Antibiotic Explorer Intermediates & Fine Chemicals Pharmaceuticals Isotope Labeled Compounds API's C13H8F2N6OD4 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-y1)-2-propanol Biozolene Difluean Elazor FCZ:UK-49858 1H-1,2,4-Triazole-1-ethanol, alpha-(2,4-difluorophenyl)-alpha-(1H-1,2,4-triazol-1-ylmethyl) Antifungal 1,3-Bis(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-2-propanol 2,4-Difluoro-α,α-bis[(1H-1,2,4-triazole-1-yl)methyl]benzenemethanol 86383-73-4 Fluconazole,2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol 2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-ol Aromatics
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