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Synopsis

Chemistry

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Also known as: 86386-73-4, Diflucan, Triflucan, Biozolene, Elazor, Biocanol
Molecular Formula
C13H12F2N6O
Molecular Weight
306.27  g/mol
InChI Key
RFHAOTPXVQNOHP-UHFFFAOYSA-N
FDA UNII
8VZV102JFY

Fluconazole
Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS.
Fluconazole is an Azole Antifungal. The mechanism of action of fluconazole is as a Cytochrome P450 2C19 Inhibitor, and Cytochrome P450 3A4 Inhibitor, and Cytochrome P450 2C9 Inhibitor.
1 2D Structure

Fluconazole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol
2.1.2 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
2.1.3 InChI Key
RFHAOTPXVQNOHP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O
2.2 Other Identifiers
2.2.1 UNII
8VZV102JFY
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apo Fluconazole

2. Apo-fluconazole

3. Bagyne

4. Diflucan

5. Fluc Hexal

6. Flucobeta

7. Flucolich

8. Fluconazol Abz

9. Fluconazol Al

10. Fluconazol Isis

11. Fluconazol Ratiopharm

12. Fluconazol Stada

13. Fluconazol Von Ct

14. Fluconazol-isis

15. Fluconazol-ratiopharm

16. Flunazul

17. Fungata

18. Lavisa

19. Loitin

20. Neofomiral

21. Oxifungol

22. Solacap

23. Triflucan

24. Uk 49858

25. Uk-49858

26. Uk49858

27. Zonal

2.3.2 Depositor-Supplied Synonyms

1. 86386-73-4

2. Diflucan

3. Triflucan

4. Biozolene

5. Elazor

6. Biocanol

7. Fluconazol

8. Fungata

9. Zoltec

10. Fluconazolum

11. Flucostat

12. Difluconazole

13. 2-(2,4-difluorophenyl)-1,3-di(1h-1,2,4-triazol-1-yl)propan-2-ol

14. 2-(2,4-difluorophenyl)-1,3-bis(1h-1,2,4-triazol-1-yl)propan-2-ol

15. Uk 49858

16. Uk-49858

17. 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol

18. Alkanazole

19. Flucazol

20. Fluconazole [usan]

21. 123631-92-5

22. Pritenzol

23. Flukezol

24. Flunizol

25. Zonal

26. Chembl106

27. Nsc-758661

28. 2-(2,4-difluorophenyl)-1,3-bis(1h-1,2,4-triazol-1-yl)-2-propanol

29. 8vzv102jfy

30. 2,4-difluoro-alpha,alpha-bis(1h-1,2,4-triazol-1-ylmethyl)benzyl Alcohol

31. 1h-1,2,4-triazole-1-ethanol, Alpha-(2,4-difluorophenyl)-alpha-(1h-1,2,4-triazol-1-ylmethyl)-

32. Uk-49,858

33. Alflucoz

34. Cryptal

35. Dimycon

36. Oxifugol

37. Canzol

38. Chebi:46081

39. Forcan

40. Syscan

41. Baten

42. Mutum

43. Zemyc

44. 2-(2,4-difluorophenyl)-1,3-di-1h-1,2,4-triazol-1-ylpropan-2-ol

45. Bayt006267

46. Bayt-006267

47. Alpha-(2,4-difluorophenyl)-alpha-(1h-1,2,4-triazol-1-ylmethyl)-1h-1,2,4-triazole-1-ethanol

48. Ncgc00095089-01

49. Flunazol

50. Fluconazol [spanish]

51. Fluconazolum [latin]

52. Loitin

53. Dsstox_cid_627

54. 2-(2,4-difluoro-phenyl)-1,3-bis-[1,2,4]triazol-1-yl-propan-2-ol

55. Dsstox_rid_75701

56. Dsstox_gsid_20627

57. Flc

58. Drg-0005

59. Diflazon

60. Fuconal

61. Triconal

62. Trican

63. 2-(2,4-difluorfenyl)-1,3-bis(1h-1,2,4-triazool-1-yl)propaan-2-ol

64. Diflucan (tn)

65. Smr000471882

66. Cas-86386-73-4

67. Flcz

68. Ccris 7211

69. Fluconazole & Hgcsf

70. Diflucan In Sodium Chloride 0.9%

71. Hsdb 7420

72. Sr-01000765440

73. Fluconazole In Sodium Chloride 0.9%

74. Unii-8vzv102jfy

75. Diflucan In Dextrose 5% In Plastic Container

76. Fluconazoli

77. Flucoral

78. Fluconazole & Mc-510,011

79. Fluconazole (f)

80. Fluconazole,(s)

81. 2,4-difluoro-,1-bis(1h-1,2,4-triazol-1-ylmethyl)benzyl Alcohol

82. Fluconazole In Dextrose 5% In Plastic Container

83. 2,4-difluoro-alpha,alpha-1-bis(1h-1,2,4-triazol-1-ylmethyl)benzyl Alcohol

84. Fluconazole- Bio-x

85. Fluzon [antifungal]

86. Mfcd00274549

87. Ks-1059

88. Fluconazole [usan:usp:inn:ban:jan]

89. Fluconazole In Sodium Chloride 0.9% In Plastic Container

90. Fluconazole In Combination With Mgcd290

91. Spectrum_001654

92. Diflucan In Sodium Chloride 0.9% In Plastic Container

93. Fluconazole [mi]

94. Spectrum2_001607

95. Spectrum3_001912

96. Spectrum4_000090

97. Spectrum5_001277

98. Fluconazole [inn]

99. Fluconazole [jan]

100. F0677

101. Fluconazole [hsdb]

102. Mgcd290 And Fluconazole

103. Fluconazole [vandf]

104. Cid_3365

105. Mg-3290 And Fluconazole

106. Schembl3151

107. Fluconazole [mart.]

108. Bspbio_003504

109. Fluconazole [usp-rs]

110. Fluconazole [who-dd]

111. Fluconazole [who-ip]

112. Kbiogr_000360

113. Kbioss_002134

114. Mls001066394

115. Mls001165780

116. Mls001195645

117. Mls001304713

118. Mls001306492

119. Mls006011884

120. Bidd:gt0799

121. Divk1c_001030

122. Spectrum1503975

123. Spbio_001613

124. Zinc4009

125. Fluconazole (jp17/usp/inn)

126. Dtxsid3020627

127. Bdbm25817

128. Hms503m21

129. Kbio1_001030

130. Kbio2_002134

131. Kbio2_004702

132. Kbio2_007270

133. Kbio3_003009

134. Fluconazole [orange Book]

135. Ninds_001030

136. Fluconazole [ep Monograph]

137. Hms1922o10

138. Hms2090i20

139. Hms2093m21

140. Hms2230o22

141. Hms3259h13

142. Hms3373i19

143. Hms3654p15

144. Hms3715f21

145. Hms3748g19

146. Pharmakon1600-01503975

147. Fluconazole [usp Monograph]

148. Fluconazoli [who-ip Latin]

149. Amy23415

150. Bcp28522

151. Fluconazole 2.0 Mg/ml In Methanol

152. Hy-b0101

153. 1,2,4-triazol-1-yl)propan-2-ol

154. Tox21_111419

155. Tox21_202240

156. Tox21_300581

157. Ac-428

158. Bbl005614

159. Ccg-39065

160. Dl-407

161. Fluconazole & Human Recombinant Granulocyte Colony Stimulating Factor

162. Nsc754343

163. Nsc758661

164. S1331

165. Stk619301

166. Akos000280854

167. Tox21_111419_1

168. Cs-1835

169. Db00196

170. Fluconazole 100 Microg/ml In Methanol

171. Fluconazole, >=98% (hplc), Powder

172. Nc00650

173. Nsc 758661

174. Nsc-754343

175. Idi1_001030

176. Ncgc00095089-02

177. Ncgc00095089-04

178. Ncgc00095089-05

179. Ncgc00095089-06

180. Ncgc00095089-07

181. Ncgc00095089-08

182. Ncgc00095089-09

183. Ncgc00095089-10

184. Ncgc00095089-11

185. Ncgc00254412-01

186. Ncgc00259789-01

187. 2-(2,4-difluorophenyl)-1,3-di(1h-

188. Bf164466

189. Fluconazole 100 Microg/ml In Acetonitrile

190. Sbi-0051880.p002

191. Uk-049858

192. Ft-0626437

193. Sw199616-2

194. En300-53634

195. C07002

196. D00322

197. Ab00052399-07

198. Ab00052399-08

199. Ab00052399_09

200. Ab00052399_10

201. 386f734

202. A841625

203. Q411478

204. Q-201120

205. Sr-01000765440-2

206. Sr-01000765440-4

207. Sr-01000765440-8

208. Uk-49858;uk 49858;uk49858

209. Brd-k05977355-001-02-6

210. Brd-k05977355-001-09-1

211. F2173-0496

212. Z235354561

213. Fluconazole, European Pharmacopoeia (ep) Reference Standard

214. 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)-2-propanol

215. Fluconazole, United States Pharmacopeia (usp) Reference Standard

216. 2-[2,4-bis(fluoranyl)phenyl]-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol

217. Fluconazole, Pharmaceutical Secondary Standard; Certified Reference Material

218. 2,4-difluoro-1',1'-bis(1h-1,2,4-triazol-1-ylmethyl)benzyl Alcohol

219. A-(2,4-difluorophenyl)-a-(1h-1,2,4-triazol-1- Ylmethyl)-1h-1,2,4-triazole-1-ethanol

220. Fluconazole For Peak Identification, European Pharmacopoeia (ep) Reference Standard

221. Fluconazole Solution, 2.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

222. .alpha.-(2,4-difluorophenyl)-.alpha.-(1h-1,2,4-triazol-1-ylmethyl)-1h-1,2,4-triazole-1-ethanol

223. 1h-1,2,4-triazole-1-ethanol, .alpha.-(2,4-difluorophenyl)-.alpha.-(1h-1,2,4-triazol-1-ylmethyl)-

224. 1h-1,2,4-triazole-1-ethanol, 1-(2,4-difluorophenyl)-1-(1h-1,2,4-triazol-1-ylmethyl)-

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 306.27 g/mol
Molecular Formula C13H12F2N6O
XLogP30.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count5
Exact Mass306.10406535 g/mol
Monoisotopic Mass306.10406535 g/mol
Topological Polar Surface Area81.6 Ų
Heavy Atom Count22
Formal Charge0
Complexity358
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameDiflucan
PubMed HealthFluconazole
Drug ClassesAntifungal
Drug LabelDIFLUCAN (fluconazole), the first of a new subclass of synthetic triazole antifungal agents, is available as tablets for oral administration, as a powder for oral suspension, and as a sterile solution for intravenous use in glass and in Viaflex P...
Active IngredientFluconazole
Dosage FormTablet; For suspension
RouteOral
Strength200mg/5ml; 200mg; 100mg; 50mg; 150mg; 50mg/5ml
Market StatusPrescription
CompanyPfizer

2 of 4  
Drug NameFluconazole
PubMed HealthFluconazole
Drug ClassesAntifungal
Drug LabelFluconazole USP, the first of a new subclass of synthetic triazole antifungal agents, is available as tablets for oral administration. Fluconazole USP is designated chemically as 2,4-difluoro-,1-bis(1H-1,2,4-triazol-1-ylmethyl) benzyl alcohol wit...
Active IngredientFluconazole
Dosage FormTablet; For suspension
RouteOral
Strength200mg/5ml; 200mg; 150mg; 50mg/5ml; 100mg; 50mg
Market StatusPrescription
CompanyRanbaxy; Teva; Apotex; Aurobindo Pharma; Taro; Unique Pharm Labs; Roxane; Glenmark Generics; Ivax Sub Teva Pharms; Aurobindo Pharm; Dr Reddys Labs; Mylan

3 of 4  
Drug NameDiflucan
PubMed HealthFluconazole
Drug ClassesAntifungal
Drug LabelDIFLUCAN (fluconazole), the first of a new subclass of synthetic triazole antifungal agents, is available as tablets for oral administration, as a powder for oral suspension, and as a sterile solution for intravenous use in glass and in Viaflex P...
Active IngredientFluconazole
Dosage FormTablet; For suspension
RouteOral
Strength200mg/5ml; 200mg; 100mg; 50mg; 150mg; 50mg/5ml
Market StatusPrescription
CompanyPfizer

4 of 4  
Drug NameFluconazole
PubMed HealthFluconazole
Drug ClassesAntifungal
Drug LabelFluconazole USP, the first of a new subclass of synthetic triazole antifungal agents, is available as tablets for oral administration. Fluconazole USP is designated chemically as 2,4-difluoro-,1-bis(1H-1,2,4-triazol-1-ylmethyl) benzyl alcohol wit...
Active IngredientFluconazole
Dosage FormTablet; For suspension
RouteOral
Strength200mg/5ml; 200mg; 150mg; 50mg/5ml; 100mg; 50mg
Market StatusPrescription
CompanyRanbaxy; Teva; Apotex; Aurobindo Pharma; Taro; Unique Pharm Labs; Roxane; Glenmark Generics; Ivax Sub Teva Pharms; Aurobindo Pharm; Dr Reddys Labs; Mylan

4.2 Therapeutic Uses

Mesh Heading: Antifungal agents

National Library of Medicine, SIS; ChemIDplus Record for Fluconazole (86386-73-4). Available from, as of April 17, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp


MEDICATION: Antifungal; Orally active bistriazole antifungal agent

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 728-9


MEDICATION (VET): Used to treat systemic mycoses, particularly CNS-related conditions in dogs.

Milne, G.W.A. Veterinary Drugs: Synonyms and Properties. Ashgate Publishing Limited, Aldershot, Hampshire, England 2002., p. 80


Fluconazole ... /is/ indicated for the prophylaxis of febrile neutropenia in patients with hematologic malignancies. /NOT included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 335


For more Therapeutic Uses (Complete) data for FLUCONAZOLE (16 total), please visit the HSDB record page.


4.3 Drug Warning

Although serious adverse hepatic effects have been reported only rarely with fluconazole, the possibility that these effects may occur during fluconazole therapy should be considered. Fluconazole therapy should be discontinued if signs and symptoms consistent with liver disease develop. If abnormal liver function test results occur during fluconazole therapy, the patient should be monitored for the development of more severe hepatic injury.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 507


Serious hepatic reactions (eg, necrosis, clinical hepatitis, cholestasis, fulminant hepatic failure) have been reported rarely in patients receiving fluconazole therapy. The manufacturer states that a clear relationship between these hepatic effects and daily dosage, duration of therapy, gender, or age has not been demonstrated. While hepatotoxicity usually has been reversible, fatalities have been reported. Fatalities principally have occurred in patients with serious underlying disease (eg, AIDS, malignancy) who were receiving fluconazole concomitantly with other drugs; however, at least one fatality involved an immunocompetent geriatric individual with renal impairment who developed fulminant hepatic necrosis within 10 days after fluconazole therapy was initiated.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 507


Mild, transient increases (1.5-3 times the upper limit of normal) in serum concentrations of AST (SGOT), ALT (SGPT), alkaline phosphatase, gamma-glutamyltransferase (GGT, gamma-glutamyl transpeptidase, GGTP), and bilirubin have been reported in about 5-7% of patients receiving fluconazole. In most reported cases, concentrations returned to pretreatment levels either during or after fluconazole therapy and were not associated with hepatotoxicity. However, higher increases in serum transaminase concentrations (8 or more times the upper limit of normal), which required discontinuance of the drug, have been reported in about 1% of patients receiving fluconazole. Any patient who develops abnormal liver function test results while receiving fluconazole should be closely monitored for the development of more severe hepatic injury.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 507


Because potentially fatal exfoliative skin disorders have been reported rarely in patients with a serious underlying disease receiving fluconazole, the possibility that these effects can occur should be considered. Immunocompromised patients (e.g., patients with HIV infections) who develop rash during fluconazole therapy should be monitored closely and the drug discontinued if the lesions progress.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 507


For more Drug Warnings (Complete) data for FLUCONAZOLE (17 total), please visit the HSDB record page.


4.4 Drug Indication

Fluconazole can be administered in the treatment of the following fungal infections: 1) Vaginal yeast infections caused by Candida 2) Systemic Candida infections 3) Both esophageal and oropharyngeal candidiasis 4) Cryptococcal meningitis 5) UTI (urinary tract infection) by Candida 6) Peritonitis (inflammation of the peritoneum) caused by Candida **A note on fungal infection prophylaxis** Patients receiving bone marrow transplantation who are treated with cytotoxic chemotherapy and/or radiation therapy may be predisposed to candida infections, and may receive fluconazole as prophylactic therapy. **A note on laboratory testing** Obtaining specimens for fungal culture and other important laboratory studies such as serology or pathology is advised before starting fluconazole therapy in order to isolate the organisms to be eliminated through treatment. It is permissible to start therapy before the results are available, however, adjusting the therapy once laboratory results confirm the causative organism may be necessary.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Fluconazole has been demonstrated to show fungistatic activity against the majority of strains of the following microorganisms, curing fungal infections: _Candida albicans, Candida glabrata (Many strains are intermediately susceptible), Candida parapsilosis, Candida tropicalis, Cryptococcus neoformans_ This is achieved through steroidal inhibition in fungal cells, interfering with cell wall synthesis and growth as well as cell adhesion, thereby treating fungal infections and their symptoms. The fungistatic activity of fluconazole has also been shown in normal and immunocompromised animal models with both systemic and intracranial fungal infections caused by _Cryptococcus neoformans_ and for systemic infections caused by Candida albicans. It is important to note that resistant organisms have been found against various strains of organisms treated with fluconazole. This further substantiates the need to perform susceptibility testing when fluconazole is considered as an antifungal therapy. **A note on steroidal effects of fluconazole** There has been some concern