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Chemistry

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Also known as: Sporanox, 84625-61-6, Oriconazole, Itrizole (tn), Sporanox (tn), Itcz
Molecular Formula
C35H38Cl2N8O4
Molecular Weight
705.6  g/mol
InChI Key
VHVPQPYKVGDNFY-ZPGVKDDISA-N
FDA UNII
304NUG5GF4

Itraconazole
A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.
Itraconazole is an Azole Antifungal. The mechanism of action of itraconazole is as a Cytochrome P450 3A4 Inhibitor, and P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor.
1 2D Structure

Itraconazole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one
2.1.2 InChI
InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1
2.1.3 InChI Key
VHVPQPYKVGDNFY-ZPGVKDDISA-N
2.1.4 Canonical SMILES
CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5COC(O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl
2.1.5 Isomeric SMILES
CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OC[C@H]5CO[C@](O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl
2.2 Other Identifiers
2.2.1 UNII
304NUG5GF4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Orungal

2. R 51211

3. R-51211

4. R51211

5. Sporanox

2.3.2 Depositor-Supplied Synonyms

1. Sporanox

2. 84625-61-6

3. Oriconazole

4. Itrizole (tn)

5. Sporanox (tn)

6. Itcz

7. Itrizole

8. Itraconazol

9. Orungal

10. Sporonox

11. Itraconazole (sporanox)

12. 2-butan-2-yl-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one

13. 873066-43-4

14. R-51211

15. Itraconazol [spanish]

16. Itraconazolum [latin]

17. Triasporin

18. Candistat

19. Canditral

20. Itralek

21. Sempera

22. Sporamelt

23. Traconal

24. Chembl22587

25. Itrac

26. Cis-itraconazole

27. Chebi:6076

28. Spherazole Cr

29. Spherazole Ir

30. R51211

31. Nsc-759239

32. Itz

33. Dsstox_cid_3180

34. Dsstox_rid_76908

35. (2r,4s)-itraconazole (mixture Of Diastereomers)

36. Dsstox_gsid_23180

37. Fungitraxx

38. Cladosal 100

39. 2-(butan-2-yl)-4-{4-[4-(4-{[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3h-1,2,4-triazol-3-one

40. 4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-sec-butyl-1,2,4-triazol-3-one

41. Cas-84625-61-6

42. 304nug5gf4

43. Intraconazole

44. Itraconazolo

45. Sporanox(tm)

46. Ncgc00018268-03

47. 3h-1,2,4-triazol-3-one, 4-(4-(4-(4-((2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-2,4-dihydro-2-(1-methylpropyl)-

48. 4-(4-{4-[4-({[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl}oxy)phenyl]piperazin-1-yl}phenyl)-2-(1-methylpropyl)-2,4-dihydro-3h-1,2,4-triazol-3-one

49. 84604-65-9

50. Itraconazole & Nyotran

51. R 51,211

52. Itraconazole [mi]

53. Itraconazole [inn]

54. Itraconazole [jan]

55. Itraconazole [inci]

56. Itraconazole [usan]

57. Itraconazole (jp17/usp)

58. Itraconazole [vandf]

59. Schembl23934

60. Itraconazole [mart.]

61. Mls006011958

62. Itraconazole [usp-rs]

63. Itraconazole [who-dd]

64. Amy922

65. Dtxsid3023180

66. Gtpl11426

67. Itraconazole [green Book]

68. Itraconazole [ep Impurity]

69. Itraconazole [orange Book]

70. Pharmakon1600-01505756

71. Itraconazole [ep Monograph]

72. 4-(4-(4-(4-((2-((1h-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-(sec-butyl)-2,4-dihydro-3h-1,2,4-triazol-3-one

73. Itraconazole [usp Monograph]

74. Tox21_110854

75. Ac-542

76. Bdbm50127138

77. Nsc759239

78. S2476

79. Akos015842738

80. Akos015961385

81. Tox21_110854_1

82. Ccg-270391

83. Db01167

84. Ks-1268

85. Ncgc00274068-01

86. Ncgc00274068-02

87. Ncgc00274068-07

88. 1-(butan-2-yl)-4-{4-[4-(4-{[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1h-1,2,4-triazol-5-one

89. 4-(4-(4-(4-(((2r,4s)-2-((1h-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-(sec-butyl)-2,4-dihydro-3h-1,2,4-triazol-3-one

90. Hy-17514

91. Smr001827898

92. Itraconazole & Nyotran(liposomal Nystatin)

93. Sbi-0206914.p001

94. Itraconazole (ema Epar: Veterinary)

95. Sw219756-1

96. Itraconazole 2.0 Mg/ml In Dimethyl Sulfoxide

97. D00350

98. Suba-itraconazole Component Itraconazole

99. Ab01274818-01

100. Ab01274818_02

101. Ab01274818_03

102. A933954

103. Itraconazole Component Of Suba-itraconazole

104. Q411229

105. Brd-a23067620-001-01-7

106. (+/-)-1-sec-butyl-4-(p-(4-(p-(((2r*,4s*)-2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-.delta.(sup 2)-1,2,4-triazolin-5-one

107. 3h-1,2,4-triazol-3-one, 4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-pipera-zinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)

108. 4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazole-1-ylmethyl)-1,3-dioxolane-4-yl]methoxy]phenyl]piperazino]phenyl]-2-(1-methylpropyl)-4h-1,2,4-triazole-3(2h)-one

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 705.6 g/mol
Molecular Formula C35H38Cl2N8O4
XLogP35.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count9
Rotatable Bond Count11
Exact Mass704.2393071 g/mol
Monoisotopic Mass704.2393071 g/mol
Topological Polar Surface Area101 Ų
Heavy Atom Count49
Formal Charge0
Complexity1120
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count1
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 NameItraconazole
PubMed HealthItraconazole (By mouth)
Drug ClassesAntifungal
Drug LabelSPORANOX is the brand name for itraconazole, a synthetic triazole antifungal agent. Itraconazole is a 1:1:1:1 racemic mixture of four diastereomers (two enantiomeric pairs), each possessing three chiral centers. It may be represented by the followi...
Active IngredientItraconazole
Dosage FormCapsule
RouteOral
Strength100mg
Market StatusPrescription
CompanyMylan Pharms; Sandoz

2 of 4  
Drug NameSporanox
PubMed HealthItraconazole (By mouth)
Drug ClassesAntifungal
Drug LabelSPORANOX is the brand name for itraconazole, a synthetic triazole antifungal agent. Itraconazole is a 1:1:1:1 racemic mixture of four diastereomers (two enantiomeric pairs), each possessing three chiral centers. It may be represented by the followi...
Active IngredientItraconazole
Dosage FormCapsule; Solution
Routeoral; Oral
Strength10mg/ml; 100mg
Market StatusPrescription
CompanyJanssen Pharms; Janssen Pharma

3 of 4  
Drug NameItraconazole
PubMed HealthItraconazole (By mouth)
Drug ClassesAntifungal
Drug LabelSPORANOX is the brand name for itraconazole, a synthetic triazole antifungal agent. Itraconazole is a 1:1:1:1 racemic mixture of four diastereomers (two enantiomeric pairs), each possessing three chiral centers. It may be represented by the followi...
Active IngredientItraconazole
Dosage FormCapsule
RouteOral
Strength100mg
Market StatusPrescription
CompanyMylan Pharms; Sandoz

4 of 4  
Drug NameSporanox
PubMed HealthItraconazole (By mouth)
Drug ClassesAntifungal
Drug LabelSPORANOX is the brand name for itraconazole, a synthetic triazole antifungal agent. Itraconazole is a 1:1:1:1 racemic mixture of four diastereomers (two enantiomeric pairs), each possessing three chiral centers. It may be represented by the followi...
Active IngredientItraconazole
Dosage FormCapsule; Solution
Routeoral; Oral
Strength10mg/ml; 100mg
Market StatusPrescription
CompanyJanssen Pharms; Janssen Pharma

4.2 Therapeutic Uses

Antifungal Agents; Antiprotozoal Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Itraconazole capsules are indicated for the treatment of the following fungal infections in immunocompromised and non-immunocompromised patients: Blastomycosis, pulmonary and extrapulmonary; Histoplasmosis, including chronic cavitary pulmonary disease and disseminated, non-meningeal histoplasmosis and Aspergillosis, pulmonary and extrapulmonary, in patients who are intolerant of or who are refractory to amphotericin B therapy. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Itraconazole (itraconazole) capsule (February 2010). Available from, as of September 27, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=16279


Itraconazole capsules are also indicated for the treatment of the following fungal infections in non-immunocompromised patients: Onychomycosis of the toenail, with or without fingernail involvement, due to dermatophytes (tinea unguium) and Onychomycosis of the fingernail due to dermatophytes (tinea unguium). /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Itraconazole (itraconazole) capsule (February 2010). Available from, as of September 27, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=16279


4.3 Drug Warning

/BOXED WARNING/ Congestive Heart Failure, Cardiac Effects: Itraconazole capsules should not be administered for the treatment of onychomycosis in patients with evidence of ventricular dysfunction such as congestive heart failure (CHF) or a history of CHF. If signs or symptoms of congestive heart failure occur during administration of itraconazole capsules, discontinue administration. When itraconazole was administered intravenously to dogs and healthy human volunteers, negative inotropic effects were seen.

US Natl Inst Health; DailyMed. Current Medication Information for Itraconazole (itraconazole) capsule (Updated: June 2014). Available from, as of April 24, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d343050e-00bb-440c-a24b-7cd18c97e184


/BOXED WARNING/ Drug Interactions: Coadministration of the following drugs are contraindicated with itraconazole capsules: methadone, disopyramide, dofetilide, dronedarone, quinidine, ergot alkaloids (such as dihydroergotamine, ergometrine (ergonovine), ergotamine, methylergometrine (methylergonovine)), irinotecan, lurasidone, oral midazolam, pimozide, triazolam, felodipine, nisoldipine, ranolazine, eplerenone, cisapride, lovastatin, simvastatin and, in subjects with renal or hepatic impairment, colchicine. Coadministration with itraconazole can cause elevated plasma concentrations of these drugs and may increase or prolong both the pharmacologic effects and/or adverse reactions to these drugs. For example, increased plasma concentrations of some of these drugs can lead to QT prolongation and ventricular tachyarrhythmias including occurrences of torsades de pointes, a potentially fatal arrhythmia.

US Natl Inst Health; DailyMed. Current Medication Information for Itraconazole (itraconazole) capsule (Updated: June 2014). Available from, as of April 24, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d343050e-00bb-440c-a24b-7cd18c97e184


Itraconazole is contraindicated in patients with known hypersensitivity to the drug or any ingredient in the formulation. Although information concerning cross-sensitivity between itraconazole and other triazole or imidazole antifungal agents is not available, the manufacturer states that itraconazole should be used with caution in individuals hypersensitive to other azoles.

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 531


Adverse GI effects have been reported in about 1-11% of patients receiving IV or oral itraconazole for the treatment of systemic fungal infections or oropharyngeal or esophageal candidiasis or for empiric anti-fungal therapy. These adverse GI effects usually are transient and respond to symptomatic treatment without alteration o