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1. Ketoconazole
2. R 41400
3. R-41400
4. R41,400
5. R41400
1. Ketoconazole
2. Levoketoconazole
3. Panfungol
4. Ketoderm
5. Fungarest
6. Fungoral
7. Ketoisdin
8. Normocort
9. Extina
10. Orifungal M
11. (-)-ketoconazole
12. 65277-42-1
13. Ketoconazol
14. Ketozole
15. 142128-57-2
16. 2s,4r Ketoconazole
17. 2s,4r-ketoconazole
18. Cor-003
19. Ketoconazole, (2s,4r)-
20. (2s,4r)-ketoconazole
21. Cor003
22. Xolegel
23. (-)-(2s,4r)-ketoconazole
24. Levoketoconazole [usan]
25. Dio-902
26. 2dj8r0nt7k
27. Ketocanazole
28. Ketoconazolum
29. Kuric
30. Chembl295698
31. Chebi:47518
32. R9400w927i
33. 1-[4-[4-[[(2s,4r)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
34. R-41400
35. Nizoral A-d
36. 1-(4-(4-(((2s,4r)-2-((1h-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethan-1-one
37. 1-acetyl-4-(4-{[(2s,4r)-2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine
38. Cis-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine
39. Ethanone, 1-(4-(4-(((2s,4r)-2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)-
40. Piperazine, 1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, Cis-
41. Brizoral
42. Sebazole
43. Teryzolin
44. Terzolin
45. Onofin K
46. Nsc 317629
47. Ketoconazol [inn-spanish]
48. Ketoconazolum [inn-latin]
49. (+-)-cis-1-acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1- Ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine
50. 1-[4-(4-{[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
51. Piperazine, 1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, Cis-
52. R 41,400
53. Unii-2dj8r0nt7k
54. J02ab02
55. Recorlev
56. (+)-(2r,4s)-ketoconazole
57. Feoris, Nizoral
58. Unii-r9400w927i
59. Hsdb 7447
60. (-)-ketoconazol
61. Ncgc00016907-01
62. R 41400
63. Einecs 265-667-4
64. Nizoral (tn)
65. Xolegel (tn)
66. Cas-65277-42-1
67. Kw-1414
68. Brn 4303081
69. Ketoconazole [usan:usp:inn:ban:jan]
70. Ketoconazole [mi]
71. Lopac-k-1003
72. Ketoconazole [inn]
73. Ketoconazole [jan]
74. Ketoconazole [hsdb]
75. Ketoconazole [inci]
76. Ketoconazole [usan]
77. Ketoconazole (jp17/usp)
78. Ketoconazole [vandf]
79. Schembl41473
80. Ketoconazole [mart.]
81. Levoketoconazole (usan/inn)
82. Mls006010227
83. Ketoconazole [usp-rs]
84. Ketoconazole [who-dd]
85. Levoketoconazole [inn]
86. Cort-001
87. Bdbm31768
88. Gtpl11829
89. Hy-b0105b
90. Dtxsid60161949
91. Levoketoconazole [who-dd]
92. Ketoconazole [ep Impurity]
93. Ketoconazole [orange Book]
94. Zinc643153
95. Ketoconazole [ep Monograph]
96. Ketoconazole [usp Impurity]
97. Act02655
98. Ketoconazole [usp Monograph]
99. Ketoconazolum [who-ip Latin]
100. Akos022172422
101. Db05667
102. Ds-6676
103. Ncgc00015577-01
104. Ncgc00016907-02
105. Ncgc00016907-03
106. Ncgc00016907-04
107. Ncgc00161836-01
108. Ncgc00161836-02
109. (+-)-cis-1-acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine
110. Smr001819845
111. Cs-0016830
112. D00351
113. D10950
114. Q27120779
115. (-)-r 41400
116. (+/-)-cis-1-acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine
117. (2s,4r)-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine
118. 1-[4-(4-{[(2s,4r)-2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
119. 72093-26-6
120. Cis-1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1h- Imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-ketoconazol
121. Ethanone, 1-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]-, Rel-
122. Piperazine, (-)-1-acetyl-4-[4-[[(2s,4r)-2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-
123. Piperazine, 1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1h- Imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, Cis-
| Molecular Weight | 531.4 g/mol |
|---|---|
| Molecular Formula | C26H28Cl2N4O4 |
| XLogP3 | 4.3 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 7 |
| Exact Mass | 530.1487608 g/mol |
| Monoisotopic Mass | 530.1487608 g/mol |
| Topological Polar Surface Area | 69.1 Ų |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Complexity | 735 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Antifungal agents
National Library of Medicine's Medical Subject Headings. Ketoconazole. Online file (MeSH, 2014). Available from, as of August 28, 2014: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html
Nizoral Tablets should be used only when other effective antifungal therapy is not available or tolerated and the potential benefits are considered to outweigh the potential risks. Nizoral (ketoconazole) Tablets are indicated for the treatment of the following systemic fungal infections in patients who have failed or who are intolerant to other therapies: blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. Nizoral Tablets should not be used for fungal meningitis because it penetrates poorly into the cerebrospinal fluid. /Included in US product label/
NIH; DailyMed. Current Medication Information for Nizoral (Ketoconazole) Tablet (Revised: March 2014). Available from, as of November 11, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=090660c1-6e6d-457f-adb5-046ddfcd1465
Oral ketoconazole has been used for the palliative treatment of Cushing's syndrome (hypercortisolism), including adrenocortical hyperfunction associated with adrenal or pituitary adenoma or ectopic corticotropin-secreting tumors. Based on ketoconazole's endocrine effects, the drug has been used in the treatment of advanced prostatic carcinoma. Safety and efficacy of ketoconazole have not been established for either of these indications. Oral ketoconazole also has been used in the treatment of hypercalcemia in patients with sarcoidosis and the treatment of tuberculosis-associated hypercalcemia and idiopathic infantile hypercalcemia and hypercalciuria. /NOT included in US product label/
American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014
Ketoconazole has been used for the treatment of sporotrichosis caused by Sporothrix schenckii; however, the drug is not recommended since it is less effective and associated with more adverse effects than some other azoles. Oral itraconazole is considered the drug of choice for the treatment of cutaneous, lymphocutaneous, or mild pulmonary or osteoarticular sporotrichosis and for follow-up therapy in more severe infections after a response has been obtained with IV amphotericin B. /NOT included in US product label/
American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014
For more Therapeutic Uses (Complete) data for KETOCONAZOLE (18 total), please visit the HSDB record page.
/BOXED WARNING/ WARNING. Nizoral Tablets should be used only when other effective antifungal therapy is not available or tolerated and the potential benefits are considered to outweigh the potential risks. Hepatotoxicity: Serious hepatotoxicity, including cases with a fatal outcome or requiring liver transplantation has occurred with the use of oral ketoconazole. Some patients had no obvious risk factors for liver disease. Patients receiving this drug should be informed by the physician of the risk and should be closely monitored. QT Prolongation and Drug Interactions Leading to QT Prolongation: Co-administration of the following drugs with ketoconazole is contraindicated: dofetilide, quinidine, pimozide, cisapride, methadone, disopyramide, dronedarone, ranolazine. Ketoconazole can cause elevated plasma concentrations of these drugs and may prolong QT intervals, sometimes resulting in life-threatening ventricular dysrhythmias such as torsades de pointes.
NIH; DailyMed. Current Medication Information for Nizoral (Ketoconazole) Tablet (Revised: March 2014). Available from, as of November 11, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=090660c1-6e6d-457f-adb5-046ddfcd1465
Transient increases in serum AST, ALT, and alkaline phosphatase concentrations may occur during ketoconazole therapy. Serious hepatotoxicity has occurred in patients receiving oral ketoconazole, including cases that were fatal or required liver transplantation. Hepatotoxicity may be hepatocellular (in most cases), cholestatic, or a mixed pattern of injury. Although ketoconazole-induced hepatotoxicity usually is reversible following discontinuance of the drug, recovery may take several months and rarely death has occurred. Symptomatic hepatotoxicity usually is apparent within the first few months of ketoconazole therapy, but occasionally may be apparent within the first week of therapy. Some patients with ketoconazole-induced hepatotoxicity had no obvious risk factors for liver disease. Serious hepatotoxicity has been reported in patients receiving high oral ketoconazole dosage for short treatment durations and in patients receiving low oral dosage of the drug for long durations. Many of the reported cases of hepatotoxicity occurred in patients who received the drug for the treatment of tinea unguium (onychomycosi or the treatment of chronic, refractory dermatophytoses. Ketoconazole-induced hepatitis has been reported in some children.
American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014, p. 521
Coadministration of a number of CYP3A4 substrates such as dofetilide, quinidine cisapride and pimozide is contraindicated with Nizoral Tablets. Coadministration with ketoconazole can cause elevated plasma concentrations of these drugs and may increase or prolong both therapeutic and adverse effects to such an extent that a potentially serious adverse reaction may occur. For example, increased plasma concentrations of some of these drugs can lead to QT prolongation and sometimes resulting in life-threatening ventricular tachyarrhythmias including occurrences of torsades de pointes, a potentially fatal arrhythmia. Additionally, the following other drugs are contraindicated with Nizoral Tablets: methadone, disopyramide, dronedarone, ergot alkaloids such as dihydroergotamine, ergometrine, ergotamine, methylergometrine, irinotecan, lurasidone, oral midazolam, alprazolam, triazolam, felodipine, nisoldipine, ranolazine, tolvaptan, eplerenone, lovastatin, simvastatin and colchicine.
NIH; DailyMed. Current Medication Information for Nizoral (Ketoconazole) Tablet (Revised: March 2014). Available from, as of November 11, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=090660c1-6e6d-457f-adb5-046ddfcd1465
The use of Nizoral Tablets is contraindicated in patients with acute or chronic liver disease.
NIH; DailyMed. Current Medication Information for Nizoral (Ketoconazole) Tablet (Revised: March 2014). Available from, as of November 11, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=090660c1-6e6d-457f-adb5-046ddfcd1465
For more Drug Warnings (Complete) data for KETOCONAZOLE (46 total), please visit the HSDB record page.
Investigated for use/treatment in diabetes mellitus type 2.
Ketoconazole HRA is indicated for the treatment of endogenous Cushings syndrome in adults and adolescents above the age of 12 years.
14-alpha Demethylase Inhibitors
Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism. (See all compounds classified as 14-alpha Demethylase Inhibitors.)
Antifungal Agents
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)
Cytochrome P-450 CYP3A Inhibitors
Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inhibitors.)
J02AB02
D - Dermatologicals
D01 - Antifungals for dermatological use
D01A - Antifungals for topical use
D01AC - Imidazole and triazole derivatives
D01AC08 - Ketoconazole
G - Genito urinary system and sex hormones
G01 - Gynecological antiinfectives and antiseptics
G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids
G01AF - Imidazole derivatives
G01AF11 - Ketoconazole
H - Systemic hormonal preparations, excl. sex hormones and insulins
H02 - Corticosteroids for systemic use
H02C - Antiadrenal preparations
H02CA - Anticorticosteroids
H02CA03 - Ketoconazole
J - Antiinfectives for systemic use
J02 - Antimycotics for systemic use
J02A - Antimycotics for systemic use
J02AB - Imidazole derivatives
J02AB02 - Ketoconazole
Ketoconazole is rapidly absorbed from the GI tract. Following oral administration, ketoconazole is dissolved in gastric secretions and converted to the hydrochloride salt prior to absorption from the stomach.
American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014
The effect of food on the rate and extent of GI absorption of ketoconazole has not been clearly determined. Some clinicians have reported that administration of ketoconazole to fasting individuals results in higher plasma concentrations of the drug than does administration with food. However, the manufacturer states that administration of ketoconazole with food increases the extent of absorption and results in more consistent plasma concentrations of the drug. The manufacturer suggests that food increases absorption of ketoconazole by increasing the rate and/or extent of dissolution of ketoconazole (e.g., by increasing bile secretions) or by delaying stomach emptying.
American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014
Ketoconazole is a weak dibasic agent and thus requires acidity for dissolution and absorption.
NIH; DailyMed. Current Medication Information for Nizoral (Ketoconazole) Tablet (Revised: March 2014). Available from, as of November 11, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=090660c1-6e6d-457f-adb5-046ddfcd1465
The bioavailability of oral ketoconazole depends on the pH of the gastric contents in the stomach; an increase in the pH results in decreased absorption of the drug. Decreased bioavailability of ketoconazole has been reported in patients with acquired immunodeficiency syndrome (AIDS), probably because of gastric hypochlorhydria associated with this condition; concomitant administration of dilute hydrochloric acid solution normalized absorption of the drug in these patients.198 Concomitant administration of an acidic beverage may increase bioavailability of oral ketoconazole in some individuals with achlorhydria.
American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014
For more Absorption, Distribution and Excretion (Complete) data for KETOCONAZOLE (19 total), please visit the HSDB record page.
Ketoconazole is partially metabolized, in the liver, to several inactive metabolites by oxidation and degradation of the imidazole and piperazine rings, by oxidative O-dealkylation, and by aromatic hydroxylation.
American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014
Plasma concentrations of ketoconazole appear to decline in a biphasic manner with a half-life of approximately 2 hours in the initial phase and approximately 8 hours in the terminal phase.
American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014
Elimination from plasma is biphasic with a half-life of 2 hours during the first 10 hours and 8 hours thereafter.
NIH; DailyMed. Current Medication Information for Nizoral (Ketoconazole) Tablet (Revised: March 2014). Available from, as of November 11, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=090660c1-6e6d-457f-adb5-046ddfcd1465
Preliminary data suggests that DIO-902 increases insulin sensitivity by lowering cortisol levels. The primary mechanism of action is via inhibition of the 11--hydroxylase enzyme, the terminal step in cortisol synthesis in the adrenal gland. DIO-902 has also been shown to lower total and LDL-cholesterol by inhibiting 14--demethylase, a key enzyme in cholesterol synthesis. In combination with a typical glucose-lowering agent, such as metformin, DIO-902 may enhance glucose control and improve total and LDL-cholesterol. [DiObex Press Release]
Ketoconazole blocks the synthesis of ergosterol, a key component of the fungal cell membrane, through the inhibition of cytochrome P-450 dependent enzyme lanosterol 14alpha-demethylase responsible for the conversion of lanosterol to ergosterol in the fungal cell membrane. This results in an accumulation of methylated sterol precursors and a depletion of ergosterol within the cell membrane thus weakening the structure and function of the fungal cell membrane.
NIH; DailyMed. Current Medication Information for Nizoral (Ketoconazole) Tablet (Revised: March 2014). Available from, as of November 11, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=090660c1-6e6d-457f-adb5-046ddfcd1465
Like other azole antifungal agents, ketoconazole presumably exerts its antifungal activity by altering cellular membranes, resulting in increased membrane permeability, secondary metabolic effects, and growth inhibition. Although the exact mechanism of action of ketoconazole has not been fully determined, it has been suggested that the fungistatic activity of the drug may result from interference with ergosterol synthesis, probably via inhibition of C-14 demethylation of sterol intermediates (e.g., lanosterol). The fungicidal activity of ketoconazole at high concentrations may result from a direct physiochemical effect of the drug on the fungal cell membrane.
American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014
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