| Drug Name: | Ketoconazole (65277-42-1) |
|---|---|
| PubChem ID: | 5702077 |
| SMILES: | CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl |
| InchiKey: | XMAYWYJOQHXEEK-NASUQTAISA-N |
| Therapeutic Category: | 14-alpha Demethylase Inhibitors, Anti-Infective Agents, Antifungal Agents, Cytochrome P-450 CYP3A Inhibitors, Cytochrome P-450 Enzyme Inhibitors, Enzyme Inhibitors, Hormone Antagonists, Hormones |
| Molecular Weight (dalton) | : | 531.44 |
| LogP | : | 4.2058 |
| Ring Count | : | 3 |
| Hydrogen Bond Acceptor Count | : | 7 |
| Hydrogen Bond Donor Count | : | 0 |
| Total Polar Surface Area | : | 69.06 |
This panel provides information on interacting drugs and their ADRs along with references
| Interacting drug | Toxicity | Interaction Type | Mechanism | Reference |
|---|---|---|---|---|
| Docetaxel (114977-28-5) | Neutropenia | Synergistic | Metabolism of docetaxel is mainly mediated by the cytochrome P450 isoenzyme CYP3A family, ketoconazole inhibitor of CYP3A | Effect of cytochrome P450 3A4 inhibition on the pharmacokinetics of docetaxel |
| Dofetilide (115256-11-6) | Torsade De Pointes | Antagonistic | Ketoconazole may inhibit the active renal tubular secretion mechanism by which dofetilide is eliminated, so reducing its loss from the body. Ketoconazole also inhibits the metabolism of dofetilide by the cytochrome P450 isoenzyme CYP3A4. Both of these mechanisms contribute to the increase in dofetilide plasma levels. There is a linear relationship between plasma dofetilide concentrations and prolongation of the QT interval, which increases the risk for torsade de pointes | Dofetilide (Tikosyn): a new drug to control atrial fibrillation |
| Imatinib (152459-95-5) | Skin rash | Synergistic | Ketoconazole is a potent inhibitor of the cytochrome P450 isoenzyme CYP3A4, which is involved in the metabolism of imatinib | Can nifedipine and estrogen interaction with imatinib be responsible for gallbladder stone development? |
| Etoposide (33419-42-0) | Increase The Effects And Toxicity Of Etoposide | Synergistic | inhibit the metabolism (3?-demethylation) of etoposide by the cytochrome P450 isoenzyme CYP3A4 | A Study on the Metabolism of Etoposide and Possible Interactions with Antitumor or Supporting Agents by Human Liver Microsomes |
| Propafenone (54063-53-5) | Seizure | Antagonistic | Ketoconazole inhibits the metabolism of the propafenone in effect, may have developed an overdose. Ketoconazole is an inhibitor of the cytochrome P450 isoenzyme CYP3A4, by which propafenone is metabolised to N-depropylpropafenone. Propafenone is also extensively metabolised by CYP2D6 to 5-hydroxypropafenone but it was suggested that if CYP2D6 activity is low, propafenone metabolism may be shifted to the CYP3A4 pathway increasing the possibility of an interaction with ketoconazole. Drugs that inhibit CYP2D6 and CYP3A4, such as ketoconazole, might lead to increased levels of propafenone | Convulsive seizures in a patient treated with propafenone and ketoconazole |
| Astemizole (68844-77-9) | Torsade De Pointes | Synergistic | In vitro studies have shown that ketoconazole inhibits the metabolism of astemizole. | Combined use of astemizole and ketoconazole resulting in torsade de pointes |
This panel provides drug-protein interaction and their ADRs along with references
| Toxicity | Interacting Protein | Mechanism | Reference |
|---|---|---|---|
| Dangerous Side Effects | Cytochrome P450 3A4 (P08684) | Terfenadine inhibits CYP3A4 enzyme activity@ thus reduces clearance of ketoconazole that is CYP3A4 substrate and causes dangerous side effects [ ADR Type 4 ] | Use of terfenadine and contraindicated drugs |
This panel provides drug-food interactions and their ADRs along with references
| Food | Toxicity | Reference |
|---|
This panel provides information on metabolites and their ADRs along with references
| Metabolite | Toxicity | Place of Metabolism | Mechanism | Reference |
|---|
This panel provides information on drug category