Details of the Drug

General Information of Drug (ID: DM8HJX6)

Drug Name
Tipranavir
Synonyms
Aptivus; TPV; PNU 140690; U 140690; Aptivus (Boehringer Ingelheim); Aptivus (TN); Aptivus(TM); PNU-140690; PNU-140690E; Tipranavir (INN); U-140690; N-[3-[(1R)-1-[(2R)-6-hydroxy-4-oxo-2-phenethyl-2-propyl-3H-pyran-5-yl]propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide; N-(3-{(1R)-1-[(6R)-4-HYDROXY-2-OXO-6-PHENETHYL-6-PROPYL-5,6-DIHYDRO-2H-PYRAN-3-YL]PROPYL}PHENYL)-5-(TRIFLUOROMETHYL)-2-PYRIDINESULFONAMIDE
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus infection 1C62 Approved [1]
Therapeutic Class
Anti-HIV Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 602.7
Topological Polar Surface Area (xlogp) 7
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 10
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Elimination
0.1% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 5 - 6 hours [3]
Metabolism
The drug is metabolized via the hepatic [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 23.704 micromolar/kg/day [5]
Chemical Identifiers
Formula
C31H33F3N2O5S
IUPAC Name
N-[3-[(1R)-1-[(2R)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3H-pyran-5-yl]propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide
Canonical SMILES
CCC[C@]1(CC(=C(C(=O)O1)[C@H](CC)C2=CC(=CC=C2)NS(=O)(=O)C3=NC=C(C=C3)C(F)(F)F)O)CCC4=CC=CC=C4
InChI
InChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1
InChIKey
SUJUHGSWHZTSEU-FYBSXPHGSA-N
Cross-matching ID
PubChem CID
54682461
ChEBI ID
CHEBI:63628
CAS Number
174484-41-4
DrugBank ID
DB00932
TTD ID
D0EV6T
VARIDT ID
DR00962
INTEDE ID
DR1601

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human immunodeficiency virus Protease (HIV PR) TT5FNQT POL_HV1B1 Modulator [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [7]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [7]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Tipranavir
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Cobicistat DM6L4H2 Moderate Decreased metabolism of Tipranavir caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [45]
Dolutegravir DMCZGRE Major Increased metabolism of Tipranavir caused by Dolutegravir mediated induction of UGT. Human immunodeficiency virus disease [1C60-1C62] [46]
Etravirine DMGV8QU Major Increased metabolism of Tipranavir caused by Etravirine mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [47]
Raltegravir DMYURI6 Minor Increased metabolism of Tipranavir caused by Raltegravir mediated induction of UGT. Human immunodeficiency virus disease [1C60-1C62] [47]
Coadministration of a Drug Treating the Disease Different from Tipranavir (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Ivosidenib DM8S6T7 Moderate Increased metabolism of Tipranavir caused by Ivosidenib mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [48]
Midostaurin DMI6E0R Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Midostaurin. Acute myeloid leukaemia [2A60] [49]
Arn-509 DMT81LZ Moderate Increased metabolism of Tipranavir caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [48]
Gilteritinib DMWQ4MZ Moderate Accelerated clearance of Tipranavir due to the transporter induction by Gilteritinib. Acute myeloid leukaemia [2A60] [50]
Dronedarone DMA8FS5 Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Dronedarone. Angina pectoris [BA40] [51]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Tipranavir and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [52]
Cilostazol DMZMSCT Major Increased risk of bleeding by the combination of Tipranavir and Cilostazol. Arterial occlusive disease [BD40] [47]
Clarithromycin DM4M1SG Moderate Decreased metabolism of Tipranavir caused by Clarithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [47]
Erdafitinib DMI782S Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Erdafitinib. Bladder cancer [2C94] [53]
Talazoparib DM1KS78 Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Talazoparib. Breast cancer [2C60-2C6Y] [49]
Esterified estrogens DM9KZDO Moderate Increased risk of skin rash by the combination of Tipranavir and Esterified estrogens. Breast cancer [2C60-2C6Y] [47]
Tucatinib DMBESUA Moderate Decreased metabolism of Tipranavir caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [54]
Quinestrol DMJ6H1Z Moderate Increased risk of skin rash by the combination of Tipranavir and Quinestrol. Breast cancer [2C60-2C6Y] [47]
Trastuzumab Emtansine DMU1LXS Major Increased risk of bleeding by the combination of Tipranavir and Trastuzumab Emtansine. Breast cancer [2C60-2C6Y] [55]
Atorvastatin DMF28YC Major Decreased metabolism of Tipranavir caused by Atorvastatin mediated inhibition of CYP450 enzyme. Cardiovascular disease [BA00-BE2Z] [56]
PF-04449913 DMSB068 Moderate Decreased clearance of Tipranavir due to the transporter inhibition by PF-04449913. Chronic myelomonocytic leukaemia [2A40] [49]
Revefenacin DMMP5SI Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Revefenacin. Chronic obstructive pulmonary disease [CA22] [57]
Anisindione DM2C48U Major Increased risk of bleeding by the combination of Tipranavir and Anisindione. Coagulation defect [3B10] [47]
Regorafenib DMHSY1I Major Increased risk of bleeding by the combination of Tipranavir and Regorafenib. Colorectal cancer [2B91] [47]
Intedanib DMSTA36 Major Accelerated clearance of Tipranavir due to the transporter induction by Intedanib. Colorectal cancer [2B91] [58]
Mestranol DMG3F94 Moderate Increased risk of skin rash by the combination of Tipranavir and Mestranol. Contraceptive management [QA21] [55]
Ardeparin DMYRX8B Major Increased risk of bleeding by the combination of Tipranavir and Ardeparin. Coronary thrombosis [BA43] [47]
Ivacaftor DMZC1HS Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Ivacaftor. Cystic fibrosis [CA25] [59]
Danaparoid DM6CLBN Major Increased risk of bleeding by the combination of Tipranavir and Danaparoid. Deep vein thrombosis [BD71] [47]
Rivaroxaban DMQMBZ1 Major Increased risk of bleeding by the combination of Tipranavir and Rivaroxaban. Deep vein thrombosis [BD71] [47]
[3H]estrone-3-sulphate DMGPF0N Moderate Increased risk of skin rash by the combination of Tipranavir and [3H]estrone-3-sulphate. Discovery agent [N.A.] [55]
SODIUM CITRATE DMHPD2Y Moderate Decreased absorption of Tipranavir due to altered gastric pH caused by SODIUM CITRATE. Discovery agent [N.A.] [47]
Felbamate DM1V5ZS Moderate Increased metabolism of Tipranavir caused by Felbamate mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [48]
Cenobamate DMGOVHA Moderate Increased metabolism of Tipranavir caused by Cenobamate mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [48]
Stiripentol DMMSDOY Moderate Decreased metabolism of Tipranavir caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [60]
Fosphenytoin DMOX3LB Moderate Increased metabolism of Tipranavir caused by Fosphenytoin mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [48]
Phenobarbital DMXZOCG Moderate Increased metabolism of Tipranavir caused by Phenobarbital mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [48]
Eslicarbazepine DMZREFQ Moderate Increased metabolism of Tipranavir caused by Eslicarbazepine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [48]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Tipranavir and Cannabidiol. Epileptic encephalopathy [8A62] [49]
Tazemetostat DMWP1BH Major Increased risk of bleeding by the combination of Tipranavir and Tazemetostat. Follicular lymphoma [2A80] [47]
Itraconazole DMCR1MV Moderate Decreased metabolism of Tipranavir caused by Itraconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [47]
Miconazole DMPMYE8 Moderate Decreased metabolism of Tipranavir caused by Miconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [47]
Ketoconazole DMPZI3Q Moderate Decreased metabolism of Tipranavir caused by Ketoconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [47]
Avapritinib DMK2GZX Major Increased risk of bleeding by the combination of Tipranavir and Avapritinib. Gastrointestinal stromal tumour [2B5B] [47]
Sulfinpyrazone DMEV954 Major Increased risk of bleeding by the combination of Tipranavir and Sulfinpyrazone. Gout [FA25] [47]
PSI-7977 DMLSUWZ Major Accelerated clearance of Tipranavir due to the transporter induction by PSI-7977. Hepatitis virus infection [1E50-1E51] [45]
Simeprevir DMLUA9D Major Increased metabolism of Tipranavir caused by Simeprevir mediated induction of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [61]
Rifampin DMA8J1G Major Increased metabolism of Tipranavir caused by Rifampin mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [62]
Rifapentine DMCHV4I Major Increased metabolism of Tipranavir caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [48]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Tipranavir and Brentuximab vedotin. Hodgkin lymphoma [2B30] [63]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Tipranavir and Mipomersen. Hyper-lipoproteinaemia [5C80] [64]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Tipranavir and Teriflunomide. Hyper-lipoproteinaemia [5C80] [55]
BMS-201038 DMQTAGO Major Decreased metabolism of Tipranavir caused by BMS-201038 mediated inhibition of CYP450 enzyme. Hyper-lipoproteinaemia [5C80] [45]
Felodipine DMOSW35 Moderate Accelerated clearance of Tipranavir due to the transporter induction by Felodipine. Hypertension [BA00-BA04] [47]
Dipyridamole DMXY30O Major Increased risk of bleeding by the combination of Tipranavir and Dipyridamole. Hypertension [BA00-BA04] [47]
Tolvaptan DMIWFRL Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Tolvaptan. Hypo-osmolality/hyponatraemia [5C72] [45]
Lesinurad DMUR64T Moderate Increased metabolism of Tipranavir caused by Lesinurad mediated induction of CYP450 enzyme. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [48]
Amobarbital DM0GQ8N Moderate Increased metabolism of Tipranavir caused by Amobarbital mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [48]
Eluxadoline DMYZ0P1 Major Decreased clearance of Tipranavir due to the transporter inhibition by Eluxadoline. Irritable bowel syndrome [DD91] [49]
Brigatinib DM7W94S Moderate Increased metabolism of Tipranavir caused by Brigatinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [65]
PF-06463922 DMKM7EW Moderate Increased metabolism of Tipranavir caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [48]
BIBW 2992 DMTKD7Q Moderate Accelerated clearance of Tipranavir due to the transporter induction by BIBW 2992. Lung cancer [2C25] [66]
Capmatinib DMYCXKL Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Capmatinib. Lung cancer [2C25] [67]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Tipranavir and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [68]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Tipranavir and Idelalisib. Mature B-cell leukaemia [2A82] [69]
Acalabrutinib DM7GCVW Major Increased risk of bleeding by the combination of Tipranavir and Acalabrutinib. Mature B-cell lymphoma [2A85] [47]
Ibrutinib DMHZCPO Major Increased risk of bleeding by the combination of Tipranavir and Ibrutinib. Mature B-cell lymphoma [2A85] [47]
Arry-162 DM1P6FR Major Increased risk of bleeding by the combination of Tipranavir and Arry-162. Melanoma [2C30] [47]
Vemurafenib DM62UG5 Moderate Increased metabolism of Tipranavir caused by Vemurafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [48]
LGX818 DMNQXV8 Major Increased risk of bleeding by the combination of Tipranavir and LGX818. Melanoma [2C30] [47]
Ethinyl estradiol DMODJ40 Moderate Increased risk of skin rash by the combination of Tipranavir and Ethinyl estradiol. Menopausal disorder [GA30] [55]
Lasmiditan DMXLVDT Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Lasmiditan. Migraine [8A80] [70]
Exjade DMHPRWG Moderate Decreased metabolism of Tipranavir caused by Exjade mediated inhibition of CYP450 enzyme. Mineral absorption/transport disorder [5C64] [71]
Panobinostat DM58WKG Major Increased risk of bleeding by the combination of Tipranavir and Panobinostat. Multiple myeloma [2A83] [45]
Fedratinib DM4ZBK6 Major Increased risk of bleeding by the combination of Tipranavir and Fedratinib. Myeloproliferative neoplasm [2A20] [47]
Nilotinib DM7HXWT Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Nilotinib. Myeloproliferative neoplasm [2A20] [72]
Dasatinib DMJV2EK Major Increased risk of bleeding by the combination of Tipranavir and Dasatinib. Myeloproliferative neoplasm [2A20] [47]
Prasugrel DM7MT6E Major Increased risk of bleeding by the combination of Tipranavir and Prasugrel. Myocardial infarction [BA41-BA43] [47]
Rolapitant DM8XP26 Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Rolapitant. Nausea/vomiting [MD90] [73]
Orlistat DMRJSP8 Moderate Altered absorption of Tipranavir caused by Orlistat. Obesity [5B80-5B81] [74]
Aspirin DM672AH Major Increased risk of bleeding by the combination of Tipranavir and Aspirin. Pain [MG30-MG3Z] [55]
Abametapir DM2RX0I Moderate Decreased metabolism of Tipranavir caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [75]
Lefamulin DME6G97 Moderate Decreased metabolism of Tipranavir caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [76]
Lonafarnib DMGM2Z6 Moderate Decreased metabolism of Tipranavir caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [77]
Enzalutamide DMGL19D Moderate Increased metabolism of Tipranavir caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [48]
Relugolix DMK7IWL Moderate Accelerated clearance of Tipranavir due to the transporter induction by Relugolix. Prostate cancer [2C82] [78]
Epoprostenol DMUTYR2 Major Increased risk of bleeding by the combination of Tipranavir and Epoprostenol. Pulmonary hypertension [BB01] [47]
Iloprost DMVPZBE Major Increased risk of bleeding by the combination of Tipranavir and Iloprost. Pulmonary hypertension [BB01] [47]
Dexamethasone DMMWZET Moderate Decreased metabolism of Tipranavir caused by Dexamethasone mediated inhibition of CYP450 enzyme. Rheumatoid arthritis [FA20] [45]
Telotristat ethyl DMDIYFZ Moderate Increased metabolism of Tipranavir caused by Telotristat ethyl mediated induction of CYP450 enzyme. Small intestine developmental anomaly [DA90] [49]
Larotrectinib DM26CQR Moderate Accelerated clearance of Tipranavir due to the transporter induction by Larotrectinib. Solid tumour/cancer [2A00-2F9Z] [45]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Tipranavir and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [49]
Pitolisant DM8RFNJ Moderate Increased metabolism of Tipranavir caused by Pitolisant mediated induction of CYP450 enzyme. Somnolence [MG42] [49]
Plicamycin DM7C8YV Major Increased risk of bleeding by the combination of Tipranavir and Plicamycin. Testicular cancer [2C80] [47]
Fostamatinib DM6AUHV Moderate Decreased clearance of Tipranavir due to the transporter inhibition by Fostamatinib. Thrombocytopenia [3B64] [79]
Caplacizumab DMPUKA7 Major Increased risk of bleeding by the combination of Tipranavir and Caplacizumab. Thrombocytopenia [3B64] [47]
Apixaban DM89JLN Major Increased risk of bleeding by the combination of Tipranavir and Apixaban. Thrombosis [DB61-GB90] [47]
Cangrelor DM8JRH0 Major Increased risk of bleeding by the combination of Tipranavir and Cangrelor. Thrombosis [DB61-GB90] [47]
Brilinta DMBR01X Major Increased risk of bleeding by the combination of Tipranavir and Brilinta. Thrombosis [DB61-GB90] [47]
Cabozantinib DMIYDT4 Major Increased risk of bleeding by the combination of Tipranavir and Cabozantinib. Thyroid cancer [2D10] [47]
Elagolix DMB2C0E Moderate Increased metabolism of Tipranavir caused by Elagolix mediated induction of CYP450 enzyme. Uterine fibroid [2E86] [48]
Betrixaban DM2C4RF Major Increased risk of bleeding by the combination of Tipranavir and Betrixaban. Venous thromboembolism [BD72] [47]
⏷ Show the Full List of 97 DDI Information of This Drug

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64 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
65 Product Information. Alunbrig (brigatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
66 Product Information. Gilotrif (afatinib). Boehringer Ingelheim, Ridgefield, CT.
67 Product Information. Tabrecta (capmatinib). Novartis Pharmaceuticals, East Hanover, NJ.
68 Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
69 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
70 Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
71 Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
72 Product Information. Tasigna (nilotinib). Novartis Pharmaceuticals, East Hanover, NJ.
73 Product Information. Varubi (rolapitant). Tesaro Inc., Waltham, MA.
74 MHRA. Medicines and Healthcare Products Regulatory Agency "Orlistat: theoretical interaction with antiretroviral HIV medicines.".
75 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
76 Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
77 Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
78 Product Information. Orgovyx (relugolix). Myovant Sciences, Inc., Brisbane, CA.
79 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.