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]
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Therapeutic Class

Anti-HIV Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

602.7

Logarithm of the Partition Coefficient (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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 []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 23.704 micromolar/kg/day [4]

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

Combinatorial Drugs (CBD)

Click to Jump to the Detailed CBD Information of This Drug

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	[5]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[6]
Cytochrome P450 2D6 (CYP2D6)	DECB0K3	CP2D6_HUMAN	Substrate	[6]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[6]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[7]
Phosphatidylcholine translocator ABCB4 (ABCB4)	OTE6PY83	MDR3_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

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]	[9]
Dolutegravir	DMCZGRE	Major	Increased metabolism of Tipranavir caused by Dolutegravir mediated induction of UGT.	Human immunodeficiency virus disease [1C60-1C62]	[10]
Etravirine	DMGV8QU	Major	Increased metabolism of Tipranavir caused by Etravirine mediated induction of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[11]
Raltegravir	DMYURI6	Minor	Increased metabolism of Tipranavir caused by Raltegravir mediated induction of UGT.	Human immunodeficiency virus disease [1C60-1C62]	[11]
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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]	[12]
Midostaurin	DMI6E0R	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Midostaurin.	Acute myeloid leukaemia [2A60]	[13]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Tipranavir caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[12]
Gilteritinib	DMTI0ZO	Moderate	Accelerated clearance of Tipranavir due to the transporter induction by Gilteritinib.	Acute myeloid leukaemia [2A60]	[14]
Dronedarone	DMA8FS5	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Dronedarone.	Angina pectoris [BA40]	[15]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Tipranavir and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[16]
Cilostazol	DMZMSCT	Major	Increased risk of bleeding by the combination of Tipranavir and Cilostazol.	Arterial occlusive disease [BD40]	[11]
Clarithromycin	DM4M1SG	Moderate	Decreased metabolism of Tipranavir caused by Clarithromycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[11]
Erdafitinib	DMI782S	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Erdafitinib.	Bladder cancer [2C94]	[17]
Talazoparib	DM1KS78	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Talazoparib.	Breast cancer [2C60-2C6Y]	[13]
Esterified estrogens	DM9KZDO	Moderate	Increased risk of skin rash by the combination of Tipranavir and Esterified estrogens.	Breast cancer [2C60-2C6Y]	[11]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Tipranavir caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[18]
Quinestrol	DMJ6H1Z	Moderate	Increased risk of skin rash by the combination of Tipranavir and Quinestrol.	Breast cancer [2C60-2C6Y]	[11]
Trastuzumab Emtansine	DMU1LXS	Major	Increased risk of bleeding by the combination of Tipranavir and Trastuzumab Emtansine.	Breast cancer [2C60-2C6Y]	[19]
Atorvastatin	DMF28YC	Major	Decreased metabolism of Tipranavir caused by Atorvastatin mediated inhibition of CYP450 enzyme.	Cardiovascular disease [BA00-BE2Z]	[20]
PF-04449913	DMSB068	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by PF-04449913.	Chronic myelomonocytic leukaemia [2A40]	[13]
Revefenacin	DMMP5SI	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Revefenacin.	Chronic obstructive pulmonary disease [CA22]	[21]
Anisindione	DM2C48U	Major	Increased risk of bleeding by the combination of Tipranavir and Anisindione.	Coagulation defect [3B10]	[11]
Regorafenib	DMHSY1I	Major	Increased risk of bleeding by the combination of Tipranavir and Regorafenib.	Colorectal cancer [2B91]	[11]
Intedanib	DMSTA36	Major	Accelerated clearance of Tipranavir due to the transporter induction by Intedanib.	Colorectal cancer [2B91]	[22]
Mestranol	DMG3F94	Moderate	Increased risk of skin rash by the combination of Tipranavir and Mestranol.	Contraceptive management [QA21]	[19]
Ardeparin	DMYRX8B	Major	Increased risk of bleeding by the combination of Tipranavir and Ardeparin.	Coronary thrombosis [BA43]	[11]
Ivacaftor	DMZC1HS	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Ivacaftor.	Cystic fibrosis [CA25]	[23]
Danaparoid	DM6CLBN	Major	Increased risk of bleeding by the combination of Tipranavir and Danaparoid.	Deep vein thrombosis [BD71]	[11]
Rivaroxaban	DMQMBZ1	Major	Increased risk of bleeding by the combination of Tipranavir and Rivaroxaban.	Deep vein thrombosis [BD71]	[11]
[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.]	[19]
SODIUM CITRATE	DMHPD2Y	Moderate	Decreased absorption of Tipranavir due to altered gastric pH caused by SODIUM CITRATE.	Discovery agent [N.A.]	[11]
Felbamate	DM1V5ZS	Moderate	Increased metabolism of Tipranavir caused by Felbamate mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Cenobamate	DM8KLU9	Moderate	Increased metabolism of Tipranavir caused by Cenobamate mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Tipranavir caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[24]
Fosphenytoin	DMOX3LB	Moderate	Increased metabolism of Tipranavir caused by Fosphenytoin mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Phenobarbital	DMXZOCG	Moderate	Increased metabolism of Tipranavir caused by Phenobarbital mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Eslicarbazepine	DMZREFQ	Moderate	Increased metabolism of Tipranavir caused by Eslicarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Tipranavir and Cannabidiol.	Epileptic encephalopathy [8A62]	[13]
Tazemetostat	DMWP1BH	Major	Increased risk of bleeding by the combination of Tipranavir and Tazemetostat.	Follicular lymphoma [2A80]	[11]
Itraconazole	DMCR1MV	Moderate	Decreased metabolism of Tipranavir caused by Itraconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[11]
Miconazole	DMPMYE8	Moderate	Decreased metabolism of Tipranavir caused by Miconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[11]
Ketoconazole	DMPZI3Q	Moderate	Decreased metabolism of Tipranavir caused by Ketoconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[11]
Avapritinib	DMK2GZX	Major	Increased risk of bleeding by the combination of Tipranavir and Avapritinib.	Gastrointestinal stromal tumour [2B5B]	[11]
Sulfinpyrazone	DMEV954	Major	Increased risk of bleeding by the combination of Tipranavir and Sulfinpyrazone.	Gout [FA25]	[11]
PSI-7977	DMLSUWZ	Major	Accelerated clearance of Tipranavir due to the transporter induction by PSI-7977.	Hepatitis virus infection [1E50-1E51]	[9]
Simeprevir	DMLUA9D	Major	Increased metabolism of Tipranavir caused by Simeprevir mediated induction of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[25]
Rifampin	DMA8J1G	Major	Increased metabolism of Tipranavir caused by Rifampin mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[26]
Rifapentine	DMCHV4I	Major	Increased metabolism of Tipranavir caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[12]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Tipranavir and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[27]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Tipranavir and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[28]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Tipranavir and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[19]
BMS-201038	DMQTAGO	Major	Decreased metabolism of Tipranavir caused by BMS-201038 mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[9]
Felodipine	DMOSW35	Moderate	Accelerated clearance of Tipranavir due to the transporter induction by Felodipine.	Hypertension [BA00-BA04]	[11]
Dipyridamole	DMXY30O	Major	Increased risk of bleeding by the combination of Tipranavir and Dipyridamole.	Hypertension [BA00-BA04]	[11]
Tolvaptan	DMIWFRL	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Tolvaptan.	Hypo-osmolality/hyponatraemia [5C72]	[9]
Lesinurad	DMUR64T	Moderate	Increased metabolism of Tipranavir caused by Lesinurad mediated induction of CYP450 enzyme.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[12]
Amobarbital	DM0GQ8N	Moderate	Increased metabolism of Tipranavir caused by Amobarbital mediated induction of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[12]
Eluxadoline	DMYZ0P1	Major	Decreased clearance of Tipranavir due to the transporter inhibition by Eluxadoline.	Irritable bowel syndrome [DD91]	[13]
Brigatinib	DM7W94S	Moderate	Increased metabolism of Tipranavir caused by Brigatinib mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[29]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Tipranavir caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[12]
BIBW 2992	DMTKD7Q	Moderate	Accelerated clearance of Tipranavir due to the transporter induction by BIBW 2992.	Lung cancer [2C25]	[30]
Capmatinib	DMYCXKL	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Capmatinib.	Lung cancer [2C25]	[31]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Tipranavir and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[32]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Tipranavir and Idelalisib.	Mature B-cell leukaemia [2A82]	[33]
Acalabrutinib	DM7GCVW	Major	Increased risk of bleeding by the combination of Tipranavir and Acalabrutinib.	Mature B-cell lymphoma [2A85]	[11]
Ibrutinib	DMHZCPO	Major	Increased risk of bleeding by the combination of Tipranavir and Ibrutinib.	Mature B-cell lymphoma [2A85]	[11]
Arry-162	DM1P6FR	Major	Increased risk of bleeding by the combination of Tipranavir and Arry-162.	Melanoma [2C30]	[11]
Vemurafenib	DM62UG5	Moderate	Increased metabolism of Tipranavir caused by Vemurafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[12]
LGX818	DMNQXV8	Major	Increased risk of bleeding by the combination of Tipranavir and LGX818.	Melanoma [2C30]	[11]
Ethinyl estradiol	DMODJ40	Moderate	Increased risk of skin rash by the combination of Tipranavir and Ethinyl estradiol.	Menopausal disorder [GA30]	[19]
Lasmiditan	DMXLVDT	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Lasmiditan.	Migraine [8A80]	[34]
Exjade	DMHPRWG	Moderate	Decreased metabolism of Tipranavir caused by Exjade mediated inhibition of CYP450 enzyme.	Mineral absorption/transport disorder [5C64]	[35]
Panobinostat	DM58WKG	Major	Increased risk of bleeding by the combination of Tipranavir and Panobinostat.	Multiple myeloma [2A83]	[9]
Fedratinib	DM4ZBK6	Major	Increased risk of bleeding by the combination of Tipranavir and Fedratinib.	Myeloproliferative neoplasm [2A20]	[11]
Nilotinib	DM7HXWT	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Nilotinib.	Myeloproliferative neoplasm [2A20]	[36]
Dasatinib	DMJV2EK	Major	Increased risk of bleeding by the combination of Tipranavir and Dasatinib.	Myeloproliferative neoplasm [2A20]	[11]
Prasugrel	DM7MT6E	Major	Increased risk of bleeding by the combination of Tipranavir and Prasugrel.	Myocardial infarction [BA41-BA43]	[11]
Rolapitant	DM8XP26	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Rolapitant.	Nausea/vomiting [MD90]	[37]
Orlistat	DMRJSP8	Moderate	Altered absorption of Tipranavir caused by Orlistat.	Obesity [5B80-5B81]	[38]
Aspirin	DM672AH	Major	Increased risk of bleeding by the combination of Tipranavir and Aspirin.	Pain [MG30-MG3Z]	[19]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Tipranavir caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[39]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Tipranavir caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[40]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Tipranavir caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[41]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Tipranavir caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[12]
Relugolix	DMK7IWL	Moderate	Accelerated clearance of Tipranavir due to the transporter induction by Relugolix.	Prostate cancer [2C82]	[42]
Epoprostenol	DMUTYR2	Major	Increased risk of bleeding by the combination of Tipranavir and Epoprostenol.	Pulmonary hypertension [BB01]	[11]
Iloprost	DMVPZBE	Major	Increased risk of bleeding by the combination of Tipranavir and Iloprost.	Pulmonary hypertension [BB01]	[11]
Dexamethasone	DMMWZET	Moderate	Decreased metabolism of Tipranavir caused by Dexamethasone mediated inhibition of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[9]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Tipranavir caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[13]
Larotrectinib	DM26CQR	Moderate	Accelerated clearance of Tipranavir due to the transporter induction by Larotrectinib.	Solid tumour/cancer [2A00-2F9Z]	[9]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Tipranavir and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[13]
Pitolisant	DM8RFNJ	Moderate	Increased metabolism of Tipranavir caused by Pitolisant mediated induction of CYP450 enzyme.	Somnolence [MG42]	[13]
Plicamycin	DM7C8YV	Major	Increased risk of bleeding by the combination of Tipranavir and Plicamycin.	Testicular cancer [2C80]	[11]
Fostamatinib	DM6AUHV	Moderate	Decreased clearance of Tipranavir due to the transporter inhibition by Fostamatinib.	Thrombocytopenia [3B64]	[43]
Caplacizumab	DMPUKA7	Major	Increased risk of bleeding by the combination of Tipranavir and Caplacizumab.	Thrombocytopenia [3B64]	[11]
Apixaban	DM89JLN	Major	Increased risk of bleeding by the combination of Tipranavir and Apixaban.	Thrombosis [DB61-GB90]	[11]
Cangrelor	DM8JRH0	Major	Increased risk of bleeding by the combination of Tipranavir and Cangrelor.	Thrombosis [DB61-GB90]	[11]
Brilinta	DMBR01X	Major	Increased risk of bleeding by the combination of Tipranavir and Brilinta.	Thrombosis [DB61-GB90]	[11]
Cabozantinib	DMIYDT4	Major	Increased risk of bleeding by the combination of Tipranavir and Cabozantinib.	Thyroid cancer [2D10]	[11]
Elagolix	DMB2C0E	Moderate	Increased metabolism of Tipranavir caused by Elagolix mediated induction of CYP450 enzyme.	Uterine fibroid [2E86]	[12]
Betrixaban	DM2C4RF	Major	Increased risk of bleeding by the combination of Tipranavir and Betrixaban.	Venous thromboembolism [BD72]	[11]
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