tipranavir ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
HIV protease inhibitors 3609 174484-41-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tipranavir
  • aptivus
  • PNU-140690
  • PNU 140690
Tipranavir is an HIV-1 protease inhibitor that inhibits the virus-specific processing of the viral Gag and Gag-Pol polyproteins in HIV-1 infected cells, thus preventing formation of mature virions. There was some evidence of in vitro activity against SARS-CoV-2, but no clinical trial data was found to support use in the treatment of COVID-19.
  • Molecular weight: 602.67
  • Formula: C31H33F3N2O5S
  • CLOGP: 7.76
  • LIPINSKI: 2
  • HAC: 7
  • HDO: 2
  • TPSA: 105.59
  • ALOGS: -6.47
  • ROTB: 11

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 23.70 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
June 22, 2005 FDA BOEHRINGER INGELHEIM

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hypomania 298.93 233.24 57 1217 4448 50599402
Jaundice cholestatic 291.75 233.24 57 1217 5054 50598796
Schizophrenia 270.73 233.24 57 1217 7340 50596510

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Acquired immunodeficiency syndrome 63.98 38.68 11 830 416 29573270
Virologic failure 63.54 38.68 15 826 2832 29570854
Dyschromatopsia 59.87 38.68 10 831 317 29573369
Drug resistance 47.07 38.68 19 822 21521 29552165
HIV infection 47.06 38.68 10 831 1171 29572515
Viral load increased 46.78 38.68 11 830 2038 29571648

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hypomania 295.45 68.32 57 1316 5597 64491762
Jaundice cholestatic 271.15 68.32 57 1316 8613 64488746
Schizophrenia 256.77 68.32 57 1316 11111 64486248
Hepatotoxicity 206.14 68.32 62 1311 39900 64457459
Psychotic disorder 197.23 68.32 58 1315 34520 64462839
Cholelithiasis 181.52 68.32 58 1315 45448 64451911
Blood bilirubin increased 172.05 68.32 59 1314 57494 64439865
Hepatic enzyme increased 138.03 68.32 63 1310 129880 64367479
Viral mutation identified 110.14 68.32 23 1350 3323 64494036
Drug resistance 74.48 68.32 28 1345 35074 64462285

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J05AE09 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Protease inhibitors
FDA MoA N0000000246 HIV Protease Inhibitors
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000998 Antiviral Agents
FDA EPC N0000175889 Protease Inhibitor
CHEBI has role CHEBI:35660 HIV protease inhibitors
CHEBI has role CHEBI:36044 antiviral drugs

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Intracranial hemorrhage contraindication 1386000
Hypercholesterolemia contraindication 13644009
Hyperbilirubinemia contraindication 14783006 DOID:2741
Hereditary factor VIII deficiency disease contraindication 28293008 DOID:12134
Hereditary factor IX deficiency disease contraindication 41788008 DOID:12259
Hepatic failure contraindication 59927004
Chronic type B viral hepatitis contraindication 61977001
Blood coagulation disorder contraindication 64779008 DOID:1247
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Procedure on central nervous system contraindication 118679007
Neoplasm of brain contraindication 126952004 DOID:1319
Inflammatory disease of liver contraindication 128241005
Chronic hepatitis C contraindication 128302006
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Lesion of brain contraindication 301766008
Hypertriglyceridemia contraindication 302870006
Surgical procedure contraindication 387713003
Breastfeeding (mother) contraindication 413712001
Traumatic injury contraindication 417746004




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.13 acidic
pKa2 6.12 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Multidrug resistance protein 1 Transporter WOMBAT-PK
Cathepsin D Enzyme Ki 4.82 CHEMBL
Cathepsin E Enzyme Ki 5.05 CHEMBL
Pepsin A-5 Enzyme Ki 5.70 CHEMBL
Pol polyprotein Enzyme INHIBITOR IC50 7.52 CHEMBL CHEMBL
CAAX prenyl protease 1 homolog Enzyme IC50 5.92 CHEMBL

External reference:

IDSource
4024917 VUID
N0000171602 NUI
D08605 KEGG_DRUG
4024917 VANDF
C0663733 UMLSCUI
CHEBI:63628 CHEBI
TPV PDB_CHEM_ID
CHEMBL222559 ChEMBL_ID
DB00932 DRUGBANK_ID
C107201 MESH_SUPPLEMENTAL_RECORD_UI
7774 INN_ID
ZZT404XD09 UNII
54682461 PUBCHEM_CID
190548 RXNORM
20182 MMSL
69882 MMSL
d05538 MMSL
010844 NDDF
418721002 SNOMEDCT_US
419409009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Aptivus HUMAN PRESCRIPTION DRUG LABEL 1 0597-0002 SOLUTION 100 mg ORAL NDA 32 sections
Aptivus HUMAN PRESCRIPTION DRUG LABEL 1 0597-0003 CAPSULE, LIQUID FILLED 250 mg ORAL NDA 32 sections