TIPRANAVIR DISODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C31H31F3N2O5S.2Na
Molecular Weight	646.628
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[Na+].[Na+].CCC[C@@]2(CCC1=CC=CC=C1)CC([O-])=C([C@H](CC)C3=CC=CC([N-]S(=O)(=O)C4=NC=C(C=C4)C(F)(F)F)=C3)C(=O)O2

InChI

InChIKey=ZBWMQTUSVWBMQE-KPHXKKTMSA-M

InChI=1S/C31H32F3N2O5S.2Na/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;;/h5-14,18,20,25H,3-4,15-17,19H2,1-2H3,(H,37,38);;/q-1;2*+1/p-1/t25-,30-;;/m1../s1

HIDE SMILES / InChI

Description

Tipranavir (PNU-140690, trade mark APTIVUS) is a potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class. Tipranavir has potent in vitro activity against a variety of HIV-1 laboratory strains and clinical isolates, including those resistant to ritonavir, as well as HIV-2. The drug is launched in several countries, including the US and in the EU. APTIVUS, co-administered with ritonavir, is indicated for combination antiretroviral treatment of HIV-1 infected patients who are treatment-experienced and infected with HIV-1 strains resistant to more than one protease inhibitor.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 protease 36	Inhibitor 8,504		8.0 pM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156	Primary		Approved 8,583	APTIVUS

C_max

Value	Dose	Co-administered	Analyte	Population
94.8 μM	500 mg 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens
77.6 μM	500 mg 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens
135 μM	375 mg/m² 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
851 μM × h	500 mg 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens
710 μM × h	500 mg 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens
1190 μM × h	375 mg/m² 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.5 h	500 mg 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens
6 h	500 mg 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens
8.1 h	375 mg/m² 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.1%	500 mg 2 times / day steady-state, oral	Ritonavir	TIPRANAVIR plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
500 mg 2 times / day multiple, oral Recommended	unhealthy, 18–65	Disc. AE: Gastrointestinal disorder NOS, Gastrointestinal disorder NOS...
1200 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 35.2
500 mg 2 times / day multiple, oral Recommended	unhealthy	Disc. AE: Hepatitis, Hepatic decompensation...
500 mg 2 times / day multiple, oral Recommended	unhealthy	Disc. AE: Rash...

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AEs

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AE	Significance	Dose	Population
Gastrointestinal disorder NOS	grade 1, 1% Disc. AE	500 mg 2 times / day multiple, oral Recommended	unhealthy, 18–65
Transaminases increased	grade 1, 1% Disc. AE	500 mg 2 times / day multiple, oral Recommended	unhealthy, 18–65
Transaminases increased	moderate, 1.6% Disc. AE	500 mg 2 times / day multiple, oral Recommended	unhealthy, 18–65
Gastrointestinal disorder NOS	moderate, 2.1% Disc. AE	500 mg 2 times / day multiple, oral Recommended	unhealthy, 18–65
Gastrointestinal disorder NOS	severe, 1% Disc. AE	500 mg 2 times / day multiple, oral Recommended	unhealthy, 18–65

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 substrate 1,946 inducer 1,087	inducer 440 inhibitor 2,438	inhibitor 2,507 substrate 1,388	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A 227 P-gp 1,741 CYP1A2 2,153 CYP2C19 2,057 OATP2B1 157 UGT enzymes 4 Ca2+ channels 59	P-gp 2,052	P-gp 301 CYP1A2 832 UGT enzymes 2 CYP2C19 329

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 2,333	inducer 1,966	inconclusive
CYP2C19 2,141	inducer 1,966	inconclusive
CYP2C9 2,497	inducer 1,966	inconclusive
Ca2+ channels 62	inhibitor 4,027	inconclusive
UGT enzymes 4	inducer 1,966	inconclusive

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP2D6 1,388	substrate 4,014	no
P-gp 2,052	substrate 4,014	yes
CYP3A4 1,946	substrate 4,014	yes	yes (co-administration study)

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63628	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63628
ChemicalBook	CB9501005	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9501005
eMolecules	36754763	https://www.emolecules.com/cgi-bin/more?vid=36754763
MolPort	MolPort-003-850-561	https://www.molport.com/shop/molecule-link/MolPort-003-850-561
ZINC	ZINC000100016058	http://zinc15.docking.org/substances/ZINC000100016058

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PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

Adults: 500 mg APTIVUS® (tipranavir), co-administered with 200 mg ritonavir, twice daily. Pediatric patients (age 2 to 18 years): Dosing is based on body weight or body surface area not to exceed adult dose.

Route of Administration: Oral

In Vitro Use Guide

Tipranavir inhibits the replication of laboratory strains of HIV-1 and clinical isolates in acute models of T-cell infection, with EC50 ranging from 0.03 to 0.07 µM (18-42 ng/mL)

Show entries

Name

Type

Language

TIPRANAVIR SODIUM

Preferred Name

English

TIPRANAVIR DISODIUM

Official Name

English

TIPRANAVIR SODIUM [MART.]

Common Name

English

TIPRANAVIR DISODIUM [USAN]

Common Name

English

Tipranavir Sodium [WHO-DD]

Common Name

English

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Classification Tree

Code System

Code

Anti-HIV Agent

NCI_THESAURUS

C97366

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Code System

Code

Type

Description

USAN

JJ-76

PRIMARY

SMS_ID

300000055366

PRIMARY

EPA CompTox

DTXSID80940718

PRIMARY

PUBCHEM

163296

PRIMARY

CAS

191150-83-1

PRIMARY

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ACTIVE MOIETY


					ZZT404XD09

TIPRANAVIR

SUBSTANCE RECORD


					9BAN2XG1ZW

TIPRANAVIR DISODIUM

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator