Tipranavir

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Tipranavir
Systematic (IUPAC) name
[R-(R,R)]-N-[3-[1-[5,6-dihydro-4- hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl] propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide
Identifiers
CAS number	174484-41-4
ATC code	J05AE09
PubChem	65027
DrugBank	APRD01306
Chemical data
Formula	C₃₁H₃₃F₃N₂O₅S
Mol. mass	602.66 g/mol
Pharmacokinetic data
Bioavailability	?
Protein binding	99.9%
Metabolism	Hepatic
Half life	5–6 hours
Excretion	Fecal
Therapeutic considerations
Licence data	EU, US
Pregnancy cat.	C(US)
Legal status	POM(UK) ℞-only(US)
Routes	Oral

Tipranavir, or tipranavir disodium, is a nonpeptidic protease inhibitor (PI) manufactured by Boehringer-Ingelheim under the trade names Aptivus. It is administered with ritonavir in combination therapy to treat HIV infection and is given as two 250mg capsules together with 200mg of ritonavir twice daily.

Tipranavir has the ability to inhibit the replication of viruses that are resistant to other protease inhibitors and it recommended for patients who are resistant to other treatments. Resistance to tipranavir itself seems to require multiple mutations.^[1]

Tipranavir was approved by the Food and Drug Administration (FDA) on June 22, 2005. Like lopinavir and atazanavir, it is very potent and is effective in salvage therapy for patients with some drug resistance. However, side effects of tipranavir can be more severe than other anti-retrovirals. Some side effects include intracranial hemorraging^{[citation needed]}, hepatitis^[2], and diabetes mellitus^{[citation needed]}. The drug has also been shown to cause increases in total cholesterol and triglycerides^{[citation needed]}.

[edit] References

^ Doyon L, Tremblay S, Bourgon L, Wardrop E, Cordingley M (2005). "Selection and characterization of HIV-1 showing reduced susceptibility to the non-peptidic protease inhibitor tipranavir.". Antiviral Res 68 (1): 27–35. doi:10.1016/j.antiviral.2005.07.003. PMID 16122817.
^ "Aptivus (tipranavir) Capsules, 250 mg, Prescribing Information", Boehringer Ingelheim, 2007. Revised February 5, 2007.

v • d • e Antivirals used against HIV (HAART) (primarily J05)

Nucleoside & Nucleotide Reverse Transcriptase Inhibitors (NRTI)	Abacavir (ABC)° • Emtricitabine° • Lamivudine (3TC)° • Tenofovir° • Didanosine • Zidovudine (AZT) • Apricitabine^† • Stampidine^† • Elvucitabine^† • Racivir^† • Amdoxovir^† • Stavudine^‡ • Zalcitabine^‡

Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTI)	Efavirenz° • Nevirapine • Etravirine • Rilpivirine^† • Loviride^‡ • Delavirdine^‡

Protease Inhibitors (PI)	Atazanavir° • Fosamprenavir° • Lopinavir° • Darunavir • Nelfinavir • Ritonavir • Saquinavir • Tipranavir • Amprenavir^‡ • Indinavir^‡

Entry/fusion inhibitors	Enfuvirtide • Maraviroc • Vicriviroc^† • PRO 140^† • Ibalizumab^†

Integrase inhibitors	Raltegravir • Elvitegravir^†

Maturation inhibitors	Bevirimat^† • Vivecon™^†

Combined formulations	Combivir • Atripla • Trizivir • Truvada • Kaletra • Epzicom

Other & experimental agents	Foscarnet • Hydroxyurea • Synergistic enhancers • Epigallocatechin gallate • Portmanteau inhibitors • Globoidnan A • Griffithsin • Diarylpyrimidines • Calanolide A • Cyanovirin-N • Miltefosine • R-roscovitine^†

°DHHS preferred first-line agent. ^†Undergoing clinical trials, not FDA approved. ^‡Formerly or rarely used agent.