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QuickView for Darunavir (compound)


PubChem
Name: darunavir
PubChem Compound ID: 213039
Molecular formula: C27H37N3O7S
Molecular weight: 547.665 g/mol
Synonyms:
Darunavir; TMC-114; 206361-99-1; 618109-00-5; Prezista; UIC-94017; (3R,3aS,6aR)-Hexahydrofuro(2,3-b)furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N1-isobutylsulfanilamido)propyl)carbamate; UIC 94017; AIDS-073035; TMC 114.
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DrugBank
Identification
Name: darunavir
Name (isomeric): DB01264
Drug Type: small molecule
Synonyms:
Darunavirum [INN-latin]; TMC-114; UIC-94017; TMC114; AIDS073035
Brand: Prezista
Category: HIV Protease Inhibitors, Antiviral Agents
CAS number: 206361-99-1
Pharmacology
Indication: Darunavir, co-administered with ritonavir, and with other antiretroviral agents, is indicated for the treatment of human immunodeficiency virus (HIV) infection in antiretroviral treatment-experienced adult patients, such as those with HIV-1 strains resistant to more than one protease inhibitor.
Pharmacology:
Darunavir is an inhibitor of the human immunodeficiency virus (HIV) protease. In studies, the drug, co-administered with ritonavir in combination therapy, significantly reduced viral load and increased CD4 cell counts in this treatment-experienced patient population (Tibotec, 2006, Product Monograph, Prezista 2006). Darunavir is used as an adjunct...
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Mechanism of Action:
Darunavir is a HIV protease inhibitor which prevents HIV replication by binding to the enzyme's active site, thereby preventing the dimerization and the catalytic activity of the HIV-1 protease. Darunavir selectively inhibits the cleavage of HIV encoded Gag-Pol polyproteins in virus-infected cells, which prevents the formation of mature infectious ...
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Absorption: The absolute oral bioavailability of a single 600 mg dose of darunavir alone and after co-administration with 100 mg ritonavir twice daily was 37% and 82%, respectively.
Protein binding: Darunavir is approximately 95% bound to plasma proteins. Darunavir binds primarily to plasma alpha 1-acid glycoprotein (AAG).
Biotransformation: Hepatic. Darunavir is extensively metabolized by CYP enzymes, primarily by CYP3A.
Route of elimination: Darunavir is primarily metabolized by CYP3A. Darunavir is extensively metabolized by CYP enzymes, primarily by CYP3A. A mass balance study in healthy volunteers showed that after single dose administration of 400 mg 14C-darunavir, co-administered with 100 mg ritonavir, approximately 79.5% and 13.9% of the administered dose of 14C-darunavir was recovered in the feces and urine, respectively.
Half Life: The terminal elimination half-life of darunavir was approximately 15 hours when combined with ritonavir.
Clearance: 32.8 L/hr [Healthy volunteers receiving intravenous administration of 400 mg of darunavir] 5.9 L/hr [Healthy volunteers receiving intravenous administrations of 400 mg of darunavir and 100 mg of ritonavir twice daily]
Affected organisms: Human Immunodeficiency Virus
Interactions
Food interaction:
Take with food - better absorption (+30%).
Drug interaction:
TramadolDarunavir may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
SaquinavirDecreased levels of darunavir
TacrolimusThe protease inhibitor, Darunavir, may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Darunavir therapy is initiated, discontinued or altered.
ZopicloneDarunavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zopiclone by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if darunavir is initiated, discontinued or dose changed.
TadalafilDarunavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
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Targets


Enzymes