QuickView for lopinavir (compound)

Summary
General Info

PubChem

PubChem Compound 11979606

Name:	Lopinavir
PubChem Compound ID:	11979606
Description:	An antiretroviral drug of the protease inhibitor class used as a fixed-dose combination with RITONAVIR.
Molecular formula:	C₇₄H₉₆N₁₀O₁₀S₂
Molecular weight:	1349.75 g/mol
Synonyms:	LPV/r; 2,4,7,12-Tetraazatridecan-13-oic acid, 10-hydroxy-2-methyl-5-(1-methylethyl)-1-(2-(1-methylethyl)-4-thiazolyl)-3,6-dioxo-8,11-bis(phenylmethyl)-, 5-thiazolylmethyl ester, (5S,8S,10S,11S)-, mixt. with (aS)-N-((1S,3S,4S)-4-(((2,6-dimethylphenoxy)acetyl)amin; D02498; ABT-378 & ABT-538; Kaletra (TN); Kaletra; Lopinavir & Ritonavir; Lopinavir & Norvir; AIDS-003688; AIDS003688. show more » LPV/r; 2,4,7,12-Tetraazatridecan-13-oic acid, 10-hydroxy-2-methyl-5-(1-methylethyl)-1-(2-(1-methylethyl)-4-thiazolyl)-3,6-dioxo-8,11-bis(phenylmethyl)-, 5-thiazolylmethyl ester, (5S,8S,10S,11S)-, mixt. with (aS)-N-((1S,3S,4S)-4-(((2,6-dimethylphenoxy)acetyl)amin; D02498; ABT-378 & ABT-538; Kaletra (TN); Kaletra; Lopinavir & Ritonavir; Lopinavir & Norvir; AIDS-003688; AIDS003688; Lopinavir/Ritonavir; 369372-47-4; Lopinavir-Ritonavir mixt show less «

DrugBank

Identification

Name:	Lopinavir
Name (isomeric):	DB01601
Drug Type:	small molecule
Description:	An antiretroviral drug of the protease inhibitor class used as a fixed-dose combination with RITONAVIR.
Synonyms:	ABT-378; LPV
Brand:	Koletra, Aluviran
Brand name mixture:	Kaletra(Lopinavir + Ritonavir)
Category:	HIV Protease Inhibitors, Anti-HIV Agents
CAS number:	192725-17-0

Pharmacology

Indication:	Indicated in combination with other antiretroviral agents for the treatment of HIV-infection.
Pharmacology:	Lopinavir is an antiretroviral of the protease inhibitor class. Inhibiting HIV-1 protease (responsible for protein cleavage), results in selectively inhibiting the cleavage of HIV gag and gag-pol polyproteins, thereby preventing viral maturation.
Mechanism of Action:	Lopinavir inhibits the HIV viral protease enzyme. This prevents cleavage of the gag-pol polyprotein and, therefore, improper viral assembly results. This subsequently results in non-infectious, immature viral particles.
Absorption:	Administered alone, lopinavir has insufficient bioavailability; however, like several HIV protease inhibitors, its blood levels are greatly increased by low doses of ritonavir, a potent inhibitor of cytochrome P450 3A4.
Protein binding:	Lopinavir is highly bound to plasma proteins (98-99%).
Biotransformation:	Hepatic. Lopinavir is extensively metabolized by the hepatic cytochrome P450 system, almost exclusively by the CYP3A isozyme.
Toxicity:	Although human experience of acute overdosage with lopinavir is limited, accidental ingestion of the product by a young child could result in significant alcohol-related toxicity and could approach the potential lethal dose of alcohol.
Affected organisms:	Human Immunodeficiency Virus

Interactions

Food interaction:

Avoid St.John's Wort.

Take with food.

Drug interaction:

Fosphenytoin	Levels of both drugs are affected
Tolterodine	Lopinavir may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Venlafaxine	Lopinavir, a CYP2D6 and CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 and CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Lopinavir is initiated, discontinued, or dose changed.
Vincristine	Lopinavir, a strong CYP3A4 and p-glycoprotein inhibitor, may increase the serum concentration of Vincristine by decreasing its metabolism and/or increasing its efflux. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Lopinavir is initiated, discontinued or dose changed.
Zolpidem	Lopinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if lopinavir is initiated, discontinued or dose changed.

Fosphenytoin	Levels of both drugs are affected
Tolterodine	Lopinavir may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Venlafaxine	Lopinavir, a CYP2D6 and CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 and CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Lopinavir is initiated, discontinued, or dose changed.
Vincristine	Lopinavir, a strong CYP3A4 and p-glycoprotein inhibitor, may increase the serum concentration of Vincristine by decreasing its metabolism and/or increasing its efflux. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Lopinavir is initiated, discontinued or dose changed.
Zolpidem	Lopinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if lopinavir is initiated, discontinued or dose changed.
Telithromycin	Lopinavir may increase the plasma concentration of Telithromycin. Consider alternate therapy or monitor therapeutic/adverse effects.
Vardenafil	Lopinavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
Temsirolimus	Lopinavir may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
Tramadol	Lopinavir may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Lopinavir may decrease the effect of Tramadol by decreasing active metabolite production.
Darunavir	Decreased levels of darunavir
Abacavir	The serum concentration of Abacavir may be decreased by protease inhibitors such as Lopinavir. The antiviral response should be closely monitored.
Topotecan	The p-glycoprotein inhibitor, Lopinavir, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
Tamoxifen	Lopinavir may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
Trimipramine	The strong CYP3A4/CYP2D6 inhibitor, Lopinavir, may decrease the metabolism and clearance of Trimipramine, a CYP3A4/CYP2D6 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Lopinavir is initiated, discontinued or dose changed.
Dantrolene	Lopinavir may increase the serum concentration of dantrolene by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of dantrolene if lopinavir is initiated, discontinued or dose changed.
Tipranavir	Tipranavir, co-administered with Ritonavir, may decrease the plasma concentration of Lopinavir. Consider alternate therapy.
Zonisamide	Lopinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zonisamide by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zonisamide if lopinavir is initiated, discontinued or dose changed.
Vinblastine	Lopinavir, a strong CYP3A4 inhibitor, may decrease the metabolism of Vinblastine. Consider alternate therapy to avoid Vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of Vinblastine if Lopinavir is initiated, discontinued or dose changed.
Phenytoin	Levels of both drugs are affected
Tadalafil	Lopinavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
Vinorelbine	Lopinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Vinorelbine by decreasing its metabolism. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Lopinavir is initiated, discontinued or dose changed.
Tamsulosin	Lopinavir, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Lopinavir is initiated, discontinued, or dose changed.
Tacrolimus	The protease inhibitor, Lopinavir, may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Lopinavir therapy is initiated, discontinued or altered.
Bromazepam	Lopinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if lopinavir is initiated, discontinued or dose changed. Dosage adjustments may be required.
Verapamil	Lopinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Lopinavir is initiated, discontinued or dose changed.
Tiagabine	The strong CYP3A4 inhibitor, Lopinavir, may decrease the metabolism and clearance of Tiagabine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tiagabine if Lopinavir is initiated, discontinued or dose changed.
Trazodone	The protease inhibitor, Lopinavir, may increase the efficacy/toxicity of Trazodone by inhibiting Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Lopinavir is initiated, discontinued or dose changed.
Zuclopenthixol	Lopinavir, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if lopinavir is initiated, discontinued or dose changed.
Voriconazole	Lopinavir may reduce serum concentration and efficacy of voriconazole. This combination should be avoided unless the potential benefits outweigh the risk of reduced voriconazole efficacy.
Zopiclone	Lopinavir, 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 lopinavir is initiated, discontinued or dose changed.
Teniposide	The strong CYP3A4 inhibitor, Lopinavir, may decrease the metabolism and clearance of Teniposide, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Teniposide if Lopinavir is initiated, discontinued or dose changed.

Targets

Enzymes

Transporters

Multidrug resistance protein 1