Lopinavir

Lopinavir
Clinical data
Pronunciation	/loʊˈpɪnəvɪər/; loh-PIN-ə-veer
Other names	ABT-378
AHFS/Drugs.com	International Drug Names
MedlinePlus	a602015
License data	EU EMA: by INN; US DailyMed: Lopinavir;
Routes of; administration	By mouth
ATC code	J05AR10 (WHO) (with ritonavir);
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	Unknown
Protein binding	98-99%
Metabolism	Liver
Elimination half-life	5 to 6 hours
Excretion	Mostly fecal
Identifiers
	IUPAC name (2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide;
CAS Number	192725-17-0 ;
PubChem CID	92727;
DrugBank	DB01601 ;
ChemSpider	83706 ;
UNII	2494G1JF75;
KEGG	D01425 ;
ChEMBL	ChEMBL729 ;
CompTox Dashboard (EPA)	DTXSID8046456 ;
ECHA InfoCard	100.281.362
Chemical and physical data
Formula	C37H48N4O5
Molar mass	628.814 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N[C@@H](Cc1ccccc1)[C@@H](O)C[C@@H](NC(=O)[C@@H](N2C(=O)NCCC2)C(C)C)Cc3ccccc3)COc4c(cccc4C)C;
	InChI InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1 ; Key:KJHKTHWMRKYKJE-SUGCFTRWSA-N ;
	(verify)

Lopinavir is an antiretroviral of the protease inhibitor class. It is used against HIV infections as a fixed-dose combination with another protease inhibitor, ritonavir (lopinavir/ritonavir).

It was patented in 1995 and approved for medical use in 2000. Considered now as second-line therapy in the West, it is still prescribed in LMIC, especially among children living with HIV. Lopinavir and ritonavir can be taken as a tablet or an oral solution, a preferred option in children. In the early stages of COVID-19 pandemics, lopinavir was repurposed against the SARS-CoV-2 virus in the hope of disturbing its protease activity.

Clinical data


Pronunciation	/loʊˈpɪnəvɪər/ loh-PIN-ə-veer
Other names	ABT-378
AHFS/Drugs.com	International Drug Names
MedlinePlus	a602015
License data	EU EMA: by INN US DailyMed: Lopinavir
Routes of administration	By mouth
ATC code	J05AR10 (WHO) (with ritonavir)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Unknown
Protein binding	98-99%
Metabolism	Liver
Elimination half-life	5 to 6 hours
Excretion	Mostly fecal
Identifiers
IUPAC name (2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide
CAS Number	192725-17-0^Y
PubChem CID	92727
DrugBank	DB01601^Y
ChemSpider	83706^Y
UNII	2494G1JF75
KEGG	D01425^Y
ChEMBL	ChEMBL729^Y
CompTox Dashboard (EPA)	DTXSID8046456
ECHA InfoCard	100.281.362
Chemical and physical data
Formula	C₃₇H₄₈N₄O₅
Molar mass	628.814 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(N[C@@H](Cc1ccccc1)[C@@H](O)C[C@@H](NC(=O)[C@@H](N2C(=O)NCCC2)C(C)C)Cc3ccccc3)COc4c(cccc4C)C
InChI InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1^Y Key:KJHKTHWMRKYKJE-SUGCFTRWSA-N^Y
(verify)