LOPINAVIR


Synonyms	A-157378-0 A-157378.0 ABT-378 Aluviran Kaletra Koletra Lopinavir Lopinavir, (s-(2s,4s,5s))- Lopinavir- Lopinavirum
Status
Molecule Category	Free-form
UNII	2494G1JF75
EPA CompTox	DTXSID8046456

Structure


InChI Key	KJHKTHWMRKYKJE-SUGCFTRWSA-N
Smiles	Cc1cccc(C)c1OCC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)C[C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)N1CCCNC1=O
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C37H48N4O5
Molecular Weight	628.81
AlogP	4.33
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	15.0
Polar Surface Area	120.0
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	46.0

Pharmacology

Mechanism of Action	Action	Reference
Human immunodeficiency virus type 1 protease inhibitor	INHIBITOR	FDA

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4	-	-	-	410	-
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A2A subfamily	-	25	0.1	0.0013-6.1	93-93
Enzyme Protease Cysteine protease Cysteine protease PAC clan Cysteine protease C3A subfamily	-	2.5-25	0.0013-1.1	0.005-1.4	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	84.6-86.4
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	-	-	-	50

	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Homo sapiens	100-104	35	-	410	50-86.4
Human immunodeficiency virus	32-385	-	-	-	-
Human immunodeficiency virus 1	1-807	1-400	0.0013-1.1	0.004-130	93-93
Human immunodeficiency virus 2	2.6-515	4-524	-	-	-
Human immunodeficiency virus type 1 (BRU ISOLATE)	-	30	-	-	-
Human immunodeficiency virus type 2 (ISOLATE ROD)	28	20	-	-	-

Environmental Exposure

Environmental Exposure Map

Countries
Croatia
Czech Republic
Romania
Serbia
South Africa

Cross References

Resources	Reference
ChEBI	31781
ChEMBL	CHEMBL729
DrugBank	DB01601
DrugCentral	1601
FDA SRS	2494G1JF75
Human Metabolome Database	HMDB0015539
KEGG	C12871
PDB	AB1
PharmGKB	PA450264
PubChem	92727
SureChEMBL	SCHEMBL21775
ZINC	ZINC000003951740

CONTENTS


PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains. Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).