AB1

N-{1-BENZYL-4-[2-(2,6-DIMETHYL-PHENOXY)-ACETYLAMINO]-3-HYDROXY-5-PHENYL-PENTYL}-3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRAMIDE

Created:	2002-09-24
Last modified:	2020-05-26

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15 entries where AB1 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	94
Chiral Atom Count	4
Bond Count	97
Aromatic Bond Count	18

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Chemical Component Summary
Name	N-{1-BENZYL-4-[2-(2,6-DIMETHYL-PHENOXY)-ACETYLAMINO]-3-HYDROXY-5-PHENYL-PENTYL}-3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRAMIDE
Synonyms	ABT-378; LOPINAVIR
Systematic Name (OpenEye OEToolkits)	(2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)ethanoylamino]-4-hydroxy-1,6-diphenyl-hexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide
Formula	C₃₇ H₄₈ N₄ O₅
Molecular Weight	628.801
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(NC(Cc1ccccc1)C(O)CC(NC(=O)C(N2C(=O)NCCC2)C(C)C)Cc3ccccc3)COc4c(cccc4C)C
SMILES	CACTVS	3.341	CC(C)[CH](N1CCCNC1=O)C(=O)N[CH](C[CH](O)[CH](Cc2ccccc2)NC(=O)COc3c(C)cccc3C)Cc4ccccc4
SMILES	OpenEye OEToolkits	1.5.0	Cc1cccc(c1OCC(=O)NC(Cc2ccccc2)C(CC(Cc3ccccc3)NC(=O)C(C(C)C)N4CCCNC4=O)O)C
Canonical SMILES	CACTVS	3.341	CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)COc3c(C)cccc3C)Cc4ccccc4
Canonical SMILES	OpenEye OEToolkits	1.5.0	Cc1cccc(c1OCC(=O)N[C@@H](Cc2ccccc2)[C@H](C[C@H](Cc3ccccc3)NC(=O)[C@H](C(C)C)N4CCCNC4=O)O)C
InChI	InChI	1.03	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
InChIKey	InChI	1.03	KJHKTHWMRKYKJE-SUGCFTRWSA-N

Drug Info: DrugBank

DrugBank ID	DB01601
Name	Lopinavir
Groups	approved
Description	Lopinavir is an antiretroviral protease inhibitor used in combination with other antiretrovirals in the treatment of HIV-1 infection.[L11163] Lopinavir is marketed and administered exclusively in combination with [ritonavir] - this combination, first marketed by Abbott under the brand name Kaletra in 2000, is necessary due to lopinavir's poor oral bioavailability and extensive biotransformation. Ritonavir is a potent inhibitor of the enzymes responsible for lopinavir metabolism, and its co-administration "boosts" lopinavir exposure and improves antiviral activity.[L11163] Like many other protease inhibitors (e.g. [saquinavir], [nelfinavir]), lopinavir is a peptidomimetic molecule - it contains a hydroxyethylene scaffold that mimics the peptide linkage typically targeted by the HIV-1 protease enzyme but which itself cannot be cleaved, thus preventing the activity of the HIV-1 protease.[A191757] Lopinavir was previously under investigation in combination with ritonavir for the treatment of COVID-19 caused by SARS-CoV-2.[L12012]
Synonyms	Lopinavir
Brand Names	Lopinavir and ritonavir Lopinavir/ritonavir Mylan Lopinavir-Ritonavir Lopinavir and Ritonavir Kaletra
Indication	The combination product lopinavir/ritonavir, marketed under the brand name Kaletra, is indicated in combination with other antiretrovirals for the treatment of HIV-1 infection in adults and pediatric patients ≥14 days old.[L11163]
Categories	Anti-HIV Agents Anti-Infective Agents Anti-Retroviral Agents Antiinfectives for Systemic Use Antiviral Agents Antivirals for Systemic Use Antivirals used in combination for the treatment of HIV infections BSEP/ABCB11 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2B6 Inhibitors Cytochrome P-450 CYP2B6 Inhibitors (strength unknown) Cytochrome P-450 CYP2B6 Inhibitors (weak) Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 Inhibitors (weak) Cytochrome P-450 CYP2C9 Inducers Cytochrome P-450 CYP2C9 Inducers (strength unknown) Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (weak) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strong) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Direct Acting Antivirals Enzyme Inhibitors Experimental Unapproved Treatments for COVID-19 HIV Protease Inhibitors Hyperglycemia-Associated Agents Nephrotoxic agents OATP1B1/SLCO1B1 Inhibitors OATP1B3 inhibitors Organic Anion Transporting Polypeptide 1B1 Inhibitors P-glycoprotein inducers P-glycoprotein inhibitors Potential QTc-Prolonging Agents Protease Inhibitors Pyrimidinones QTc Prolonging Agents Viral Protease Inhibitors
ATC-Code	J05AR10
CAS number	192725-17-0

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Human immunodeficiency virus type 1 protease	PQVTLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKMIGGI...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate,inhibitor
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	inhibitor
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	inhibitor,inducer
Cytochrome P450 3A Subfamily	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	inhibitor
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor,inducer
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	inhibitor
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682