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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H48N4O5
Molecular Weight 628.8008
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOPINAVIR

SMILES

CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](CC2=CC=CC=C2)NC(=O)COC3=C(C)C=CC=C3C)CC4=CC=CC=C4

InChI

InChIKey=KJHKTHWMRKYKJE-SUGCFTRWSA-N
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

HIDE SMILES / InChI
Molecular Formula C37H48N4O5
Molecular Weight 628.8008
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:39:15 UTC 2023
Edited
by admin
on Fri Dec 15 15:39:15 UTC 2023
Record UNII
2494G1JF75
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOPINAVIR
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
LOPINAVIR, (S-(2S,4S,5S))-
Common Name English
KOLETRA
Common Name English
Lopinavir [WHO-DD]
Common Name English
LOPINAVIR COMPONENT OF KALETRA
Common Name English
(S)-N-((2S,4S,5S)-5-(2-(2,6-DIMETHYLPHENOXY)ACETAMIDO)-4-HYDROXY-1,6-DIPHENYLHEXAN-2-YL)-3-METHYL-2-(2-OXOTETRAHYDROPYRIMIDIN-1(2H)-YL)BUTANAMIDE
Systematic Name English
ALUVIRAN
Common Name English
A-157378.0
Code English
lopinavir [INN]
Common Name English
LOPINAVIR [ORANGE BOOK]
Common Name English
A-157378-0
Code English
LOPINAVIR [USP MONOGRAPH]
Common Name English
LOPINAVIR [WHO-IP]
Common Name English
LOPINAVIR [EMA EPAR]
Common Name English
(1S-(1R*(R*),3R*,4R*))-N-(4-(((2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYL-1-(PHENYLMETHYL)PENTYL)TETRAHYDRO-.ALPHA.-(1-METHYLETHYL)-2-OXO-1(2H)-PYRIMIDINEACETAMIDE
Common Name English
KALETRA COMPONENT LOPINAVIR
Common Name English
LOPINAVIR [MI]
Common Name English
LOPINAVIR [VANDF]
Common Name English
LOPINAVIR [USAN]
Common Name English
ABT-378
Code English
LOPINAVIR [USP-RS]
Common Name English
(αS)-Tetrahydro-N-[(αS)-α-[(2S,3S)-2-hydroxy-4-phenyl-3-[2-(2,6-xylyloxy)acetamido]butyl]phenethyl]-α-isopropyl-2-oxo-1(2H)-pyrimidineacetamide
Common Name English
LOPINAVIR [MART.]
Common Name English
LOPINAVIRUM [WHO-IP LATIN]
Common Name English
LOPINAVIR [EP MONOGRAPH]
Common Name English
LOPINAVIR [JAN]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AE06
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
WHO-ATC J05AR10
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
LIVERTOX NBK547961
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
NDF-RT N0000000246
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
EMA ASSESSMENT REPORTS LOPINAVIR (AUHTORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
WHO-VATC QJ05AR10
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LPV/R)
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
EMA ASSESSMENT REPORTS KALETRA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
NDF-RT N0000175889
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
NCI_THESAURUS C97366
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
Code System Code Type Description
SMS_ID
100000089405
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
INN
7798
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
EVMPD
SUB02970MIG
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
DRUG CENTRAL
1601
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
LOPINAVIR
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY Description: A white or almost white powder.Solubility: Freely soluble in methanol and dichloromethane, practically insoluble in water.Category: Antiretroviral (Protease Inhibitor).Storage: Lopinavir should be kept in a tightly closed container, protected from light.Additional information: Lopinavir is hygroscopic and is usually obtained in a hydrated form ; it may exhibit polymorphism.Definition: Lopinavir contains not less than 98.5% and not more than 101.5% of lopinavir (C37H48N4O5), calculated with reference to the anhydrous substance.
NDF-RT
N0000185503
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY P-Glycoprotein Inhibitors [MoA]
HSDB
8138
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
CHEBI
31781
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
DRUG BANK
DB01601
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
RXCUI
195088
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID8046456
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
NDF-RT
N0000190114
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
FDA UNII
2494G1JF75
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
LACTMED
Lopinavir
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
CAS
192725-17-0
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
MERCK INDEX
m6900
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C2095
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
RS_ITEM_NUM
1370101
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
MESH
D061466
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
ChEMBL
CHEMBL729
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
NDF-RT
N0000190107
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]
WIKIPEDIA
LOPINAVIR
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
USAN
KK-30
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
DAILYMED
2494G1JF75
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
PUBCHEM
92727
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
Related Record Type Details
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
Structure of LOPINAVIR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1
TARGET ORGANISM->INHIBITOR
OATP-8
TRANSPORTER -> INHIBITOR
OATP1B1
TRANSPORTER -> INHIBITOR
Structure of LOPINAVIR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Structure of LOPINAVIR MONOHYDRATE
SOLVATE->ANHYDROUS
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 PROTEASE
TARGET -> INHIBITOR
Related Record Type Details
Structure of DES(2-OXO-TETRAHYDROPYRIMIDINYL)-2-OXO-4-HYDROXY-TETRAHYDROPYRIMIDINYL LOPINAVIR
METABOLITE -> PARENT
MAJOR
Structure of 4-OXO-LOPINAVIR
METABOLITE -> PARENT
MAJOR
Structure of DES(2-OXO-TETRAHYDROPYRIMIDINYL)-2-OXO-4-HYDROXY-TETRAHYDROPYRIMIDINYL LOPINAVIR
METABOLITE -> PARENT
LOPINAVIR Impurity C. Amount not specified.
Related Record Type Details
Structure of ISOLOPINAVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of LOPINAVIR N-FORMYLAMINOALCOHOL
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (2S)-N-((1S,3S,4S)-1-BENZYL-4-((2-(2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYLPENTYL)-2-(3-(2-(2,6-DIMETHYLPHENOXY)ACETYL)-2-OXOTETRAHYDROPYRIMIDIN-1(2H)-YL)-3-METHYLBUTANAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of TS-97
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N-((2S,3S,5S)-5-ACETAMIDO-3-HYDROXY-1,6-DIPHENYLHEXAN-2-YL)-2-(2,6-DIMETHYLPHENOXY)ACETAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N,N'-(ETHENE-1,2-DIYL)BIS(2-(2,6-DIMETHYLPHENOXY)ACETAMIDE), (Z)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N,N'-(ETHENE-1,2-DIYL)BIS(2-(2,6-DIMETHYLPHENOXY)ACETAMIDE), (Z)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of LOPINAVIR 2,4-PHENOXY ISOMER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N-((S)-1-((4S,6S)-4-BENZYL-2-OXO-1,3-OXAZINAN-6-YL)-2-PHENYLETHYL)-2-(2,6-DIMETHYLPHENOXY)ACETAMIDE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of SULFOLOPINAVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N-((2S,3S,5S)-5-AMINO-3-HYDROXY-1,6-DIPHENYLHEXAN-2-YL)-2-(2,6-DIMETHYLPHENOXY)ACETAMIDE
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of TS-97
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of TS-97
IMPURITY -> PARENT
LOPINAVIR Impurity H. Amount not specified.
Structure of LOPINAVIR, (2R,4R) DIASTEREOMER-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of LOPINAVIR DIVALINATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of LOPINAVIR, (4R) EPIMER-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of LOPINAVIR 2,4-PHENOXY ISOMER
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of N-((2S,3S,5S)-5-ACETAMIDO-3-HYDROXY-1,6-DIPHENYLHEXAN-2-YL)-2-(2,6-DIMETHYLPHENOXY)ACETAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ISOLOPINAVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2-(2,6-DIMETHYLPHENOXY)-N-((2S,3S,5S)-5-FORMAMIDO-3-HYDROXY-1,6-DIPHENYLHEXAN-2-YL)ACETAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N,N'-BIS((1S,3S,4S)-1-BENZYL-4-((2-(2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYLPENTYL)UREA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N-((1S,3S,4S)-4-((2-(2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYL-1-(PHENYLMETHYL)PENTYL)TETRAHYDRO-.ALPHA.-(2-METHYLPROPYL)-2-OXO-1(2H)-PYRIMIDINEACETAMIDE, (.ALPHA.S)-
IMPURITY -> PARENT
LOPINAVIR Impurity G. Amount not specified.
Structure of N,N'-BIS((1S,3S,4S)-1-BENZYL-4-((2-(2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYLPENTYL)UREA
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of Lopinavir carboxymethyl dimer
IMPURITY -> PARENT
LOPINAVIR Impurity D. Amount not specified.
Structure of LOPINAVIR, (4R) EPIMER-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of LOPINAVIR FREE AMINE
IMPURITY -> PARENT
LOPINAVIR Impurity A. Amount not specified.
Structure of N-((S)-1-((4S,6S)-4-BENZYL-2-OXO-1,3-OXAZINAN-6-YL)-2-PHENYLETHYL)-2-(2,6-DIMETHYLPHENOXY)ACETAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2-(2-(2,6-DIMETHYLPHENOXY)ACETAMIDO)-5-((S)-3-METHYL-2-(2-OXOTETRAHYDROPYRIMIDIN-1(2H)-YL)BUTANAMIDO(-1,6-DIPHENYLHEXAN-3-YL 2-(2,6-DIMETHYLPHENOXY)ACETATE, (2S,3S,5S)-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of (2,6-DIMETHYLPHENOXY)ACETIC ACID
IMPURITY -> PARENT
LOPINAVIR Impurity B. Amount not specified.
Structure of LOPINAVIR (2R) EPIMER
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 2-(2-(2,6-DIMETHYLPHENOXY)ACETAMIDO)-5-((S)-3-METHYL-2-(2-OXOTETRAHYDROPYRIMIDIN-1(2H)-YL)BUTANAMIDO(-1,6-DIPHENYLHEXAN-3-YL 2-(2,6-DIMETHYLPHENOXY)ACETATE, (2S,3S,5S)-
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of LOPINAVIR, (2R,4R) DIASTEREOMER-
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of LOPINAVIR, D-VALINE DIASTEREOMER-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of LOPINAVIR (2R) EPIMER
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (2S)-N-((1S,3S,4S)-1-BENZYL-4-((2-(2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYLPENTYL)-2-(3-(2-(2,6-DIMETHYLPHENOXY)ACETYL)-2-OXOTETRAHYDROPYRIMIDIN-1(2H)-YL)-3-METHYLBUTANAMIDE
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (2S)-N-((1S,3S,4S)-1-BENZYL-4-((2-(2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYLPENTYL)-2-(3-(2-(2,6-DIMETHYLPHENOXY)ACETYL)-2-OXOTETRAHYDROPYRIMIDIN-1(2H)-YL)-3-METHYLBUTANAMIDE
IMPURITY -> PARENT
LOPINAVIR Impurity I. Amount not specified.
Structure of 4-OXO-LOPINAVIR
IMPURITY -> PARENT
Structure of 2-(2,6-DIMETHYLPHENOXY)-N-((2S,3S,5S)-5-FORMAMIDO-3-HYDROXY-1,6-DIPHENYLHEXAN-2-YL)ACETAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of LOPINAVIR FREE AMINE
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.6
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of LOPINAVIR, D-VALINE DIASTEREOMER-
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
Structure of LOPINAVIR
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