LOPINAVIR

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Lopinavir (ABT-378) is an antiretroviral of the protease inhibitor class. It is used against HIV infections as a fixed-dose combination with another protease inhibitor, ritonavir, under the trade names Kaletra.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 protease 36	Inhibitor 8,504		1.3 pM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV infection 21	Primary		Approved 8,583	KALETRA
HPV positive with high grade squamous intraepithelial lesions 2	Primary		Phase II 1,147	LOPIMUNE

C_max

Value	Dose	Co-administered	Analyte	Population
6539 ng/mL	400 mg 2 times / day steady-state, oral	RITONAVIR	LOPINAVIR plasma	Homo sapiens
11.8 μg/mL	800 mg 1 times / day steady-state, oral	RITONAVIR	LOPINAVIR plasma	Homo sapiens
9.8 μg/mL	400 mg 2 times / day steady-state, oral	RITONAVIR	LOPINAVIR plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
60328 ng × h/mL	400 mg 2 times / day steady-state, oral	RITONAVIR	LOPINAVIR plasma	Homo sapiens
154.1 μg × h/mL	800 mg 1 times / day steady-state, oral	RITONAVIR	LOPINAVIR plasma	Homo sapiens
92.6 μg × h/mL	400 mg 2 times / day steady-state, oral	RITONAVIR	LOPINAVIR plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.4 h	400 mg 2 times / day steady-state, oral	RITONAVIR	LOPINAVIR plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.5%	400 mg 2 times / day steady-state, oral	RITONAVIR	LOPINAVIR plasma	Homo sapiens

Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31781	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31781
eMolecules	6719306	https://www.emolecules.com/cgi-bin/more?vid=6719306
MolPort	MolPort-003-848-410	https://www.molport.com/shop/molecule-link/MolPort-003-848-410
Selleck Chemicals	Lopinavir	http://www.selleckchem.com/products/Lopinavir.html
ZINC	ZINC000003951740	http://zinc15.docking.org/substances/ZINC000003951740

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PubMed

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Title	Date	PubMed
		12361546
Simultaneous determination of the new HIV protease inhibitor lopinavir (ABT 378) and of indinavir(1), amprenavir, saquinavir, ritonavir (ABT 538)(2) and nelfinavir(3) in human plasma by gradient HPLC.	2001	11596909
Antiviral drugs: current state of the art.	2001 Aug	11418355
Lopinavir/ritonavir.	2001 Mar-Apr	11296724
Resistant to everything.	2001 May	11682786

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Patents

Sample Use Guides

In Vivo Use Guide

Kaletra (combination of lopinavir and ritonavir) capsules and oral solution should be adminstered orally with food. Dosage for therapy-naïve adult patients KALETRA 400/100 mg (3 capsules or 5.0 mL) twice-daily taken with food or KALETRA 800/200 mg (6 capsules or 10 mL) once-daily taken with food. For therapy-experienced patients KALETRA 400/100 mg (3 capsules or 5.0 mL) twice-daily taken with food.

Route of Administration: Oral

In Vitro Use Guide

MT4 cells and wild-type virus stocks were obtained through the AIDS Research and Reference Reagent Program, AIDS Program, National Institute of Allergy and Infectious Diseases. For drug susceptibility assays, viruses were propagated in CEM cells and titers were determined in MT4 cells. Inhibition of viral replication and compound cytotoxicity were determined in parallel in MT4 cells by a standard colorimetric assay. The EC50s of lopinavir in the absence and presence of 50% human serum were 17 ± 4 and 102 ± 44 nM, respectively.

Substance Class	Chemical
Record UNII	2494G1JF75
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOPINAVIR

Official Name

English

KALETRA COMPONENT LOPINAVIR

Preferred Name

English

LOPINAVIR, (S-(2S,4S,5S))-

Common Name

English

KOLETRA

Common Name

English

Lopinavir [WHO-DD]

Common Name

English

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Classification Tree

Code System

Code

Protease inhibitors

WHO-ATC

J05AE06

Antivirals for treatment of HIV infections, combinations

WHO-ATC

J05AR10

Antiviral: HIV

LIVERTOX

NBK547961

Protease Inhibitors

NDF-RT

N0000000246

SEXUALLY TRANSMITTED DISEASES, VIRAL

EMA ASSESSMENT REPORTS

LOPINAVIR (AUHTORIZED: HIV INFECTIONS)

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Code System

Code

Type

Description

SMS_ID

100000089405

PRIMARY

INN

7798

PRIMARY

EVMPD

SUB02970MIG

PRIMARY

DRUG CENTRAL

1601

PRIMARY

WHO INTERNATIONAL PHARMACOPEIA

LOPINAVIR

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.

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