CAS 192725-17-0|Lopinavir

Introduction：Basic information about CAS 192725-17-0|Lopinavir, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Lopinavir BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles3
6. Synonyms

Common Name	Lopinavir
CAS Number	192725-17-0	Molecular Weight	628.801
Density	1.2±0.1 g/cm3	Boiling Point	924.2±65.0 °C at 760 mmHg
Molecular Formula	C₃₇H₄₈N₄O₅	Melting Point	124-127°C
MSDS	ChineseUSA	Flash Point	512.7±34.3 °C

Names

Name	lopinavir
Synonym	More Synonyms

Lopinavir BiologicalActivity

Description	Lopinavir is a potent HIV protease inhibitor with Ki of 1.3 pM.Target: HIV proteaseLopinavir is a potent inhibitor of Rh123 efflux in Caco-2 monolayers with IC50 of 1.7 mM. Lopinavir exposure (72 hours) in LS 180V cells reduces the content of intracellular Rh123. Lopinavir induces P-glycoprotein immunoreactive protein and messenger RNA levels in LS 180V cells. Lopinavir inhibits subtype C clone C6 with IC50 of 9.4 nM. Lopinavir inhibits CYP3A with IC50 of 7.3 mM in human liver microsomes, while produces negligible or weak inhibition of human CYP1A2, 2B6, 2C9, 2C19 and 2D6. Lopinavir (10 mg/kg, orally) results in Cmax of 0.8 μg/mL and oral bioavailability of 25% in rats.
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>HIV ProteaseSignaling Pathways >>Anti-infection >>HIVResearch Areas >>Inflammation/Immunology
References	[1]. Vishnuvardhan, D., et al., Lopinavir: acute exposure inhibits P-glycoprotein; extended exposure induces P-glycoprotein. AIDS, 2003. 17(7): p. 1092-4. [2]. Gonzalez, L.M., et al., In vitro hypersusceptibility of human immunodeficiency virus type 1 subtype C protease to lopinavir. Antimicrob Agents Chemother, 2003. 47(9): p. 2817-22. [3]. Weemhoff, J.L., et al., Apparent mechanism-based inhibition of human CYP3A in-vitro by lopinavir. J Pharm Pharmacol, 2003. 55(3): p. 381-6. [4]. Sham, H.L., et al., ABT-378, a highly potent inhibitor of the human immunodeficiency virus protease. Antimicrob Agents Chemother, 1998. 42(12): p. 3218-24.

Description

Lopinavir is a potent HIV protease inhibitor with Ki of 1.3 pM.Target: HIV proteaseLopinavir is a potent inhibitor of Rh123 efflux in Caco-2 monolayers with IC50 of 1.7 mM. Lopinavir exposure (72 hours) in LS 180V cells reduces the content of intracellular Rh123. Lopinavir induces P-glycoprotein immunoreactive protein and messenger RNA levels in LS 180V cells. Lopinavir inhibits subtype C clone C6 with IC50 of 9.4 nM. Lopinavir inhibits CYP3A with IC50 of 7.3 mM in human liver microsomes, while produces negligible or weak inhibition of human CYP1A2, 2B6, 2C9, 2C19 and 2D6. Lopinavir (10 mg/kg, orally) results in Cmax of 0.8 μg/mL and oral bioavailability of 25% in rats.

Related Catalog

Signaling Pathways >>Metabolic Enzyme/Protease >>HIV ProteaseSignaling Pathways >>Anti-infection >>HIVResearch Areas >>Inflammation/Immunology

References

[1]. Vishnuvardhan, D., et al., Lopinavir: acute exposure inhibits P-glycoprotein; extended exposure induces P-glycoprotein. AIDS, 2003. 17(7): p. 1092-4.

[2]. Gonzalez, L.M., et al., In vitro hypersusceptibility of human immunodeficiency virus type 1 subtype C protease to lopinavir. Antimicrob Agents Chemother, 2003. 47(9): p. 2817-22.

[3]. Weemhoff, J.L., et al., Apparent mechanism-based inhibition of human CYP3A in-vitro by lopinavir. J Pharm Pharmacol, 2003. 55(3): p. 381-6.

[4]. Sham, H.L., et al., ABT-378, a highly potent inhibitor of the human immunodeficiency virus protease. Antimicrob Agents Chemother, 1998. 42(12): p. 3218-24.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	924.2±65.0 °C at 760 mmHg
Melting Point	124-127°C
Molecular Formula	C₃₇H₄₈N₄O₅
Molecular Weight	628.801
Flash Point	512.7±34.3 °C
Exact Mass	628.362488
PSA	120.00000
LogP	6.26
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.577
InChIKey	KJHKTHWMRKYKJE-SUGCFTRWSA-N
SMILES	Cc1cccc(C)c1OCC(=O)NC(Cc1ccccc1)C(O)CC(Cc1ccccc1)NC(=O)C(C(C)C)N1CCCNC1=O
Storage condition	Hygroscopic, -20°C Freezer, Under inert atmosphere
Stability	Hygroscopic

Safety Information

Hazard Codes	Xi
RIDADR	NONH for all modes of transport

Articles3

ABT-378, a highly potent inhibitor of the human immunodeficiency virus protease.

Antimicrob. Agents Chemother. 42(12) , 3218-24, (1998)

The valine at position 82 (Val 82) in the active site of the human immunodeficiency virus (HIV) protease mutates in response to therapy with the protease inhibitor ritonavir. By using the X-ray crysta...

HIV-1 subtype influences susceptibility and response to monotherapy with the protease inhibitor lopinavir/ritonavir.

J. Antimicrob. Chemother. 70(1) , 243-8, (2015)

PI susceptibility results from a complex interplay between protease and Gag proteins, with Gag showing wide variation across HIV-1 subtypes. We explored the impact of pre-treatment susceptibility on t...

Antiretroviral therapy response among HIV-2 infected patients: a systematic review.

BMC Infect. Dis. 14 , 461, (2014)

Few data are available on antiretroviral therapy (ART) response among HIV-2 infected patients. We conducted a systematic review on treatment outcomes among HIV-2 infected patients on ART, focusing on ...

Synonyms

1(2H)-Pyrimidineacetamide, N-[(1S,3S,4S)-4-[[2-(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-α-(1-methylethyl)-2-oxo-, (αS)-

(2S)-N-[(2S,4S,5S)-5-{[(2,6-Dimethylphenoxy)acetyl]amino}-4-hydroxy-1,6-diphenyl-2-hexanyl]-3-methyl-2-(2-oxotetrahydro-1(2H)-pyrimidinyl)butanamide

(2S)-N-[(1S,3S,4S)-1-benzyl-4-{[(2,6-diméthylphénoxy)acétyl]amino}-3-hydroxy-5-phénylpentyl]-3-méthyl-2-(2-oxotétrahydropyrimidin-1(2H)-yl)butanamide

ABT 378

(2S)-N-[(1S,3S,4S)-1-Benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-hydroxy-5-phenylpentyl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamid

Lopinavir

Aluviran

1(2H)-pyrimidineacetamide, N-[(1S,3S,4S)-4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-α-(1-methylethyl)-2-oxo-, (αS)-

(aS)-Tetrahydro-N-((aS)-a-((2S,3S)-2-hydroxy-4-phenyl-3-(2-(2,6-xylyloxy)acetamido)butyl)phenethyl)-a-isopropyl-2-oxo-1(2H)-pyrimidineacetamide

Koletr

(2S)-N-[(1S,3S,4S)-1-benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-hydroxy-5-phenylpentyl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide

(2S)-N-[(2S,4S,5S)-5-{[(2,6-Dimethylphenoxy)acetyl]amino}-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide

ABT 378/r

Koletra

MFCD04973616

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