CAS No.192725-17-0,Lopinavir Suppliers

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Basic Information

Molecular Structure:
CAS No.:	192725-17-0
Name:	Lopinavir
Article Data:	20

Formula:	C₃₇H₄₈N₄O₅
Molecular Weight:	628.812
Synonyms:	1(2H)-Pyrimidineacetamide,N-[(1S,3S,4S)-4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-a-(1-methylethyl)-2-oxo-, (aS)- (9CI);1(2H)-Pyrimidineacetamide,N-[4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-a-(1-methylethyl)-2-oxo-, [1S-[1R(R),3R,4R]]-;A157378.0;ABT 378;Aluviran;Koletra;1(2H)-Pyrimidineacetamide,N-[(1S,3S,4S)-4-[[2-(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-a-(1-methylethyl)-2-oxo-, (aS)-;Intermediates of Lopinavir;
Density:	1.163 g/cm³
Melting Point:	124-127 °C
Boiling Point:	924.1 °C at 760 mmHg
Flash Point:	512.7 °C
Appearance:	white crystalline solid
Hazard Symbols:	Xi
PSA:	120.00000
LogP:	4.39310

Synthetic route

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

: C13H14N2O2

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
In ethyl acetate at 25℃; for 8h; Solvent;	97%

: C28H40N4O2*C5H7NO3

: C13H14N2O2

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
In dichloromethane at 25℃; for 8h; Solvent;	96%

: 224648-11-7
N-(2,6-dimethyl-phenyloxy acetyloxy)succinimide

: C28H40N4O2*C5H7NO3

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	96%

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

: 224648-11-7
N-(2,6-dimethyl-phenyloxy acetyloxy)succinimide

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	96%

: 192800-77-4
2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride

: 192725-49-8
(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With 1H-imidazole In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃; Reagent/catalyst; Inert atmosphere;	92%
With 1H-imidazole; dmap In ethyl acetate; N,N-dimethyl-formamide at 0 - 10℃; for 14h;

: C28H40N4O2*C5H7NO3

: C19H19NO5

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	92%

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

: C19H19NO5

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	92%

: 192725-49-8
(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane

: 192725-50-1
(S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Stage #1: (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane; (S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid With thionyl chloride In dichloromethane at 0℃; for 2h; Reflux; Stage #2: With triethylamine In dichloromethane at 0 - 20℃; for 5h;	90.1%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide	70%

: C28H40N4O2*C5H7NO3

: C18H15NO5

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 25℃; for 8h; Solvent;	89%

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

: C18H15NO5

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	89%

Raw Materials

72-18-4

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Chemistry

IUPAC Name: (2S)-N-[(2S,4S,5S)-5-[[2-(2,6-Dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide
Formula: C₃₇H₄₈N₄O₅
Molecular Weight: 628.8 g/mol
Molecular Structure of Lopinavir (CAS NO.192725-17-0):

Melting Point: 124-127 °C
Flash Point: 512.7 °C
Boiling Point: 924.1 °C at 760 mmHg
Density: 1.163 g/cm³
Enthalpy of Vaporization: 140.81 kJ/mol
Appearance: white crystalline solid
Index of Refraction: 1.577
Molar Refractivity: 179.17 cm³
Molar Volume: 540.4 cm³
Surface Tension: 49.4 dyne/cm
XLogP3-AA: 5.9
H-Bond Donor: 4
H-Bond Acceptor: 5
Rotatable Bond Count: 15
Tautomer Count: 8
Exact Mass: 628.362471
MonoIsotopic Mass: 628.362471
Topological Polar Surface Area: 120
Heavy Atom Count: 46
Product Categories: Anti-viral Compounds;Anti-virals;Intermediates & Fine Chemicals;Non-nucleoside Reverse Transcriptase;Pharmaceuticals

History

In an attempt to improve on the HIV resistance and serum protein-binding properties of the company's earlier protease inhibitor, ritonavir, Lopinavir was developed by Abbott. Abbott pursued a strategy of co-administering lopinavir with sub-therapeutic doses of ritonavir, and lopinavir is only marketed as a co-formulation with ritonavir. It is the first multi-drug capsule to contain a drug not available individually. Lopinavir/ritonavir was approved by the US FDA on 15 September 2000, and in Europe in April 2001. On June 26, 2016, Its patent will expire in the US. Abbott Laboratories was one of the earliest users of the Advanced Photon Source, a national synchrotron-radiation light source at Argonne National Laboratory. One of the early research projects undertaken at the Advanced Photon Source was the Human Immunodeficiency Virus. Using X-ray crystallography, researchers found the points of attack of the HIV protease inhibitors–agents that block the breakdown of proteins. Protease inhibitors stop HIV from making new copies of itself by blocking the last step in the process, when the virus attempts to replicate - and out of that discovery came the drug Kaletra.

Uses

Lopinavir (CAS NO.192725-17-0) is used as a selective HIV protease inhibitor. It is also used as an analogue of Ritonavir.

Specification

The chemical synonyms of Lopinavir (CAS NO.192725-17-0) is also named as (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 ; (alphaS)-Tetrahydro-N-((alphaS)-alpha-((2S,3S)-2-hydroxy-4-phenyl-3-(2-(2,6-xylyloxy)acetamido)butyl)phenethyl)-alpha-isopropyl-2-oxo-1(2H)-pyrimidineacetamide ; A 157378.0 ; ABT 378 ; ABT-378 ; UNII-2494G1JF75 .