Nelfinavir mesylate

Modify Date: 2024-01-03 10:43:16

Nelfinavir mesylate Structure
Nelfinavir mesylate structure
 Common Name Nelfinavir mesylate
CAS Number 159989-65-8 Molecular Weight 663.888
Density N/A Boiling Point 786.8ºC at 760 mmHg
Molecular Formula C33H49N3O7S2 Melting Point 131-135ºC
MSDS Chinese USA Flash Point 429.7ºC

 Use of Nelfinavir mesylate


Nelfinavir(AG-1341) is a potent and orally bioavailable human immunodeficiency virus HIV-1 protease inhibitor (Ki=2 nM) and is widely prescribed in combination with HIV reverse transcriptase inhibitors for the treatment of HIV infection. IC50 Valur: 2 nM (Ki for HIV-1 protease) [2]Target: HIV Proteasein vitro: In vitro exposure (72 hours) of HAECs to NEL (0.25-2 μg/mL) decreased both basal (2.5-fold) and insulin-induced NO production (4- to 5-fold). NEL suppressed insulin-induced phosphorylation of both Akt and eNOS at serine residues 473 and 1177, respectively. NEL decreased tyrosine phosphorylation of IR-β, IRS-1, and PI3K. Coexposure to troglitazone (TRO; 250 nM) ameliorated the suppressive effects of NEL on insulin signaling and NO production. Coexposure to TRO also increased eNOS expression in NEL-treated HAECs [1]. AG1343 is a potent enzyme inhibitor (Ki = 2 nM) and antiviral agent (HIV-1 ED50 = 14 nM). An X-ray cocrystal structure of the enzyme-AG1343 complex reveals how the novel thiophenyl ether and phenol-amide substituents of the inhibitor interact with the S1 and S2 subsites of HIV-1 protease, respectively [2].in vivo: In vivo studies indicate that AG1343 is well absorbed orally in a variety of species and possesses favorable pharmacokinetic properties in humans [2].

 Names

Name nelfinavir mesylate
Synonym More Synonyms

 Nelfinavir mesylate Biological Activity

Description Nelfinavir(AG-1341) is a potent and orally bioavailable human immunodeficiency virus HIV-1 protease inhibitor (Ki=2 nM) and is widely prescribed in combination with HIV reverse transcriptase inhibitors for the treatment of HIV infection. IC50 Valur: 2 nM (Ki for HIV-1 protease) [2]Target: HIV Proteasein vitro: In vitro exposure (72 hours) of HAECs to NEL (0.25-2 μg/mL) decreased both basal (2.5-fold) and insulin-induced NO production (4- to 5-fold). NEL suppressed insulin-induced phosphorylation of both Akt and eNOS at serine residues 473 and 1177, respectively. NEL decreased tyrosine phosphorylation of IR-β, IRS-1, and PI3K. Coexposure to troglitazone (TRO; 250 nM) ameliorated the suppressive effects of NEL on insulin signaling and NO production. Coexposure to TRO also increased eNOS expression in NEL-treated HAECs [1]. AG1343 is a potent enzyme inhibitor (Ki = 2 nM) and antiviral agent (HIV-1 ED50 = 14 nM). An X-ray cocrystal structure of the enzyme-AG1343 complex reveals how the novel thiophenyl ether and phenol-amide substituents of the inhibitor interact with the S1 and S2 subsites of HIV-1 protease, respectively [2].in vivo: In vivo studies indicate that AG1343 is well absorbed orally in a variety of species and possesses favorable pharmacokinetic properties in humans [2].
Related Catalog
References

[1]. Mondal D, et al. Nelfinavir suppresses insulin signaling and nitric oxide production by human aortic endothelial cells: protective effects of thiazolidinediones. Ochsner J. 2013 Spring;13(1):76-90.

[2]. Kaldor SW, et al. Viracept (nelfinavir mesylate, AG1343): a potent, orally bioavailable inhibitor of HIV-1 protease. J Med Chem. 1997 Nov 21;40(24):3979-85.

 Chemical & Physical Properties

Boiling Point 786.8ºC at 760 mmHg
Melting Point 131-135ºC
Molecular Formula C33H49N3O7S2
Molecular Weight 663.888
Flash Point 429.7ºC
Exact Mass 663.301208
PSA 189.95000
LogP 6.05210
Storage condition Store at +4°C

 Safety Information

Hazard Statements H413
Hazard Codes Xi
RIDADR NONH for all modes of transport

 Synthetic Route

Methanesulfonic acid structure

Methanesulfonic acid

CAS#:75-75-2
Nelfinavir structure

Nelfinavir

CAS#:159989-64-7

~99%

Nelfinavir mesylate Structure

Nelfinavir mesylate

CAS#:159989-65-8
Literature: AUROBINDO PHARMA LIMITED Patent: WO2008/41087 A1, 2008 ; Location in patent: Page/Page column 6 ;
ethyl-isopropyl ether structure

ethyl-isopropyl...

CAS#:67000-01-5
Nelfinavir structure

Nelfinavir

CAS#:159989-64-7

~97%

Nelfinavir mesylate Structure

Nelfinavir mesylate

CAS#:159989-65-8
Literature: Japan Tobacco Inc.; Agouron Pharmaceuticals, Inc. Patent: US5962704 A1, 1999 ;

 Synonyms

Methansulfonsäure--(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-{[(3-hydroxy-2-methylphenyl)carbonyl]amino}-4-(phenylsulfanyl)butyl]decahydroisochinolin-3-carboxamid(1:1)
Nelfinavir mesylate
(3S,4aS,8aS)-N-tert-Butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylsulfanyl)butyl]decahydroisoquinoline-3-carboxamide methanesulfonate (1:1)
(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylsulfanylbutyl]-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide,methanesulfonic acid
acide méthanesulfonique - (3S,4aS,8aS)-N-(1,1-diméthyléthyl)-2-[(2R,3R)-2-hydroxy-3-{[(3-hydroxy-2-méthylphényl)carbonyl]amino}-4-(phénylsulfanyl)butyl]décahydroisoquinoléine-3-carboxamide (1:1)
3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-, (3S,4aS,8aS)-, methanesulfonate (1:1) (salt)
MFCD00931436
(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide methanesulfonate (salt)
(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-{[(3-hydroxy-2-methylphenyl)carbonyl]amino}-4-(phenylsulfanyl)butyl]decahydroisoquinoline-3-carboxamide methanesulfonate (salt)
Nelfinavir mesylate hydrate
AZT/3TC/NLFR combination
(3S-(2(2S*,3S*),3-a,4ab,8ab))-N-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-3-isoquinolinecarboxamide monomethanesulfonate (salt)
(3S,4aS,8aS)-2-[(2R,3R)-2-Hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylsulfanyl)butyl]-N-(2-methyl-2-propanyl)decahydro-3-isoquinolinecarboxamide methanesulfonate (1:1)
Nelfinavir (Mesylate)
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