Saquinavir mesylate

Names

[ Name ]:
Saquinavir mesylate

[Synonym ]:
L-aspartamide, N-[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-N-(2-quinolinylcarbonyl)-, methanesulfonate (1:1)
Saquinavir mesilate
acide méthanesulfonique - (2S)-N-{(1S,2R)-1-benzyl-3-[(3S,4aS,8aS)-3-[(1,1-diméthyléthyl)carbamoyl]octahydroisoquinoléin-2(1H)-yl]-2-hydroxypropyl}-2-[(quinoléin-2-ylcarbonyl)amino]butanediamide (1:1)
Saquinavir monomethanesulfonate salt
N-{(2S,3R)-3-Hydroxy-4-[(3S,4aS,8aS)-3-[(2-methyl-2-propanyl)carbamoyl]octahydro-2(1H)-isoquinolinyl]-1-phenyl-2-butanyl}-N-(2-quinolinylcarbonyl)-L-aspartamide methanesulfonate (1:1)
N-{(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-Butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}-N-(quinolin-2-ylcarbonyl)-L-aspartamide methanesulfonate (1:1)
N-{(1S,2R)-1-benzyl-3-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-2-hydroxypropyl}-N-(quinolin-2-ylcarbonyl)-L-aspartamide methanesulfonate (salt)
(2S)-N-{(1S,2R)-1-benzyl-3-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-2-hydroxypropyl}-2-[(quinolin-2-ylcarbonyl)amino]butanediamide methanesulfonate (salt)
Methansulfonsäure--(2S)-N-{(1S,2R)-1-benzyl-3-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisochinolin-2(1H)-yl]-2-hydroxypropyl}-2-[(chinolin-2-ylcarbonyl)amino]butandiamid(1:1)
Saquinavir Mesylate
MFCD00944907
L-aspartamide, N-[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-N-(2-quinolinylcarbonyl)-, methanesulfonate (1:1) (salt)
N1-{(1S,2R)-1-benzyl-3-[(3S,4aS,8aS)-3-[(tert-butylamino)carbonyl]octahydroisoquinolin-2(1H)-yl]-2-hydroxypropyl}-N2-(quinolin-2-ylcarbonyl)-L-aspartamide methanesulfonate (salt)
acide méthanesulfonique - (2S)-N-{(1S,2R)-1-benzyl-3-[(3S,4aS,8aS)-3-[(1,1-diméthyléthyl)carbamoyl]octahydroisoquinoléin-2(1H)-yl]-2-hydroxypropyl}-2-[(quinoléin-2-ylcarbonyl)amino]butanediamide (1
L-Aspartamide, N-[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-N-(2-quinolinylcarbonyl)-, methanesulfonate (1:1) ; (salt)

Biological Activity

[Description]:

Saquinavir mesylate is an HIV Protease Inhibitor used in antiretroviral therapy. IC50 Value:Target: HIV ProteaseSaquinavir is a protease inhibitor. Proteases are enzymes that cleave protein molecules into smaller fragments. HIV protease is vital for both viral replication within the cell and release of mature viral particles from an infected cell. Saquinavir binds to the active site of the viral protease and prevents cleavage of viral polyproteins, preventing maturation of the virus. Saquinavir inhibits both HIV-1 and HIV-2 proteases.Studies have also looked at Saquinavir as a possible anti-cancer agent.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> HIV Protease

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

[References]

[1]. Kaldor et al (1995) Isophthalic acid derivatives: amino acid surrogates for the inhibition of HIV-1 protease. Bioorg.Med.Chem.Lett. 5 721.

[2]. Yerino GA, Halabe EK, Zini E, Feleder EC.Bioequivalence study of two oral tablet formulations containing saquinavir mesylate boosted with ritonavir in healthy male subjects.Arzneimittelforschung. 2011;61(8):481-7.

[3]. Branham ML, Moyo T, Govender T.Preparation and solid-state characterization of ball milled saquinavir mesylate for solubility enhancement.Eur J Pharm Biopharm. 2012 Jan;80(1):194-202.

[4]. Brouwers J, Vermeire K, Grammen C, Schols D, Augustijns P.Early identification of availability issues for poorly water-soluble microbicide candidates in biorelevant media: a case study with saquinavir.Antiviral Res. 2011 Aug;91(2):217-23.

[5]. Knechten H, Lutz T, Pulik P, Martin T, Tappe A, Jaeger H.Safety and Efficacy in HIV-1-Infected Patients Treated with Ritonavir-Boosted Saquinavir Mesylate.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
1015ºC at 760 mmHg

[ Molecular Formula ]:
C₃₉H₅₄N₆O₈S

[ Molecular Weight ]:
766.946

[ Flash Point ]:
567.7ºC

[ Exact Mass ]:
766.372375

[ PSA ]:
229.50000

[ LogP ]:
5.48810

[ Vapour Pressure ]:
0mmHg at 25°C

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

Intranasal in situ gel loaded with saquinavir mesylate nanosized microemulsion: preparation, characterization, and in vivo evaluation.

Int. J. Pharm. 475(1-2) , 191-7, (2014)

Saquinavir mesylate (SM) is a protease inhibitor with activity against human immunodeficiency virus type 1 (HIV-1) and is available in tablet form, which has three major problems. First, the drug unde...

Saquinavir-NO-targeted S6 protein mediates sensitivity of androgen-dependent prostate cancer cells to TRAIL.

Cell Cycle 11(6) , 1174-82, (2012)

We previously reported that the NO-modified form of HIV protease inhibitor Saquinavir (Saq) is a potent antitumoral agent efficient against numerous tumor cell lines in vitro and in vivo. In acute tox...

Can inhibition of proteasomes or NF-kappaB help control idiopathic nephrotic syndrome?

Nephrol. Dial. Transplant. 27(5) , 1698-701, (2012)