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S8451

Sigma-Aldrich

Saquinavir mesylate

≥98% (HPLC), powder

Synonym(s):

(2S)-N1[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-Dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]butanediamide methanesulfonate, Ro-31-8959

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About This Item

Empirical Formula (Hill Notation):
C38H50N6O5·CH4O3S
CAS Number:
149845-06-7
Molecular Weight:
766.95
MDL number:
MFCD00944907
UNSPSC Code:
12352200
PubChem Substance ID:
329824603
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to tan

solubility

DMSO: ≥5 mg/mL

originator

Roche

storage temp.

2-8°C

SMILES string

CS(O)(=O)=O.CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@@H](O)[C@H](Cc3ccccc3)NC(=O)[C@H](CC(N)=O)NC(=O)c4ccc5ccccc5n4

InChI

1S/C38H50N6O5.CH4O3S/c1-38(2,3)43-37(49)32-20-26-14-7-8-15-27(26)22-44(32)23-33(45)30(19-24-11-5-4-6-12-24)41-36(48)31(21-34(39)46)42-35(47)29-18-17-25-13-9-10-16-28(25)40-29;1-5(2,3)4/h4-6,9-13,16-18,26-27,30-33,45H,7-8,14-15,19-23H2,1-3H3,(H2,39,46)(H,41,48)(H,42,47)(H,43,49);1H3,(H,2,3,4)/t26-,27+,30-,31-,32-,33+;/m0./s1

InChI key

IRHXGOXEBNJUSN-YOXDLBRISA-N

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General description

Saquinavir is a peptidomimetic hydroxyethylamine inhibitor, which is used to treat human immunodeficiency virus (HIV) infection.

Application

Saquinavir mesylate may be used in cell signaling and immunology studies.

Biochem/physiol Actions

Saquinavir is an HIV Protease Inhibitor used in antiretroviral therapy. It inhibits both HIV-1 and HIV-2 proteases. Studies have also looked at saquinavir as a possible anti-cancer agent.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Filip Petković et al.
Journal of neuroimmunology, 259(1-2), 55-65 (2013-04-23)
NO-hybridization of the HIV protease inhibitor Saquinavir generates a new chemical entity named Saq-NO, that retains the anti-viral activity and exerts lower toxicity. We show that Saq-NO inhibited the generation of various cytokines in ConA-stimulated unfractionated murine spleen cells and
Ana Beloqui et al.
Journal of controlled release : official journal of the Controlled Release Society, 166(2), 115-123 (2012-12-26)
The aims of this work were (i) to evaluate the potential of nanostructured lipid carriers (NLCs) as a tool to enhance the oral bioavailability of poorly soluble compounds using saquinavir (SQV), a BCS class IV drug and P-gp substrate as
Martha Stefanidou et al.
Antimicrobial agents and chemotherapy, 56(8), 4381-4390 (2012-06-06)
The maturation of newly formed human immunodeficiency virus type 1 (HIV-1) virions is a critical step for the establishment of productive infection. We investigated the potential of saquinavir (SQV), a protease inhibitor (PI) used in highly active antiretroviral therapy (HAART)
David A Davis et al.
Antimicrobial agents and chemotherapy, 56(7), 3620-3628 (2012-04-18)
Inhibitors of HIV protease have proven to be important drugs in combination anti-HIV therapy. These inhibitors were designed to target mature protease and prevent viral particle maturation by blocking Gag and Gag-Pol processing by mature protease. Currently there are few
Zhiying Wang et al.
Journal of pharmaceutical sciences, 101(9), 3199-3213 (2012-05-23)
In an approach to overcome biological barriers mediated by P-glycoprotein (P-gp) and cytochrome P450 3A (CYP3A), a series of stereoisomeric valine-valine prodrugs of saquinavir (SQV) were synthesized and investigated with respect to affinity for efflux pump P-gp, and resistance to
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