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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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Can inhibition of proteasomes or NF-kappaB help control idiopathic nephrotic syndrome?
Scott E Wenderfer
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association, 27(5), 1698-1701 (2012-05-02)
Rowena E Martin et al.
Antimicrobial agents and chemotherapy, 56(5), 2283-2289 (2012-02-23)
The antiretroviral protease inhibitors (APIs) ritonavir, saquinavir, and lopinavir, used to treat HIV infection, inhibit the growth of Plasmodium falciparum at clinically relevant concentrations. Moreover, it has been reported that these APIs potentiate the activity of chloroquine (CQ) against this
Rosanna Coppo et al.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association, 27(5), 1902-1910 (2012-03-21)
Some difficult cases of idiopathic nephrotic syndrome (NS) have been treated with a HIV protease inhibitor provided with proteasome-inhibiting activity. The objective of this study was to limit nuclear factor κB (NF-κB) activation which is up-regulated in these patients, aiming
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
Danijela Maksimovic-Ivanic et al.
Immunologic research, 52(1-2), 157-168 (2012-03-13)
Development of resistance to TRAIL-induced toxicity is one of the strategies used from tumor cells to escape destruction from the immune system. This process may occur through aberrant expression of functional receptors, overexpression of decoy receptors on tumor cell membrane
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