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Saquinavir mesylate (Ro-31-8959; Invirase; Fortovase),an HIV Protease Inhibitor, is an antiretroviral drug used together with other medications to treat or prevent HIV/AIDS. Typically it is used with ritonavir or lopinavir/ritonavir to increase its affect. It is in the protease inhibitor class and works by blocking the HIV protease. Saquinavir was first sold in 1995.
Physicochemical Properties
| Molecular Formula | C39H54N6O8S |
| Molecular Weight | 766.9465 |
| Exact Mass | 766.372 |
| Elemental Analysis | C, 61.08; H, 7.10; N, 10.96; O, 16.69; S, 4.18 |
| CAS # | 149845-06-7 |
| Related CAS # | Saquinavir;127779-20-8 |
| PubChem CID | 60934 |
| Appearance | White to off-white solid powder |
| Boiling Point | 1015ºC at 760 mmHg |
| Flash Point | 567.7ºC |
| Vapour Pressure | 0mmHg at 25°C |
| LogP | 5.488 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 13 |
| Heavy Atom Count | 54 |
| Complexity | 1230 |
| Defined Atom Stereocenter Count | 6 |
| SMILES | S(C([H])([H])[H])(=O)(=O)O[H].O=C([C@]1([H])C([H])([H])[C@]2([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]2([H])C([H])([H])N1C([H])([H])[C@]([H])([C@]([H])(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])N([H])C([C@]([H])(C([H])([H])C(N([H])[H])=O)N([H])C(C1C([H])=C([H])C2=C([H])C([H])=C([H])C([H])=C2N=1)=O)=O)O[H])N([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] |
| InChi Key | IRHXGOXEBNJUSN-YOXDLBRISA-N |
| InChi Code | 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 |
| Chemical Name | (S)-N1-((2S,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-phenylbutan-2-yl)-2-(quinoline-2-carboxamido)succinamide mesylate |
| Synonyms | trade names: Invirase and Fortovase; Ro 31-8959; Ro 31-8959/000; Ro 318959; Sch 52852; Sch-52852; Sch52852; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References |
[1]. Kaldor\net al (1995) Isophthalic acid derivatives: amino acid surrogates for\nthe inhibition of HIV-1 protease. Bioorg.Med.Chem.Lett. 5 721. [2]. Yerino\nGA, Halabe EK, Zini E, Feleder EC.\nBioequivalence study of two oral tablet formulations containing\nsaquinavir mesylate boosted with ritonavir in healthy male subjects.\nArzneimittelforschung. 2011;61(8):481-7. [3]. Branham ML, Moyo T, Govender T.\nPreparation and solid-state characterization of ball milled saquinavir mesylate for solubility enhancement.\nEur J Pharm Biopharm. 2012 Jan;80(1):194-202. [4]. Brouwers\nJ, Vermeire K, Grammen C, Schols D, Augustijns P.\nEarly identification of availability issues for poorly water-soluble\nmicrobicide candidates in biorelevant media: a case study with\nsaquinavir.\nAntiviral Res. 2011 Aug;91(2):217-23. |
| Additional Infomation |
Saquinavir mesylate is an organic molecular entity. Saquinavir Mesylate is the mesylate salt form of saquinavir, a peptidomimetic inhibitor of human immunodeficiency virus (HIV) protease. An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A. See also: Saquinavir (has active moiety). |
Solubility Data
| Solubility (In Vitro) | DMSO: ~20 mg/mL (~26.08 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2 mg/mL (2.61 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2 mg/mL (2.61 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2 mg/mL (2.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.3039 mL | 6.5193 mL | 13.0387 mL | |
| 5 mM | 0.2608 mL | 1.3039 mL | 2.6077 mL | |
| 10 mM | 0.1304 mL | 0.6519 mL | 1.3039 mL |