Saquinavir

  Saquinavir (CAS No.127779-20-8) was the first protease inhibitor (and sixth antiretroviral) ,which was approved on December 6, 1995 by the Food and Drug Administration (FDA) .
  It was approved again on Nov 7, 1997 as Fortovase, a soft gel capsule reformulated for improved bioavailability.
  Roche announced in May 2005 that, owing to reduction in demand, Fortovase would cease being marketed early in 2006 in favour of Invirase boosted with ritonavir.

The Saquinavir, with the CAS registry number 127779-20-8, is also known as 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. It belongs to the product categories of Active Pharmaceutical Ingredients; Saquinavir. This chemical's molecular formula is C₃₈H₅₀N₆O₅ and molecular weight is 670.84. What's more, its IUPAC name is called (2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-Butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinoline-2-carbonylamino)butanediamide. The production is an antiretroviral drug used in HIV therapy. In addition, it falls in the protease inhibitor class. The most frequent adverse events with saquinavir in either formulation are mild gastrointestinal symptoms, including diarrhea, nausea, loose stools & abdominal discomfort. This chemical can be prepared by N-Phthalic acyl-(S)-styrene-acrylic ammonia carbonyl chlorides with 1,1,2-Tris(trimethylsilyloxy)ethene. This reaction needs reagent HCl and solvents ethyl acetate, hexane.

Physical properties about Saquinavir are: (1)ACD/LogP: 4.03; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 1.96; (4)ACD/LogD (pH 7.4): 3.61; (5)ACD/BCF (pH 5.5): 5.79; (6)ACD/BCF (pH 7.4): 260.25; (7)ACD/KOC (pH 5.5): 31.52; (8)ACD/KOC (pH 7.4): 1417.08; (9)#H bond acceptors: 11; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 106.6 Å²; (13)Index of Refraction: 1.598; (14)Molar Refractivity: 189.12 cm³; (15)Molar Volume: 553.8 cm³; (16)Surface Tension: 54.2 dyne/cm; (17)Density: 1.211 g/cm³; (18)Flash Point: 567.7 °C; (19)Enthalpy of Vaporization: 155.26 kJ/mol; (20)Boiling Point: 1015 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(N)C[C@H](NC(=O)c1nc2c(cc1)cccc2)C(=O)N[C@@H](Cc3ccccc3)[C@H](O)CN5[C@H](C(=O)NC(C)(C)C)C[C@@H]4CCCC[C@@H]4C5
(2) InChI: InChI=1S/C38H50N6O5/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/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)/t26-,27+,30-,31-,32-,33+/m0/s1
(3) InChIKey: QWAXKHKRTORLEM-UGJKXSETSA-N