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127779-20-8

Basic Information
CAS No.: 127779-20-8
Name: Saquinavir
Article Data: 6
Molecular Structure:
Molecular Structure of 127779-20-8 (Saquinavir)
Formula: C38H50N6O5
Molecular Weight: 670.852
Synonyms: Butanediamide,N1-[3-[3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-,[3S-[2[1R*(R*),2S*],3a,4ab,8ab]]-;(S)-N-[(aS)-a-[(1R)-2-[(3S,4aS,8aS)-3-(tert-Butylcarbamoyl)octahydro-2(1H)-isoquinolyl]-1-hydroxyethyl]phenethyl]-2-quinaldamidosuccinamide;Fortovase;Ro 31-8959/000;Sch 52852;
EINECS: 1806241-263-5
Density: 1.211 g/cm3
Melting Point: 91.5oC
Boiling Point: 1015 °C at 760 mmHg
Flash Point: 567.7 °C
Solubility: 35.8mg/L(25 oC)
PSA: 166.75000
LogP: 4.90330
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History

  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.

Specification

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