Indinavir
Structural Formula Vector Image
Title: Indinavir
CAS Registry Number: 150378-17-9
CAS Name: 2,3,5-Trideoxy-N-[(1S,2R)-2,3-dihydro-2-hydroxy-1H-inden-1-yl]-5-[(2S)-2-[[(1,1-dimethylethyl)amino]carbonyl]-4-(3-pyridinylmethyl)-1-piperazinyl]-2-(phenylmethyl)-D-erythro-pentonamide
Additional Names: (aR,gS,2S)-a-benzyl-2-(tert-butylcarbamoyl)-g-hydroxy-N-[(1S,2R)-2-hydroxy-1-indanyl]-4-(3-pyridylmethyl)-1-piperazinevaleramide; N-(2(R)-hydroxy-1(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-hydroxy-5-[1-[4-(3-pyridylmethyl)-2(S)-(N-tert-butylcarbamoyl)piperazinyl]]pentanamide
Molecular Formula: C36H47N5O4
Molecular Weight: 613.79
Percent Composition: C 70.45%, H 7.72%, N 11.41%, O 10.43%
Literature References: Member of the novel hydroxyaminopentane amide class of HIV-1 protease inhibitors. Prepn: J. P. Vacca et al., EP 541168; eidem, US 5413999 (1993, 1995 both to Merck & Co.); B. D. Dorsey et al., J. Med. Chem. 37, 3443 (1994). Diastereoselective synthesis: D. Askin et al., Tetrahedron Lett. 35, 673 (1994); P. E. Maligres et al., ibid. 36, 2195 (1995). Crystal structure of HIV-II protease complex: Z. Chen et al., J. Biol. Chem. 269, 26344 (1994). Antiviral activity and pharmacokinetics: J. P. Vacca et al., Proc. Natl. Acad. Sci. USA 91, 4096 (1994). HPLC determn in plasma and urine: E. Woolf et al., J. Chromatogr. A 692, 45 (1995). Metabolism in humans: S. K. Balani et al., Drug Metab. Dispos. 23, 266 (1995).
Properties: Occurs as monohydrate, crystals from wet ethyl or isopropyl acetate, loss of water below 100° followed by recrystallization of anhydrous form with mp 153-154°; second anhydrous form, mp 167.5-168°. Soly in water (mg/ml): 0.015 (unbuffered), >1.5 (pH 4.0). [a]D22 +24.1° (c = 0.0133 in chloroform).
Melting point: mp 153-154°; mp 167.5-168°
Optical Rotation: [a]D22 +24.1° (c = 0.0133 in chloroform)
 
Derivative Type: Sulfate
CAS Registry Number: 157810-81-6
Manufacturers' Codes: MK-639
Trademarks: Crixivan (Merck & Co.)
Molecular Formula: C36H47N5O4.H2SO4
Molecular Weight: 711.87
Percent Composition: C 60.74%, H 6.94%, N 9.84%, O 17.98%, S 4.50%
Properties: Occurs as the monoethanolate, crystals from absolute ethanol, softens at 135°, mp 150-153° (dec). Converts to hydrate upon loss of ethanol and exposure to moist air.
Melting point: mp 150-153° (dec)
 
Therap-Cat: Antiviral.
Keywords: Antiviral; Peptidomimetics; HIV Protease Inhibitor.

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