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MedKoo CAT#: 315293
CAS#: 206361-99-1 (free)
Description: Darunavir is a drug used to treat HIV infection. It is in the protease inhibitor class. Prezista is an OARAC recommended treatment option for treatment-naÃ¯ve and treatment-experienced adults and adolescents. Developed by pharmaceutical company Tibotec, darunavir is named after Arun K. Ghosh, the chemist who discovered the molecule at the University of Illinois at Chicago. It was approved by the Food and Drug Administration (FDA) on June 23, 2006. .
MedKoo Cat#: 315293
CAS#: 206361-99-1 (free)
Chemical Formula: C27H37N3O7S
Exact Mass: 547.23522
Molecular Weight: 547.66
Elemental Analysis: C, 59.21; H, 6.81; N, 7.67; O, 20.45; S, 5.85
Related CAS #: 206361-99-1 (free) 635728-49-3 (Ethanolate)
Synonym: TMC114; TMC 114; TMC-114; Darunavir; brand name Prezista.
IUPAC/Chemical Name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate
InChi Key: CJBJHOAVZSMMDJ-HEXNFIEUSA-N
InChi Code: InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1
SMILES Code: O=C(O[C@@H]1[C@@]2([H])[C@@](OCC2)([H])OC1)N[C@H]([C@H](O)CN(CC(C)C)S(=O)(C3=CC=C(N)C=C3)=O)CC4=CC=CC=C4
PREZISTA (darunavir) is an inhibitor of the human immunodeficiency virus (HIV) protease. PREZISTA (darunavir), in the form of darunavir ethanolate, has the following chemical name: [(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester monoethanolate. Its molecular formula is C27H37N3O7S Â• C2H5OH and its molecular weight is 593.73. Darunavir ethanolate is a white to off-white powder with a solubility of approximately 0.15 mg/mL in water at 20Â°C.
Darunavir is a second-generation protease inhibitor (PIs), designed specifically to overcome problems with the older agents in this class, such as indinavir. Early PIs often have severe side effects and drug toxicities, require a high therapeutic dose, are costly to manufacture, and show a disturbing susceptibility to drug resistant mutations. Such mutations can develop in as little as a year of use, and effectively render the drugs useless. Darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including strains from treatment-experienced patients with multiple resistance mutations to PIs. Darunavir received much attention at the time of its release, as it represents an important treatment option for patients with drug-resistant HIV. Patient advocacy groups pressured developer Tibotec not to follow the previous trend of releasing new drugs at prices higher than existing drugs in the same class. Darunavir was priced to match other common PIs already in use, such as kaletra. The drug costs around $9000 for a one year supply. (Source: http://en.wikipedia.org/wiki/Darunavir).
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