Darunavir

• CAT Number: I002590
• CAS Number: 206361-99-1
• Molecular Formula: C27H37N3O7S
• Molecular Weight: 547.7
• Purity: ≥95%
• Synonyms: (E)-(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl hydrogen ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbonimidate
• Target: HIV Protease
• Solubility: DMSO: soluble20 mg/mL, clear
• Storage: Store at -20°C
• IUPAC Name: [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
• InChI: 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
• InChIKey: CJBJHOAVZSMMDJ-HEXNFIEUSA-N
• SMILES: CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2COC3C2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)N

Darunavir(TMC114) (CAS 206361-99-1) is an HIV protease inhibitor.Upon oral administration, darunavir selectively targets and binds to the active site of HIV-1 protease, and inhibits the dimerization and catalytic activity of HIV-1 protease. This inhibits the proteolytic cleavage of viral Gag and Gag-Pol polyproteins in HIV-infected cells. This inhibition leads to the production of immature, non-infectious viral proteins that are unable to form mature virions, and prevents HIV replication.
IC50 Value:
Target: HIV Protease
Darunavir HIV-1 antiviral structurally is similar to amprenavir and it is second generation HIV-1-protease inhibitor. Darunavir(brand namePrezista, formerly known as TMC114) is a drug used to treat HIV infection. It is in the protease inhibitor class. Prezista is an OARAC recommended treatment option for treatment-nave and treatment-experienced adults and adolescents.
 

Overview of Clinical Research

Darunavir is a HIV protease inhibitor developed by Gilead Sciences and Janssen R&D Ireland.

Reference

[1]. Meher, Biswa Ranjan; Wang, Yixuan. Interaction of I50V Mutant and I50L/A71V Double Mutant HIV-Protease with Inhibitor TMC114 (Darunavir): Molecular Dynamics Simulation and Binding Free Energy Studies. Journal of Physical Chemistry B (2012), 116(6), 1884-1900.
[2]. Kakuda, Thomas; Sekar, Vanitha; Vis, Peter; Coate et al. Pharmacokinetics and pharmacodynamics of darunavir and etravirine in HIV-1-infected, treatment-experienced patients in the gender, race, and clinical experience (GRACE) trial AIDS Research and Treatment (2012), 186987, 10 pp..
[3]. Valantin, M. A.; Lambert-Niclot, S.; Flandre, P.; et al.Long-term efficacy of darunavir/ritonavir monotherapy in patients with HIV-1 viral suppression: week 96 results from the MONOI ANRS 136 study. Journal of Antimicrobial Chemotherapy (2012), 67(3), 691-695.
[4]. Lambert-Niclot S, Flandre P, Valantin MA, Soulie C, Fourati S, Wirden M, Sayon S, Pakianather S, Bocket L, Masquelier B, Dos Santos G, Katlama C, Calvez V, Marcelin AG. Similar Evolution of Cellular HIV-1 DNA Level in Darunavir/Ritonavir Monotherapy versus Triple Therapy in MONOI -ANRS136 Trial over 96 Weeks. PLoS One. 2012;7(7):e41390.
[5]. Ruela Corrêa JC, D/'Arcy DM, Dos Reis Serra CH, Nunes Salgado HR. Darunavir: a critical review of its properties, use and drug interactions. Pharmacology. 2012;90(1-2):102-9.