TMC-310911

TMC-310911 (also known as ASC-09) is an antiviral drug which was originally researched as a treatment for HIV/AIDS. It is a protease inhibitor related to darunavir.[1][2] While TMC-310911 was not ultimately developed as a medication for the treatment of AIDS, research has continued into potential applications in the treatment of other viral diseases, and in March 2020 it was entered into clinical trials for the treatment of COVID-19.[3][4]

TMC-310911
Legal status
Legal status
  • US: Investigational drug
Identifiers
IUPAC name
  • [(3As,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[[2-[(1-cyclopentylpiperidin-4-yl)amino]-1,3-benzothiazol-6-yl]sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
Chemical and physical data
FormulaC38H53N5O7S2
Molar mass755.99 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CO[C@@H]3[C@H]2CCO3)O)S(=O)(=O)C4=CC5=C(C=C4)N=C(S5)NC6CCN(CC6)C7CCCC7
InChI
  • InChI=1S/C38H53N5O7S2/c1-25(2)22-43(23-33(44)32(20-26-8-4-3-5-9-26)41-38(45)50-34-24-49-36-30(34)16-19-48-36)52(46,47)29-12-13-31-35(21-29)51-37(40-31)39-27-14-17-42(18-15-27)28-10-6-7-11-28/h3-5,8-9,12-13,21,25,27-28,30,32-34,36,44H,6-7,10-11,14-20,22-24H2,1-2H3,(H,39,40)(H,41,45)/t30-,32-,33+,34-,36+/m0/s1
  • Key:JQUNFHFWXCXPRK-AMMMHQJVSA-N

See also

References
  1. Dierynck I, Van Marck H, Van Ginderen M, Jonckers TH, Nalam MN, Schiffer CA, Raoof A, Kraus G, Picchio G (December 2011). "TMC310911, a novel human immunodeficiency virus type 1 protease inhibitor, shows in vitro an improved resistance profile and higher genetic barrier to resistance compared with current protease inhibitors". Antimicrobial Agents and Chemotherapy. 55 (12): 5723–31. doi:10.1128/AAC.00748-11. PMC 3232804. PMID 21896904.
  2. Ghosh AK, Brindisi M (April 2015). "Organic carbamates in drug design and medicinal chemistry". Journal of Medicinal Chemistry. 58 (7): 2895–940. doi:10.1021/jm501371s. PMC 4393377. PMID 25565044.
  3. Catapang JK, Billones JB (March 2020). "On the Generation of Novel Ligands for SARS-CoV-2 Protease and ACE2 Receptor via Constrained Graph Variational Autoencoders". ChemRxiv. doi:10.26434/chemrxiv.12011157.v3.
  4. McGrath J (2 April 2020). "All the COVID-19 vaccines and treatments currently in clinical trials". Digital Trends. Retrieved 6 April 2020.
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