TMC-310911

Chemical compound
  • US: Investigational drug
Identifiers
  • [(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
  • 1000287-05-7
PubChem CID
  • 53361968
DrugBank
  • DB15623
ChemSpider
  • 34554561
UNII
  • 0151W500HP
Chemical and physical dataFormulaC38H53N5O7S2Molar mass755.99 g·mol−13D model (JSmol)
  • Interactive image
  • 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

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]

See also

  • Brecanavir
  • TMC-647055

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.
  • v
  • t
  • e
Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)
Capsid inhibitorsEntry/fusion inhibitors
(Discovery and development)Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))Maturation inhibitorsProtease Inhibitors (PI)
(Discovery and development)
1st generation
2nd generation
Reverse-transcriptase
inhibitors (RTIs)
Nucleoside and
nucleotide (NRTI)
Non-nucleoside (NNRTI)
(Discovery and development)
1st generation
2nd generation
Combined formulations
Pharmacokinetic boostersExperimental agents
Uncoating inhibitors
Transcription inhibitors
  • Tat antagonists
Translation inhibitors
BNAbs
Other
Failed agents
°DHHS recommended initial regimen options. ◊Formerly or rarely used agent.