TMC-310911

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	1000287-05-7;
PubChem CID	53361968;
DrugBank	DB15623;
ChemSpider	34554561;
UNII	0151W500HP;
Chemical and physical data
Formula	C38H53N5O7S2
Molar mass	755.99 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References

^ 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.
^ 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.
^ 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.
^ McGrath J (2 April 2020). "All the COVID-19 vaccines and treatments currently in clinical trials". Digital Trends. Retrieved 6 April 2020.

[pmid21896904-1] 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.

[pmid25565044-2] 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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See also

References