TMC-310911

{{Short description|Chemical compound}}

{{Drugbox

| 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

| image = TMC-310911.svg

| width = 240

| tradename =

| legal_US = Investigational drug

| legal_status =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 1000287-05-7

| PubChem = 53361968

| UNII = 0151W500HP

| ChemSpiderID = 34554561

| DrugBank = DB15623

| C=38 | H=53 | N=5 | O=7 | S=2

| 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

| StdInChI=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

| StdInChIKey = 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.{{cite journal | vauthors = Dierynck I, Van Marck H, Van Ginderen M, Jonckers TH, Nalam MN, Schiffer CA, Raoof A, Kraus G, Picchio G | title = 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 | journal = Antimicrobial Agents and Chemotherapy | volume = 55 | issue = 12 | pages = 5723–31 | date = December 2011 | pmid = 21896904 | pmc = 3232804 | doi = 10.1128/AAC.00748-11 }}{{cite journal | vauthors = Ghosh AK, Brindisi M | title = Organic carbamates in drug design and medicinal chemistry | journal = Journal of Medicinal Chemistry | volume = 58 | issue = 7 | pages = 2895–940 | date = April 2015 | pmid = 25565044 | pmc = 4393377 | doi = 10.1021/jm501371s }} 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.{{cite journal | vauthors = Catapang JK, Billones JB | title = On the Generation of Novel Ligands for SARS-CoV-2 Protease and ACE2 Receptor via Constrained Graph Variational Autoencoders | journal = ChemRxiv | date = March 2020 | doi = 10.26434/chemrxiv.12011157.v3| doi-access = free }}{{cite web | first = Jenny | last = McGrath | name-list-style = vanc |title=All the COVID-19 vaccines and treatments currently in clinical trials |url=https://www.digitaltrends.com/health-fitness/coronavirus-covid-19-vaccines-treatments-list/ |publisher=Digital Trends |access-date=6 April 2020 |date=2 April 2020}}