Cyclic adenosine-inosine monophosphate explained

Drug Name:	Cyclic adenosine-inosine monophosphate
C:	20
H:	23
N:	9
O:	13
P:	2
Iupac Name:	9-[(1S,6R,8R,9R,10S,15R,17R,18R)-17-(6-aminopurin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ<sup>5</sup>,12λ<sup>5</sup>-diphosphatricyclo[13.3.0.0<sup>6,10</sup>]octadecan-8-yl]-1H-purin-6-one
Cas Number:	1507367-51-2
Chembl:	4776666
Pubchem:	136247207
Smiles:	C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=CNC4=O)O)OP(=O)(OC[C@@H]5[C@H]([C@H]([C@@H](O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)O)O
Stdinchi:	1S/C20H23N9O13P2/c21-15-9-16(23-3-22-15)28(5-26-9)19-11(30)13-7(39-19)1-37-44(35,36)42-14-8(2-38-43(33,34)41-13)40-20(12(14)31)29-6-27-10-17(29)24-4-25-18(10)32/h3-8,11-14,19-20,30-31H,1-2H2,(H,33,34)(H,35,36)(H2,21,22,23)(H,24,25,32)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
Stdinchikey:	SBNULQXUGGEMOY-XPWFQUROSA-N

Cyclic adenosine-inosine monophosphate (cAIMP, CL-592) is an experimental antiviral drug. It is the best studied of a range of related analogues which act as agonists of the Stimulator of interferon genes (STING) receptor which mediates interferon production by the immune system. It shows broad spectrum antiviral activity against a range of viruses including SARS-CoV-2 and enterovirus 68, and in studies on mice prevented the development of arthritis following infection with Chikungunya virus.^[1] ^[2] ^[3] ^[4]

Notes and References

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Ding C, Song Z, Shen A, Chen T, Zhang A . Small molecules targeting the innate immune cGAS‒STING‒TBK1 signaling pathway . Acta Pharmaceutica Sinica. B . 10 . 12 . 2272–2298 . December 2020 . 33354501 . 10.1016/j.apsb.2020.03.001 . 7745059 .
Garcia G, Irudayam JI, Jeyachandran AV, Dubey S, Chang C, Castillo Cario S, Price N, Arumugam S, Marquez AL, Shah A, Fanaei A, Chakravarty N, Joshi S, Sinha S, French SW, Parcells MS, Ramaiah A, Arumugaswami V . Innate immune pathway modulator screen identifies STING pathway activation as a strategy to inhibit multiple families of arbo and respiratory viruses . Cell Reports. Medicine . 4 . 5 . 101024 . May 2023 . 37119814 . 10.1016/j.xcrm.2023.101024 . 10213809 .
Wang M, Fan B, Lu W, Ryde U, Chang Y, Han D, Lu J, Liu T, Gao Q, Chen C, Xu Y . Unraveling the Binding Mode of Cyclic Adenosine-Inosine Monophosphate (cAIMP) to STING through Molecular Dynamics Simulations . Molecules . 29 . 11 . June 2024 . 38893524 . 10.3390/molecules29112650 . free . 11173896 .