A-286501

A-286501
Identifiers
	IUPAC name (1S,2R,3S,5R)-3-amino-5-(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)cyclopentane-1,2-diol;
CAS Number	483341-15-7;
PubChem CID	9862222;
ChemSpider	8037918;
UNII	8G293B8TT7;
Chemical and physical data
Formula	C11H14BrN5O2
Molar mass	328.170 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1[C@@H]([C@H]([C@H]([C@@H]1N2C=C(C3=C(N=CN=C32)N)Br)O)O)N;
	InChI InChI=1S/C11H14BrN5O2/c12-4-2-17(6-1-5(13)8(18)9(6)19)11-7(4)10(14)15-3-16-11/h2-3,5-6,8-9,18-19H,1,13H2,(H2,14,15,16)/t5-,6+,8+,9-/m0/s1; Key:FKFYQPGMXTXSTC-LWIVVEGESA-N;

A-286501 is an experimental drug that acts as a selective inhibitor of the enzyme adenosine kinase. In animal studies it has analgesic and antiinflammatory effects.^[1]^[2]^[3]

References

^ Fleurisson C, Benedetti E, Micouin L (2021). "Cyclic cis-1,3-Diamines Derived from Bicyclic Hydrazines: Synthesis and Applications" (PDF). Synlett. 32 (9): 858–874. doi:10.1055/s-0040-1707324.
^ Jarvis MF, Yu H, McGaraughty S, Wismer CT, Mikusa J, Zhu C, et al. (March 2002). "Analgesic and anti-inflammatory effects of A-286501, a novel orally active adenosine kinase inhibitor". Pain. 96 (1–2): 107–118. doi:10.1016/s0304-3959(01)00435-3. PMID 11932067.
^ Jarvis MF, Mikusa J, Chu KL, Wismer CT, Honore P, Kowaluk EA, et al. (October 2002). "Comparison of the ability of adenosine kinase inhibitors and adenosine receptor agonists to attenuate thermal hyperalgesia and reduce motor performance in rats". Pharmacology, Biochemistry, and Behavior. 73 (3): 573–581. doi:10.1016/s0091-3057(02)00840-7. PMID 12151032.