Chemistry:Bucladesine

Short description: Chemical compound

Bucladesine

Clinical data
Other names	Dibutyryl cyclic adenosine monophosphate (N6,2'-O-dibutyryl)-adenosine-3',5'-mono-phosphate Dibutyryl cAMP DcAMP DBcAMP
AHFS/Drugs.com	International Drug Names
ATC code	C01CE04 (WHO)
Identifiers
IUPAC name boring(3aR,4R,6R,6aR)-4-(6-butanamido-9H-purin-9-yl)-6-[(butanoyloxy)methyl]-2-oxo-tetrahydro-2H-1,3,5,2λ5-furo[3,4-d][1,3,2]dioxaphosphol-2-olate
CAS Number	362-74-3 Y
PubChem CID	28177
IUPHAR/BPS	5485
ChemSpider	9306 Y
UNII	63X7MBT2LQ
ChEBI	CHEBI:50095 Y
ChEMBL	ChEMBL485980 Y
Chemical and physical data
Formula	C18H23N5NaO8P
Molar mass	491.373 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(Nc4ncnc1c4ncn1[C@@H]2O[C@@H]3COP(=O)(O[C@H]3[C@H]2OC(=O)CCC)O)CCC
InChI InChI=1S/C18H24N5O8P/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24)/t10-,14-,15-,18-/m1/s1 Y Key:CJGYSWNGNKCJSB-YVLZZHOMSA-N Y
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Bucladesine is a cyclic nucleotide derivative which mimics the action of endogenous cAMP and is a phosphodiesterase inhibitor.

Bucladesine is a cell permeable cAMP analog. The compound is used in a wide variety of research applications because it mimics cAMP and can induce normal physiological responses when added to cells in experimental conditions. cAMP is only able to elicit minimal responses in these situations.

The neurite outgrowth instigated by bucladesine in cell cultures has been shown to be enhanced by nardosinone.

Bucladesine and seizure

The effect of bucladesine as a cAMP analog has been studied on the pentylenetetrazol-induced seizure in the wild-type mice. The data showed that bucladesine (300nM/mouse) reduced the seizure latency and threshold. In addition they found that combination of bucladesine and pentoxyfillin has additive effect on seizure latency and threshold.

Bucladesine and morphine withdrawal syndrome

Bucladesine (50-100nM/mouse) showed significant attenuation in the morphine withdrawal syndrome in the wild-type mice. In addition, its high dose (200nM/mouse) combination with H-89, as a protein kinase inhibitor, had additive attenuating effect on withdrawal syndromes.

External links

• Bucladesine at the US National Library of Medicine Medical Subject Headings (MeSH)