Bucladesine

Bucladesine
Clinical data
Other namesDibutyryl cyclic adenosine monophosphate
(N6,2'-O-dibutyryl)-adenosine-3',5'-mono-phosphate
Dibutyryl cAMP
DcAMP
DBcAMP
AHFS/Drugs.comInternational Drug Names
ATC code
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
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.046
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Chemical and physical data
FormulaC18H23N5NaO8P
Molar mass491.373 g·mol−1
3D model (JSmol)
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 checkY
  • Key:CJGYSWNGNKCJSB-YVLZZHOMSA-N checkY
  (verify)

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.[1]

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.[2]

References

  1. ↑ Hosseini-Zare MS, Salehi F, Seyedi SY, Azami K, Ghadiri T, Mobasseri M, Gholizadeh S, Beyer C, Sharifzadeh M (2011). "Effects of pentoxifylline and H-89 on epileptogenic activity of bucladesine in pentylenetetrazol-treated mice". European Journal of Pharmacology. 670 (2–3): 464–70. doi:10.1016/j.ejphar.2011.09.026. PMID 21946102.
  2. ↑ Seyedi SY, Salehi F, Payandemehr B, Hossein S, Hosseini-Zare MS, Nassireslami E, Yazdi BB, Sharifzadeh M (2014). "Dual effect of cAMP agonist on ameliorative function of PKA inhibitor in morphine-dependent mice". Fundamental & Clinical Pharmacology. 28 (4): 445–54. doi:10.1111/fcp.12045. PMID 24033391.
  • Bucladesine at the US National Library of Medicine Medical Subject Headings (MeSH)


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