Bucladesine

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 ;
PubChem CID	28177;
IUPHAR/BPS	5485;
ChemSpider	9306 ;
UNII	63X7MBT2LQ;
ChEBI	CHEBI:50095 ;
ChEMBL	ChEMBL485980 ;
CompTox Dashboard (EPA)	DTXSID1040459 ;
ECHA InfoCard	100.006.046
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 ; Key:CJGYSWNGNKCJSB-YVLZZHOMSA-N ;
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Bucladesine is a cyclic nucleotide derivative which mimics the action of endogenous cAMP and is a phosphodiesterase inhibitor.

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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.

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 (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]

[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 U.S. National Library of Medicine Medical Subject Headings (MeSH)

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[1] [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] [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.

[1]

[2]

Bucladesine

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Bucladesine and seizure

Bucladesine and morphine withdrawal syndrome

References

External links