Structure via PubChem · Public domain (PubChem)
bucladesine
Sign in to saveAlso known as actosin, cyclic AMP dibutyrate, dbcAMP, dibutyryl cAMP, N(6),O(2')-dibutyryl-3',5'-cyclic AMP, dibutyryl 3',5'-cyclic AMP, N(6),O(2')-dibutyryl adenosine 3',5'-cyclic monophosphate, dibutyryladenosine cyclic monophosphate
Bucladesine is a cyclic nucleotide derivative which mimics the action of endogenous cAMP and is a phosphodiesterase inhibitor.
Chemical data
- Formula
- C18H24N5O8P
- Molecular weight
- 469.4 g/mol
- IUPAC name
- [(4aR,6R,7R,7aR)-6-[6-(butanoylamino)purin-9-yl]-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate
- SMILES
- CCCC(=O)NC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)OC(=O)CCC
- InChIKey
- CJGYSWNGNKCJSB-YVLZZHOMSA-N
- XLogP
- -0.5
- Polar surface area
- 164 Ų
- H-bond donors
- 2
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- cardiovascular disease
via ChEMBL · EBI
Research
9,786 papers- Reduction of autophagy markers mediated protective effects of JNK inhibitor and bucladesine on memory deficit induced by Aβ in rats.Naunyn-Schmiedeberg's archives of pharmacology · 2016
- Dual effect of cAMP agonist on ameliorative function of PKA inhibitor in morphine-dependent mice.Fundamental & clinical pharmacology · 2014
- Local interstitial chemotherapy with sustained release bucladesine in de novo glioblastoma multiforme: a preliminary study.Journal of neuro-oncology · 2002
- Post-training intrahippocampal infusion of nicotine-bucladesine combination causes a synergistic enhancement effect on spatial memory retention in rats.European journal of pharmacology · 2007
- Reversal of cancer.Lancet (London, England) · 1983
via PubMed
Wikidata facts
- Mass
- 469.136
Show 5 more facts
- canonical SMILES
- CCCC(=O)NC1=NC=NC2=C1N=CN2C3C(C4C(O3)COP(=O)(O4)O)OC(=O)CCC
- isomeric SMILES
- CCCC(=O)NC1=NC=NC2=C1N=CN2[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)OC(=O)CCC
- chemical formula
- C₁₈H₂₄N₅O₈P
- Commons category
- Bucladesine
- World Health Organisation international non-proprietary name
- bucladesine
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Bucladesine and seizure
- Bucladesine and morphine withdrawal syndrome
- References
- External links
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.
Excerpted from Wikipedia’s “bucladesine” article, available under the CC BY-SA 4.0 licence.