Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | 2C18H23N5O8P.Ca |
| Molecular Weight | 976.833 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Ca++].CCCC(=O)NC1=NC=NC2=C1N=CN2[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3OC(=O)CCC.CCCC(=O)NC5=NC=NC6=C5N=CN6[C@@H]7O[C@@H]8COP([O-])(=O)O[C@H]8[C@H]7OC(=O)CCC
InChI
InChIKey=RCFZVVHQICKFQW-NGVPHMJWSA-L
InChI=1S/2C18H24N5O8P.Ca/c2*1-3-5-11(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;/h2*8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24);/q;;+2/p-2/t2*10-,14-,15-,18-;/m11./s1
Bucladesine is a cyclic nucleotide derivative which mimics the action of endogenous cAMP and is a phosphodiesterase inhibitor. 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. Recently, 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 is more lipophilic than cAMP and in contrast to cAMP capable of penetrating cell membranes. Bucladesine interferes with different protein kinases which are normally activated by cAMP. Bucladesine has undergone in the past clinical developments as systemic treatment for cardioprotection and as topical treatment to improve wound healing. In Japan, a bucladesine ointment (Actosin® ointment; Daiichi Pharmaceutical Co., Ltd., Tokyo, Japan) was marketed to treat skin ulcers. Clinical studies have shown favourable effects on diabetic foot ulcers or decubitus, but the compound was later withdrawn despite good tolerability. One possible reason for the withdrawal may be the odour of the cream formulation which can be related to the hydrolytic cleavage in aqueous solutions resulting in release of butyric acid.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Myelin contributes to the parallel orientation of axonal growth on white matter in vitro. | 2001 |
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| A cyclic AMP-regulated negative feedforward system for neuritogenesis revealed in a neuroblastomaxglioma hybrid cell line. | 2001 |
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| Cannabinoid receptor activation and elevated cyclic AMP reduce glutamate neurotoxicity. | 2001 Apr |
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| Transforming growth factor-beta suppresses tumor necrosis factor alpha-induced matrix metalloproteinase-9 expression in monocytes. | 2001 Apr |
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| Effect of the blood substitute diaspirin crosslinked hemoglobin in rat mesenteric and human radial collateral arteries. | 2001 Apr |
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| Up-regulation of cyclooxygenase-1 in neuroblastoma cell lines by retinoic acid and corticosteroids. | 2001 Apr |
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| Gonadotrophins inhibit and activin induces expression of inhibin/activin beta(B) subunit mRNA in cultured human granulosa-luteal cells. | 2001 Apr |
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| The water channel aquaporin-8 is mainly intracellular in rat hepatocytes, and its plasma membrane insertion is stimulated by cyclic AMP. | 2001 Apr 13 |
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| Meiotic maturation of the mouse oocyte requires an equilibrium between cyclin B synthesis and degradation. | 2001 Apr 15 |
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| Cyclic AMP- and IL6-signaling cross talk: comodulation of proliferation and apoptosis in the 7TD1 B cell hybridoma. | 2001 Apr 15 |
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| A gap-junction-mediated signal, rather than an external paracrine factor, predominates during meiotic induction in isolated mouse oocytes. | 2001 Feb |
|
| Characterization of a KATP channel-independent pathway involved in potentiation of insulin secretion by efaroxan. | 2001 Feb |
|
| Regulation of interleukin-10 secretion by histamine in TH2 cells and splenocytes. | 2001 Jan |
|
| The effects of histamine on interferon gamma production are dependent on the stimulatory signals. | 2001 Jan |
|
| Induction of apoptosis by a Newcastle disease virus vaccine (MTH-68/H) in PC12 rat phaeochromocytoma cells. | 2001 Jan-Feb |
|
| Shear stress regulates occludin content and phosphorylation. | 2001 Jul |
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| Modulation of alpha-ENaC and alpha1-Na+-K+-ATPase by cAMP and dexamethasone in alveolar epithelial cells. | 2001 Jul |
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| Distinct effect of diazoxide on insulin secretion stimulated by protein kinase A and protein kinase C in rat pancreatic islets. | 2001 Jul |
|
| Molecular dynamics of point mutated I-A(k) molecules expressed on lymphocytes. | 2001 Jul 2 |
|
| Promoter regulatory elements and DNase I-hypersensitive sites involved in serglycin proteoglycan gene expression in human erythroleukemia, CHRF 288-11, and HL-60 cells. | 2001 Jul 6 |
|
| Modulation of thapsigargin-induced calcium mobilisation by cyclic AMP-elevating agents in human lymphocytes is insensitive to the action of the protein kinase A inhibitor H-89. | 2001 Jun |
|
| Serine protease inhibitor causes F-actin redistribution and inhibition of calcium-mediated secretion in pancreatic acini. | 2001 Jun |
|
| An immortalized jimpy oligodendrocyte cell line: defects in cell cycle and cAMP pathway. | 2001 Jun |
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| Cold suppression of follicle-stimulating hormone activity on proliferation and survival of newt spermatogonia. | 2001 Jun |
|
| Helicobacter pylori induces pepsinogen secretion by rat gastric cells in culture via a cAMP signal pathway. | 2001 Jun |
|
| Differential effects of apical and basolateral uridine triphosphate on intestinal epithelial chloride secretion. | 2001 Jun |
|
| Inhibitor of nuclear factor-kappaB induction by cAMP antagonizes interleukin-1-induced human macrophage-colony-stimulating-factor expression. | 2001 Jun 1 |
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| Aromatase expression in prepuberal Sertoli cells: effect of thyroid hormone. | 2001 Jun 10 |
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| Peroxisomes exist in growth cones and move anterogradely and retrogradely in neurites of PC12D cells. | 2001 Jun 10 |
|
| Characterization of a steroidogenic factor-1-binding site found in promoter of sterol carrier protein-2 gene. | 2001 Mar |
|
| Quantitative analysis of the proliferation of epidermal cells using a human skin organ culture system and the effect of DbcAMP using markers of proliferation (BrdU, Ki-67, PCNA). | 2001 Mar |
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| Stimulation by nitric oxide of gastric acid secretion in bullfrog fundic mucosa in vitro. | 2001 Mar |
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| Stimuli that induce a cholinergic neuronal phenotype of NG108-15 cells upregulate ChAT and VAChT mRNAs but fail to increase VAChT protein. | 2001 Mar 1 |
|
| Interactions of cyclic AMP and its dibutyryl analogue with model membrane: X-ray diffraction and Raman spectroscopic study using cubic liquid-crystalline phases of monoolein. | 2001 Mar 15 |
|
| Dual effect of cAMP on the writhing response in mice. | 2001 Mar 30 |
|
| The role of cyclic AMP in the pathogenesis of glucose desensitization in rat pancreatic islets. | 2001 May |
|
| Hypoxia reverses dibutyryl-cAMP-induced stellation of cultured astrocytes via activation of the endothelin system. | 2001 May |
|
| The properties of ryanodine-sensitive Ca(2+) release in mouse gastric smooth muscle cells. | 2001 May |
|
| Impact of epididymal maturation on the tyrosine phosphorylation patterns exhibited by rat spermatozoa. | 2001 May |
|
| The Drosophila melanogaster homologue of an insect calcitonin-like diuretic peptide stimulates V-ATPase activity in fruit fly Malpighian tubules. | 2001 May |
|
| Effects of cyclic adenosine-monophosphate on growth and PSA secretion of human prostate cancer cell line. | 2001 May |
|
| The influence of cAMP before or during bovine oocyte maturation on embryonic developmental competence. | 2001 May 1 |
|
| Overexpression of rat neuronal calcium sensor-1 in rodent NG108-15 cells enhances synapse formation and transmission. | 2001 May 1 |
|
| Regulation of TNFalpha and interleukin-10 production by prostaglandins I(2) and E(2): studies with prostaglandin receptor-deficient mice and prostaglandin E-receptor subtype-selective synthetic agonists. | 2001 May 1 |
|
| Reactive nitrogen species inhibit alveolar epithelial fluid transport after hemorrhagic shock in rats. | 2001 May 15 |
|
| Multiple transcription factors regulate the inducible expression of the human complement receptor 2 promoter. | 2001 May 15 |
|
| Nitric oxide regulates actin reorganization through cGMP and Ca(2+)/calmodulin in RAW 264.7 cells. | 2001 May 28 |
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| Multipathways for transdifferentiation of human prostate cancer cells into neuroendocrine-like phenotype. | 2001 May 28 |
|
| GATA DNA-binding protein expressed in mouse I-10 Leydig testicular tumor cells. | 2001 May 4 |
|
| Effects of diabetes and insulin on hepatic delta6 desaturase gene expression. | 2001 May 4 |
Patents
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| Code System | Code | Type | Description | ||
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7J3JCE9A9U
Created by
admin on Sat Dec 16 15:42:01 GMT 2023 , Edited by admin on Sat Dec 16 15:42:01 GMT 2023
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44514776
Created by
admin on Sat Dec 16 15:42:01 GMT 2023 , Edited by admin on Sat Dec 16 15:42:01 GMT 2023
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100000172823
Created by
admin on Sat Dec 16 15:42:01 GMT 2023 , Edited by admin on Sat Dec 16 15:42:01 GMT 2023
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938448-87-4
Created by
admin on Sat Dec 16 15:42:01 GMT 2023 , Edited by admin on Sat Dec 16 15:42:01 GMT 2023
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PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
