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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
Structure of BUCLADESINE CALCIUM

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

HIDE SMILES / InChI

Molecular Formula C18H23N5O8P
Molecular Weight 468.3777
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Ca
Molecular Weight 40.078
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Differential expression of small heat shock proteins in reactive astrocytes after focal ischemia: possible role of beta-adrenergic receptor.
1999 Nov 15
Dibutyryl cyclic AMP-induced enhancement of RB protein degradation in human hepatoma cells.
1999 Nov-Dec
Myelin contributes to the parallel orientation of axonal growth on white matter in vitro.
2001
Upregulation of gap junctional intercellular communication and connexin 43 expression by cyclic-AMP and all-trans-retinoic acid is associated with glutathione depletion and chemosensitivity in neuroblastoma cells.
2001
Cannabinoid receptor activation and elevated cyclic AMP reduce glutamate neurotoxicity.
2001 Apr
Effect of the blood substitute diaspirin crosslinked hemoglobin in rat mesenteric and human radial collateral arteries.
2001 Apr
The water channel aquaporin-8 is mainly intracellular in rat hepatocytes, and its plasma membrane insertion is stimulated by cyclic AMP.
2001 Apr 13
Cyclic AMP- and IL6-signaling cross talk: comodulation of proliferation and apoptosis in the 7TD1 B cell hybridoma.
2001 Apr 15
Age-related differences in messenger ribonucleic acid expression of key proteins involved in adipose cell differentiation and metabolism.
2001 Feb
Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes.
2001 Feb
Thyroid hormone activation in human vascular smooth muscle cells: expression of type II iodothyronine deiodinase.
2001 Feb 16
The effects of histamine on interferon gamma production are dependent on the stimulatory signals.
2001 Jan
Meiosis-activating sterol and the maturation of isolated mouse oocytes.
2001 Jan
Cyclic AMP regulates the calcium transients released from IP(3)-sensitive stores by activation of rat kappa-opioid receptors expressed in CHO cells.
2001 Jan
CREB is involved in mouse annexin A1 regulation by cAMP and glucocorticoids.
2001 Jan
Blockade of NGF-induced neurite outgrowth by a dominant-negative inhibitor of the egr family of transcription regulatory factors.
2001 Jan 1
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
Helicobacter pylori induces pepsinogen secretion by rat gastric cells in culture via a cAMP signal pathway.
2001 Jun
Inhibitor of nuclear factor-kappaB induction by cAMP antagonizes interleukin-1-induced human macrophage-colony-stimulating-factor expression.
2001 Jun 1
Monocyte membrane type 1-matrix metalloproteinase. Prostaglandin-dependent regulation and role in metalloproteinase-2 activation.
2001 Jun 1
Effects of short- and long-term exposure to c-AMP and c-GMP on the noradrenaline transporter.
2001 Mar
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
Control of CYP11B2 gene expression through differential regulation of its promoter by atypical and conventional protein kinase C isoforms.
2001 Mar 16
In vitro differentiation of human marrow stromal cells into early progenitors of neural cells by conditions that increase intracellular cyclic AMP.
2001 Mar 23
Melatonin inhibits the expression of steroidogenic acute regulatory protein and steroidogenesis in MA-10 cells.
2001 Mar-Apr
Nitric oxide regulates actin reorganization through cGMP and Ca(2+)/calmodulin in RAW 264.7 cells.
2001 May 28
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
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 15:42:00 GMT 2023
Edited
by admin
on Sat Dec 16 15:42:00 GMT 2023
Record UNII
7J3JCE9A9U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUCLADESINE CALCIUM
Common Name English
CALCIUM N6-2'-O-DIBUTYRYL CYCLIC ADENOSINE-3',5'-MONOPHOSPHATE
Common Name English
ADENOSINE, N-(1-OXOBUTYL)-, CYCLIC 3',5'-(HYDROGEN PHOSPHATE) 2'-BUTANOATE, CALCIUM SALT (2:1)
Systematic Name English
Bucladesine calcium [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
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
PRIMARY
PUBCHEM
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
PRIMARY
SMS_ID
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
PRIMARY
CAS
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
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY