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362-74-3 , Calcium Dibutyacyladenosine Cyclophosphate, CAS:362-74-3

362-74-3 , Calcium Dibutyacyladenosine Cyclophosphate,
CAS:362-74-3
C18H24N5O8P / 469.386

二丁酰环磷腺苷钙,

Calcium Dibutyacyladenosine Cyclophosphate

Dibutyryladenosine cyclic 3',5'-monophosphate (DBACMP) is a mitochondrial function regulator that inhibits the synthesis of ATP by binding to the methyltransferase enzyme. DBACMP also has an inhibitory effect on other enzymes, such as dna binding activity and enzyme activities involved in cellular energy metabolism. DBACMP inhibits infectious diseases by altering signal pathways, which leads to the production of cytokines and chemokines that have pro-inflammatory effects and stimulate axonal growth. The drug may also bind to the atp-binding cassette transporter and inhibit mitochondrial calcium uptake. DBACMP binds to polymorphonuclear leucocytes and alters cytosolic calcium levels, which may lead to an increased production of protein genes for cell growth.

Bucladesine is a cyclic nucleotide derivative which mimics the action of endogenous cAMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. Bucladesine 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.

Title: Bucladesine

CAS Registry Number: 362-74-3

CAS Name: N-(1-Oxobutyl)adenosine cyclic 3¢,5¢-(hydrogen phosphate) 2¢-butanoate

Additional Names: N-(9-b-D-ribofuranosyl-9H-purin-6-yl)butyramide cyclic 3¢,5¢-(hydrogen phosphate) 2¢-butyrate; N6,2¢-O-dibutyryladenosine 3¢,5¢-cyclic monophosphate; N6,2¢-O-dibutyryl cAMP; DBcAMP

Molecular Formula: C18H24N5O8P

Molecular Weight: 469.39

Percent Composition: C 46.06%, H 5.15%, N 14.92%, O 27.27%, P 6.60%

Literature References: Vasodilating cyclic nucleotide derivative which can permeate the cell membrane. Mimics the action of endogenous cyclic AMP, q.v. Prepn: Th. Posternak et al., Biochim. Biophys. Acta 65, 558 (1962); O. Nagase et al., JP Kokai 76 113896, C.A. 86, 140409r (1977); T. Hirayama et al., JP Kokai 77 39698; JP 77 39699, C.A. 87, 136330m-136331n (1977) (1976, 1977, 1977 all to Daiichi Seiyaku). Pharmacology: H. S. White et al., Eur. J. Pharmacol. 57, 107 (1979); J. D. Johnson et al., ibid. 91, 343 (1983); N. Bondar et al., J. Physiol. 355, 33 (1984). Clinical trial in congestive heart failure: S. Matsui et al., Am. J. Cardiol. 51, 1364 (1983); after cardiopulmonary bypass surgery: T. Yoshitake et al., Prog. Clin. Biol. Res. 111, 211 (1983).

 

Derivative Type: Sodium salt

CAS Registry Number: 16980-89-5

Manufacturers' Codes: DC-2797

Trademarks: Actosin (Daiichi Seiyaku)

Molecular Formula: C18H23N5NaO8P

Molecular Weight: 491.37

Percent Composition: C 44.00%, H 4.72%, N 14.25%, Na 4.68%, O 26.05%, P 6.30%

 

Derivative Type: Barium salt

CAS Registry Number: 18837-96-2

Molecular Formula: C36H46BaN10O16P2

Molecular Weight: 1074.08

Percent Composition: C 40.26%, H 4.32%, Ba 12.79%, N 13.04%, O 23.83%, P 5.77%

Properties: uv max (ethanol-0.5M ammonium acetate, 5:2) 270 nm.

Absorption maximum: uv max (ethanol-0.5M ammonium acetate, 5:2) 270 nm

 

Therap-Cat: Cardiotonic.

Keywords: Cardiotonic.

CAS Number362-74-3
Product NameBucladesine
IUPAC Name[(4aR,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
Molecular FormulaC18H24N5O8P
Molecular Weight469.386 g/mol
InChIInChI=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
InChI KeyCJGYSWNGNKCJSB-QMJNRFBBSA-N
SMILESCCCC(=O)NC1=C2C(=NC=N1)N(C=N2)C3C(C4C(O3)COP(=O)(O4)O)OC(=O)CCC
SolubilitySoluble in DMSO
Synonyms(But)(2) cAMP, Adenosine-3',5'-Monophosphate, Dibutyryl, AMP, Dibutyryl Cyclic, Bucladesine, Bucladesine, Barium (1:1) Salt, Bucladesine, Disodium Salt, Bucladesine, Monosodium Salt, Bucladesine, Sodium Salt, Cyclic AMP, Dibutyryl, DBcAMP, Dibutyryl Adenosine 3',5' Monophosphate, Dibutyryl Adenosine 3,5 Monophosphate, Dibutyryl Adenosine-3',5'-Monophosphate, Dibutyryl Cyclic AMP, Disodium Salt Bucladesine, Monosodium Salt Bucladesine, N',O' Dibutyryl cAMP, N',O'-Dibutyryl-cAMP, N(6),0(2')-Dibutyryl Cyclic AMP, Sodium Salt Bucladesine
Canonical SMILESCCCC(=O)NC1=C2C(=NC=N1)N(C=N2)C3C(C4C(O3)COP(=O)(O4)O)OC(=O)CCC
Isomeric SMILESCCCC(=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


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