CAS 16980-89-5|Bucladesine (sodium salt)

Introduction：Basic information about CAS 16980-89-5|Bucladesine (sodium salt), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Bucladesine (sodium salt) BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles41
7. Synonyms

Common Name	Bucladesine (sodium salt)
CAS Number	16980-89-5	Molecular Weight	491.367
Density	/	Boiling Point	/
Molecular Formula	C₁₈H₂₃N₅NaO₈P	Melting Point	/
MSDS	ChineseUSA	Flash Point	/

Names

Name	Bucladesine Sodium Salt
Synonym	More Synonyms

Bucladesine (sodium salt) BiologicalActivity

Description	Bucladesine sodium salt is a cell-permeable cyclic AMP (cAMP) analog that activates cAMP dependent protein kinase (PKA).
Related Catalog	Signaling Pathways >>Protein Tyrosine Kinase/RTK >>PKASignaling Pathways >>Stem Cell/Wnt >>PKAResearch Areas >>Others
References	[1]. Sharifzadeh, M., et al., Post-training intrahippocampal infusion of nicotine-bucladesine combination causes a synergistic enhancement effect on spatial memory retention in rats. Eur J Pharmacol, 2007. 562(3): p. 212-20. [2]. Azami, K., et al., The quantitative evaluation of cholinergic markers in spatial memory improvement induced by nicotine-bucladesine combination in rats. Eur J Pharmacol, 2010. 636(1-3): p. 102-7. [3]. Mafune, E., M. Takahashi, and N. Takasugi, Effect of vehicles on percutaneous absorption of bucladesine (dibutyryl cyclic AMP) in normal and damaged rat skin. Biol Pharm Bull, 1995. 18(11): p. 1539-43. [4]. Rundfeldt, C., et al., The stable cyclic adenosine monophosphate analogue, dibutyryl cyclo-adenosine monophosphate (bucladesine), is active in a model of acute skin inflammation. Arch Dermatol Res, 2012.

Description

Bucladesine sodium salt is a cell-permeable cyclic AMP (cAMP) analog that activates cAMP dependent protein kinase (PKA).

Related Catalog

Signaling Pathways >>Protein Tyrosine Kinase/RTK >>PKASignaling Pathways >>Stem Cell/Wnt >>PKAResearch Areas >>Others

References

[1]. Sharifzadeh, M., et al., Post-training intrahippocampal infusion of nicotine-bucladesine combination causes a synergistic enhancement effect on spatial memory retention in rats. Eur J Pharmacol, 2007. 562(3): p. 212-20.

[2]. Azami, K., et al., The quantitative evaluation of cholinergic markers in spatial memory improvement induced by nicotine-bucladesine combination in rats. Eur J Pharmacol, 2010. 636(1-3): p. 102-7.

[3]. Mafune, E., M. Takahashi, and N. Takasugi, Effect of vehicles on percutaneous absorption of bucladesine (dibutyryl cyclic AMP) in normal and damaged rat skin. Biol Pharm Bull, 1995. 18(11): p. 1539-43.

[4]. Rundfeldt, C., et al., The stable cyclic adenosine monophosphate analogue, dibutyryl cyclo-adenosine monophosphate (bucladesine), is active in a model of acute skin inflammation. Arch Dermatol Res, 2012.

Chemical & Physical Properties

Molecular Formula	C₁₈H₂₃N₅NaO₈P
Molecular Weight	491.367
Exact Mass	491.118195
PSA	176.63000
LogP	2.20120
InChIKey	KRBZRVBLIUDQNG-JBVYASIDSA-M
SMILES	CCCC(=O)Nc1ncnc2c1ncn2C1OC2COP(=O)([O-])OC2C1OC(=O)CCC.[Na+]
Storage condition	−20°C
Water Solubility	H2O: 50 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: ES5055500

CHEMICAL NAME :: Butyramide, N-(9-beta-D-ribofuranosyl-9H-purin-6-yl)-, cyclic hydrogen phosphate, butyrate (ester), monosodium salt

CAS REGISTRY NUMBER :: 16980-89-5

LAST UPDATED :: 199612

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C18-H23-N5-O8-O.Na

MOLECULAR WEIGHT :: 476.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 36,357,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 18,2543,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 515 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,1140,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 487 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,1140,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 448 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,1140,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 36,357,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1024 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 36,357,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 678 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,1140,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 543 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,1140,1984 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 840 mg/kg

SEX/DURATION :: female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 27,571,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 2200 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - sex ratio Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 27,585,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 138 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 27,585,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 340 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 28 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 27,599,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 630 mg/kg

SEX/DURATION :: male 9 week(s) pre-mating female 2 week(s) pre-mating female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 27,571,1984

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	C
Safety Phrases	24/25
RIDADR	NONH for all modes of transport
WGK Germany	2
RTECS	ES5055500

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Synonyms

sodium N6,O2'-dibutyryl-O3',O5'-hydroxyphosphoryl-adenosine

N6,2‘-O-Dibutyryladenosine 3’,5‘-cyclic monophosphate sodium salt

EINECS 241-059-4

Butanoic acid, (4aR,6R,7R,7aR)-tetrahydro-2-hydroxy-2-oxido-6-[6-[(1-oxobutyl)amino]-9H-purin-9-yl]-4H-furo[3,2-d]-1,3,2-dioxaphosphorin-7-yl ester, sodium salt (1:1)

N6,2'-O-Dibutyryladenosine 3',5'-cyclic monophosphate sodium salt

dibutyryl cyclic AMP sodium salt

Bucladesine sodium salt

N-(1-Oxobutyl)adenosine Cyclic 3',5'-(Hydrogen Phosphate)-2'-butanoate Monosodium Salt

sodium dibutyryl camp

sodium salt of N6,2'-O-dibutyryl adenosine 3',5'-cyclic monophosphate

N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)butyramide Cyclic Hydrogen Phosphate Butyrate (Ester) Monosodium Salt

sodium bucladesine

Bucladesine sodium

Dibutyl cAMP sodium salt

Dibutyl cyclic AMP sodium

Sodium dibutyryl 3',5'-cyclic AMP

MFCD00005843

Dibutyryl cAMP sodium salt

sodium N6,O2'-dibutyryl cyclic adenosinemonophosphate

Dibutyryl cyclic-AMP sodium salt

Sodium (4aR,6R,7R,7aR)-6-[6-(butyrylamino)-9H-purin-9-yl]-7-(butyryloxy)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-olate 2-oxide

Bucladesine (sodium salt)

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