7-Deazaadenosine(Tubercidin)

Modify Date: 2024-01-01 19:04:58

7-Deazaadenosine(Tubercidin) structure	Common Name	7-Deazaadenosine(Tubercidin)
	CAS Number	69-33-0	Molecular Weight	266.253
	Density	1.9±0.1 g/cm3	Boiling Point	648.8±55.0 °C at 760 mmHg
	Molecular Formula	C₁₁H₁₄N₄O₄	Melting Point	247-248 °C (decomp)
	MSDS	Chinese USA	Flash Point	346.2±31.5 °C
	Symbol	GHS06	Signal Word	Danger

Use of 7-Deazaadenosine(Tubercidin)

Tubercidin (7-Deazaadenosine) is an adenosine analog, is an antibiotic obtained from Streptomyces tubercidicus.Target: AntibacterialTubercidin inhibits the growth of Streptococcus faecalis by 50 % at a concentration of 20 nM. Tubercidin is not subject to cleavage by adenosine phosphorylase or to deamination by adenosine deaminase. The antibiotic served as a substrate for numerous enzymes involved in the anabolism of adenosine, as demonstrated by its incorporation into RNA and DNA, and by the formation of nicotinamide-deaza-adenine dinucleotide. Tubercidin proves to be a weak inhibitor of adenosine phosphorylase, and interfered with the phosphorylation of adenosine and AMP. The inhibition of the growth of S. faecalis by Tubercidin is prevented by purine and pyrimidine nucleosides, ribose 5-phosphate, pyruvate, and certain amino acids. In the presence of Tubercidin, growing cultures of the test organism used pyruvate instead of glucose, whereas in the absence of the antibiotic glucose served as the main source of energy. It is suggested, therefore, that the impairment of growth is due primarily to the interference of Tubercidin with the utilization of glucose.

Name	tubercidin
Synonym	More Synonyms

Description	Tubercidin (7-Deazaadenosine) is an adenosine analog, is an antibiotic obtained from Streptomyces tubercidicus.Target: AntibacterialTubercidin inhibits the growth of Streptococcus faecalis by 50 % at a concentration of 20 nM. Tubercidin is not subject to cleavage by adenosine phosphorylase or to deamination by adenosine deaminase. The antibiotic served as a substrate for numerous enzymes involved in the anabolism of adenosine, as demonstrated by its incorporation into RNA and DNA, and by the formation of nicotinamide-deaza-adenine dinucleotide. Tubercidin proves to be a weak inhibitor of adenosine phosphorylase, and interfered with the phosphorylation of adenosine and AMP. The inhibition of the growth of S. faecalis by Tubercidin is prevented by purine and pyrimidine nucleosides, ribose 5-phosphate, pyruvate, and certain amino acids. In the presence of Tubercidin, growing cultures of the test organism used pyruvate instead of glucose, whereas in the absence of the antibiotic glucose served as the main source of energy. It is suggested, therefore, that the impairment of growth is due primarily to the interference of Tubercidin with the utilization of glucose.
Related Catalog	Signaling Pathways >> Anti-infection >> Bacterial Natural Products >> Others Research Areas >> Infection
References	[1]. Bloch A, et al. On the mode of action of 7-deaza-adenosine (Tubercidin). Biochim Biophys Acta. 1967 Mar 29;138(1):10-25.

Density	1.9±0.1 g/cm3
Boiling Point	648.8±55.0 °C at 760 mmHg
Melting Point	247-248 °C (decomp)
Molecular Formula	C₁₁H₁₄N₄O₄
Molecular Weight	266.253
Flash Point	346.2±31.5 °C
Exact Mass	266.101501
PSA	126.65000
LogP	-0.12
Vapour Pressure	0.0±2.0 mmHg at 25°C
Index of Refraction	1.834

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY8870000

CHEMICAL NAME :: 7H-Pyrrolo(2,3-d)pyrimidine, 4-amino-7-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 69-33-0

BEILSTEIN REFERENCE NO. :: 0038498

LAST UPDATED :: 199612

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C11-H14-N4-O4

MOLECULAR WEIGHT :: 266.29

WISWESSER LINE NOTATION :: T56 BN GN INJ FZ I- BT5OTJ CQ DQ E1Q

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 :: 16 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - pleural effusion Gastrointestinal - other changes Lungs, Thorax, or Respiration - pleural effusion

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - pleural effusion Gastrointestinal - peritonitis Liver - other changes

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 28320 ug/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6 mg/kg

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

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 45 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 48 mg/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 48 mg/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: Dominant lethal test

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - rabbit Kidney

DOSE/DURATION :: 30 ug/L

REFERENCE :: BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 38,1771,1989

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H300
Precautionary Statements	P264-P301 + P310
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T+: Very toxic;
Risk Phrases	R28
Safety Phrases	S45;S36/S37/S39
RIDADR	UN 3462 6.1/PG 2
WGK Germany	3
RTECS	UY8870000
Packaging Group	II
Hazard Class	6.1(a)
HS Code	29419090

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EINECS 200-703-4

Tubercidine

sparsomycina

7H-pyrrolo[2,3-d]pyrimidin-4-amine, 7-β-D-ribofuranosyl-

MFCD00056012

TUBERCIDIN

4-amino-7-(D-ribofuranosyl)-7H-pyrrolo{2,3-d}pyrimidine

7-Deazaadenosine

Sparsomycine A

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China
Product Name: Tubercidin
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