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69-33-0

69-33-0 structure
69-33-0 structure
  • Name: 7-Deazaadenosine(Tubercidin)
  • Chemical Name: tubercidin
  • CAS Number: 69-33-0
  • Molecular Formula: C11H14N4O4
  • Molecular Weight: 266.253
  • Catalog: Biochemical Nucleoside drugs Nucleoside intermediate
  • Create Date: 2018-08-25 15:17:20
  • Modify Date: 2024-01-01 19:04:58
  • 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
Synonyms 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
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
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
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