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Name |
Streptomycin |
EINECS | 223-286-0 |
CAS No. | 57-92-1 | Density | 1.982 g/cm3 |
PSA | 331.43000 | LogP | -4.96900 |
Solubility | N/A | Melting Point |
194 °C |
Formula | C21H39N7O12 | Boiling Point | 948.247 °C at 760 mmHg |
Molecular Weight | 581.58 | Flash Point | 527.281 °C |
Transport Information | N/A | Appearance | Crystalline powder |
Safety | Risk Codes | N/A | |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
Streptomycin (8CI);2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-a-glucopyranosyl)-3-formylpentofuranoside;Agrept;Agrimycin;NSC 14083;Neodiestreptopab;Streptomycin A; |
Article Data | 5 |
Conditions | Yield |
---|---|
With water pH 7.0-7.2; | |
With methanol |
n-Dodecylamine
streptomicin
(1R)-N,N'-dicarbamimidoyl-O4-[3-(dodecylamino-methyl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine
hexadecylamine
streptomicin
(1R)-N,N'-dicarbamimidoyl-O4-[3-(hexadecylamino-methyl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine
1-aminodecane
streptomicin
(1R)-N,N'-dicarbamimidoyl-O4-[3-(decylamino-methyl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine
Conditions | Yield |
---|---|
With water |
streptomicin
N,N'-Dibenzylethylenediamine
(1R)-N,N'-bis-carbamimidoyl-O4-[3-(1,3-dibenzyl-imidazolidin-2-yl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine
streptomicin
dihydrostreptomycin
Conditions | Yield |
---|---|
With sulfuric acid; water bei der elektrochemischen Reduktion an einer Cadmium-Amalgam-Kathode; | |
With sulfuric acid; water bei der elektrochemischen Reduktion an einer Quecksilber-Kathode; | |
With sulfuric acid; water bei der elektrochemischen Reduktion an einer Blei-Kathode; | |
With sulfuric acid; water bei der elektrochemischen Reduktion an einer Blei-Amalgam-Kathode; |
Conditions | Yield |
---|---|
With potassium hydroxide; 2-hydroxyethanethiol; sodium sulfite In water at 100℃; for 0.166667h; |
Streptomycin (CAS NO.57-92-1) was first isolated on October 19, 1943 by Albert Schatz, a graduate student, in the laboratory of Selman Abraham Waksman at Rutgers University. Waksman and his laboratory discovered several antibiotics, including actinomycin, clavacin, streptothricin, streptomycin, grisein, neomycin, fradicin, candicidin and candidin. Of these, streptomycin and neomycin found extensive application in the treatment of numerous infectious diseases. Streptomycin was the first antibiotic that could be used to cure the disease tuberculosis; early production of the drug was dominated by Merck & Co. under George W. Merck.
The first randomized trial of streptomycin against pulmonary tuberculosis was carried out in 1947 by the MRC Tuberculosis Research Unit. Whilst neither double-blind nor placebo-controlled, results showed efficacy against TB, albeit with minor toxicity and acquired bacterial resistance to the drug.
EPA Genetic Toxicology Program.
The Streptomycin, with the CAS registry number 57-92-1, is also known as 2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-a-L-glucopyranosyl)-3-C-formyl-b-L-lyxopentanofuranoside. It belongs to the product categories of Oligosaccharide Compounds; Intermediates & Fine Chemicals; Oligosaccharides; Pharmaceuticals. Its EINECS number is 223-286-0. This chemical's molecular formula is C21H39N7O12 and molecular weight is 581.57. What's more, its systematic name is 5-(2,4-diguanidino-3,5,6-trihydroxy-cyclohexoxy)- 4-[4,5-dihydroxy-6-(hydroxymethyl)-3-methylamino-tetrahydropyran-2-yl] oxy-3-hydroxy-2-methyl-tetrahydrofuran-3-carbaldehyde. Its classification codes are: (1)Agricultural Chemical; (2)Anti-Bacterial Agents; (3)Anti-Infective Agents; (4)Drug / Therapeutic Agent; (5)Enzyme Inhibitors; (6)Fungicide, bactericide, wood preservative; (7)Human Data; (8)Mutation data; (9)Natural Product; (10)Protein synthesis inhibitors; (11)Reproductive Effect. Its storage temperature is 2-8 °C. It is an antibiotic produced by the soil actinomycete Streptomyces griseus. It acts by inhibiting the initiation and elongation processes during protein synthesis. It is also used as a pesticide, to combat the growth of bacteria, fungi and algae.
Physical properties of Streptomycin are: (1)# of Rule of 5 Violations: 3; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 19; (7)#H bond donors: 16; (8)#Freely Rotating Bonds: 16; (9)Polar Surface Area: 336.43 Å2; (10)Index of Refraction: 1.762; (11)Molar Refractivity: 121.037 cm3; (12)Molar Volume: 293.483 cm3; (13)Polarizability: 47.983×10-24cm3; (14)Surface Tension: 92.673 dyne/cm; (15)Density: 1.982 g/cm3; (16)Flash Point: 527.281 °C; (17)Enthalpy of Vaporization: 156.549 kJ/mol; (18)Boiling Point: 948.247 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(C=O)O
(2)Std. InChI: InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
(3)Std. InChIKey: UCSJYZPVAKXKNQ-HZYVHMACSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | intravenous | 150mg/kg (150mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978. | |
cat | LDLo | oral | 2gm/kg (2000mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978. | |
cat | LDLo | subcutaneous | 600mg/kg (600mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978. | |
dog | LDLo | subcutaneous | 300mg/kg (300mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978. | |
guinea pig | LDLo | subcutaneous | 600mg/kg (600mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978. | |
human | TDLo | intraperitoneal | 143mg/kg (143mg/kg) | VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | British Medical Journal. Vol. 1, Pg. 556, 1961. |
human | TDLo | oral | 400mg/kg/28D- (400mg/kg) | SENSE ORGANS AND SPECIAL SENSES: CHANGES IN VESTIBULAR FUNCTIONS: EAR | Revue Medicale de la Suisse Romande. Vol. 73, Pg. 854, 1953. |
human | TDLo | parenteral | 28mg/kg/D (28mg/kg) | BLOOD: EOSINOPHILIA | Revue Medicale de la Suisse Romande. Vol. 73, Pg. 820, 1953. |
monkey | LDLo | subcutaneous | 400mg/kg (400mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978. | |
mouse | LD50 | intraperitoneal | 525mg/kg (525mg/kg) | Strahlentherapie. Vol. 127, Pg. 245, 1965. | |
mouse | LD50 | intravenous | 90200ug/kg (90.2mg/kg) | Antibiotiki. Vol. 18, Pg. 249, 1973. | |
mouse | LD50 | oral | 500mg/kg (500mg/kg) | Yakkyoku. Pharmacy. Vol. 38, Pg. 1493, 1987. | |
mouse | LD50 | subcutaneous | 520mg/kg (520mg/kg) | British Journal of Pharmacology and Chemotherapy. Vol. 15, Pg. 496, 1960. | |
mouse | LD50 | unreported | 90mg/kg (90mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955. | |
rabbit | LDLo | intravenous | 175mg/kg (175mg/kg) | Naturwissenschaften. Vol. 43, Pg. 183, 1956. | |
rabbit | LDLo | subcutaneous | 600mg/kg (600mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978. | |
rat | LD50 | oral | 9gm/kg (9000mg/kg) | "Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson Publications, 1976/77 revisionVol. 4, Pg. 35, 1976/1977. | |
rat | LDLo | intravenous | 175mg/kg (175mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978. | |
rat | LDLo | subcutaneous | 600mg/kg (600mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 570, 1978. |