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Streptomycin

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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 Molecular Structure of 57-92-1 (Streptomycin) 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

Streptomycin Synthetic route

54-85-3

isoniazid

57-92-1

streptomicin

4480-58-4

streptomycin-isonicotinoylhydrazone

Conditions
ConditionsYield
With water pH 7.0-7.2;
With methanol
124-22-1

n-Dodecylamine

57-92-1

streptomicin

56222-71-0

(1R)-N,N'-dicarbamimidoyl-O4-[3-(dodecylamino-methyl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

2016-42-4

tetradecylamine

57-92-1

streptomicin

(1R)-N,N'-dicarbamimidoyl-O4-[O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-3-(tetradecylamino-methyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

143-27-1

hexadecylamine

57-92-1

streptomicin

56222-72-1

(1R)-N,N'-dicarbamimidoyl-O4-[3-(hexadecylamino-methyl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

111-86-4

n-Octylamine

57-92-1

streptomicin

(1R)-N,N'-dicarbamimidoyl-O4-[O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-3-(octylamino-methyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

2016-57-1

1-aminodecane

57-92-1

streptomicin

56222-69-6

(1R)-N,N'-dicarbamimidoyl-O4-[3-(decylamino-methyl)-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine

5351-23-5

4-hydroxybenzoic acid hydrazide

57-92-1

streptomicin

(1R)-N,N'-dicarbamimidoyl-O4-{3-[(4-hydroxy-benzoylhydrazono)-methyl]-O2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-5-deoxy-α-L-lyxofuranosyl}-streptamine

Conditions
ConditionsYield
With water
57-92-1

streptomicin

140-28-3

N,N'-Dibenzylethylenediamine

47896-20-8

(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

57-92-1

streptomicin

128-46-1, 82443-21-8

dihydrostreptomycin

Conditions
ConditionsYield
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;
119-53-9

2-hydroxy-2-phenylacetophenone

57-92-1

streptomicin

C49H55N7O12

Conditions
ConditionsYield
With potassium hydroxide; 2-hydroxyethanethiol; sodium sulfite In water at 100℃; for 0.166667h;

Streptomycin History

  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.

Streptomycin Consensus Reports

EPA Genetic Toxicology Program.

Streptomycin Specification

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.

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