Streptomycin

  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: