Streptomycin

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Streptomycin
Category Antibiotics
Catalog number BBF-03487
CAS 57-92-1
Molecular Weight 581.57
Molecular Formula C21H39N7O12
Purity 95%

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Description

Streptomycin is an aminoglycoside antibiotic produced by Str. griseus. Broad-spectrum anti-bacterial antibiotics. It has the activity against gram-positive bacteria, negative bacteria and mycobacteria. Clinically, it is widely used in bacterial infections and Mycobacterium tuberculosis infections, with good curative effects, but bacteria are prone to drug resistance after contact with streptomycin.

Specification

Related CAS 6160-32-3 (hydrochloride) 3810-74-0 (sulfate)
Synonyms O-2-Deoxy-2-(methylamino)-α-L-glucopyranosyl-(1→2)-O-5-deoxy-3-C-formyl-α-L-lyxofuranosyl-(1→4)-N1,N3-bis(aminoiminomethyl)-D-streptamine; 2,4-Diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-α-glucopyranosyl)-3-formylpentofuranoside; Agrept; Agrimycin; Neodiestreptopab; NSC 14083; Poushamycin; Streptomycin A
Storage Store at 2-8°C
IUPAC Name 2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine
Canonical SMILES CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(C=O)O
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
InChI Key UCSJYZPVAKXKNQ-HZYVHMACSA-N

Properties

Appearance Solid powder
Application Streptomycin is typically used for treatment of active tuberculosis, always in combination with other antituberculosis agents.
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; mycobacteria
Boiling Point 948.2°C at 760 mmHg
Melting Point 194 °C
Density 1.98 g/cm3
Solubility Soluble in DMSO, Methanol

Reference Reading

1.[Persistence of a ST6 clone of Enterococcus faecalis genotype vanB2 in two Hospitals in Aragon (Spain)].
Alonso CA1, Rezusta A2, Seral C3, Ferrer I2, Castillo FJ3, Torres C4. Enferm Infecc Microbiol Clin. 2016 Apr 5. pii: S0213-005X(16)30005-2. doi: 10.1016/j.eimc.2016.02.020. [Epub ahead of print]
INTRODUCTION: In order to study the evolution of the outbreak that occurred between 2009 and 2010 in 3 hospitals in Zaragoza, all vancomycin-resistant clinical Enterococcus faecalis isolates identified between 2011 and 2013 at these hospitals were characterised.
2.Quantifying Attachment and Antibiotic Resistance of from Conventional and Organic Swine Manure.
Zwonitzer MR, Soupir ML, Jarboe LR, Smith DR. J Environ Qual. 2016 Mar;45(2):609-17. doi: 10.2134/jeq2015.05.0245.
Broad-spectrum antibiotics are often administered to swine, contributing to the occurrence of antibiotic-resistant bacteria in their manure. During land application, the bacteria in swine manure preferentially attach to particles in the soil, affecting their transport in overland flow. However, a quantitative understanding of these attachment mechanisms is lacking, and their relationship to antibiotic resistance is unknown. The objective of this study is to examine the relationships between antibiotic resistance and attachment to very fine silica sand in collected from swine manure. A total of 556 isolates were collected from six farms, two organic and four conventional (antibiotics fed prophylactically). Antibiotic resistance was quantified using 13 antibiotics at three minimum inhibitory concentrations: resistant, intermediate, and susceptible. Of the 556 isolates used in the antibiotic resistance assays, 491 were subjected to an attachment assay.
3.[In vitro susceptibility of Trichomonas vaginalis to metronidazole, ornidazole and proton pump inhibitors pantoprazole and esomeprazole].
Aksoy Gökmen A1, Girginkardeşler N, Kilimcioğlu AA, Şirin MC, Özbilgin A. Mikrobiyol Bul. 2016 Jan;50(1):133-9.
The current treatment of trichomoniasis is based on the use of 5-nitroimidazole derivatives. Although metronidazole is reliable, inexpensive and highly effective against anaerobic microorganisms and protozoa, the development of metronidazole-resistant T.vaginalis strains pose to an increasing problem. Nitroimidazoles are compounds having azomycin (2-nitroimidazole) chemical structure and are obtained from Streptomyces strains. Benzimidazole, which is found in the structure of proton pump inhibitors, is also present in the other components that have antiprotozoal activity. In this study, the in vitro susceptibility of T.vaginalis against metronidazole, ornidazole, and the proton pump inhibitors which are tested recently as antiprotozoal agents; pantoprazole and esomeprazole was investigated. For this purpose a clinical T.vaginalis strain which was formerly isolated and stored after cryopreservation process in our laboratory was used. Minimum inhibitory concentration (MIC) and minimum lethal concentration (MLC) values of those agents against to this strain were determined in vitro by dilution method in 24-well cell culture plates.
4.Epidemiological Trends of Drug-Resistant Tuberculosis in China From 2007 to 2014: A Retrospective Study.
He XC1, Zhang XX, Zhao JN, Liu Y, Yu CB, Yang GR, Li HC. Medicine (Baltimore). 2016 Apr;95(15):e3336.
The emergence and spread of drug-resistant tuberculosis (DR-TB) has become the major concern in global TB control nowadays due to its limited therapy options and high mortality. A comprehensive evaluation for the epidemiological trends of DR-TB in mainland China, of which TB incidences remain high, is essential but lacking. This study aimed to describe the trends of DR-TB overtime, especially multidrug-resistant TB (MDR-TB); and to identify unique characteristics of MDR-TB cases compared with drug-susceptible TB cases in Mainland China.We retrospectively analyzed surveillance data collected from 36 TB prevention and control institutions in Shandong Province, China over an 8-year period. Unique characteristics of MDR-TB were identified; Chi-square test for trends and linear regression were used to assess the changes in proportions of different resistance patterns overtime.The overall MDR rate was 6.2% in our sample population. There were no statistically significant changes in the percentage of drug-susceptible, isoniazid (INH) resistance, ethambutol (EMB) resistance, streptomycin (SM) resistance, and MDR TB during our study period except that the overall rifampin (RFP) resistance and rifampin monoresistance (RMR) increased at a yearly rate of 0.

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