Streptomycin

Base Information

• Chemical Name: Streptomycin
• CAS No.: 57-92-1
• Deprecated CAS: 12672-24-1,82958-69-8,47814-83-5,47816-81-9,364062-67-9,47814-83-5,47816-81-9
• Molecular Formula: C21H39N7O12
• Molecular Weight: 581.58
• Hs Code.: 2941200000
• European Community (EC) Number: 200-355-3
• UNII: Y45QSO73OB
• DSSTox Substance ID: DTXSID4023597
• Nikkaji Number: J4.500D
• Wikipedia: Streptomycin
• Wikidata: Q192717
• NCI Thesaurus Code: C61952
• RXCUI: 10109
• Metabolomics Workbench ID: 43315
• ChEMBL ID: CHEMBL372795
• Mol file: 57-92-1.mol

Synonyms:Estreptomicina CEPA;Estreptomicina Clariana;Estreptomicina Normon;Strepto Fatol;Strepto Hefa;Strepto-Fatol;Strepto-Hefa;Streptomycin;Streptomycin Grünenthal;Streptomycin Sulfate;Streptomycin Sulfate (2:3) Salt;Streptomycin Sulphate;Streptomycine Panpharma

Chemical Property of Streptomycin

Chemical Property:

• Appearance/Colour: Crystalline powder
• Melting Point: 194 °C
• Refractive Index: 1.6800 (estimate)
• Boiling Point: 948.247 °C at 760 mmHg
• PKA: pKa 7.84(H2O t = 25 I = 0.1) (Uncertain);11.54(H2O t = 25 I = 0.1) (Uncertain);>12(H2O t = 25 I = 0.1) (Uncertain)
• Flash Point: 527.281 °C
• PSA: 331.43000
• Density: 1.982 g/cm³
• LogP: -4.96900
• Storage Temp.: 2-8°C
• XLogP3: -8
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 9
• Exact Mass: 581.26566970
• Heavy Atom Count: 40
• Complexity: 940

Purity/Quality:

99.0% ^*data from raw suppliers

Streptomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Antituberculosis Agents
• 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
• Isomeric 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
• Recent ClinicalTrials: Ciprofloxacin Versus an Aminoglycoside Followed by Ciprofloxacin for Bubonic Plague
• Description: The antibiotic streptomycin is an important and effective chemical for the management of bacterial diseases of fruit trees (especially apple), woody ornamentals, and vegetables. Streptomycin was initially discovered in 1944 and was one of the first antibiotics to be utilized in clinical medicine to control human diseases, and is still important as a feed amendment for growth promotion in agricultural animals. The widespread and diverse usage of streptomycin has contributed to the currently observed global streptomycin resistance (SmR) problem. This problem is especially critical in plant disease management, as there are few alternatives to streptomycin available and, as a consequence of increased usage, SmR has been increasingly observed among bacterial plant pathogens.
• Uses: Control of bacterial shot-hole, bacterial rots, bacterial canker, bacterial wilts, fire blight, and other diseases caused by gram-positive species of bacteria in pome fruit, stone fruit, citrus fruit, olives, vegetables, potatoes, tobacco, cotton, and ornamentals. Chlorosis may occur on grapes, pears, peaches, and some ornamentals. Formulation types WP; Liquid. Incompatible with pyrethrins and alkaline materials. A mixture of streptomycin and oxytetracycline is highly effective for the control of bacterial canker of peach, citrus canker, soft rot of vegetables, and various other bacterial diseases. Selected tradenames “Agrimycin 17” (sesquisulfate); “AS-50” (sesquisulfate). Streptomycin is the most commonly utilized bactericidal antibiotic for the management of plant pathogens and has been used most frequently on apple, pear, sweet pepper, and ornamental trees.
• Indications: Streptomycin, an aminoglycoside antibiotic was the first drug shown to reduce tuberculosis mortality. Streptomycin is bactericidal against M. tuberculosis in vitro but is inactive against intracellular organisms. Most M. tuberculosis strains and nontuberculosis species, such as M. kansasii and M. aviumintracellulare, are sensitive. Spontaneous resistance to streptomycin, seen in approximately 1 in 106 tubercle bacilli, is related to a point mutation that involves the gene (rpsl or rrs) that encodes for ribosomal proteins and binding sites.About 80% of strains that are resistant to isoniazid and rifampin are also resistant to streptomycin.
• Therapeutic Function: Antitubercular
• Clinical Use: Streptomycin is indicated as a fourth drug in combination with isoniazid, rifampin, and pyrazinamide in patients at high risk for drug resistance. It is also used in the treatment of streptomycin-susceptible MDR tuberculosis. Tuberculosis (in combination with other antituberculosis drugs) Infections caused by M. kansasii (in combination with other antimycobacterial agents) Plague and tularemia, including tularemia pneumonia Bacterial endocarditis (in combination with a penicillin) Brucellosis Whipple’s disease (in combination with other antibiotics) The most important use of streptomycin is in the treatment of tuberculosis . Depression of vestibular function by streptomycin has been used in the treatment of patients suffering from Ménière’s disease.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: increased risk of nephrotoxicity with colistimethate or polymyxins and possibly cephalosporins; increased risk of ototoxicity and nephrotoxicity with capreomycin or vancomycin. Ciclosporin: increased risk of nephrotoxicity. Cytotoxics: increased risk of nephrotoxicity and ototoxicity with platinum compounds. Loop diuretics: increased risk of ototoxicity. Muscle relaxants: enhanced effects of nondepolarising muscle relaxants and suxamethonium. Parasympathomimetics: neostigmine and pyridostigmine antagonised by aminoglycosides. Tacrolimus: increased risk of nephrotoxicity.

Technology Process of Streptomycin

There total 1 articles about Streptomycin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ streptomicin (57-92-1)

Guidance literature:

Reference yield:

streptomicin (57-92-1) → dihydrostreptomycin (128-46-1,82443-21-8,77093-29-9)

Guidance literature:

With sulfuric acid; water; bei der elektrochemischen Reduktion an einer Cadmium-Amalgam-Kathode;

Reference yield:

2-(aminooxy)-N-(3,5-dibromo-2-hydroxyphenyl)acetamide + streptomicin (57-92-1) → C29H45Br2N9O14

Guidance literature:

at 20 ℃; for 3h;

Downstream raw materials:

streptomycin-isonicotinoylhydrazone

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

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

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

Refernces

Synthesis, pharmacological activities and molecular docking studies of pyrazolyltriazoles as anti-bacterial and anti-inflammatory agents

10.1016/j.bmc.2017.08.042

The research focuses on the synthesis, pharmacological activities, and molecular docking studies of pyrazolyltriazoles as potential anti-bacterial and anti-inflammatory agents. The purpose of the study was to prepare and evaluate a series of novel pyrazolyl alcohols, pyrazolyl azides, and pyrazolyltriazoles for their bioactivity profile, specifically targeting anti-bacterial and anti-inflammatory properties. The conclusions drawn from the research indicated that compound 5c exhibited potent anti-bacterial activity against Micrococcus luteus, while compounds 5f, 8b, and 8h demonstrated significant in vitro anti-inflammatory activity. Notably, compound 8h was effective in an in vivo LPS-induced sepsis model in mice, showing a significant reduction in TNF-α levels. The chemicals used in the process included various acetophenones, phenylhydrazine hydrochlorides, Vilsmeier-Haack reagents, sodium borohydride, and a range of alkynes and azides for the synthesis of the target pyrazolyltriazoles, as well as standard drugs like streptomycin and dexamethasone for comparative analysis in the biological assays.

Synthesis, biological evaluation and QSAR studies of new thieno[2,3-d]pyrimidin-4(3H)-one derivatives as antimicrobial and antifungal agents

10.1016/j.bioorg.2020.104509

The research focuses on the synthesis, biological evaluation, and QSAR studies of new thieno[2,3-d]pyrimidin-4(3H)-one derivatives as potential antimicrobial and antifungal agents. The purpose of the study was to develop new compounds that exhibit excellent activity against gram-positive and gram-negative bacteria, as well as fungal species, and to understand their structure-activity relationships. The majority of the synthesized compounds showed promising antimicrobial and antifungal activity, surpassing the potency of control compounds like streptomycin and ampicillin. Particularly, compound 22, with a m-methoxyphenyl group and an ethylenediamine side chain, demonstrated broad-spectrum antibacterial activity, while compound 15, with a m-methoxyphenyl group and a 2-(2-mercaptoethoxy)ethan-1-ol side chain, showed the best antifungal activity. Both compounds 15 and 22 showed no toxic effects in vitro on HFL-1 human embryonic primary cells and in vivo in the nematode C. elegans at their respective MIC concentrations.