SRY

STREPTOMYCIN


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Chemical Component Summary

NameSTREPTOMYCIN
SynonymsSTREPTOMYCIN A
Identifiers1-[(1R,2R,3S,4R,5R,6S)-3-carbamimidamido-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-methylamino-oxan-2-yl]oxy-4-hydroxy-4-methanoyl-5-methyl-oxolan-2-yl]oxy-2,5,6-trihydroxy-cyclohexyl]guanidine
FormulaC21 H39 N7 O12
Molecular Weight581.574
TypeNON-POLYMER
Isomeric SMILES[H]/N=C(/N)\N[C@@H]1[C@H]([C@@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2[C@@H]([C@]([C@@H](O2)C)(C=O)O)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)N/C(=N\[H])/N)O
InChIInChI=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
InChIKeyUCSJYZPVAKXKNQ-HZYVHMACSA-N

Chemical Details

Formal Charge0
Atom Count79
Chiral Atom Count15
Bond Count81
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB01082 
NameStreptomycin
Groups
  • approved
  • vet_approved
DescriptionStreptomycin, an antibiotic derived from _Streptomyces griseus_, was the first aminoglycoside to be discovered and used in practice in the 1940s.[A233325,A233390] Selman Waksman and eventually Albert Schatz were recognized with the Nobel Prize in Medicine for their discovery of streptomycin and its antibacterial activity.[A233325,A232294] Although streptomycin was the first antibiotic determined to be effective against mycobacterium tuberculosis, it has fallen out of favor due to resistance and is now primarily used as adjunctive treatment in cases of multi-drug resistant tuberculosis.[A233325]
Synonyms
  • Estreptomicina
  • Streptomycin Sulfate
  • Streptomyzin
  • 2,4-diguanidino-3,5,6-trihydroxycyclohexyl 5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-C-formyl-beta-L-lyxopentanofuranoside
  • Streptomicina
Brand Names
  • Streptomycin
  • Streptomycin for Injection USP
  • Streptomycin Sulfate Injection USP 1g/2.5ml
  • Streptomycin Sulfate
IndicationAlthough streptomycin was the first antibiotic available for the treatment of mycobacterium tuberculosis, it is now largely a second line option due to resistance and toxicity.[A233320] Streptomycin may also be used to treat a variety of other infections caused by susceptible strains of aerobic bacteria where other less toxic agents are ineffective. Examples include: _Yersinia pestis_, _Francisella tularensis_, _Brucella_, _Calymmatobacterium granulomatis_ (donovanosis, granuloma inguinale), _H. ducreyi_ (chancroid), _H. influenzae_ (in respiratory, endocardial, and meningeal infections - concomitantly with another antibacterial agents). _K. pneumoniae_ pneumonia (concomitantly with another antibacterial agent), _E.coli_, _Proteus_, _A.aerogenes_, _K. pneumoniae_, and _Enterococcus faecalis_ in urinary tract infections, _Streptococcus viridans_, _Enterococcus faecalis_ (in endocardial infections - concomitantly with penicillin), and Gram-negative bacillary bacteremia (concomitantly with another antibacterial agent).
Categories
  • Agents that produce neuromuscular block (indirect)
  • Alimentary Tract and Metabolism
  • Aminoglycoside Antibacterials
  • Anti-Bacterial Agents
  • Anti-Infective Agents
ATC-Code
  • J04AM01
  • J01GA01
  • A07AA54
  • A07AA04
CAS number57-92-1

Drug Targets

NameTarget SequencePharmacological ActionActions
16S ribosomal RNA-unknowninhibitor
23S ribosomal RNA-unknowninhibitor
30S ribosomal protein S12MATVNQLVRKPRARKVAKSNVPALEACPQKRGVCTRVYTTTPKKPNSALR...unknowninhibitor
Cytoplasmic membrane-unknownincorporation into and destabilization
Bacterial outer membrane-unknownincorporation into and destabilization
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 19649
ChEMBL CHEMBL372795
ChEBI CHEBI:17076