Chemical Component Summary | |
|---|---|
| Name | STREPTOMYCIN |
| Synonyms | STREPTOMYCIN A |
| Identifiers | 1-[(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 |
| Formula | C21 H39 N7 O12 |
| Molecular Weight | 581.574 |
| Type | NON-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 |
| 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 |
| InChIKey | UCSJYZPVAKXKNQ-HZYVHMACSA-N |
Chemical Details | |
|---|---|
| Formal Charge | 0 |
| Atom Count | 79 |
| Chiral Atom Count | 15 |
| Bond Count | 81 |
| Aromatic Bond Count | 0 |
Drug Info: DrugBank
| DrugBank ID | DB01082? |
|---|---|
| Name | Streptomycin |
| Groups |
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| Description | Streptomycin, 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 |
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| Brand Names |
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| Indication | Although 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 |
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| ATC-Code |
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| CAS number | 57-92-1 |
Drug Targets
| Name | Target Sequence | Pharmacological Action | Actions |
|---|---|---|---|
| 16S ribosomal RNA | - | unknown | inhibitor |
| 23S ribosomal RNA | - | unknown | inhibitor |
| 30S ribosomal protein S12 | MATVNQLVRKPRARKVAKSNVPALEACPQKRGVCTRVYTTTPKKPNSALR... | unknown | inhibitor |
| Cytoplasmic membrane | - | unknown | incorporation into and destabilization |
| Bacterial outer membrane | - | unknown | incorporation 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 Name | Reference |
|---|---|
| PubChem | 19649 |
| ChEMBL | CHEMBL372795 |
| ChEBI | CHEBI:17076 |
