Spectinomycin
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| Systematic (IUPAC) name | |
| (1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one | |
| Clinical data | |
| Trade names | Trobicin |
| AHFS/Drugs.com | monograph |
| Pregnancy cat. | B (US) |
| Legal status | not available in US |
| Identifiers | |
| CAS number | 1695-77-8  |
| ATC code | J01XX04 |
| PubChem | CID 15541 |
| DrugBank | APRD01232 |
| ChemSpider | 14785 |
| UNII | 93AKI1U6QF |
| KEGG | D08526 |
| ChEMBL | CHEMBL1167 |
| Synonyms | (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)decahydro-4H-pyrano[2,3-b][1,4]benzodioxin-4-one |
| Chemical data | |
| Formula | C14H24N2O7 |
| Mol. mass | 332.35 g/mol |
| SMILES | eMolecules & PubChem |
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Spectinomycin (marketed as the hydrochloride salt spectinomycin hydrochloride under the trade name Trobicin) is an aminocyclitol antibiotic, closely related to the aminoglycosides, produced by the bacterium Streptomyces spectabilis.
There was a disruption in the supply in 2001.[1]
Contents |
[edit] Mechanism
Spectinomycin binds to the 30S subunit of the bacterial ribosome and interrupts protein synthesis.
One form of resistance has emerged in the 16S ribosomal RNA in Pasteurella multocida.[2]
[edit] Uses
It is given by injection to treat gonorrhea, especially in patients who are allergic to penicillins. This antibiotic is no longer available in the United States.
A resistance-conferring gene for spectinomycin can also be used as a selection marker in bacteria for molecular cloning purposes.
[edit] Side effects
Side effects include itching, chills, stomach-ache, and red rash.
[edit] References
- ^ "From the Centers for Disease Control and Prevention. Update on spectinomycin availability in the United States". JAMA 286 (11): 1308–9. September 2001. doi:10.1001/jama.286.11.1308. PMID 11575327. http://jama.ama-assn.org/cgi/pmidlookup?view=long&pmid=11575327.
- ^ Kehrenberg C, Schwarz S (June 2007). "Mutations in 16S rRNA and ribosomal protein S5 associated with high-level spectinomycin resistance in Pasteurella multocida". Antimicrob. Agents Chemother. 51 (6): 2244–6. doi:10.1128/AAC.00229-07. PMC 1891365. PMID 17371823. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1891365.
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