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 | DB00919 |
| 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
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| (what is this?) (verify) | |
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. Spectinomycin is produced in nature by many organisms including cyanobacteria and various plant species. It is present in the genome or plastome of many plastids as the spc operon, which is usually 2–10 amino acids long (this has been known to vary). The difference in size may be due to the elimination of obsolete genes or the takeover of its function by nuclear genes. Spectinomycin is mainly produced by organisms as a defence mechanism against predators.
Mechanism of action
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.[1]
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. Furthermore, Spectinomycin is used as a selection agent for transformed plant cells that contain the selectable marker gene Spcr.[2]
Side effects
Side effects include itching, chills, stomach-ache, and red rash.
History
There was a disruption in the supply in 2001.[3]
References
- ↑ 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.
- ↑ "Spectinomycin Hydrochloride" (pdf). Toku-E. 2010-10-10. Retrieved 2012-06-11.
- ↑ "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.
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