Spectinomycin

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Spectinomycin
Spectinomycin.svg
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 YesY
ATC code J01XX04
PubChem CID 15541
DrugBank DB00919
ChemSpider 14785 YesY
UNII 93AKI1U6QF YesY
KEGG D08526 YesY
ChEBI CHEBI:9215 N
ChEMBL CHEMBL1167 YesY
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
 N (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[edit]

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[edit]

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[edit]

Side effects include itching, chills, stomach-ache, and red rash.

History[edit]

There was a disruption in the supply in 2001.[3]

References[edit]