Spectinomycin

Spectinomycin

File: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
Pregnancy category	US: B (No risk in non-human studies)
Legal status
Legal status	not available in US
Identifiers
CAS Number	1695-77-8
ATC code	J01XX04 (WHO)
PubChem	CID 15541
DrugBank	APRD01232
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
Molar mass	332.35 g/mol[[]]

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.

Mechanism

It binds to the 30S ribosomal subunit in invading bacteria and interrupts protein synthesis.

One form of resistance has emerged in the 16S ribosomal RNA in Pasteurella multocida.

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.

It can also be used as a selection marker in bacteria for cloning purposes.

Side effects

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

References

de:Spectinomycin ja:スペクチノマイシン