Chemical Properties
White Powder
Uses
An antibiotic used in the treatment and control of infectious bacterial enteritis in animals. Used in drug testing against nonreplicating mycobacterium tuberculosis.
Uses
Antibacterial;Ribosomal protein
Definition
ChEBI: A hydrochloride obtained by combining spectinomycin with two molar equivalents of hydrochloric acid. An antibiotic that is active against gram-negative bacteria and used (as its pentahydrate) to treat gonorrhea.
Clinical Use
The aminocyclitol antibiotic spectinomycin hydrochloride(Trobicin), isolated from Streptomyces spectabilis andonce called actinospectocin, was first described by Lewisand Clapp. Its structure and absolute stereochemistryhave been confirmed by x-ray crystallography. It occursas the white, crystalline dihydrochloride pentahydrate,which is stable in the dry form and very soluble in water.Solutions of spectinomycin, a hemiacetal, slowly hydrolyzeon standing and should be prepared freshly andused within 24 hours. It is administered by deep intramuscularinjection.
Spectinomycin is a broad-spectrum antibiotic withmoderate activity against many Gram-positive and Gramnegativebacteria. It differs from streptomycin and thestreptamine-containing aminoglycosides in chemical and antibacterialproperties. Like streptomycin, spectinomycininterferes with the binding of transfer RNA (tRNA) to the ribosomesand thus with the initiation of protein synthesis.Unlike streptomycin or the streptamine-containing antibiotics,however, it does not cause misreading of the messenger.Spectinomycin exerts a bacteriostatic action and isinferior to other aminoglycosides for most systemic infections.Currently, it is recommended as an alternative to penicillinG salts for the treatment of uncomplicated gonorrhea.A cure rate of more than 90% has been observed in clinicalstudies for this indication. Many physicians prefer to use atetracycline or erythromycin for prevention or treatment ofsuspected gonorrhea in penicillin-sensitive patients because,unlike these agents, spectinomycin is ineffective againstsyphilis. Furthermore, it is considerably more expensive thanerythromycin and most of the tetracyclines.
Purification Methods
The salt is purified by recrystallisation from aqueous Me2CO and is soluble in H2O, MeOH and dilute acid and base, but only slightly soluble in Me2CO, EtOH, CHCl3 and *C6H6. The free base is an amorphous solid, m 184-194o with []D -20o (H2O). [Wiley et al. J Am Chem Soc 93 2652 1963, X-ray: Cochran et al. J Chem Soc Chem Commun 494 1972.] It is an aminoglycoside antibiotic which interacts with 16S ribosomal RNA [Moazet & Noller Nature 327 389 1987] and is used for the treatment of gonorrhea [Rinehart J Infect Dis 119 345 1969].
