Spectinomycin

Source: Wikipedia, the free encyclopedia.
Spectinomycin
Clinical data
Trade namesTrobicin
Other names(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 , SPT/SPE/SC/SP[1]
AHFS/Drugs.comMonograph
Routes of
administration		IM
ATC code
Legal status
Legal status
  • US: not available
Identifiers
  • (1R,3S,5R,8R,10S,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
JSmol)
Melting point184 to 194 °C (363 to 381 °F)
  • O=C1[C@@]2(O[C@@H]3[C@@H](NC)[C@@H](O)[C@@H](NC)[C@H](O)[C@H]3O[C@@H]2O[C@@H](C1)C)O
  • InChI=1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1 checkY
  • Key:UNFWWIHTNXNPBV-WXKVUWSESA-N checkY
 ☒NcheckY (what is this?)  (verify)

Spectinomycin, sold under the tradename Trobicin among others, is an

gonorrhea infections.[2] It is given by injection into a muscle.[2]

Common side effects include pain at the area of injection, rash, nausea, fever, and trouble sleeping.

allergic reactions may occasionally occur.[2] It is generally safe to use during pregnancy.[2] It may be used by those who are allergic to penicillin or cephalosporins.[2] It is in the aminocyclitol class of drugs and works by stopping the making of protein by certain bacteria.[2]

Spectinomycin was discovered in 1961.

bacterium Streptomyces spectabilis.[2]

Medical uses

It is given by intramuscular injection to treat gonorrhea, especially in patients who are allergic to penicillins.

This antibiotic is no longer available in the United States for human use, but is still available for veterinary use.

Side effects

Side effects include

itching, chills, stomach ache, and red rash
.

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.[5]

Biosynthetic mechanism

Proposed spectinomycin biosynthesis

Biosynthesis of spectinomycin begins similar to all aminoglycosides, with the formation of an

S-adenosyl methionine
molecules (5a). With this methylation, the glucose ring is finally ready to be converted into an inositol ring through inositol cyclase (6a). This can then be hydrolyzed to get rid of the phosphate group, making the inositol ring necessary for spectinomycin (7a).

While all this happens, an alternate pathway is occurring creating the sugar functional group from a similar starting product. In this pathway,

glucose-1-phosphate is used as the starting product (1b). This is converted into a TDP-glucose through TDP synthase (2b). TDP glucose then has the hydroxyl removed from C6 through a hydratase enzyme (3b), which is then reduced through NADH at C4 creating a new product (4b). With this ketone present, PLP and glutamine can come in to convert it to a primary amine (5b) which can then be removed through a deaminase (6b). This conversion to 6b is also accompanied by a double reduction at C4 and C3 through two more NADH molecules, giving the final product necessary to form the aminoglycoside. With this, products 7a and 6b can come together, removing the TDP functional group and combining with the sugar molecule to form the aminoglycoside spectinomycin.[6]

Nature

It is in

defence mechanism
against predators.

History

Spectinomycin was discovered 1961.[3] A disruption in the supply occurred in 2001.[7]

References

  1. ^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
  2. ^ a b c d e f g h i "Spectinomycin Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 2015-09-24. Retrieved Sep 6, 2015.
  3. ^
    ISBN 9781439882405. Archived
    from the original on 2015-10-03.
  4. hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  5. PMID 17371823
    .
  6. ISBN 9780470741689
    .
  7. PMID 11575327
    .

External links

  • "Spectinomycin". Drug Information Portal. U.S. National Library of Medicine.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Spectinomycin&oldid=1216898231"