Tue . 19 Jun 2019

Spectinomycin

spectinomycin, spectinomycin for cattle
Spectinomycin, sold under the tradename Trobicin among others, is an antibiotic useful for the treatment of gonorrhea infections It is given by injection into a muscle

Common side effects include pain at the area of injection, rash, nausea, fever, and trouble sleeping Severe allergic reactions may occasionally occur It is generally safe to use during pregnancy It may be used by those who are allergic to penicillin or cephalosporins It is in the aminocyclitol class of drugs and works by stopping the making of protein by certain bacteria

Spectinomycin was discovered 1961 It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system The wholesale cost in the developing world is about US$5 per dose It is not available in the United States It is made from the bacterium Streptomyces spectabilis

Contents

  • 1 Medical uses
  • 2 Side effects
  • 3 Mechanism of action
  • 4 Biosynthetic mechanism
    • 41 Nature
  • 5 History
  • 6 References

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

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

Biosynthetic mechanism

Proposed spectinomycin biosynthesis

Biosynthesis of spectinomycin begins similar to all aminoglycosides, with the formation of an inositol ring The difference is the initial modification that forms the inositol ring of spectinomycin The process begins with a glucose-6-phosphate 1a, which is reduced by NADH to form a ketone at C2 2a This ketone is then formed into a primary amine group through PLP and glutamine transamination 3a This process is repeated again at C4 to form a second primary amine 4a Once these two amines are present, the glucose ring is ready to be methylated through two 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

Nature

It is in aminocyclitol class, closely related to the aminoglycosides Spectinomycin is industrially produced by fermentation of 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 two to 10 genes long 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

History

Spectinomycin was discovered 1961 A disruption in the supply occurred in 2001

References

  1. ^ 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 
  2. ^ a b Textbook of Drug Design and Discovery, Fourth Edition CRC Press 2009 p 438 ISBN 9781439882405 Archived from the original on 2015-10-03 
  3. ^ "WHO Model List of Essential Medicines 19th List" PDF World Health Organization April 2015 Archived PDF from the original on 13 December 2016 Retrieved 8 December 2016 
  4. ^ "Spectinomycin" International Drug Price Indicator Guide Retrieved 7 September 2015 
  5. ^ 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:101128/AAC00229-07 PMC 1891365  PMID 17371823 
  6. ^ Dewick, Paul M 4 Feb 2009 Medicinal Natural Products: A Biosynthetic Approach, 3rd Edition Wiley Online Library: Wiley pp 485–508 ISBN 9780470741689 Archived from the original on 10 March 2014 Retrieved 29 May 2014 
  7. ^ "From the Centers for Disease Control and Prevention Update on spectinomycin availability in the United States" JAMA 286 11: 1308–9 September 2001 doi:101001/jama286111308 PMID 11575327 
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Spectinomycin Information about

Spectinomycin


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    Spectinomycin beatiful post thanks!

    29.10.2014


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