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Colistin information


Colistin
Clinical data
Trade namesXylistin, Coly-Mycin M, Colobreathe, others
AHFS/Drugs.comMonograph
MedlinePlusa682860
License data
  • US DailyMed: Colistimethate
Routes of
administration
Topical, by mouth, intravenous, intramuscular, inhalation
ATC code
  • A07AA10 (WHO) J01XB01 (WHO), QA07AA10 (WHO), QA07AA98 (WHO), QG51AG07 (WHO), QJ01XB01 (WHO), QJ51XB01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only[1]
  • UK: POM (Prescription only)[2][3][4]
  • US: ℞-only[5]
  • EU: Rx-only[6]
Pharmacokinetic data
Bioavailability0%
Elimination half-life5 hours
Identifiers
IUPAC name
  • N-(4-amino-1-(1-(4-amino-1-oxo-1-(3,12,23-tris(2-aminoethyl)- 20-(1-hydroxyethyl)-6,9-diisobutyl-2,5,8,11,14,19,22-heptaoxo- 1,4,7,10,13,18-hexaazacyclotricosan-15-ylamino)butan-2-ylamino)- 3-hydroxybutan-2-ylamino)-1-oxobutan-2-yl)-N,5-dimethylheptanamide
CAS Number
  • 1066-17-7 checkY
  • as salt: 8068-28-8 checkY
PubChem CID
  • 5311054
DrugBank
  • DB00803 checkY
ChemSpider
  • 4470591 checkY
UNII
  • Z67X93HJG1
  • as salt: XW0E5YS77G checkY
KEGG
  • D02138 checkY
  • as salt: D02049 checkY
ChEMBL
  • ChEMBL501505 ☒N
CompTox Dashboard (EPA)
  • DTXSID1040663 Edit this at Wikidata
ECHA InfoCard100.012.644 Edit this at Wikidata
Chemical and physical data
FormulaC52H98N16O13
Molar mass1155.455 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC1)[C@H](O)C)CCN)CCN)CC(C)C)CC(C)C)CCN)CCN)[C@H](O)C)CCN)CCCC(C)CC
InChI
  • InChI=1S/C52H98N16O13/c1-9-29(6)11-10-12-40(71)59-32(13-19-53)47(76)68-42(31(8)70)52(81)64-35(16-22-56)44(73)63-37-18-24-58-51(80)41(30(7)69)67-48(77)36(17-23-57)61-43(72)33(14-20-54)62-49(78)38(25-27(2)3)66-50(79)39(26-28(4)5)65-45(74)34(15-21-55)60-46(37)75/h27-39,41-42,69-70H,9-26,53-57H2,1-8H3,(H,58,80)(H,59,71)(H,60,75)(H,61,72)(H,62,78)(H,63,73)(H,64,81)(H,65,74)(H,66,79)(H,67,77)(H,68,76)/t29?,30-,31-,32+,33+,34+,35+,36+,37+,38+,39-,41+,42+/m1/s1 checkY
  • Key:YKQOSKADJPQZHB-QNPLFGSASA-N checkY
 ☒NcheckY (what is this?)  (verify)

Colistin, also known as polymyxin E, is an antibiotic medication used as a last-resort treatment for multidrug-resistant Gram-negative infections including pneumonia.[7][8] These may involve bacteria such as Pseudomonas aeruginosa, Klebsiella pneumoniae, or Acinetobacter.[9] It comes in two forms: colistimethate sodium can be injected into a vein, injected into a muscle, or inhaled, and colistin sulfate is mainly applied to the skin or taken by mouth.[10] Colistimethate sodium[11] is a prodrug; it is produced by the reaction of colistin with formaldehyde and sodium bisulfite, which leads to the addition of a sulfomethyl group to the primary amines of colistin. Colistimethate sodium is less toxic than colistin when administered parenterally. In aqueous solutions it undergoes hydrolysis to form a complex mixture of partially sulfomethylated derivatives, as well as colistin. Resistance to colistin began to appear as of 2015.[12]

Common side effects of the injectable form include kidney problems and neurological problems.[8] Other serious side effects may include anaphylaxis, muscle weakness, and Clostridium difficile-associated diarrhea.[8] The inhaled form may result in constriction of the bronchioles.[8] It is unclear if use during pregnancy is safe for the fetus.[13] Colistin is in the polymyxin class of medications.[8] It works by breaking down the cytoplasmic membrane, which generally results in bacterial cell death.[8]

Colistin was discovered in 1947 and colistimethate sodium was approved for medical use in the United States in 1970.[9][8] It is on the World Health Organization's List of Essential Medicines.[14] The World Health Organization classifies colistin as critically important for human medicine.[15] It is available as a generic medication.[16] It is derived from bacteria of the genus Paenibacillus.[10]

  1. ^ "Drug Product Database". Health Canada. 25 April 2012. Retrieved 13 January 2022.
  2. ^ "Colobreathe 1,662,500 IU inhalation powder, Hard Capsules – Summary of Product Characteristics (SmPC)". (emc). Retrieved 16 November 2020.
  3. ^ "Colomycin 1 million International Units (IU) Powder for solution for injection, infusion or inhalation – Summary of Product Characteristics (SmPC)". (emc). 27 May 2020. Retrieved 16 November 2020.
  4. ^ "Promixin 1 million International Units (IU) Powder for Nebuliser Solution – Summary of Product Characteristics (SmPC)". (emc). 23 September 2020. Retrieved 16 November 2020.
  5. ^ "Coly-Mycin M- colistimethate injection". DailyMed. 3 December 2018. Retrieved 16 November 2020.
  6. ^ "Colobreathe EPAR". European Medicines Agency. 17 September 2018. Retrieved 16 November 2020.
  7. ^ Pogue JM, Ortwine JK, Kaye KS (April 2017). "Clinical considerations for optimal use of the polymyxins: A focus on agent selection and dosing". Clinical Microbiology and Infection. 23 (4): 229–233. doi:10.1016/j.cmi.2017.02.023. PMID 28238870.
  8. ^ a b c d e f g "Colistimethate Sodium Monograph for Professionals". Drugs.com. Retrieved 6 November 2019.
  9. ^ a b Falagas ME, Grammatikos AP, Michalopoulos A (October 2008). "Potential of old-generation antibiotics to address current need for new antibiotics". Expert Review of Anti-Infective Therapy. 6 (5): 593–600. doi:10.1586/14787210.6.5.593. PMID 18847400. S2CID 13158593.
  10. ^ a b Bennett JE, Dolin R, Blaser MJ, Mandell GL (2009). Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases E-Book. Elsevier Health Sciences. p. 469. ISBN 9781437720600.
  11. ^ Bergen PJ, Li J, Rayner CR, Nation RL (June 2006). "Colistin methanesulfonate is an inactive prodrug of colistin against Pseudomonas aeruginosa". Antimicrobial Agents and Chemotherapy. 50 (6): 1953–1958. doi:10.1128/AAC.00035-06. PMC 1479097. PMID 16723551.
  12. ^ Hasman H, Hammerum AM, Hansen F, Hendriksen RS, Olesen B, Agersø Y, et al. (2015-12-10). "Detection of mcr-1 encoding plasmid-mediated colistin-resistant Escherichia coli isolates from human bloodstream infection and imported chicken meat, Denmark 2015". Euro Surveillance. 20 (49): 30085. doi:10.2807/1560-7917.ES.2015.20.49.30085. PMID 26676364.
  13. ^ "Colistimethate (Coly Mycin M) Use During Pregnancy". Drugs.com. Retrieved 11 November 2019.
  14. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  15. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.
  16. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 547. ISBN 9780857113382.

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Colistin

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Colistin, also known as polymyxin E, is an antibiotic medication used as a last-resort treatment for multidrug-resistant Gram-negative infections including...

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Polymyxin

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Polymyxins are antibiotics. Polymyxins B and E (also known as colistin) are used in the treatment of Gram-negative bacterial infections. They work mostly...

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List of antibiotics

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Fluoroquinolones: particularly levofloxacin, ciprofloxacin Polymyxins: Colistin, Polymyxin B Aztreonam (monobactam) Aminoglycosides - particularly tobramycin...

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Chinchilla

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digestive problems. Sulfonamides dissolved in drinking water may be used. Colistin can be an effective antibiotic. Roach, N.; Kennerley, R. (2016). "Chinchilla...

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Pig farming

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countries. China once used colistin (an antibiotic) as growth promoter (subtherapeutic antibiotic use) but discovered a colistin-resistant form of E. coli...

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Gardnerella vaginalis

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agar; it also grows on HBT agar. A selective medium for G. vaginalis is colistin-oxolinic acid blood agar. G. vaginalis is a facultatively anaerobic Gram-variable...

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Elizabethkingia meningoseptica

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oxidizer. Most strains do not grow on colistin nalidixic acid agar because, although they are resistant to colistin, they are susceptible to quinolones...

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Tyrothricin

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pharmacologically related group of polypeptide antibiotic compounds including colistin, polymyxin B, and bacitracin. There is no cross-resistance to these three...

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Klebsiella pneumoniae

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gram-negative pathogens in the ICU have invoked the re-emergence of colistin. However, colistin-resistant strains of K. pneumoniae have been reported in ICUs...

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Polypeptide antibiotic

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polypeptide chains. Examples of this class include actinomycin, bacitracin, colistin, and polymyxin B. Actinomycin-D has found use in cancer chemotherapy. Most...

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Cyclic peptide

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example in bacitracin; the carboxyl end and a side chain, for example in colistin; or two side chains or more complicated arrangements, for example in alpha-amanitin...

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Acinetobacter baumannii

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fall back on polymyxins, particularly colistin although tetracyclines have shown promise in MDR A. baumannii. Colistin is considered a drug of last resort...

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Antibiotic

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an E. coli "superbug" was identified in the United States resistant to colistin, "the last line of defence" antibiotic. In recent years, even anaerobic...

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Amikacin

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meropenem for meningitis caused by Acinetobacter, as an adjunct to imipenem or colistin for neonatal meningitis caused by Streptococcus agalactiae or Listeria...

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Anaerococcus murdochii

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Resistance or reduced susceptibility to several antibiotics, such as colistin sulphate, clindamycin and kanamycin A or penicillin has been reported....

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New York City agar

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vancomycin, colistin, nystatin and trimethoprim, to suppress the accompanying flora. Vancomycin is inhibitory for gram-positive bacteria. Colistin inhibits...

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Timeline of antibiotics

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vancomycin, the first glycopeptide 1956 – phenoxymethylpenicillin 1958 – colistin, the first polymyxin 1958 – demeclocycline 1959 – virginiamycin 1960 –...

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Acinetobacter

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two (4%) were resistant to all drugs tested. One antimicrobial agent, colistin (polymyxin E), has been used to treat infections with multidrug-resistant...

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Cystic fibrosis

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Frijlink HW, Heijerman HG (March 2004). "Effect of nebulized colistin sulphate and colistin sulphomethate on lung function in patients with cystic fibrosis:...

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Sepsis

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for antibiotics with low volume distribution (vancomycin, teicoplanin, colistin), a loading dose is required to achieve an adequate therapeutic level to...

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Mobiluncus

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sensitive to vancomycin, erythromycin and ampicillin, but resistant to colistin. These organisms are found in the human vagina, particularly in association...

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Morganella morganii

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second-generation cephalosporins, macrolides, lincosamides, fosfomycin, colistin, and polymyxin B. The emergence of highly resistant strains of M. morganii...

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Carbapenem

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Enterobacteriaceae has led to a renaissance of the use of antibiotics such as colistin, which was discovered in the 1950s but rarely used until recently due to...

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Bacteriophage

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strains was being treated with a cocktail of Azithromycin, Rifampicin, and Colistin for 4 months without results and overall rapidly declining health. Because...

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Antibiotic use in livestock

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cephalosporins, glycopeptides, macrolides and ketolides, polymyxins including colistin, and quinolones including fluoroqinolones.[citation needed] The European...

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Burkholderia cepacia complex

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ceftolozane-tazobactam can also be effective. BCC intrinsically resistant to colistin and usually resistant to aminoglycosides. In people with cystic fibrosis...

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