Colistin

Colistin
Clinical data
Trade namesXylistin, Coly-Mycin M, Colobreathe, others
AHFS/Drugs.comMonograph
MedlinePlusa682860
License data
Routes of
administration		Topical, by mouth, intravenous, intramuscular, inhalation
ATC code
Legal status
Legal status
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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.644
Chemical and physical data
FormulaC52H98N16O13
Molar mass1155.455 g·mol−1
3D model (JSmol)
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 Y
  • Key:YKQOSKADJPQZHB-QNPLFGSASA-N Y
 NY (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, carbapenem-resistant Klebsiella pneumoniae (CRKP), 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 Clostridioides 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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