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Details

Stereochemistry ABSOLUTE
Molecular Formula C57H108N16O25S4
Molecular Weight 1545.82
Optical Activity UNSPECIFIED
Defined Stereocenters 13 / 13
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COLISTIN-1,3,5,9-TETRAMETHANESULFONIC A ACID

SMILES

[H][C@](NC(=O)[C@H](CCNCS(O)(=O)=O)NC(=O)CCCC[C@@H](C)CC)([C@@H](C)O)C(=O)N[C@@H](CCNCS(O)(=O)=O)C(=O)N[C@H]1CCNC(=O)[C@@]([H])(NC(=O)[C@H](CCNCS(O)(=O)=O)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCNCS(O)(=O)=O)NC1=O)[C@@H](C)O

InChI

InChIKey=ZXYYNNMHQSUIER-UKUNXGILSA-N
InChI=1S/C57H108N16O25S4/c1-9-34(6)12-10-11-13-45(76)64-38(15-21-59-28-99(87,88)89)52(81)73-47(36(8)75)57(86)69-40(17-23-61-30-101(93,94)95)49(78)68-42-19-25-63-56(85)46(35(7)74)72-53(82)41(18-24-62-31-102(96,97)98)67-48(77)37(14-20-58)65-54(83)43(26-32(2)3)71-55(84)44(27-33(4)5)70-51(80)39(66-50(42)79)16-22-60-29-100(90,91)92/h32-44,46-47,59-62,74-75H,9-31,58H2,1-8H3,(H,63,85)(H,64,76)(H,65,83)(H,66,79)(H,67,77)(H,68,78)(H,69,86)(H,70,80)(H,71,84)(H,72,82)(H,73,81)(H,87,88,89)(H,90,91,92)(H,93,94,95)(H,96,97,98)/t34-,35+,36+,37-,38-,39-,40-,41-,42-,43-,44+,46-,47-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=317cc880-73fe-4561-897e-41489108b3ba http://www.drugbank.ca/drugs/DB00803 http://www.rxlist.com/coly-mycin-s-otic-drug.htm https://www.niaid.nih.gov/topics/antimicrobialResistance/Pages/colistin.aspx

Colistin sulfate is a polypeptide antibiotic which penetrates into and disrupts the bacterial cell membrane. It is a cyclic polypeptide antibiotic from Bacillus colistinus. It is composed of Polymyxins E1 and E2 (or Colistins A, B, and C). Colistin was first isolated in Japan in 1949 from a flask of fermenting Bacillus polymyxa var. colistinus and became available for clinical use in 1959. The following local adverse events have been reported with topical corticosteroids, especially under occlusive dressings: burning, itching, irritation, dryness, folliculitis, hypertrichosis, etc. Healthcare providers had largely stopped using colistin in the 1970s because of its toxicity. However, with antibacterial resistance on the rise, colistin is increasingly being used today to treat severe, multidrug-resistant Gram-negative bacterial infections, particularly among intensive care-based patients. The problem with re-introducing an older drug, such as colistin, though, is that techniques for evaluating new drugs have evolved since the 1950s, and therefore, little is known about the dose needed to effectively fight infection while limiting the potential emergence of antimicrobial resistance and reducing potentially toxic side effects. More data are needed to guide optimal use of these older medications. An international team of NIAID-funded researchers is making progress in obtaining better dosing information about colistin and how best to use the antibiotic to treat Gram-negative bacterial infections. Resistance to colistin is rare. The first colistin-resistance gene that is carried in a plasmid and can be transferred between bacterial strains was described in 2016. This plasmid-borne mcr-1 gene has since been isolated in China, Europeand the United States.

Originator

Curator's Comment: Colistin was first discovered by Koyama et al. in 1949.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Bacterial outer membrane
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
COLY-MYCIN S

Approved Use

Cortisporin®-TC Otic Suspension is indicated for the treatment of superficial bacterial infections of the external auditory canal, caused by organisms susceptible to the action of the antibiotics; and for the treatment of infections of mastoidectomy and fenestration cavities, caused by organisms susceptible to the antibiotics.

Launch Date

1962
Curative
COLY-MYCIN S

Approved Use

Cortisporin®-TC Otic Suspension is indicated for the treatment of superficial bacterial infections of the external auditory canal, caused by organisms susceptible to the action of the antibiotics; and for the treatment of infections of mastoidectomy and fenestration cavities, caused by organisms susceptible to the antibiotics.

Launch Date

1962
PubMed

PubMed

TitleDatePubMed
Antibacterial agents in renal failure.
1971 May 29
Myopathy caused by polymyxin E: functional disorder of the cell membrane.
1974 Dec
Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation.
1975 Dec
Further studies on effects of irrigation solutions on rat bladders.
1976 Dec
Deafness and biochemical imbalance after burns treatment with topical antibiotics in young children. Report of 6 cases.
1978 Apr
Antimycobacterial spectrum of colistin (polymixin E).
1986 Jan-Feb
Screening for inhibitors of avian myeloblastosis virus reverse transcriptase and effect on the replication of AIDS-virus.
1987 Jan
Early prediction of polymyxin-induced nephrotoxicity with next-generation urinary kidney injury biomarkers.
2014 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Therapy with Coly-Mycin S (Colistin-containing suspension) should be limited to 10 days.
For adults, 5 drops of the suspension into the affected ear 3 or 4 times daily. For pediatric patients, 4 drops are suggested.
Route of Administration: Otic (auricular)
In Vitro Use Guide
Lethal concentrations of colistin of 50 and 100 µg/ml caused about 90 and 99% cell death, respectively.
Name Type Language
COLISTIN-1,3,5,9-TETRAMETHANESULFONIC A ACID
Common Name English
POLYMYXIN E1, 1-(N2-(6-METHYL-1-OXOOCTYL)-N4-(SULFOMETHYL)-L-2,4-DIAMINOBUTANOIC ACID)-3-(N4-(SULFOMETHYL)-L-2,4-DIAMINOBUTANOIC ACID)-5-(N4-(SULFOMETHYL)-L-2,4-DIAMINOBUTANOIC ACID)-9-(N4-(SULFOMETHYL)-L-2,4-DIAMINOBUTANOIC ACID)-
Systematic Name English
COLISTIN A, 1-(L-2-(6-METHYLOCTANAMIDO)-4-((SULFOMETHYL)AMINO)BUTYRIC ACID)-3-(L-2-AMINO-4-((SULFOMETHYL)AMINO)BUTYRIC ACID)-5-(L-2-AMINO-4-((SULFOMETHYL)AMINO)BUTYRIC ACID)-9-(L-2-AMINO-4-((SULFOMETHYL)AMINO)BUTYRIC ACID)-
Systematic Name English
POLYMYXIN E1, 1-((2S)-2-((6-METHYL-1-OXOOCTYL)AMINO)-4-((SULFOMETHYL)AMINO)BUTANOIC ACID)-3-((2S)-2-AMINO-4-((SULFOMETHYL)AMINO)BUTANOIC ACID)-5-((2S)-2-AMINO-4-((SULFOMETHYL)AMINO)BUTANOIC ACID)-9-((2S)-2-AMINO-4-((SULFOMETHYL)AMINO)BUTANOIC ACID)-
Systematic Name English
Code System Code Type Description
PUBCHEM
112500431
Created by admin on Sat Dec 16 08:15:55 GMT 2023 , Edited by admin on Sat Dec 16 08:15:55 GMT 2023
PRIMARY
FDA UNII
76Z8VB787C
Created by admin on Sat Dec 16 08:15:55 GMT 2023 , Edited by admin on Sat Dec 16 08:15:55 GMT 2023
PRIMARY
CAS
30387-39-4
Created by admin on Sat Dec 16 08:15:55 GMT 2023 , Edited by admin on Sat Dec 16 08:15:55 GMT 2023
PRIMARY