Identification
- Summary
Colistin is a polymyxin antibiotic used to treat bacterial infections caused by susceptible Gram negative bacteria.
- Brand Names
- Cortisporin-TC
- Generic Name
- Colistin
- DrugBank Accession Number
- DB00803
- Background
Cyclic polypeptide antibiotic from Bacillus colistinus. It is composed of Polymyxins E1 and E2 (or Colistins A, B, and C) which act as detergents on cell membranes. Colistin is less toxic than Polymyxin B, but otherwise similar; the methanesulfonate is used orally.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Colistin (DB00803)
- Weight
- Average: 1155.455
Monoisotopic: 1154.74992728 - Chemical Formula
- C52H98N16O13
- Synonyms
- Colimycin
- Colistin
- Colistina
- Colistine
- Colistinum
- Kolimycin
- Polymyxin E
Pharmacology
- Indication
For the treatment of acute or chronic infections due to sensitive strains of certain gram-negative bacilli, particularly Pseudomonas aeruginosa.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Ear infection bacterial Combination Product in combination with: Neomycin (DB00994), Hydrocortisone (DB00741) •••••••••••• •••••••••• Used in combination to treat External ear infection Combination Product in combination with: Hydrocortisone acetate (DB14539), Neomycin (DB00994), Thonzonium (DB09552) •••••••••••• - Contraindications & Blackbox Warnings
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Colistin is a polymyxin antibiotic agent. Polymyxins are cationic polypeptides that disrupt the bacterial cell membrane through a detergentlike mechanism. With the development of less toxic agents, such as extended-spectrum penicillins and cephalosporins, parenteral polymyxin use was largely abandoned, except for the treatment of multidrug-resistant pulmonary infections in patients with cystic fibrosis. More recently, however, the emergence of multidrug-resistant gram-negative bacteria, such as Pseudomonas aeruginosa and Acinetobacter baumannii, and the lack of new antimicrobial agents have led to the revived use of the polymyxins.
- Mechanism of action
Colistin is a surface active agent which penetrates into and disrupts the bacterial cell membrane. Colistin is polycationic and has both hydrophobic and lipophilic moieties. It interacts with the bacterial cytoplasmic membrane, changing its permeability. This effect is bactericidal. There is also evidence that polymyxins enter the cell and precipitate cytoplasmic components, primarily ribosomes.
Target Actions Organism ABacterial outer membrane incorporation into and destabilizationBacteria - Absorption
Very poor absorption from gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
As 80% of the dose can be recovered unchanged in the urine, and there is no biliary excretion, it can be assumed that the remaining drug is inactivated in the tissues, however the mechanism is unknown.
- Route of elimination
Not Available
- Half-life
5 hours
- Clearance
Not Available
- Adverse Effects
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Oral LD50 in rats is 5450 mg/kg. Overdosage with colistimethate can cause neuromuscular blockade characterized by paresthesia, lethargy, confusion, dizziness, ataxia, nystagmus, disorders of speech and apnea. Respiratory muscle paralysis may lead to apnea, respiratory arrest and death.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Colistin which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Colistin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Colistin which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Colistin is combined with Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Colistin which could result in a higher serum level. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Colistin sulfate WP15DXU577 1264-72-8 ZJIWRHLZXQPFAD-LRYSGCCDSA-N - International/Other Brands
- Alfacolin (Catalysis) / Alficetin (Nova Argentia) / ColiFin (Pari Pharma) / Colimicina (Quimifar) / Colimycine (Sanofi Aventis) / Coliracin (Rafa) / Colistate (Atlantic Lab) / Colomycin (Forest) / Coly-Mycin (King Pharmaceuticals) / Diarönt mono (CNP) / Promixin (Profile Pharma) / Tadim (Allertec) / Walamycin (Wallace)
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image COLISTINA SULFATO+HIDROCORTISONA ACETATO+NEOMICINA SULFATO Colistin sulfate (1.538 mg) + Hydrocortisone (0.5 mg) + Neomycin (5 mg) Suspension Auricular (otic) ARBOFARMA S.A.S 2010-02-11 2020-07-01 Colombia 
Coly-Mycin S Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL) + Thonzonium bromide (0.5 mg/1mL) Suspension Auricular (otic) Par Pharmaceutical 2007-11-01 2017-06-18 US 
Coly-Mycin S Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL) + Thonzonium bromide (0.5 mg/1mL) Suspension Auricular (otic) Physicians Total Care, Inc. 2007-11-01 2012-06-30 US Coly-Mycin S Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL) + Thonzonium bromide (0.5 mg/1mL) Suspension Auricular (otic) Endo Pharmaceuticals Inc. 2016-04-18 2020-04-30 US Cortisporin TC Colistin sulfate (3 mg/1mL) + Hydrocortisone acetate (10 mg/1mL) + Neomycin sulfate (3.3 mg/1mL) + Thonzonium bromide (0.5 mg/1mL) Suspension Auricular (otic) Endo Pharmaceuticals, Inc. 2019-06-03 Not applicable US
Categories
- ATC Codes
- J01XB01 — Colistin
- J01XB — Polymyxins
- J01X — OTHER ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Alimentary Tract and Metabolism
- Amino Acids, Peptides, and Proteins
- Aminoglycoside Antibacterials
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antiinfectives for Systemic Use
- Antimicrobial Cationic Peptides
- Antimicrobial Peptides
- Drugs that are Mainly Renally Excreted
- Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index
- Intestinal Antiinfectives
- Lipids
- Lipopeptides
- Membrane Proteins
- Narrow Therapeutic Index Drugs
- Nephrotoxic agents
- Peptides
- Peptides, Cyclic
- Polymyxins
- Pore Forming Cytotoxic Proteins
- Proteins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Cyclic peptides
- Alternative Parents
- Cyclic carboximidic acids / Secondary alcohols / Propargyl-type 1,3-dipolar organic compounds / Polyols / Azacyclic compounds / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic heteromonocyclic compound / Amine / Azacycle / Carboximidic acid / Carboximidic acid derivative / Cyclic alpha peptide / Cyclic carboximidic acid / Hydrocarbon derivative / Organic 1,3-dipolar compound
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Gram-negative bacilli
Chemical Identifiers
- UNII
- Z67X93HJG1
- CAS number
- 1066-17-7
- InChI Key
- YKQOSKADJPQZHB-BRLOSWAASA-N
- 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
- IUPAC Name
- N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(6R,9S,12R,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl]carbamoyl}propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}propyl]-5-methylheptanamide
- SMILES
- CCC(C)CCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)C(NC(=O)[C@@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O)[C@@H](C)O
References
- General References
- Not Available
- External Links
- KEGG Drug
- D02138
- KEGG Compound
- C13768
- PubChem Compound
- 131704173
- PubChem Substance
- 46505467
- 2709
- ChEMBL
- CHEMBL407135
- Therapeutic Targets Database
- DAP001324
- PharmGKB
- PA164760862
- Wikipedia
- Colistin
- MSDS
- Download (72.2 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Bacterial Infections 1 4 Completed Prevention Hematological Infection 1 4 Completed Treatment Bronchiectasis 1 4 Completed Treatment Colistin / Colistin Adverse Reaction / Gram-Negative Bacterial Infections / MIC / Pediatric Cancer 1 4 Completed Treatment Cystic Fibrosis (CF) 2
Pharmacoeconomics
- Manufacturers
- Parke davis div warner lambert co
- Packagers
- Paddock Labs
- Dosage Forms
Form Route Strength Powder, for solution Oral 100 mg/g Injection, powder, for solution 1000000 UI/4ML Solution / drops Oral 4000000 U/3.5ML Tablet 1500.000 U Granule Oral 10 % Injection, powder, for solution 1000.000 U.I. Injection, powder, for solution 2000.000 U.I. Powder, for solution Oral 1000000 UI Powder, for solution Oral 2000000 UI Injection, powder, for solution 1000000 UI Injection, powder, for solution 2000000 UI Granule Oral Tablet Powder, for solution Oral 150 MIU Powder, for solution Oral 75 mg/g Suspension Auricular (otic) Powder Solution Oral Powder, for solution Oral Injection, powder, for solution Injection, powder, for solution 1000.000 UI Injection, powder, for solution 2000.000 UI Granule Oral 10 % w/w Solution Oral 2.4 MIU/ML Powder, for solution Oral 2 MIU/G - Prices
Unit description Cost Unit Colistin sulfate powder 513.26USD each Coly-Mycin S 3.3-3-10 mg/ml Suspension 5ml Bottle 49.17USD bottle DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 200-220 °C Not Available water solubility 5.64E+005 mg/L Not Available logP -2.4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.238 mg/mL ALOGPS logP -1.3 ALOGPS logP -8.1 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 11.6 Chemaxon pKa (Strongest Basic) 10.23 Chemaxon Physiological Charge 5 Chemaxon Hydrogen Acceptor Count 18 Chemaxon Hydrogen Donor Count 18 Chemaxon Polar Surface Area 490.66 Å2 Chemaxon Rotatable Bond Count 28 Chemaxon Refractivity 297.67 m3·mol-1 Chemaxon Polarizability 123.32 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7444 Blood Brain Barrier - 0.9752 Caco-2 permeable - 0.7492 P-glycoprotein substrate Substrate 0.8048 P-glycoprotein inhibitor I Non-inhibitor 0.7514 P-glycoprotein inhibitor II Non-inhibitor 0.8582 Renal organic cation transporter Non-inhibitor 0.9525 CYP450 2C9 substrate Non-substrate 0.893 CYP450 2D6 substrate Non-substrate 0.7907 CYP450 3A4 substrate Non-substrate 0.513 CYP450 1A2 substrate Non-inhibitor 0.9372 CYP450 2C9 inhibitor Non-inhibitor 0.9387 CYP450 2D6 inhibitor Non-inhibitor 0.929 CYP450 2C19 inhibitor Non-inhibitor 0.9139 CYP450 3A4 inhibitor Non-inhibitor 0.8879 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9937 Ames test Non AMES toxic 0.8807 Carcinogenicity Non-carcinogens 0.8947 Biodegradation Not ready biodegradable 0.9515 Rat acute toxicity 3.0728 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9855 hERG inhibition (predictor II) Non-inhibitor 0.8646
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 318.8137 predictedDeepCCS 1.0 (2019) [M+H]+ 320.4669 predictedDeepCCS 1.0 (2019) [M+Na]+ 326.6238 predictedDeepCCS 1.0 (2019)
Targets
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1. Bacterial outer membrane
Yes
Incorporation into and destabilization
References
- Vaara M: Polymyxins and their novel derivatives. Curr Opin Microbiol. 2010 Oct;13(5):574-81. doi: 10.1016/j.mib.2010.09.002. Epub 2010 Sep 24. [Article]
- Soon RL, Nation RL, Cockram S, Moffatt JH, Harper M, Adler B, Boyce JD, Larson I, Li J: Different surface charge of colistin-susceptible and -resistant Acinetobacter baumannii cells measured with zeta potential as a function of growth phase and colistin treatment. J Antimicrob Chemother. 2011 Jan;66(1):126-33. doi: 10.1093/jac/dkq422. Epub 2010 Nov 16. [Article]
- Evans ME, Feola DJ, Rapp RP: Polymyxin B sulfate and colistin: old antibiotics for emerging multiresistant gram-negative bacteria. Ann Pharmacother. 1999 Sep;33(9):960-7. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54