Polymyxin B
Identification
- Summary
Polymyxin B is a polymyxin antibiotic used to treat a wide variety of infections in the body.
- Brand Names
- Casporyn HC, Cortisporin, Dioptrol, Diosporin, Maxitrol, Neo-polycin, Neo-polycin HC, Neosporin Ointment, Neosporin Plus Maximum Strength, Neosporin Plus Maximum Strength Cream, Neosporin Solution, Polycin-B, Polysporin, Polytrim, Procomycin, Statrol, Triple Antibiotic
- Generic Name
- Polymyxin B
- DrugBank Accession Number
- DB00781
- Background
Polymyxin B was discovered in the 1940s5. They are basic polypeptides of about eight amino acids and have cationic detergent action on cell membranes4. Polymyxin B is used for infections with gram-negative organisms, but may be neurotoxic and nephrotoxic4,Label. All gram-positive bacteria, fungi, and the gram-negative cocci, are resistant4. It is appropriate for treatment of infections of the urinary tract, meninges, and blood stream, caused by susceptible strains of Pseudomonas aeruginosaLabel. Polymyxin B has a narrow therapeutic index and so its use is limited and unlikely to be used first line5.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Polymyxin B (DB00781)
- Weight
- Average: 1203.499
Monoisotopic: 1202.74992728 - Chemical Formula
- C56H98N16O13
- Synonyms
- Polimixina B
- Polymyxin B
- Polymyxine B
- Polymyxinum B
Pharmacology
- Indication
Polymyxin B is indicated for the treatment of infections of the urinary tract, meninges, and blood stream, caused by susceptible strains of Pseudomonas aeruginosaLabel.
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- Acute Otitis Media
- Bacteremia caused by Enterobacter aerogenes
- Bacterial Conjunctivitis
- Bacterial Infections
- Chronic Otitis Media
- Escherichia urinary tract infection
- Klebsiella bacteraemia
- Meningitis caused by Haemophilus influenzae
- Meningitis, Bacterial
- Ocular Inflammation
- Otitis Externa
- Otorrhoea
- Superficial ocular infections of the conjunctiva caused by susceptible bacteria
- Superficial ocular infections of the cornea caused by susceptible bacteria
- Urinary Tract Infection
- Ocular bacterial infections
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Polymyxin B is an antibiotic that disrupts the outer cell membrane of Gram negative bacteria, binds and neutralizes lipopolysaccharide, and inhibits respiration of Gram-negative bacterial cells4. Polymyxin B can be given by a number of routes to treat susceptible Gram negative bacterial infections4. Absorption of the drug is poor (though not necessary for most of its activity) and the excreted drug is unchanged by metabolic processes6,1. Polymyxin B is generally indicated for susceptible Gram negative infections of the urinary tract, meninges, and blood streamLabel.
- Mechanism of action
The alpha and gamma diaminobutyric acid of a positively charged polymyxin B forms an electrostatic interaction with the phosphate groups of a negatively charged lipid A on the outer membrane of a Gram negative bacterium4. Calcium and Magnesium ions are displaced from phosphates of the membrane lipids, destabalising the lipopolysaccharide (LPS), increasing membrane permeability, causing cytoplasmic leaking, and killing the cell4.
Polymyxin B can also bind and neutralize LPS released during bacterial lysis, preventing reactions to endotoxin4.
A third activity of polymyxin B is the inhibition of type II NADH-quinone oxidoreductases in the bacterial inner membrane, which are essential for respiration4.
Polymyxin is active against common Gram negative bacteria but not Gram negative cocci, Gram positive bacteria, or anaerobic bacteria4.
Target Actions Organism ABacterial outer membrane incorporation into and destabilizationBacteria - Absorption
Administration by the oral route does not lead to absorption4.
- Volume of distribution
1 compartment models estimate the volume of distribution to be 34.3L to 47.2L1. However, the general consensus is that the volume of distribution is yet to be determined8.
- Protein binding
Polymyxin B is 79% to 92% bound to proteins8. Polymyxin B is likely 92 to 99% protein bound in circulation, though the exact proteins have not been identified3.
- Metabolism
There is little data available for the metabolism of polymyxin B6. In one study, <1% of polymyxin B was eliminated through the kidneys and it had not been metabolised6. Polymyxin B has also been found in bile, not having undergone metabolic processes1.
- Route of elimination
Polymyxin B is proposed to be primarily eliminated through renal tubular reabsorption and non-renal pathways1,8. Urine collection in humans and animals show <5% of polymyxin B eliminated from the kidneys1. However, a Canadian product monograph states the drug is primarily eliminated through the kidneys and that 60% of polymyxin B is recovered in the urine8. This discrepancy can be explained by the 12 to 24 hour lag time between administration and significant elimination of polymyxin B8. Non-renal elimination is not well understood but all 4 components of polymyxin B have been detected in bile1.
- Half-life
In one study the half life was 9 to 11.5 hours1. However, a Canadian monograph states the half life to be 6 hours, and 48-72 hours in patients with renal insufficiency8.
- Clearance
1 compartment models estimate clearance to be 2.37L/h to 2.5L/h1.
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
Nephrotoxicity can occur in patients as polymyxin B is thought to accumulate in renal cells after renal tubular reabsorption1. This accumulation can lead to apoptosis of renal cells and decrease in renal function2. In recent studies, acute kidney injury (AKI) has been seen in 31.3% to 39.4% of patients receiving polymyxin B2.
Overdose cases can cause neuromuscular block leading to apnea, muscular weakness, vertigo, transient facial parasthesia, slurred speed, vasomotor instability, visual disturbance, confusion, psychosis, and respiratory arrest8. Renal failure has also been seen through decreased urine output, and increased serum concentrations of blood urea nitrogen8.
Overdose of polymyxin B is treated by stopping the drug and beginning symptomatic treatment8. Intravenous administration of mannitol may enhance renal clearance, and hemodialysis may manage renal complications8.
Safety of polymyxin B has not been established in pregnancy, breast feeding, pediatrics, and geriatrics8. Polymyxin B should no be used in pregnancy unless the benefit outweighs the risk8. Nursing mothers should either stop nursing or stop polymyxin B treatment depending on the risks to both the mother and child8. Pediatric patients should be frequently monitored for renal function and no dosing information is available in children under 2 years of age8. Geriatric patients should have renal function assessed before and regularly during therapy8.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 softwareAceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Polymyxin B. Acemetacin The risk or severity of adverse effects can be increased when Acemetacin is combined with Polymyxin B. Acenocoumarol The risk or severity of bleeding can be increased when Polymyxin B is combined with Acenocoumarol. Acetophenazine Acetophenazine may increase the neurotoxic activities of Polymyxin B. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Polymyxin B. Acyclovir The risk or severity of adverse effects can be increased when Acyclovir is combined with Polymyxin B. Adefovir dipivoxil The risk or severity of adverse effects can be increased when Adefovir dipivoxil is combined with Polymyxin B. Alclofenac The risk or severity of adverse effects can be increased when Alclofenac is combined with Polymyxin B. Alimemazine Alimemazine may increase the neurotoxic activities of Polymyxin B. Amikacin The risk or severity of adverse effects can be increased when Amikacin is combined with Polymyxin B. 
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- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Polymyxin B sulfate 19371312D4 1405-20-5 HFMDLUQUEXNBOP-OLYKAHIFSA-N - International/Other Brands
- Aerosporin (GlaxoSmithKline) / Metamyxin (Pola Pharma) / Polomyxin B (Fuji Yakuhin) / Poly-Rx (X-Gen) / Polyfax (Intra) / Polyxx (Celon)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aerosporin Sterile Powder Powder, for solution 500000 unit / vial Intramuscular; Intrathecal; Intravenous; Respiratory (inhalation); Topical Glaxo Wellcome 1952-12-31 1998-07-30 Canada 
Polymyxin B for Injection USP Powder, for solution 50 mg / vial Intramuscular; Intrathecal; Intravenous; Ophthalmic Sterimax Inc 2012-05-03 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Polymyxin B Injection, powder, lyophilized, for solution 500000 [iU]/1 Intramuscular; Intrathecal; Intravenous; Ophthalmic Alvogen Inc. 2017-09-23 Not applicable US 
Polymyxin B Injection, powder, lyophilized, for solution 500000 [USP'U]/1 Intramuscular; Intrathecal; Intravenous; Ophthalmic AuroMedics Pharma LLC 2016-04-04 Not applicable US Polymyxin B Injection 500000 1/1 Intramuscular; Intrathecal; Intravenous Xellia Pharmaceuticals ApS 2014-01-24 Not applicable US Polymyxin B Injection, powder, lyophilized, for solution 500000 [USP'U]/1 Intramuscular; Intravenous X-GEN Pharmaceuticals, Inc. 2014-04-25 2020-02-25 US Polymyxin B Injection, powder, for solution 500000 [USP'U]/1 Intramuscular; Intrathecal; Intravenous; Ophthalmic Xellia Pharmaceuticals USA LLC 2018-10-01 Not applicable US Polymyxin B Injection, powder, lyophilized, for solution 500000 [iU]/1 Intramuscular; Intrathecal; Intravenous; Ophthalmic Athenex Pharmaceutical Division, Llc. 2019-07-15 Not applicable US Polymyxin B Injection, solution 500000 1/1 Intramuscular; Intrathecal; Intravenous; Ophthalmic Breckenridge Pharmaceutical, Inc. 2016-06-01 2019-03-31 US Polymyxin B Injection, powder, lyophilized, for solution 500000 [USP'U]/1 Intramuscular; Intrathecal; Intravenous; Ophthalmic Fresenius Kabi USA, LLC 2009-11-17 Not applicable US Polymyxin B Injection, powder, lyophilized, for solution 500000 [USP'U]/1 Intramuscular; Intrathecal; Intravenous; Ophthalmic Fresenius Kabi USA, LLC 2015-09-09 Not applicable US Polymyxin B Injection, powder, for solution 500000 [iU]/1 Intramuscular; Intrathecal; Intravenous; Ophthalmic Bedford Pharmaceuticals 1998-06-01 2014-03-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 10 Person ANSI Polymyxin B sulfate (5000 [iU]/1g) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ibuprofen (200 mg/1) + Lidocaine (0.5 1/100g) + Neomycin sulfate (5 mg/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Topical Genuine First Aid 2010-04-24 Not applicable US 25 Person ANSI Polymyxin B sulfate (5000 [iU]/1g) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ethanol (62 g/100g) + Ibuprofen (200 mg/1) + Isopropyl alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Topical Genuine First Aid 2010-04-25 Not applicable US 4032 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc 2018-10-18 Not applicable US 4042 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4050 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4064 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4065 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4066 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4067 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4125 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc 2018-10-18 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 4032 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc 2018-10-18 Not applicable US 4042 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4050 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4064 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4065 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4066 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4067 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4125 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc 2018-10-18 Not applicable US 4135 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL) Kit Ophthalmic; Respiratory (inhalation); Topical Honeywell Safety Products USA, Inc. 2018-09-13 Not applicable US 4138 First Aid Kit Polymyxin B sulfate (5000 [iU]/1g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (2 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Topical Honeywell Safety Products USA, Inc. 2018-09-13 Not applicable US
Categories
- ATC Codes
- S02AA11 — Polymyxin bS03AA03 — Polymyxin b
- S03AA — Antiinfectives
- S03A — ANTIINFECTIVES
- S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
- S — SENSORY ORGANS
- J01XB — Polymyxins
- J01X — OTHER ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A07AA — Antibiotics
- A07A — INTESTINAL ANTIINFECTIVES
- A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Alimentary Tract and Metabolism
- Amino Acids, Peptides, and Proteins
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antiinfectives for Systemic Use
- Antimicrobial Cationic Peptides
- Intestinal Antiinfectives
- Lipopeptides
- Neurotoxic agents
- Ophthalmological and Otological Preparations
- Ophthalmologicals
- Otologicals
- Peptides
- Peptides, Cyclic
- Polymyxin-class Antibacterial
- Polymyxins
- Pore Forming Cytotoxic Proteins
- Proteins
- Sensory Organs
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- J2VZ07J96K
- CAS number
- 1404-26-8
- InChI Key
- WQVJHHACXVLGBL-BPJDFBQWSA-N
- InChI
- InChI=1S/C56H98N16O13/c1-7-32(4)13-11-12-16-44(75)63-36(17-23-57)51(80)72-46(34(6)74)56(85)68-39(20-26-60)48(77)67-41-22-28-62-55(84)45(33(5)73)71-52(81)40(21-27-61)65-47(76)37(18-24-58)66-53(82)42(29-31(2)3)69-54(83)43(30-35-14-9-8-10-15-35)70-49(78)38(19-25-59)64-50(41)79/h8-10,14-15,31-34,36-43,45-46,73-74H,7,11-13,16-30,57-61H2,1-6H3,(H,62,84)(H,63,75)(H,64,79)(H,65,76)(H,66,82)(H,67,77)(H,68,85)(H,69,83)(H,70,78)(H,71,81)(H,72,80)/t32?,33-,34-,36+,37+,38-,39+,40+,41+,42+,43-,45+,46+/m1/s1
- IUPAC Name
- N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9S,12S,15R,18R,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-(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]-6-methyloctanamide
- SMILES
- [H][C@]1(NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](CCN)NC(=O)[C@H](CCNC1=O)NC(=O)[C@H](CCN)NC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)CCCCC(C)CC)[C@@H](C)O)[C@@H](C)O
References
- General References
- Avedissian SN, Liu J, Rhodes NJ, Lee A, Pais GM, Hauser AR, Scheetz MH: A Review of the Clinical Pharmacokinetics of Polymyxin B. Antibiotics (Basel). 2019 Mar 22;8(1). pii: antibiotics8010031. doi: 10.3390/antibiotics8010031. [Article]
- Nation RL, Rigatto MHP, Falci DR, Zavascki AP: Polymyxin Acute Kidney Injury: Dosing and Other Strategies to Reduce Toxicity. Antibiotics (Basel). 2019 Mar 14;8(1). pii: antibiotics8010024. doi: 10.3390/antibiotics8010024. [Article]
- Abodakpi H, Gohlke J, Chang KT, Chow DS, Tam VH: Analytical and functional determination of polymyxin B protein binding in serum. Antimicrob Agents Chemother. 2015 Nov;59(11):7121-3. doi: 10.1128/AAC.01815-15. Epub 2015 Aug 31. [Article]
- Poirel L, Jayol A, Nordmann P: Polymyxins: Antibacterial Activity, Susceptibility Testing, and Resistance Mechanisms Encoded by Plasmids or Chromosomes. Clin Microbiol Rev. 2017 Apr;30(2):557-596. doi: 10.1128/CMR.00064-16. [Article]
- Velkov T, Roberts KD, Nation RL, Thompson PE, Li J: Pharmacology of polymyxins: new insights into an 'old' class of antibiotics. Future Microbiol. 2013 Jun;8(6):711-24. doi: 10.2217/fmb.13.39. [Article]
- Zavascki AP, Goldani LZ, Cao G, Superti SV, Lutz L, Barth AL, Ramos F, Boniatti MM, Nation RL, Li J: Pharmacokinetics of intravenous polymyxin B in critically ill patients. Clin Infect Dis. 2008 Nov 15;47(10):1298-304. doi: 10.1086/592577. [Article]
- SteriMax Inc: Polymyxin B for Injection USP Monograph [Link]
- Product Monograph: Polymyxin B For Injection USP [File]
- External Links
- ChemSpider
- 25045120
- BindingDB
- 50410807
- 8536
- ChEMBL
- CHEMBL1201283
- Wikipedia
- Polymyxin_B
- FDA label
- Download (219 KB)
- MSDS
- Download (127 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Antibiotic Allergy / Antibiotic Side Effect / Eyelid Diseases / Eyelid; Wound / Postoperative Wound Infection / Skin Cancer Face / Surgical Incisions / Surgical Site Infections / Surgical Wound, Recent 1 4 Completed Prevention End Stage Renal Disease (ESRD) 1 4 Completed Prevention Urinary Tract Infection 1 4 Completed Treatment Actinic Keratosis (AK) 1 4 Completed Treatment Conjunctivitis 1 4 Unknown Status Treatment Infections, Hospital 1 3 Completed Treatment Dermatitis, Eczematous 1 3 Recruiting Treatment Critically Ill Patients / Resistant Infection / Traumas 1 3 Unknown Status Treatment Acute / Bacterial Conjunctivitis 1 3 Unknown Status Treatment Hordeolum 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Ophthalmic; Oral; Respiratory (inhalation); Topical Kit Ophthalmic; Respiratory (inhalation); Topical Kit Oral; Respiratory (inhalation); Topical Kit Respiratory (inhalation); Topical Kit Irrigation; Ophthalmic; Respiratory (inhalation); Topical Kit Irrigation; Ophthalmic; Topical Kit Irrigation; Oral; Respiratory (inhalation); Topical Kit Irrigation; Ophthalmic; Oral; Respiratory (inhalation); Topical Kit Oral; Topical Kit Topical Powder, for solution Intramuscular; Intrathecal; Intravenous; Respiratory (inhalation); Topical 500000 unit / vial Solution / drops Oral Ointment Ointment Cutaneous Ointment; swab Topical Kit Electro-osmosis Solution Cutaneous Cream Topical Solution Auricular (otic) Suspension Topical Kit Oral Solution Auricular (otic); Topical Kit Ophthalmic; Oral; Topical Kit Ophthalmic Kit Ophthalmic; Topical Lozenge Buccal Stick Topical Suspension Conjunctival; Ophthalmic Solution Conjunctival; Ophthalmic Solution Conjunctival; Ophthalmic 1.3 mg Solution Intraocular; Ophthalmic Irrigant Irrigation Solution Irrigation Ointment Ophthalmic Suspension Ophthalmic Solution / drops Ophthalmic Solution / drops Auricular (otic) Suspension / drops Auricular (otic) Suspension / drops Ophthalmic Solution Auricular (otic); Ophthalmic Solution Urethral Gel Topical Liquid Auricular (otic) Suspension Auricular (otic) Injection, solution Intramuscular; Intrathecal; Intravenous Injection, powder, lyophilized, for solution Intramuscular; Intrathecal; Intravenous Liquid Auricular (otic); Ophthalmic Injection Intramuscular; Intrathecal; Intravenous 500000 1/1 Injection, powder, for solution Intramuscular; Intrathecal; Intravenous; Ophthalmic 500000 [iU]/1 Injection, powder, for solution Intramuscular; Intrathecal; Intravenous; Ophthalmic 500000 [USP'U]/1 Injection, powder, lyophilized, for solution Intramuscular; Intrathecal; Intravenous; Ophthalmic 500000 [iU]/1 Injection, powder, lyophilized, for solution Intramuscular; Intrathecal; Intravenous; Ophthalmic 500000 [USP'U]/1 Injection, powder, lyophilized, for solution Intramuscular; Intrathecal; Intravenous; Ophthalmic 500000 1/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous 500000 [USP'U]/1 Injection, solution Intramuscular; Intrathecal; Intravenous; Ophthalmic 500000 1/1 Powder, for solution Intramuscular; Intrathecal; Intravenous; Ophthalmic 50 mg / vial Powder Topical Solution / drops Auricular (otic); Ophthalmic Ointment Ophthalmic; Topical Injection, powder, lyophilized, for solution Intramuscular; Intrathecal; Intravenous 500000 IU Lozenge Oral Ointment Topical Solution Ophthalmic Ointment Conjunctival; Ophthalmic Swab Topical Solution Ophthalmic 1 mg Liquid Ophthalmic - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) >203 MSDS water solubility Soluble MSDS pKa 8.9 https://www.chemicalbook.com/ChemicalProductProperty_US_CB8666707.aspx - Predicted Properties
Property Value Source Water Solubility 0.0744 mg/mL ALOGPS logP -0.89 ALOGPS logP -7.2 ChemAxon logS -4.2 ALOGPS pKa (Strongest Acidic) 11.57 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 29 ChemAxon Refractivity 313.22 m3·mol-1 ChemAxon Polarizability 127.4 Å3 ChemAxon Number of Rings 2 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
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1. Bacterial outer membrane
Yes
Incorporation into and destabilization
References
- Yuan Z, Tam VH: Polymyxin B: a new strategy for multidrug-resistant Gram-negative organisms. Expert Opin Investig Drugs. 2008 May;17(5):661-8. doi: 10.1517/13543784.17.5.661 . [Article]
- Zavascki AP, Goldani LZ, Li J, Nation RL: Polymyxin B for the treatment of multidrug-resistant pathogens: a critical review. J Antimicrob Chemother. 2007 Dec;60(6):1206-15. Epub 2007 Sep 17. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- Mediates drug reabsorption in the kidney
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Lu X, Chan T, Xu C, Zhu L, Zhou QT, Roberts KD, Chan HK, Li J, Zhou F: Human oligopeptide transporter 2 (PEPT2) mediates cellular uptake of polymyxins. J Antimicrob Chemother. 2016 Feb;71(2):403-12. doi: 10.1093/jac/dkv340. Epub 2015 Oct 22. [Article]
Drug created on February 28, 2019 16:07 / Updated on July 29, 2021 06:27