Bacitracin
Identification
- Summary
Bacitracin is a cyclic polypeptide antibiotic used to prevent wound infections, treat pneumonia and empyema in infants, and to treat skin and eye infections.
- Brand Names
- Baciguent, Baciject, Cortisporin, Diosporin, Neo-polycin, Neo-polycin HC, Neosporin Ointment, Neosporin Plus Maximum Strength, Neosporin Solution, Polycin-B, Polysporin, Procomycin, Rash Relief Antibacterial, Triple Antibiotic
- Generic Name
- Bacitracin
- DrugBank Accession Number
- DB00626
- Background
Bacitracin is a combination of at least 9 bacitracins.2,3 60-80% of commercially prepared bacitracin is bacitracin A.3 The bacillus that produces bacitracin was first isolated from a knee scrape in 1945 from the knee wound of a child named Margaret Tracy.3
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Bacitracin (DB00626)
- Weight
- Average: 1422.693
Monoisotopic: 1421.748941023 - Chemical Formula
- C66H103N17O16S
- Synonyms
- Bacitracin
- Bacitracin A
- Bacitracina
- External IDs
- NSC-45737
Pharmacology
- Indication
Bacitracin is indicated in topical formulations for acute and chronic localized skin infections.4 Occasionally, it is also used intramuscularly for infantile streptococcal pneumonia and empyema.4 Bacitracin is also formulated as an ointment with neomycin and polymyxin B for over the counter use.4,10 A bacitracin ointment formulated with neomycin and polymyxin B along with hydrocortisone is indicated for the treatment of corticosteroid responsive dermatoses with secondary infection.11
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Associated Conditions
- 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
Bacitracin is a mixture of polypeptides that prevent the formation of the bacterial cell wall and oxidatively cleave DNA.1 It has a short duration of action as it must be given every 3 to 4 hours topically.10,11 Bacitracin is nephrotoxic when given intramuscularly and may lead to renal failure.4
- Mechanism of action
Bacitracin binds to a divalent metal ion such as Mn(II), Co(II), Ni(II), Cu(II), or Zn(II).1 These complexes bind C55-isoprenyl pyrophosphate, preventing the hydrolysis of a lipid dolichol pyrophosphate, which finally inhibits cell wall synthesis.1 Bacitracin metal complexes also bind and oxidatively cleave DNA.1
Target Actions Organism AC55-isoprenyl pyrophosphate antagonistGram positive and gram negative bacteria AInsulin-degrading enzyme inhibitorHumans UAlpha-2-macroglobulin inhibitorHumans - Absorption
Topical, ophthalmic, and oral formulations of bacitracin are poorly absorbed systemically.4,7 Intramuscular bacitracin is readily and completely absorbed.13
- Volume of distribution
Data regarding the volume of distribution of bacitracin in humans is not readily available.4
- Protein binding
Data regarding the protein binding of bacitracin in humans is not readily available.4
- Metabolism
Data regarding the metabolism of bacitracin in humans is not readily available.4 Because bacitracin is a protein it is expected to be metabolized into smaller polypeptides and amino acids.5 However, the structure of bacitracin may afford it some protection from the action of proteases.1
- Route of elimination
Bacitracin is mainly excreted renally with 87% of and intramuscular dose being recovered in the urine after 6 hours.6
- Half-life
Data regarding the half life of bacitracin in humans is not readily available.4
- Clearance
Data regarding the clearance of bacitracin in humans has not been well studied.4 A study of 9 subjects in 1947 shows a renal clearance of 105-283mL/min with an average renal clearance of 159mL/min.6
- 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
The oral LD50 of bacitracin in rats is >2000mg/kg.12
Specific data regarding bacitracin overdoses is not readily available.8 An overdose of bacitracin may lead to nephrotoxicity4 and patients should be treated with supportive measures.
- 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 softwareAbacavir Bacitracin may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac The risk or severity of nephrotoxicity can be increased when Bacitracin is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Bacitracin is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Bacitracin is combined with Acenocoumarol. Acetaminophen Bacitracin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Bacitracin is combined with Acetylsalicylic acid. Aclidinium Bacitracin may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Bacitracin may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir The risk or severity of nephrotoxicity can be increased when Bacitracin is combined with Acyclovir. Adefovir dipivoxil The risk or severity of nephrotoxicity can be increased when Bacitracin is combined with Adefovir dipivoxil. 
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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 Bacitracin methylene disalicylate JGV6OJ52FT 55852-84-1 Not applicable Bacitracin zinc 89Y4M234ES 1405-89-6 Not applicable - International/Other Brands
- Baciguent (Upjohn)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Baciject 50,000 Units/vial Powder, for solution 50000 unit / vial Intramuscular; Topical Sterimax Inc 2003-08-28 Not applicable Canada 
Bacitracin for Injection Powder, for solution 50000 unit / vial Intramuscular; Topical Fresenius Kabi Not applicable Not applicable Canada Bacitracin for Injection, USP Powder, for solution 50000 unit / vial Intramuscular; Topical Auro Pharma Inc Not applicable Not applicable Canada Bacitracin USP Powder, for solution 50000 unit / vial Intramuscular; Topical Pfizer Canada Ulc 1951-12-31 2021-03-31 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Baciguent Ointment 500 [USP'U]/1g Ophthalmic Woodward Pharma Services Llc 2020-04-15 Not applicable US 
BACiiM Injection, powder, lyophilized, for solution 50000 [USP'U]/1 Intramuscular X-GEN Pharmaceuticals, Inc. 1997-05-09 2020-02-07 US Bacitracin Ointment 500 [USP'U]/1g Ophthalmic Paddock Laboratories, LLC 2014-03-10 Not applicable US Bacitracin Injection, powder, for solution 50000 [USP'U]/1 Intramuscular Xellia Pharmaceuticals USA LLC 2018-10-01 Not applicable US Bacitracin Ointment 500 [iU]/1g Ophthalmic Remedy Repack 2013-02-08 2014-02-08 US Bacitracin Ointment 500 [iU]/1g Ophthalmic Rebel Distributors 2010-01-11 Not applicable US Bacitracin Injection, powder, for solution 50000 [iU]/1 Intramuscular Fresenius Kabi USA, LLC 2003-01-28 Not applicable US Bacitracin Injection, powder, for solution 5000 [USP'U]/1mL Intramuscular Pharmacia & Upjohn Company LLC 1948-07-29 2022-01-31 US Bacitracin Injection, powder, for solution 5000 [USP'U]/1mL Intramuscular Pharmacia and Upjohn Company 1948-07-29 Not applicable US Bacitracin Ointment 500 [USP'U]/1g Ophthalmic Akorn 2013-12-13 2014-02-25 US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Advanced First Aid Bacitracin Ointment 500 1/1g Topical Advanced First Aid, Inc. 2016-10-18 Not applicable US Aftate Bacitracin Zinc Ointment 500 [iU]/1g Topical Sabel Med Llc 2016-05-01 Not applicable US Ancalima Bacitracin Zinc First Aid Ointment 500 [USP'U]/1g Topical ANCALIMA LIFESCIENCES LIMITED 2019-04-08 Not applicable US Antibiotic Ointment 500 [USP'U]/1g Topical Meijer Distribution Inc 2015-04-15 Not applicable US Antibiotic Ointment 500 [USP'U]/1g Topical Topco Associates LLC 2020-04-03 Not applicable US antibiotic Bacitracin Zinc Ointment 500 [iU]/1g Topical A-S Medication Solutions 2006-05-11 2019-09-30 US antibiotic Bacitracin Zinc Ointment 500 [iU]/1g Topical Strategic Sourcing Services LLC 2006-05-11 Not applicable US Baciguent First Aid Ointment Ointment 500 unit / g Topical Johnson & Johnson Merck Consumer Pharmaceuticals Of Canada 1997-12-19 2008-08-07 Canada Baciguent First Aid Ointment 500units/gm Ointment 500 unit / g Topical Upjohn 1995-12-31 2001-07-26 Canada Baciguent Ointment 500 Units Ointment 500 unit / g Topical Upjohn 1951-12-31 1996-09-10 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 10 Person ANSI Bacitracin zinc (400 [iU]/1g) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + 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) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Topical Genuine First Aid 2010-04-24 Not applicable US 25 Person ANSI Bacitracin zinc (400 [iU]/1g) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + 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) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Oral; Topical Genuine First Aid 2010-04-25 Not applicable US 4032 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/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 Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4050 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4064 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4065 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4066 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4067 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4125 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Ammonia (0.045 g/0.3mL) + 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) + Polymyxin B sulfate (5000 [iU]/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 Bacitracin zinc (400 [iU]/1g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/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 Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4050 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4064 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 2019-10-18 US 4065 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4066 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4067 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) Kit Topical Honeywell Safety Products USA, Inc 2018-11-21 Not applicable US 4125 First Aid Kit Bacitracin zinc (400 [iU]/1g) + Ammonia (0.045 g/0.3mL) + 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) + Polymyxin B sulfate (5000 [iU]/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 Bacitracin zinc (400 [iU]/1g) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/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 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) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL) Kit Ophthalmic; Topical Honeywell Safety Products USA, Inc. 2018-09-13 Not applicable US
Categories
- ATC Codes
- J01XX10 — Bacitracin
- J01XX — Other antibacterials
- J01X — OTHER ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- D06AX — Other antibiotics for topical use
- D06A — ANTIBIOTICS FOR TOPICAL USE
- D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- Drug Categories
- Acids, Carbocyclic
- Amino Acids, Peptides, and Proteins
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Antibacterials for Systemic Use
- Antibiotics for Topical Use
- Antiinfectives for Systemic Use
- Bacitracins
- Benzene Derivatives
- Benzoates
- Decreased Cell Wall Synthesis & Repair
- Dermatologicals
- Hydroxy Acids
- Hydroxybenzoates
- Nephrotoxic agents
- Peptides
- Peptides, Cyclic
- Phenols
- Throat Preparations
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
- Kingdom
- Organic compounds
- Super Class
- Organic Polymers
- Class
- Polypeptides
- Sub Class
- Not Available
- Direct Parent
- Polypeptides
- Alternative Parents
- Cyclic peptides / Glutamic acid and derivatives / Leucine and derivatives / Isoleucine and derivatives / N-acyl-alpha amino acids and derivatives / Macrolactams / Alpha amino acid amides / Thiazolecarboxamides / Imidazolyl carboxylic acids and derivatives / Benzene and substituted derivatives show 16 more
- Substituents
- Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Azole / Benzenoid / Carbonyl group show 37 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- homodetic cyclic peptide, polypeptide (CHEBI:35862) / Non-ribosomal peptides (C15482)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- DDA3RRX0P7
- CAS number
- 1405-87-4
- InChI Key
- CLKOFPXJLQSYAH-ABRJDSQDSA-N
- InChI
- InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-/m0/s1
- IUPAC Name
- (4R)-4-[(2S)-2-{[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazol-4-yl]formamido}-4-methylpentanamido]-4-{[(1S,2S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-3-(carbamoylmethyl)-6-(carboxymethyl)-9-[(1H-imidazol-4-yl)methyl]-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
- SMILES
- CC[C@H](C)[C@H](N)C1=N[C@@H](CS1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H]1CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(O)=O)NC(=O)[C@H](CC2=CNC=N2)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](NC(=O)[C@@H](CCCN)NC1=O)[C@@H](C)CC
References
- Synthesis Reference
Brigt Oystese, "Zinc bacitracin composition for use as a feed supplement and method for making the same." U.S. Patent US4096246, issued December, 1963.
US4096246- General References
- Tay WM, Epperson JD, da Silva GF, Ming LJ: 1H NMR, mechanism, and mononuclear oxidative activity of the antibiotic metallopeptide bacitracin: the role of D-Glu-4, interaction with pyrophosphate moiety, DNA binding and cleavage, and bioactivity. J Am Chem Soc. 2010 Apr 28;132(16):5652-61. doi: 10.1021/ja910504t. [Article]
- Karala AR, Ruddock LW: Bacitracin is not a specific inhibitor of protein disulfide isomerase. FEBS J. 2010 Jun;277(11):2454-62. doi: 10.1111/j.1742-4658.2010.07660.x. Epub 2010 Apr 30. [Article]
- Toscano WA Jr, Storm DR: Bacitracin. Pharmacol Ther. 1982;16(2):199-210. [Article]
- Nguyen R, Sun Y: Bacitracin Topical . [Article]
- Katsila T, Siskos AP, Tamvakopoulos C: Peptide and protein drugs: the study of their metabolism and catabolism by mass spectrometry. Mass Spectrom Rev. 2012 Jan-Feb;31(1):110-33. doi: 10.1002/mas.20340. Epub 2011 Jun 22. [Article]
- Eagle H, Newman EV, Greif R, Burkholder TM, Goodman SC, Musselman AD: THE BLOOD LEVELS AND RENAL CLEARANCE IN RABBITS AND MAN OF AN ANTIBIOTIC DERIVED FROM B. SUBTILIS (BACITRACIN). J Clin Invest. 1947 Sep;26(5):919-28. doi: 10.1172/JCI101886. [Article]
- Authors unspecified: Bacitracin . [Article]
- 2. (2018). In Poisoning & Drug Overdose (7th ed.). McGraw-Hill Education. [ISBN:978-0-07-183979-2]
- FDA Approved Drug Products: Bacitracin Injection [Link]
- FDA Approved Drug Products: Bacitracin, Neomycin, and Polymyxin B Ophthalmic Ointment [Link]
- FDA Approved Drug Products: Bacitracin, Neomycin, Polymyxin B, and Hydrocortisone Topical Ointment [Link]
- Pfizer: Corticosporin Safety Data Sheet [Link]
- FDA Briefing Document: Bacitracin for Intramuscular Injection [Link]
- External Links
- Human Metabolome Database
- HMDB0014764
- KEGG Drug
- D00128
- KEGG Compound
- C15482
- PubChem Compound
- 10909430
- PubChem Substance
- 46504727
- ChemSpider
- 9084687
- 1291
- ChEBI
- 35862
- ChEMBL
- CHEMBL1200558
- Therapeutic Targets Database
- DAP000710
- PharmGKB
- PA448531
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Bacitracin
- AHFS Codes
- 52:04.04 — Antibacterials
- 84:04.04 — Antibiotics
- 08:12.28.08 — Bacitracins
- MSDS
- Download (71.6 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 Incision / Surgical Site Infections / Surgical Wound, Recent 1 4 Completed Prevention Arrhythmia 2 4 Completed Prevention End Stage Renal Disease (ESRD) 1 4 Completed Prevention Skin Infections 1 4 Completed Prevention Urinary Tract Infection 1 4 Completed Treatment Actinic Keratosis (AK) 1 4 Completed Treatment Arteriovenous Fistulas 1 4 Completed Treatment Burns 1 4 Recruiting Prevention Surgical Site Infections 1 4 Recruiting Treatment Partial Thickness Burn 1
Pharmacoeconomics
- Manufacturers
- X gen pharmaceuticals inc
- App pharmaceuticals llc
- Pfizer laboratories div pfizer inc
- Pharmacia and upjohn co
- Sagent pharmaceuticals inc
- Altana inc
- Eli lilly and co
- Pharmaderm div altana inc
- Pharmafair inc
- Combe inc
- Naska pharmacal co inc div rugby darby group cosmetics
- Apothekernes laboratorium a/s
- Paddock laboratories inc
- Packagers
- Amend
- APP Pharmaceuticals
- Ben Venue Laboratories Inc.
- CVS Pharmacy
- Dispensing Solutions
- DSM Corp.
- E. Fougera and Co.
- Fera Pharmaceuticals
- Ivax Pharmaceuticals
- Mckesson Corp.
- Pharmacia Inc.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Redpharm Drug
- Toku E Company
- X-Gen Pharmaceuticals
- 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 Ointment Topical 500 1/1g Kit Oral; Topical Kit Topical Ointment Ophthalmic 500 unit / g Ointment Topical 500 unit / g Cream Topical 500 U/0.9g Cream Topical 500 [iU]/1g Injection Intramuscular 50000 [iU]/1 Injection, powder, for solution Intramuscular 5000 [USP'U]/1mL Injection, powder, for solution Intramuscular 50000 [iU]/1 Injection, powder, for solution Intramuscular 50000 [USP'U]/1 Injection, powder, for solution Intramuscular 50000 [iU]/10mL Injection, powder, lyophilized, for solution Intramuscular 50000 [USP'U]/1 Ointment Ophthalmic 500 [iU]/1g Ointment Ophthalmic 500 [USP'U]/1g Ointment Topical 500 [iU]/1g Ointment Topical 500 1/1000mg Ointment Topical 500 1/1 Ointment Granule Oral Powder Not applicable 1 g/1g Powder, for solution Intramuscular; Topical 50000 unit / vial Ointment Topical 500 [USP'U]/1g Powder Not applicable 1 kg/1kg Ointment Cutaneous Ointment; swab Topical Syrup Oral Tablet Oral Kit Electro-osmosis Solution Cutaneous Kit Oral Ointment Topical .51 g/100g Kit Ophthalmic; Oral; Topical Kit Ophthalmic Kit Ophthalmic; Topical Stick Topical Powder Oral Ointment Ophthalmic Gel Topical Cream Topical 500 unit / g Powder Topical Ointment Ophthalmic; Topical Cream Topical Ointment Topical 500 U/1g Cream Topical 500 U/1g Liquid Topical Cream Ointment Topical Ointment Topical 400 [USP'U]/1g Patch Cutaneous Powder, for solution Oral Spray Topical 500 [USP'U]/1g Swab Topical Ointment Topical 500 U/1mL Cream Topical 500 [USP'U]/1g Lozenge Oral Tablet - Prices
Unit description Cost Unit Bacitracin 5mm unit powder 126.0USD each Baciim strl 50000 unit vial 19.8USD vial Bacitracin 50000 unit vial 13.31USD vial Bacitracin 500 unit/gm ointmnt 9.69USD g CVS Pharmacy bacitracin 500 unit/gm oin 0.15USD g Sm first aid bacitracin ointmn 0.1USD g 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 water solubility Freely soluble O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 166 - Predicted Properties
Property Value Source Water Solubility 0.0245 mg/mL ALOGPS logP -2.9 ALOGPS logP -6.8 ChemAxon logS -4.8 ALOGPS pKa (Strongest Acidic) 3.19 ChemAxon pKa (Strongest Basic) 9.63 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 20 ChemAxon Hydrogen Donor Count 17 ChemAxon Polar Surface Area 530.87 Å2 ChemAxon Rotatable Bond Count 31 ChemAxon Refractivity 363.14 m3·mol-1 ChemAxon Polarizability 149.32 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7857 Blood Brain Barrier - 0.9943 Caco-2 permeable - 0.7639 P-glycoprotein substrate Substrate 0.7416 P-glycoprotein inhibitor I Non-inhibitor 0.898 P-glycoprotein inhibitor II Non-inhibitor 0.9697 Renal organic cation transporter Non-inhibitor 0.9073 CYP450 2C9 substrate Non-substrate 0.7482 CYP450 2D6 substrate Non-substrate 0.7884 CYP450 3A4 substrate Non-substrate 0.5435 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9011 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9122 Ames test Non AMES toxic 0.7225 Carcinogenicity Non-carcinogens 0.9045 Biodegradation Not ready biodegradable 0.9799 Rat acute toxicity 2.8201 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9936 hERG inhibition (predictor II) Non-inhibitor 0.6586
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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Yes
Antagonist
References
- Stone KJ, Strominger JL: Mechanism of action of bacitracin: complexation with metal ion and C 55 -isoprenyl pyrophosphate. Proc Natl Acad Sci U S A. 1971 Dec;68(12):3223-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Plays a role in the cellular breakdown of insulin, IAPP, glucagon, bradykinin, kallidin and other peptides, and thereby plays a role in intercellular peptide signaling. Degrades amyloid formed by A...
- Gene Name
- IDE
- Uniprot ID
- P14735
- Uniprot Name
- Insulin-degrading enzyme
- Molecular Weight
- 117967.49 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Tumor necrosis factor binding
- Specific Function
- Is able to inhibit all four classes of proteinases by a unique 'trapping' mechanism. This protein has a peptide stretch, called the 'bait region' which contains specific cleavage sites for differen...
- Gene Name
- A2M
- Uniprot ID
- P01023
- Uniprot Name
- Alpha-2-macroglobulin
- Molecular Weight
- 163289.945 Da
References
- Maxfield FR, Davies PJ, Klempner L, Willingham MC, Pastan I: Epidermal growth factor stimulation of DNA synthesis is potentiated by compounds that inhibit its clustering in coated pits. Proc Natl Acad Sci U S A. 1979 Nov;76(11):5731-5. [Article]
- Dickson RB, Willingham MC, Pastan I: Binding and internalization of 125I-alpha 2-macroglobulin by cultured fibroblasts. J Biol Chem. 1981 Apr 10;256(7):3454-9. [Article]
- Dickson RB, Willingham MC, Gallo M, Pastan I: Inhibition by bacitracin of high affinity binding of 125I-alpha 2M to plasma membranes. FEBS Lett. 1981 Apr 20;126(2):265-8. [Article]
- Hanover JA, Cheng S, Willingham MC, Pastan IH: alpha 2-Macroglobulin binding to cultured fibroblasts. Solubilization and partial purification of binding sites. J Biol Chem. 1983 Jan 10;258(1):370-7. [Article]
- Gliemann J, Larsen TR, Sottrup-Jensen L: Cell association and degradation of alpha 2-macroglobulin-trypsin complexes in hepatocytes and adipocytes. Biochim Biophys Acta. 1983 Mar 31;756(2):230-7. [Article]
Transporters
- Kind
- Protein
- Organism
- Bacillus licheniformis
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Part of the binding-protein-dependent transport system for bacitracin that confer resistance to this antibiotic. Probably responsible for energy coupling to the transport system (By similarity).
- Specific Function
- Atp binding
- Gene Name
- bcrA
- Uniprot ID
- P42332
- Uniprot Name
- Bacitracin transport ATP-binding protein BcrA
- Molecular Weight
- 34641.065 Da
References
- Podlesek Z, Comino A, Herzog-Velikonja B, Zgur-Bertok D, Komel R, Grabnar M: Bacillus licheniformis bacitracin-resistance ABC transporter: relationship to mammalian multidrug resistance. Mol Microbiol. 1995 Jun;16(5):969-76. doi: 10.1111/j.1365-2958.1995.tb02322.x. [Article]
- Kind
- Protein
- Organism
- Bacillus licheniformis
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Part of the binding-protein-dependent transport system for bacitracin that confer resistance to this antibiotic; probably responsible for the translocation of the substrate across the membrane.
- Specific Function
- Not Available
- Gene Name
- bcrB
- Uniprot ID
- P42333
- Uniprot Name
- Bacitracin transport permease protein BCRB
- Molecular Weight
- 23323.755 Da
References
- Podlesek Z, Comino A, Herzog-Velikonja B, Zgur-Bertok D, Komel R, Grabnar M: Bacillus licheniformis bacitracin-resistance ABC transporter: relationship to mammalian multidrug resistance. Mol Microbiol. 1995 Jun;16(5):969-76. doi: 10.1111/j.1365-2958.1995.tb02322.x. [Article]
- Kind
- Protein
- Organism
- Bacillus licheniformis
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Part of the binding-protein-dependent transport system for bacitracin that confer resistance to this antibiotic; probably responsible for the translocation of the substrate across the membrane.
- Specific Function
- Undecaprenyl-diphosphatase activity
- Gene Name
- bcrC
- Uniprot ID
- P42334
- Uniprot Name
- Bacitracin transport permease protein BcrC
- Molecular Weight
- 23274.21 Da
References
- Podlesek Z, Comino A, Herzog-Velikonja B, Zgur-Bertok D, Komel R, Grabnar M: Bacillus licheniformis bacitracin-resistance ABC transporter: relationship to mammalian multidrug resistance. Mol Microbiol. 1995 Jun;16(5):969-76. doi: 10.1111/j.1365-2958.1995.tb02322.x. [Article]
Drug created on June 13, 2005 13:24 / Updated on June 23, 2021 06:08