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, Diphen, 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

Bacitracin was granted FDA approval on 29 July 1948.^4,9

Type

Small Molecule

Groups

Approved, Vet approved

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Bacitracin (DB00626)

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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

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Associated Conditions

• Acne
• Bacterial Infections of the Intestine
• Empyema
• Eye Infections
• Infection
• Inflammatory Reaction caused by Acne
• Ocular Inflammatory Disease
• Pneumonia
• Skin Ulcer
• Wound Infections
• Corticosteroid-responsive dermatoses
• Infection in minor cuts, scrapes, or burns
• Wound site

Contraindications & Blackbox Warnings

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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	antagonist	Gram positive and gram negative bacteria
AInsulin-degrading enzyme	inhibitor	Humans
UAlpha-2-macroglobulin	inhibitor	Humans

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

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	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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Food Interactions

No interactions found.

Products

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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	Powder, for solution	50000 unit / vial	Intramuscular; Topical	Sterimax Inc	2003-08-28	Not applicable
Bacitracin for Injection	Powder, for solution	50000 unit / vial	Intramuscular; Topical	Fresenius Kabi	Not applicable	Not applicable
Bacitracin for Injection, USP	Powder, for solution	50000 unit / vial	Intramuscular; Topical	Eugia Pharma Inc.	Not applicable	Not applicable
Bacitracin for Injection, USP	Powder, for solution	50000 unit / vial	Intramuscular; Topical	Auro Pharma Inc	Not applicable	Not applicable
Bacitracin USP	Powder, for solution	50000 unit / vial	Intramuscular; Topical	Pfizer Canada Ulc	1951-12-31	2021-03-31

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
BACiiM	Injection, powder, lyophilized, for solution	50000 [USP'U]/1	Intramuscular	X-GEN Pharmaceuticals, Inc.	1997-05-09	2020-02-07
Bacitracin	Injection	50000 [iU]/1	Intramuscular	Xellia Pharmaceuticals ApS	2013-01-31	Not applicable
Bacitracin	Ointment	500 [iU]/1g	Ophthalmic	E. Fougera & CO., A division of Fougera Pharmaceuticals Inc.	1971-11-09	2009-07-31
Bacitracin	Injection, powder, lyophilized, for solution	50000 [USP'U]/1	Intramuscular	X-GEN Pharmaceuticals, Inc.	2015-10-08	2020-02-07
Bacitracin	Injection, powder, for solution	50000 [USP'U]/1	Intramuscular	Civica, Inc.	2019-12-01	Not applicable
Bacitracin	Injection, powder, for solution	5000 [USP'U]/1mL	Intramuscular	Pharmacia and Upjohn Company LLC	1948-07-29	2021-03-31
Bacitracin	Injection, powder, for solution	5000 [USP'U]/1mL	Intramuscular	Akorn, Inc.	2017-10-23	Not applicable
Bacitracin	Injection, powder, for solution	50000 [iU]/10mL	Intramuscular	Sagent Pharmaceuticals	2010-08-10	2013-12-01
Bacitracin	Ointment	500 [iU]/1g	Ophthalmic	Fera Pharmaceuticals	2010-01-11	2013-06-14

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
Aftate Bacitracin Zinc	Ointment	500 [iU]/1g	Topical	Sabel Med Llc	2016-05-01	Not applicable
Ancalima Bacitracin Zinc First Aid	Ointment	500 [USP'U]/1g	Topical	ANCALIMA LIFESCIENCES LIMITED	2019-04-08	Not applicable
Antibiotic	Ointment	500 [USP'U]/1g	Topical	Meijer Distribution Inc	2015-04-15	Not applicable
Antibiotic	Ointment	500 [USP'U]/1g	Topical	Topco Associates LLC	2020-04-03	Not applicable
antibiotic Bacitracin Zinc	Ointment	500 [iU]/1g	Topical	A-S Medication Solutions	2006-05-11	2019-09-30
antibiotic Bacitracin Zinc	Ointment	500 [iU]/1g	Topical	Strategic Sourcing Services LLC	2006-05-11	Not applicable
Antibiotic Gel	Gel	500 [USP'U]/1mL	Topical	Rosemont Ventures, Inc.	2022-09-15	Not applicable
astonea First Aid	Ointment	500 [USP'U]/1g	Topical	ASTONEA LABS PRIVATE LIMITED	2022-05-02	Not applicable
Baciguent First Aid Ointment	Ointment	500 unit / g	Topical	Johnson & Johnson Merck Consumer Pharmaceuticals Of Canada	1997-12-19	2008-08-07

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
0.9g Triple Antibiotic	Bacitracin zinc (400 [USP'U]/1g) + Neomycin sulfate (0.0035 g/1g) + Polymyxin B sulfate (5000 [USP'U]/1g)	Ointment	Topical	Sled Distribution, LLC	2022-03-24	Not applicable
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
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
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)	Inhalant; Kit; Liquid; Ointment; Spray; Tablet	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
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
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
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)	Cream; Kit; Ointment; Swab	Topical	Honeywell Safety Products USA, Inc	2018-11-21	2019-10-18
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)	Cream; Kit; Ointment; Swab	Topical	Honeywell Safety Products USA, Inc	2018-11-21	Not applicable
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)	Cream; Kit; Ointment; Swab	Topical	Honeywell Safety Products USA, Inc	2018-11-21	Not applicable
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)	Cream; Kit; Ointment; Swab	Topical	Honeywell Safety Products USA, Inc	2018-11-21	Not applicable

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)	Inhalant; Kit; Liquid; Ointment; Spray; Tablet	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
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
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
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)	Cream; Kit; Ointment; Swab	Topical	Honeywell Safety Products USA, Inc	2018-11-21	2019-10-18
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)	Cream; Kit; Ointment; Swab	Topical	Honeywell Safety Products USA, Inc	2018-11-21	Not applicable
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)	Cream; Kit; Ointment; Swab	Topical	Honeywell Safety Products USA, Inc	2018-11-21	Not applicable
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)	Cream; Kit; Ointment; Swab	Topical	Honeywell Safety Products USA, Inc	2018-11-21	Not applicable
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) + Menthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Inhalant; Kit; Liquid; Ointment; Spray; Swab	Ophthalmic; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
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
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)	Gel; Kit; Liquid; Ointment; Swab	Ophthalmic; Topical	Honeywell Safety Products USA, Inc.	2018-09-13	Not applicable

Categories

ATC Codes

J01XX10 — Bacitracin

• J01XX — Other antibacterials
• J01X — OTHER ANTIBACTERIALS
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

D06AX05 — Bacitracin

• D06AX — Other antibiotics for topical use
• D06A — ANTIBIOTICS FOR TOPICAL USE
• D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
• D — DERMATOLOGICALS

R02AB04 — Bacitracin

• R02AB — Antibiotics
• R02A — THROAT PREPARATIONS
• R02 — THROAT PREPARATIONS
• R — RESPIRATORY SYSTEM

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 / Dicarboxylic acids and derivatives / N-acyl amines / Thiazolines / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Primary carboxylic acid amides / Lactams / Azacyclic compounds / Carboxylic acids / Propargyl-type 1,3-dipolar organic compounds / Organopnictogen compounds / Carbonyl compounds / Organic oxides / Monoalkylamines / Hydrocarbon 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 / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Cyclic alpha peptide / Dicarboxylic acid or derivatives / Fatty acyl / Fatty amide / Glutamic acid or derivatives / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imidazolyl carboxylic acid derivative / Isoleucine or derivatives / Lactam / Leucine or derivatives / Macrolactam / Meta-thiazoline / Monocyclic benzene moiety / N-acyl-alpha amino acid or derivatives / N-acyl-amine / N-substituted-alpha-amino acid / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Polypeptide / Primary aliphatic amine / Primary amine / Primary carboxylic acid amide / Propargyl-type 1,3-dipolar organic compound / Secondary carboxylic acid amide / Thiazole / Thiazolecarboxamide

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

1. 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]
2. 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]
3. Toscano WA Jr, Storm DR: Bacitracin. Pharmacol Ther. 1982;16(2):199-210. [Article]
4. Nguyen R, Sun Y: Bacitracin Topical . [Article]
5. 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]
6. 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]
7. Authors unspecified: Bacitracin . [Article]
8. 2. (2018). In Poisoning & Drug Overdose (7th ed.). McGraw-Hill Education. [ISBN:978-0-07-183979-2]
9. FDA Approved Drug Products: Bacitracin Injection [Link]
10. FDA Approved Drug Products: Bacitracin, Neomycin, and Polymyxin B Ophthalmic Ointment [Link]
11. FDA Approved Drug Products: Bacitracin, Neomycin, Polymyxin B, and Hydrocortisone Topical Ointment [Link]
12. Pfizer: Corticosporin Safety Data Sheet [Link]
13. 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

RxNav

1291

ChEBI

35862

ChEMBL

CHEMBL1200558

Therapeutic Targets Database

DAP000710

PharmGKB

PA448531

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Bacitracin

MSDS

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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	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	Burns	1
4	Completed	Treatment	Fistulas Arteriovenous	1
4	Recruiting	Prevention	Surgical Site Infections	1
4	Terminated	Treatment	Burns	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
Inhalant; kit; liquid; ointment; spray; tablet	Ophthalmic; Oral; Respiratory (inhalation); Topical
Cream; kit; liquid; ointment; swab	Topical
Gel; inhalant; kit; liquid; ointment	Ophthalmic; Respiratory (inhalation); Topical
Cream; kit; liquid; ointment; swab; tablet	Ophthalmic; Oral; Topical
Cream; kit; liquid; ointment; swab	Ophthalmic; Topical
Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical
Kit	Ophthalmic; Respiratory (inhalation); Topical
Kit	Oral; Respiratory (inhalation); Topical
Kit; liquid; ointment; swab	Ophthalmic; Topical
Inhalant; kit; liquid; ointment; spray; swab; tablet	Ophthalmic; Oral; Respiratory (inhalation); Topical
Kit	Respiratory (inhalation); Topical
Gel; kit; liquid; ointment; swab	Ophthalmic; Topical
Inhalant; kit; liquid; ointment; spray; swab	Ophthalmic; Respiratory (inhalation); Topical
Kit; liquid; ointment; spray; swab	Ophthalmic; Topical
Cream; kit; liquid; ointment; spray; tablet	Ophthalmic; Oral; Topical
Cream; kit; liquid; ointment; swab; tablet	Oral; Topical
Cream; kit; liquid; ointment	Topical
Gel; kit; ointment; swab	Topical
Cream; kit; ointment; swab	Topical
Gel; kit; liquid; ointment	Ophthalmic; Topical
Kit; liquid; ointment; swab; tablet	Ophthalmic; Oral; Topical
Gel; kit; liquid; ointment; solution; swab	Ophthalmic; Topical
Kit; liquid; ointment; swab	Topical
Gel; kit; liquid; ointment	Topical
Gel; kit; liquid; ointment; swab	Topical
Cream; gel; kit; liquid; ointment; swab	Ophthalmic; Topical
Kit; liquid; ointment; spray; tablet	Ophthalmic; Oral; Topical
Cream; gel; kit; liquid; ointment; spray; swab	Ophthalmic; Topical
Kit; liquid; ointment	Topical
Gel; kit; liquid; ointment; swab; tablet	Oral; Topical
Kit; liquid; ointment	Ophthalmic; Topical
Kit	Irrigation; Ophthalmic; Respiratory (inhalation); Topical
Cream; irrigant; kit; liquid; ointment; swab	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
Gel	Topical	500 [USP'U]/1mL
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 [iU]/10mL
Injection, powder, for solution	Intramuscular	50000 [USP'U]/1
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 [USP'U]/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
Ointment	Topical	250 iu/g
Syrup	Oral
Kit	Electro-osmosis
Solution	Cutaneous
Kit	Oral
Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coated	Oral; Topical
Kit	Ophthalmic; Topical
Ointment	Topical	.51 g/100g
Kit	Ophthalmic; Oral; Topical
Cloth; cream; gel; kit; ointment; solution	Ophthalmic; Topical
Kit	Ophthalmic
Stick	Topical
Powder	Oral
Ointment	Ophthalmic
Kit; ointment	Topical
Gel	Topical
Cream	Topical	500 unit / g
Tablet	Oral
Powder	Topical
Ointment	Ophthalmic; Topical
Cream	Topical
Ointment	Topical	500 U/1g
Cream	Topical	500 U/1g
Liquid	Topical
Cloth; kit; ointment	Topical
Cream
Ointment	Topical
Ointment	Topical	400 [USP'U]/1g
Jelly; kit; ointment	Topical
Kit	Cutaneous
Powder, for solution	Oral
Spray	Topical	500 [USP'U]/1g
Swab	Topical
Ointment	Topical	500 U/1mL
Spray	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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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Details1. C55-isoprenyl pyrophosphate

Kind

Small molecule

Organism

Gram positive and gram negative bacteria

Pharmacological action

Yes

Actions

Antagonist

References

1. 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]

Details2. Insulin-degrading enzyme

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

1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
2. Medina V, Kesner L, Stracher A: Purification of nonantibiotic insulinase inhibitors from bacitracin. Biochem Med Metab Biol. 1993 Apr;49(2):255-64. [Article]

Details3. Alpha-2-macroglobulin

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

1. 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]
2. 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]
3. 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]
4. 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]
5. 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]

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Drug created at June 13, 2005 13:24 / Updated at February 08, 2023 20:46