Bacitracin methylenedisalicylic acid |
![]() Last updated: 15/09/2025 |
![]() |
(Also known as: bacitracin MD) |
|
![]() |
|
A broad spectrum antibiotic used primarily against gram-positive infections often in combination with other antibacterial compounds such as tetracyclin or prednisolone | |
---|---|---|
|
Used to treart mastitis in lactating cows. Sometimes used as a growth promotor but now banned in many countries. | |
|
Meat poultry; Pigs; Sheep; Cattle; Rabbits |
Approval status |
|
Not approved | |
---|---|---|
|
Not approved |
Chemical structure |
|
Bacitracin methylenedisalicylic acid exhibits complex stereoisomerism due to its structure as a cyclic polypeptide bound to a methylenedisalicylic acid moiety. The bacitracin portion contains multiple chiral centres arising from its diverse amino acid residues, including both L- and D-configurations. These stereocentres give rise to diastereomers. Additionally, the methylenedisalicylic acid component introduces geometric and positional isomerism, particularly in the orientation of the two salicylic acid rings connected via a methylene bridge. The isomeric complexity is further amplified by the possibility of epimerization at sensitive stereocentres during synthesis or storage, which can affect the compound’s antimicrobial potency and stability. | |
---|---|---|
|
C₈₁H₁₁₇N₁₇O₂₃S | |
|
CCC(C)C(C1=NC(CS1)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CCCN)C(=O)NC(C(C)CC)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(CC3=CN=CN3)C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)N)C(=O)O)N.C1=CC=C(C(=C1)C(=O)OCOC(=O)C2=CC=CC=C2O)O | |
|
CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC2=CN=CN2)C(=O)N[C@H](CC(=O)O)C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)C3CSC(=N3)C(C(C)CC)N.C1=CC=C(C(=C1)C(=O)OCOC(=O)C2=CC=CC=C2O)O | |
|
POMORUSPLDFVEK-PHXAWWDYSA-N | |
|
InChI=1S/C66H105N17O17S.C15H12O6/c1-9-35(6)52(70)65-81-48(32-101-65)62(96)76-43(26-34(4)5)58(92)74-42(22-23-50(85)86)57(91)83-53(36(7)10-2)63(97)75-40(20-15-16-24-67)55(89)73-41(21-17-25-68)56(90)82-54(37(8)11-3)64(98)79-44(27-38-18-13-12-14-19-38)59(93)77-45(28-39-31-71-33-72-39)60(94)78-46(30-51(87)88)61(95)80-47(66(99)100)29-49(69)84;16-12-7-3-1-5-10(12)14(18)20-9-21-15(19)11-6-2-4-8-13(11)17/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67-68,70H2,1-8H3,(H2,69,84)(H,71,72)(H,73,89)(H,74,92)(H,75,97)(H,76,96)(H,77,93)(H,78,94)(H,79,98)(H,80,95)(H,82,90)(H,83,91)(H,85,86)(H,87,88)(H,99,100);1-8,16-17H,9H2/t35?,36-,37-,40-,41+,42+,43-,44+,45-,46+,47-,48?,52?,53-,54-;/m0./s1 | |
|
Yes |
General status |
|
Medicinal drug, Antibiotic, Antibacterial, Antimicrobial, Medicated feed additive | |
---|---|---|
|
Polypeptide | |
|
- | |
|
- | |
|
Natural | |
|
Inhibits the biosynthesis of bacterium cell wall | |
|
[C55-isoprenyl pyrophosphate, Antagonist], [Insulin-degrading enzyme, Antagonist]; [Alpha-2-macroglobulin, Antagonist] | |
|
55852-84-1 | |
|
259-862-3 | |
|
- | |
|
- | |
|
11980094 | |
|
Alimentary tract & metabolism: Intestinal anti-infective | |
|
QA07AA93 | |
|
No | |
|
Allowed substance (Table 1: Bovine, Rabbit) | |
|
1729.0 | |
|
- | |
|
(4R)-5-[[(2S,3S)-1-[[(2S)-6-amino-1-[[(2R)-5-amino-1-[[(2S,3S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(1S)-3-amino-1-carboxy-3-oxopropyl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-[[(2S)-2-[[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid;(2-hydroxybenzoyl)oxymethyl 2-hydroxybenzoate | |
|
- | |
|
- | |
|
Banned in EU as growth promotor; Not approved as feed additive in EU | |
|
- | |
|
- | |
|
Commercial |
|
|
|||
---|---|---|---|---|
|
Considered obsolete but may be available in some countries | |||
|
1945, isolated | |||
|
|
|||
|
|
|||
|
Often sold as a premix or soluble powder | |||
|
Bacitracin methylenedisalicylic acid is produced through a multi-step process that begins with leaching bacitracin from a premix using n-butanol as the extraction solvent. After soaking and filtering to remove microbial residues, the extract is concentrated at around 65 DegC. Separately, methylenedisalicylic acid is dissolved in n-butanol and added to the concentrated bacitracin solution to initiate complexation, typically for about 3 hours. The resulting complex is then subjected to acidic extraction using citric acid, followed by pH adjustment to 7.6 with sodium hydroxide to isolate the target compound in the aqueous phase. This solution is spray-dried to yield a crude product, which is then refined. | |||
|
Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
|
![]() |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
- | |||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
Released into the environment via the excretion of treated animals |
Degradation |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | ||||||||||
|
22.5 | R4 R = Peer reviewed scientific publications Soil & chicken manure at 20 °C for bacitracin4 = Verified data |
- | ||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
|
- |
Soil adsorption and mobility |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | ||||||||||
|
- | ||||||||||
|
- |
Fate indices |
|
|
|
|
||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||||||||||||||||||||
|
|
- | - | - | |||||||||||||||||||||||||
|
- | - |
Known soil and groundwater metabolites |
None
Other known metabolites |
|
|
|
|
||||
---|---|---|---|---|---|---|---|
desamidobasitracin | - | Chickens; Pigs | - |
|
![]() |
Terrestrial ecotoxicology |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
> 3751 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Mouse4 = Verified data |
Low | ||||||||
|
|
- | - | - | |||||||
|
- | - | |||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
- | |||||||||||
|
- | - | - | ||||||||
- | |||||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - |
Aquatic ecotoxicology |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - |
|
- | - | - | |||
|
- | - | - |
|
![]() |
General |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
High (class III) | - | - | ||||||||
|
> 3751 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Mouse4 = Verified data |
Low | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | |||||||||
|
Poisonous by intraperitoneal and intravenous routes | ||||||||||
|
Some metabolism, excreted in the urine and faeces within 24 hr | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
- |
Health issues |
|
|
||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
May cause contact dermititis or skin sensitisation May cause gastrointestinal problems May cause delayed hypersensitivity |
Handling issues |
|
|
|||
---|---|---|---|---|
|
No information available | |||
|
- | |||
|
Not listed (Not listed) | |||
|
- | |||
|
- | |||
|
- |
|
![]() |
|
|
||
---|---|---|---|
|
bacitracin methylenedisalicylic acid | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- |
Record last updated: | 15/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |