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药品详细

Bacitracin(杆菌肽)

化学结构式图
中文名
杆菌肽
英文名
Bacitracin
分子式
C66H103N17O16S
化学名
(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-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
分子量
Average: 1422.693
Monoisotopic: 1421.748941023
CAS号
1405-87-4
ATC分类
D06A 未知;R02A 未知;J01X Other Antibacterials
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy. Its unique name derives from the fact that the bacillus producing it was first isolated in 1943 from a knee scrape from a girl named Margaret Tracy. As a toxic and difficult-to-use antibiotic, bacitracin doesn’t work well orally. However, it is very effective topically.

Bacitracin is synthesised via the so-called nonribosomal peptide synthetases (NRPSs), which means that ribosomes are not involved in its synthesis.

生产厂家
  • Altana inc
  • Apothekernes laboratorium a/s
  • App pharmaceuticals llc
  • Combe inc
  • Eli lilly and co
  • Naska pharmacal co inc div rugby darby group cosmetics
  • Paddock laboratories inc
  • Pfizer laboratories div pfizer inc
  • Pharmacia and upjohn co
  • Pharmaderm div altana inc
  • Pharmafair inc
  • Sagent pharmaceuticals inc
  • X gen pharmaceuticals inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  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. Pubmed
  2. Karala AR, Ruddock LW: Bacitracin is not a specific inhibitor of protein disulfide isomerase. FEBS J. 2010 Jun;277(11):2454-62. Epub 2010 Apr 30. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
药理
Indication For the treatment of infants with pneumonia and empyema caused by staphylococci shown to be susceptible to the drug. Also used in ointment form for topical treatment of a variety of localized skin and eye infections, as well as for the prevention of wound infections. Used against gram positive bacteria. Bacitracin is also used as an inhibitor of proteases and other enzymes. However, specific activity of bactracin's inhibition of protein disulfide isomerase has been called into question.
Pharmacodynamics Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy. As a polypeptide, toxic, and difficult to use chemical, bacitracin doesn't work well orally, however is very effective topically. Bacitracin exerts pronounced antibacterial action in vitro against a variety of gram-positive and a few gram-negative organisms. However, among systemic diseases, only staphylococcal infections qualify for consideration of bacitracin therapy.
Mechanism of action Bacitracin intereferes with the dephosphorylation of the 55-carbon, biphosphate lipid transport molecule C55-isoprenyl pyrophosphate (undecaprenyl pyrophosphate), which carries the building blocks of the peptidoglycan bacterial cell wall outside the inner membrane for construction. Bacitracin binds divalent transition metal ions (Mn(II), Co(II), Ni(II), Cu(II), and Zn(II)) which binds and oxidatively cleave DNA.
Absorption Absorption of bacitracin following intramuscular injection is rapid and complete. Absorption from the gastrointestinal tract following oral administration is not appreciable. Absorption following topical application is negligible.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available
Route of elimination The drug is excreted slowly by glomerular filtration.
Half life Not Available
Clearance Not Available
Toxicity Oral, mouse: LD50 = >3750 mg/kg.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 221-225 °C Not Available
water solubility Freely soluble Not Available
logP -0.8 Not Available
Predicted Properties
Property Value Source
water solubility 2.45e-02 g/l 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 ChemAxon
rotatable bond count 31 ChemAxon
refractivity 363.14 ChemAxon
polarizability 147.15 ChemAxon
药物相互作用
食物相互作用
Not Available

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