U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C66H101N17O16S.Zn
Molecular Weight 1486.086
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BACITRACIN A ZINC

SMILES

[Zn++].[H][C@](NC(=O)[C@@H](CCC([O-])=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CSC(=N1)[C@@H](N)[C@@H](C)CC)([C@@H](C)CC)C(=O)N[C@H]2CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC([O-])=O)NC(=O)[C@H](CC3=CNC=N3)NC(=O)[C@@H](CC4=CC=CC=C4)NC(=O)[C@@]([H])(NC(=O)[C@@]([H])(CCCN)NC2=O)[C@@H](C)CC

InChI

InChIKey=UCRLQOPRDMGYOA-DFTDUNEMSA-L
InChI=1S/C66H103N17O16S.Zn/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);/q;+2/p-2/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C66H101N17O16S
Molecular Weight 1420.677
Charge -2
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 15 / 15
E/Z Centers 4
Optical Activity UNSPECIFIED

Molecular Formula Zn
Molecular Weight 65.409
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00626 | https://www.drugs.com/pro/bacitracin.html

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. Bacitracin is composed of a mixture of related compounds with varying degrees of antibacterial activity. Notable fractions include bacitracin A, A1, B, B1, B2, C, D, E, F, G, and X. Bacitracin A has been found to have the most antibacterial activity. 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. Used 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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Bacitracin

Approved Use

For the treatment of superficial ocular infections involving the conjunctiva and/or cornea caused by Bacitracin susceptible organisms.

Launch Date

5.84064E10
PubMed

PubMed

TitleDatePubMed
Enantiotracin.
2003 Jul 7
Patents

Sample Use Guides

In Vivo Use Guide
The ointment should be applied directly into the conjunctival sac 1 to 3 times daily. In blepharitis all scales and crusts should be carefully removed and the ointment then spread uniformly over the lid margins. Each gram of ointment contains 500 units of Bacitracin.
Route of Administration: Topical
Bacitracin A displays minimum inhibitory concentrations (MIC values) against Staphylococcus aureus and Staphylococcus epidermidis: 4 and 32 ug/ml, resp.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:29:08 UTC 2023
Edited
by admin
on Wed Jul 05 23:29:08 UTC 2023
Record UNII
86315B9ND7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BACITRACIN A ZINC
Common Name English
Code System Code Type Description
PUBCHEM
70687193
Created by admin on Wed Jul 05 23:29:08 UTC 2023 , Edited by admin on Wed Jul 05 23:29:08 UTC 2023
PRIMARY
FDA UNII
86315B9ND7
Created by admin on Wed Jul 05 23:29:08 UTC 2023 , Edited by admin on Wed Jul 05 23:29:08 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY