CAS 1405-87-4|bacitracin zinc|Baciguent|(4R)-4-[(2S)-2-({2-[(1S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazol-5-yl}formamido)-4-methylpentanamido]-4-{[(1S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-ami...

General Information

Structure

Molecular Formula

C₆₆H₁₀₃N₁₇O₁₆S

Molecular Mass

1422.69332

Exact Mass

1421.7489413

Charge

InChI

InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-72-32-48(100-66)63(97)80-43(26-34(4)5)59(93)75-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)76-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-73-39)77-60(94)44(27-38-18-13-12-14-19-38)81-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)74-56(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,70,73)(H,71,89)(H,74,90)(H,75,93)(H,76,98)(H,77,94)(H,78,96)(H,79,95)(H,80,97)(H,81,99)(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

InChIKey

MNJKVJAYSVAQLU-YOJCIBLDSA-N

Canonic Smiles

NCCC[C@H]1NC(=O)[C@H](CCCCNC(=O)[C@H](CC(=O)N)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)C(CC)C)Cc1ccccc1)Cc1[nH]cnc1)CC(=O)O)NC(=O)[C@H](C(CC)C)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)C1CN=C(S1)[C@H](C(CC)C)N)CC(C)C)CCC(=O)O

Isomeric Smiles

S1C(C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(=O)N[C@@H](C(CC)C)C(=O)N[C@H]2CCCCNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC2=O)CCCN)C(CC)C)Cc2ccccc2)Cc2[nH]cnc2)CC(=O)O)CC(=O)N)CCC(=O)O)CN=C1[C@@H](N)C(CC)C

Calculated Properties

JChem

Acid pKa

3.4586437

H Acceptors

H Donor

LogD (pH = 5.5)

-7.635476

LogD (pH = 7.4)

-7.1978397

Log P

-7.2495475

Molar Refractivity

363.6494

Polarizability

143.00023

Polar Surface Area

530.87

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

-2.98

LOG S

-4.75

Solubility (Water)

2.52e-02 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Brand Name

BaciguentBaciimBacitracin Bacillus licheniformis

IUPAC Traditional name

bacitracin zinc

Synonyms

Bacitracin

IUPAC name

(4R)-4-[(2S)-2-({2-[(1S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazol-5-yl}formamido)-4-methylpentanamido]-4-{[(1S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-15-(butan-2-yl)-3-(carbamoylmethyl)-6-(carboxymethyl)-9-(1H-imidazol-5-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

Names and Identifiers

Registration numbers

PubChem SID

160963971

PubChem CID

439542

CAS Number

1405-87-4

Registration numbers

Properties

Physical Property

Solubility

Freely soluble

Hydrophobicity(logP)

-0.8

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00626

Drug Groups

approved

Description

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.

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.

Pharmacology

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.

Toxicity

Oral, mouse: LD₅₀ = >3750 mg/kg.

Affected Organisms

Enteric bacteria and other eubacteria

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.

Elimination

The drug is excreted slowly by glomerular filtration.

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. [Pubmed]

• 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]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data