Bacitracin

ID: ALA1200558

Cas Number: 22601-59-8

PubChem CID: 10909430

Max Phase: Approved

First Approval: 1948

Molecular Formula: C66H103N17O16S

Molecular Weight: 1422.72

Molecule Type: Protein

Names and Identifiers

Synonyms: Bacilliquin | Bacitracin | Bacitracin(non-injectable) | Bacitracin, sterile | Bacitracinum | Fortracin | Parentracin | Penitracin | Topitracin | Tropitracin | Zutracin | NSC-755905 | Bacitracin A|Bacitracin A2a|Solu-Tracin 50|Baciguent|Fortracin|Bacitracinum|Parentracin|Penitracin|Topitracin|Zutracin|Baciim|22601-59-8|CHEBI:35862|UNII-DDA3RRX0P7|Baci-rx|DDA3RRX0P7|EINECS 245-115-9|NSC 45737|Altracin|Bacitracin A1|NSC-45737|E700|Bacitracin F, 1-(N-((2-(1-amino-2-methylbutyl)-4,5-dihydro-4-thiazolShow More⌵

Synonyms from Alternative Forms(8): Bacitracin zinc | Bacifarmin | Bacitracins zinc complex | Bacitracins, zinc complex | Bacitracinum zincum | Noptracin | Zinc bacitracin | Ziba-rx

Trade Names(6): Albac 50 | Baci-rx | Baciferm 50 | Baciguent | Baciim | Bacitracin

Canonical SMILES:  CC[C@H](C)[C@H](N)C1=N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@H]2CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(=O)O)NC(=O)[C@H](Cc3cnc[nH]3)NC(=O)[C@@H](Cc3ccccc3)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCCN)NC2=O)[C@@H](C)CC)CS1

Standard 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

Standard InChI Key:  CLKOFPXJLQSYAH-ABRJDSQDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1200558

   BACITRACIN

2. Alternative Forms:

   

   ALA1200558

   Noptracin

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Protein

Topical: Yes

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 1422.72

Molecular Weight (Monoisotopic): 1421.7489

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

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2. Sieradzki K, Chung M, Tomasz A..  (2008)  Role of a sodium-dependent symporter homologue in the thermosensitivity of beta-lactam antibiotic resistance and cell wall composition in Staphylococcus aureus.,  52  (2): [PMID:18056270] [10.1128/aac.00504-07]

3. Steidl R, Pearson S, Stephenson RE, Ledala N, Sitthisak S, Wilkinson BJ, Jayaswal RK..  (2008)  Staphylococcus aureus cell wall stress stimulon gene-lacZ fusion strains: potential for use in screening for cell wall-active antimicrobials.,  52  (8): [PMID:18541730] [10.1128/aac.00273-08]

4. Cui L, Neoh HM, Shoji M, Hiramatsu K..  (2009)  Contribution of vraSR and graSR point mutations to vancomycin resistance in vancomycin-intermediate Staphylococcus aureus.,  53  (3): [PMID:19124662] [10.1128/aac.01173-08]

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7. Katayama Y, Murakami-Kuroda H, Cui L, Hiramatsu K..  (2009)  Selection of heterogeneous vancomycin-intermediate Staphylococcus aureus by imipenem.,  53  (8): [PMID:19451283] [10.1128/aac.00834-08]

8. Collins B, Curtis N, Cotter PD, Hill C, Ross RP..  (2010)  The ABC transporter AnrAB contributes to the innate resistance of Listeria monocytogenes to nisin, bacitracin, and various beta-lactam antibiotics.,  54  (10): [PMID:20643901] [10.1128/aac.00503-10]

9. Collins B, Joyce S, Hill C, Cotter PD, Ross RP..  (2010)  TelA contributes to the innate resistance of Listeria monocytogenes to nisin and other cell wall-acting antibiotics.,  54  (11): [PMID:20713661] [10.1128/aac.00290-10]

10. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

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13. Unpublished dataset, 

14. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

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20. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

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22. WHO Anatomical Therapeutic Chemical Classification, 

23. DrugMatrix,  [10.6019/CHEMBL3885881]

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25. Mokhlesi A, Stuhldreier F, Wex KW, Berscheid A, Hartmann R, Rehberg N, Sureechatchaiyan P, Chaidir C, Kassack MU, Kalscheuer R, Brötz-Oesterhelt H, Wesselborg S, Stork B, Daletos G, Proksch P..  (2017)  Cyclic Cystine-Bridged Peptides from the Marine Sponge Clathria basilana Induce Apoptosis in Tumor Cells and Depolarize the Bacterial Cytoplasmic Membrane.,  80  (11): [PMID:29094598] [10.1021/acs.jnatprod.7b00477]

26. Elsebaei MM, Mohammad H, Abouf M, Abutaleb NS, Hegazy YA, Ghiaty A, Chen L, Zhang J, Malwal SR, Oldfield E, Seleem MN, Mayhoub AS..  (2018)  Alkynyl-containing phenylthiazoles: Systemically active antibacterial agents effective against methicillin-resistant Staphylococcus aureus (MRSA).,  148  [PMID:29459278] [10.1016/j.ejmech.2018.02.031]

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28. Unpublished dataset, 

29. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

30. Gou S, Li B, Ouyang X, Ba Z, Zhong C, Zhang T, Chang L, Zhu Y, Zhang J, Zhu N, Zhang Y, Liu H, Ni J..  (2021)  Novel Broad-Spectrum Antimicrobial Peptide Derived from Anoplin and Its Activity on Bacterial Pneumonia in Mice.,  64  (15.0): [PMID:34180670] [10.1021/acs.jmedchem.1c00614]

Source

Source(8):

• Scientific Literature
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• AstraZeneca Deposited Data
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data