Compound ID | 1946

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Cyclacillin

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Binds to bacterial penicillin-binding proteins (PBP); PBP inhibitor
Target Pathogen: Active against Gram-positive bacteria and some Enterobacteriaceae, but vulnerable to penicillinases produced by staphylococci and Escherichia coli
Description: Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA); similar to ampicillin; an aminopenicillin
Year first mentioned: 1970
Highest development stage: Approved by FDA in 1979
Development status: Withdrawn
Chemical structure(s):
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Molecular weight: 341.43
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
InChI Key: HGBLNBBNRORJKI-WCABBAIRSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)C3(CCCCC3)N
InChI: InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/19003
Guide to Pharmacology: cyclacillin
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC283732/
  • https://pubmed.ncbi.nlm.nih.gov/773605/

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