Compound ID | 1934

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Mezlocillin

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 and some Gram-negative bacteria including Pseudomonas aeruginosa, but vulnerable to beta-lactamases
Description: Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA); closely related to azlocillin; parenteral application; a ureidopenicillin
Institute where first reported: BAYER
Year first mentioned: 1976
Highest development stage: Approved by FDA in 1981
Development status: Withdrawn
Chemical structure(s):
Click here for structure editor
Molecular weight: 539.58
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCN(C4=O)S(=O)(=O)C)C(=O)O)C
InChI Key: YPBATNHYBCGSSN-VWPFQQQWSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCN(C4=O)S(=O)(=O)C
InChI: InChI=1S/C21H25N5O8S2/c1-21(2)14(18(29)30)26-16(28)13(17(26)35-21)22-15(27)12(11-7-5-4-6-8-11)23-19(31)24-9-10-25(20(24)32)36(3,33)34/h4-8,12-14,17H,9-10H2,1-3H3,(H,22,27)(H,23,31)(H,29,30)/t12-,13-,14+,17-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/656511
Guide to Pharmacology: mezlocillin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/35662337/
  • https://pubmed.ncbi.nlm.nih.gov/6369480/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1958713/pdf/brmedj02865-0068.pdf
  • https://pubmed.ncbi.nlm.nih.gov/6215872/

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