Compound ID | 1914

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Ceftriaxone

Synonym(s): Ro 13-9904

Class: Beta-lactam (cephalosporin, third generation)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Gram-positive bacteria and against many Enterobacteriaceae but vulnerable to extended-spectum beta-lactamases (ESBL)
Description: Semisynthetic Cephalosporine, derived from Cephalosporin C, longer half-live than other Cephalosporins
Year first mentioned: 1980
Highest developmental phase: Approved by FDA in 1984
Development status: Approved
Chemical structure(s):
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Molecular weight: 554.58
Iso. SMILES: CN1C(=NC(=O)C(=O)N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)O
InChI Key: VAAUVRVFOQPIGI-SPQHTLEESA-N
Can. SMILES: CN1C(=NC(=O)C(=O)N1)SCC2=C(C(=O)O)N3C(=O)[C@H]([C@H]3SC2)NC(=O)/C(=N\OC)/C4=CSC(=N4)N
InChI: InChI=1S/C18H18N8O7S3/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7/h5,9,15H,3-4H2,1-2H3,(H2,19,20)(H,21,27)(H,23,29)(H,31,32)/b24-8-/t9-,15-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5479530
Guide to Pharmacology: ceftriaxone
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/31179786/
  • https://www.cdc.gov/mmwr/volumes/69/wr/mm6950a6.htm
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7513262/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC183664/

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