Compound ID | 442

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MC-02,479

Synonym(s): MC 02479  |  RWJ 54428  |  MC-02479

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor
Combined with other compounds: Could be combined with aztreonam, fosfomycin, gentamicin or levofloxacin for empiric therapy
Description: Chamberland S, Blais J, Hoang M, et al. In vitro activities of RWJ-54428 (MC-02,479) against multiresistant gram-positive bacteria. Antimicrob Agents Chemother. 2001;45(5):1422-30.
Institute where first reported: Johnson & Johnson Pharmaceutical R&D, USA; Essential Therapeutics [Ceased]
Year first mentioned: 1997
Highest development stage: Phase 1
Development status: Inactive
Reason dropped: This was to be developed as an anti-MRSA Cephalosporin [as its prodrug]. May have been dropped in favour of ceftobiprole which J&J were also developing at the same time
Chemical structure(s):
Click here for structure editor
Molecular weight: 602.13
Iso. SMILES: C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=N\O)/C3=C(SC(=N3)N)Cl)C(=O)O)SC4=C(C=NC=C4)CSCCN
InChI Key: LTUWUNMGTLOPNC-RLQAYIIJSA-N
Can. SMILES: C1=C(C(=CN=C1)CSCCN)SC2=C(C(=O)O)N3C(=O)[C@H]([C@H]3SC2)NC(=O)/C(=N\O)/C4=C(Cl)SC(=N4)N
InChI: InChI=1S/C20H20ClN7O5S4/c21-15-11(26-20(23)37-15)12(27-33)16(29)25-13-17(30)28-14(19(31)32)10(7-35-18(13)28)36-9-1-3-24-5-8(9)6-34-4-2-22/h1,3,5,13,18,33H,2,4,6-7,22H2,(H2,23,26)(H,25,29)(H,31,32)/b27-12-/t13-,18-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9873517
Guide to Pharmacology: MC-02479
Citations:
  • https://journals.asm.org/doi/10.1128/aac.47.2.658-664.2003
  • https://doi.org/10.7164/antibiotics.53.1272

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