Compound ID | 1339

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Mecillinam

Synonym(s): Amdinocillin  |  FL 1060  |  FL-1060  |  FL1060

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Penicillin binding protein 2 inhibitor (PBP-2 inhibitor)
Target Pathogen: Active against pathogens causing urinary tract infection
Description: An amidinopenicillin; low bioavailability
Institute where first reported: Leo Pharmaceutical Products; Roche
Year first mentioned: 1972
Highest development stage: Approved by FDA in 1984
Development status: Withdrawn
Reason dropped: Discontinued in US; parenteral amdinocillin has been discontinued but prodrug pivmecillinam is still available
Chemical structure(s):
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Molecular weight: 325.43
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)O)C
InChI Key: BWWVAEOLVKTZFQ-NTZNESFSSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)N=CN3CCCCCC3
InChI: InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/t10-,11+,13-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/36273
Guide to Pharmacology: mecillinam
Citations:
  • https://accpjournals.onlinelibrary.wiley.com/doi/abs/10.1002/j.1875-9114.1985.tb04448.x
  • https://doi.org/10.1136/bmj.2.6026.14

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