A β-lactam antibiotic
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Mecillinam

Item No. 9002008

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,5R,6R)-6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
32887-01-7
Synonyms
  • Amdinocillin
  • FL 1060
  • Penicillin Hx
Molecular Formula
C15H23N3O3S
Formula Weight
325.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 30 mg/ml
λmax
221 nm
SMILES
O=C(O)[C@@H](C(C)(C)S1)N2[C@@]1([H])[C@H](N=CN3CCCCCC3)C2=O
InChi Code
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
InChi Key
BWWVAEOLVKTZFQ-NTZNESFSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Mecillinam is a β-lactam antibiotic.1 It is active against Gram-negative bacteria, including E. coli, K. pneumoniae, and N. gonorrhoeae (MIC90s = 4, 8, and 1 μg/ml, respectively). It is also active against clinical isolates of E. coli, K. pneumoniae, and P. mirabilis isolated from human urine.2 It binds to K. pneumoniae penicillin-binding protein 2 (PBP2) over PBP1A/B, PBP3, PBP4, and PBP5/6 (IC50s = <0.0075, >256, 128, >256, and >256 mg/L, respectively) in a competitive binding assay.3 Mecillinam is efficacious against susceptible E. coli strains in a systemic mouse model of infection with 50% protective dose (PD50) values ranging from less than or equal to 0.39 to 6.4 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Neu, H.C. Amdinocillin: A novel penicillin. Antibacterial activity, pharmacology and clinical use. Pharmacotherapy 5(1), 1-10 (1985).

    2. Fuchs, F., and Hamprecht, A. Results from a prospective in vitro study on the mecillinam (amdinocillin) susceptibility of Enterobacterales. Antimicrob. Agents Chemother 63(4), e02402-02418 (2019).

    3. Sutaria, D.S., Moya, B., Green, K.B., et al. First penicillin-binding protein occupancy patterns of β-lactams and β-lactamase inhibitors in Klebsiella pneumoniae. Antimicrob. Agents Chemother. 62(6), e00282-00218 (2018).

    4. Anderson, J.D., Eftekhar, F., Cleeland, R., et al. Comparative activity of mecillinam and ampicillin singly and in combination in the urinary bladder model and experimental mouse model. J. Antimicrob. Chemother. 8(2), 121-131 (1981).