A β-lactamase inhibitor
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Alternative(s)
30715Enmetazobactam (triflate)
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Enmetazobactam (iodide)

Item No. 46757

Product Insert (PDF)
Technical Information
Formal Name
3-[[(2S,3S,5R)-2-carboxy-3-methyl-4,4-dioxido-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-3-yl]methyl]-1-methyl-1H-1,2,3-triazolium, monoiodide
CAS Number
1379594-98-5
Synonyms
  • AAI-101
Molecular Formula
C11H15N4O5S • I
Formula Weight
442.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mlPBS (pH 7.2): Sparingly soluble: 1-10 mg/ml
SMILES
O=C1C[C@]2([H])N1[C@@H](C(O)=O)[C@@](C[N+]3=NN(C)C=C3)(C)S2(=O)=O.[I-]
InChi Code
InChI=1S/C11H14N4O5S.HI/c1-11(6-14-4-3-13(2)12-14)9(10(17)18)15-7(16)5-8(15)21(11,19)20;/h3-4,8-9H,5-6H2,1-2H3;1H/t8-,9+,11+;/m1./s1
InChi Key
GSBNEXCMKCGSGW-GNPQZNTHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Enmetazobactam is a β-lactamase inhibitor.1 It has greater activity against class A β-lactamases (IC50s = 0.006-0.56 µM) than class C (IC50s = 25 and 31 µM) or class D β-lactamases (IC50s = 8.7->100 µM). Enmetazobactam restores the activity of the cephalosporin antibiotic cefepime (Item No. 23633) against 223 Enterobacteriaceae clinical isolates, 208 of which were cefepime resistant.2 In vivo, enmetazobactam restores the ability of cefepime to reduce mortality in mouse models of septicemia induced by cefepime-resistant clinical isolates of K. pneumoniae or E. cloacae.1 Formulations containing enmetazobactam have previously been used in combination with cefepime in the treatment of complicated urinary tract infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Papp-Wallace, K.M., Bethel, C.R., Caillon, J., et al. Beyond piperacillin-tazobactam: Cefepime and AAI101 as a potent β-lactam-β-lactamase inhibitor combination. Antimicrob Agents Chemother. 63(5), e00105-e00119 (2019).

    2. Crandon, J.L., and Nicolau, D.P. In vitro activity of cefepime/AAI101 and comparators against cefepime non-susceptible Enterobacteriaceae. Pathogens 4(3), 620-625 (2015).