Metampicillin

Metampicillin
Clinical data
ATC code
Identifiers
IUPAC name
  • 3,3-Dimethyl-6-[[2-(methylideneamino)-2-phenylacetyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.026.696
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Chemical and physical data
FormulaC17H19N3O4S
Molar mass361.42 g·mol−1
3D model (JSmol)
SMILES
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c3ccccc3)N=C)C(=O)O)C
InChI
  • InChI=1S/C17H19N3O4S/c1-17(2)12(16(23)24)20-14(22)11(15(20)25-17)19-13(21)10(18-3)9-7-5-4-6-8-9/h4-8,10-12,15H,3H2,1-2H3,(H,19,21)(H,23,24)/t10-,11-,12+,15-/m1/s1 ☒N
  • Key:FZECHKJQHUVANE-MCYUEQNJSA-N ☒N
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Metampicillin (INN) is a penicillin antibiotic. It is prepared by the reaction of ampicillin with formaldehyde, and is hydrolysed in aqueous solution with the formation of ampicillin. Hydrolysis is rapid under acid conditions, e.g., in the stomach, less rapid in neutral media, and incomplete in solutions such as human serum.[1]

References

  1. Sutherland R, Elson S, Croydon EA (1972). "Metampicillin. Antibacterial activity and absorption and excretion in man". Chemotherapy. 17 (3): 145–60. doi:10.1159/000220849. PMID 4556172.


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