Metampicillin

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]

Metampicillin

Clinical data
ATC code	J01CA14 (WHO)
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	6489-97-0
PubChem CID	6713928
ChemSpider	5145919
UNII	G0H6U7VSTK
ChEMBL	ChEMBL1908324
CompTox Dashboard (EPA)	DTXSID5048479
ECHA InfoCard	100.026.696
Chemical and physical data
Formula	C17H19N3O4S
Molar mass	361.42 g·mol^−1
3D model (JSmol)	Interactive image
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 Key:FZECHKJQHUVANE-MCYUEQNJSA-N
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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.

External links

• ChEBI ID