Metampicillin

Chemical compound

Pharmaceutical compound

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 ^checkY
PubChem CID	6713928
ChemSpider	5145919 ^☒N
UNII	G0H6U7VSTK
ChEMBL	ChEMBL1908324 ^☒N
CompTox Dashboard (EPA)	DTXSID5048479 Edit this at Wikidata
ECHA InfoCard	100.026.696 Edit this at Wikidata
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^☒N Key:FZECHKJQHUVANE-MCYUEQNJSA-N^☒N
^☒NcheckY (what is this?) (verify)

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

[edit ]

^ 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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Antibacterials active on the cell wall and envelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) ^# Benzathine benzylpenicillin ^# Procaine benzylpenicillin ^# Phenoxymethylpenicillin (V) ^# Propicillin ^‡ Pheneticillin ^‡ Azidocillin ^‡ Clometocillin ^‡ Penamecillin ^‡
β-lactamase resistant (2nd generation)	Cloxacillin ^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin ^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin ^# Ampicillin ^# (Pivampicillin Hetacillin ^‡ Bacampicillin ^‡ Lenampicillin Metampicillin ^‡ Talampicillin ^‡) Epicillin ^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin ^‡ / Carindacillin ^‡ Temocillin ^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin ^‡ Mezlocillin ^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin ^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin ^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone ^‡ Cefazaflur ^‡ Cefradine ^‡ Cefroxadine ^‡ Ceftezole ^‡ Cefaloglycin ^‡ Cefacetrile ^‡ Cefalonium ^‡ Cefaloridine ^‡ Cefalotin Cefatrizine ^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole ^‡ Cefonicid ^‡ Ceforanide ^‡ Cefuzonam ^‡ Cephamycin (Cefoxitin Cefotetan Cefminox ^‡ Cefbuperazone ^‡ Cefmetazole ^‡) Carbacephem (Loracarbef ^‡)
3rd generation	Cefixime ^# Ceftriaxone ^# Cefotaxime ^# Antipseudomonal (Ceftazidime ^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam ^‡ Cefetamet ^‡ Cefodizime ^‡ Cefpimizole ^‡ Cefsulodin ^‡ Cefteram ^‡ Ceftiolene ^‡ Oxacephem (Flomoxef Latamoxef ^‡)
4th generation	Cefepime Cefozopran ^‡ Cefpirome Cefquinome ^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol ^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin ^§

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

External links

[edit ]

ChEBI ID

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