U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19N3O4S
Molecular Weight 361.415
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METAMPICILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=C)C3=CC=CC=C3)C(O)=O

InChI

InChIKey=FZECHKJQHUVANE-MCYUEQNJSA-N
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

HIDE SMILES / InChI
Metampicillin is the approved name for the penicillin resulting from the reaction of ampicillin with formaldehyde. Metampicillin is hydrolysed in aqueous solution with the formation of ampicillin. Metampicillin has broad spectrum of activity coupled with a marked degree of stability to bacterial penicillinase. Furthermore, metampicillin is reported to be absorbed to a greater extent than ampicillin, resulting in superior blood levels in human subjects, and also giving high levels of antibiotic in bile following parenteral administration. Metampicillin showed a spectrum and level of activity similar to that of ampicillin in vitro, and both compounds were inactive against penicillinase-producing strains of bacteria. The activity of metampicillin was markedly reduced by human serum, and the compound was less active than ampicillin in the presence of human serum. Following the oral administration of metampicillin to man, metampicillin was not detected in the blood stream nor in urine, and ampicillin alone was demonstrated in these subjects. The serum concentrations of ampicillin that were produced following the oral administration of metampicillin were somewhat lower than those obtained with equivalent doses of ampicillin. Adminstration of metampicillin by the intramuscular (i.m.) route to volunteers resulted in the appearance of both ampicillin and metampicillin in the blood, and of ampicillin alone in the urine of these subjects. When parenteraly administered, metampicillin appeared to be a particularly suitable penicillin for the treatment of biliary tract infections. Metampicillin is a cell wall biosynthesis inhibitor.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Metampicillin in oral medicine].
1972 Nov 26
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Deacetoxycephalosporin C synthase isozymes exhibit diverse catalytic activity and substrate specificity.
2003 Jan 28
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
2005 Jan
Patents

Sample Use Guides

Oral administration. Following the oral administration of a single 500-mg dose of metampicillin to fasting human subjects, metampicillin was not detected and ampicillin alone was demonstrated in the blood specimens taken 1, 2, and 3 h after dosing. Intramuscular administration. After administration of 250 mg metampicillin by the i.m. route to 2 human subjects, both metampicillin and ampicillin were observed in the blood of both subjects after 1/2 h and both penicillins were present in 1 subject 1 h after dosing.
Route of Administration: Other
Metampicillin interacted with renal peptide transporter PEPT2 with medium affinity (K(i)=0.1-5mM).
Name Type Language
METAMPICILLIN
INN   MI   WHO-DD  
INN  
Official Name English
PRAVACILIN
Brand Name English
METHYLENAMPICILLIN
Common Name English
(.ALPHA.-(METHYLENEAMINO)BENZYL)PENICILLIN
Common Name English
Metampicillin [WHO-DD]
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-6-(((2R)-(METHYLENEAMINO)PHENYLACETYL)AMINO)-7-OXO-, (2S,5R,6R)-
Common Name English
NSC-758167
Code English
MICINOVO
Brand Name English
RUTICINA
Brand Name English
FEDACILINA
Brand Name English
METAMPICILLIN [MI]
Common Name English
metampicillin [INN]
Common Name English
VIDERPEN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
WHO-VATC QJ01CA14
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
WHO-ATC J01CA14
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1718
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
FDA UNII
G0H6U7VSTK
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
MERCK INDEX
m7266
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID5048479
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
MESH
C005195
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
WIKIPEDIA
METAMPICILLIN
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
PUBCHEM
6713928
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
229-365-6
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
NCI_THESAURUS
C87368
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
CHEBI
52060
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
DRUG BANK
DB13836
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
NSC
758167
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
SMS_ID
100000081216
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL1908324
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
INN
2570
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
CAS
6489-97-0
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
EVMPD
SUB08811MIG
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY
RXCUI
29629
Created by admin on Sat Dec 16 16:45:38 GMT 2023 , Edited by admin on Sat Dec 16 16:45:38 GMT 2023
PRIMARY RxNorm