CHEBI:51208 - mecillinam

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name mecillinam
Definition A penicillin in which the 6β substituent is [(azepan-1-yl)methylidene]amino; an extended-spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2 (PBP2), and is only considered to be active against Gram-negative bacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C15H23N3O3S
Net Charge 0
Average Mass 325.42754
Monoisotopic Mass 325.14601
InChI InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/t10-,11+,13-/m1/s1
SMILES [H]C(=N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@]12[H])N1CCCCCC1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
(via penicillin )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing mecillinam (CHEBI:51208) has role antibacterial drug (CHEBI:36047)
mecillinam (CHEBI:51208) has role antiinfective agent (CHEBI:35441)
mecillinam (CHEBI:51208) is a penicillin (CHEBI:17334)
Incoming pivmecillinam (CHEBI:51210) has functional parent mecillinam (CHEBI:51208)
6β-{[(azepan-1-yl)methylidene]amino}-2,2-dimethylpenam-3α-carboxylic acid
INNs Sources
mecilinamo ChemIDplus
mecillinam ChemIDplus
mecillinamum ChemIDplus
Synonyms Sources
(2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
amdinocillin ChemIDplus
penicillin HX ChemIDplus
Brand Name Source
Coactin DrugBank
Manual Xrefs Databases
DB01163 DrugBank
DE2055531 Patent
US3957764 Patent
View more database links
Registry Numbers Types Sources
1223657 Reaxys Registry Number Reaxys
1223657 Beilstein Registry Number Beilstein
32887-01-7 CAS Registry Number ChemIDplus
Last Modified
15 March 2018