CHEBI:51208 - mecillinam

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ChEBI Name mecillinam
ChEBI ID CHEBI:51208
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 325.146
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
InChIKey BWWVAEOLVKTZFQ-NTZNESFSSA-N
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.
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)
IUPAC Name
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
LSM-5528 LINCS
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