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CHEBI:51208 - mecillinam

ChEBI IDCHEBI:51208
ChEBI Namemecillinam
Stars
DefinitionA 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.
Last Modified15 March 2018
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC15H23N3O3S
Net Charge0
Average Mass325.434
Monoisotopic Mass325.14601
SMILES[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@]12[H])N1CCCCCC1
InChIInChI=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
InChIKeyBWWVAEOLVKTZFQ-NTZNESFSSA-N
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antibacterial drug  A drug used to treat or prevent bacterial infections.
allergen  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.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antibacterial drug  A drug used to treat or prevent bacterial infections.
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
pivmecillinam (CHEBI:51210) has functional parent mecillinam (CHEBI:51208)
IUPAC Name 
6β-{[(azepan-1-yl)methylidene]amino}-2,2-dimethylpenam-3α-carboxylic acid
INNs  Source
mecilinamoChemIDplus
mecillinamumChemIDplus
mecillinamChemIDplus
Synonyms  Source
(2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidIUPAC
penicillin HXChemIDplus
amdinocillinChemIDplus
Brand Name  Source
CoactinDrugBank
Manual XrefsDatabases
DB01163DrugBank
DE2055531Patent
US3957764Patent
LSM-5528LINCS
Registry NumbersSources
Reaxys:1223657Reaxys
CAS:32887-01-7ChemIDplus