Details of the Drug

General Information of Drug (ID: DMDU0BV)

Drug Name
Pivmecillinam
Synonyms
Coactabs; PMPC; Pivamdinocillin; Pivmecilinamo; Pivmecillinamum; Selexid; Amdinocillin Pivoxil; Amdinocillin pivoxil [USAN]; Mecillinam Pivaloyl Ester; Amdinocillin pivoxil (USAN); Amdinocillin, pivaloyloxymethyl ester; Coactabs (TN); Penomax (TN); Pivmecilinamo [INN-Spanish]; Pivmecillinam (INN); Pivmecillinamum [INN-Latin]; Ro 10-9071; Selexid (TN); [(2,2-dimethylpropanoyl)oxy]methyl 6beta-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3alpha-carboxylate; [(2,2-dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; [(2,2-dimethylpropanoyl)oxy]methyl(2s,5r,6r)-6-{[(e)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; Hydroxymethyl (2S,5R,6R)-6-(((hexahydro-1H-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate pivalate (ester); 2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 2,2-dimethylpropanoyloxymethyl (5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Indication
Disease Entry ICD 11 Status REF
Urinary tract infection GC08 Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 439.6
Logarithm of the Partition Coefficient (xlogp) 3.1
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Absorption
The drug is well absorbed after oral administration []
Chemical Identifiers
Formula
C21H33N3O5S
IUPAC Name
2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C
InChI
InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1
InChIKey
NPGNOVNWUSPMDP-HLLBOEOZSA-N
Cross-matching ID
PubChem CID
115163
ChEBI ID
CHEBI:51210
CAS Number
32886-97-8
DrugBank ID
DB01605
TTD ID
D08HDY

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drug information of Pivmecillinam, 2008. eduDrugs.
2 Association between antimicrobial consumption and resistance in Escherichia coli. Antimicrob Agents Chemother. 2009 Mar;53(3):912-7.