Pivmecillinam hydrochlorideProduct ingredient for Pivmecillinam

Name
Pivmecillinam hydrochloride
Drug Entry
Pivmecillinam

Pivmecillinam is a mecillinam prodrug, a pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin. [PubChem]

Accession Number
DBSALT001943
Structure
Synonyms
Amdinocillin pivoxil hydrochloride
UNII
48FX7N21H2
CAS Number
32887-03-9
Weight
Average: 476.03
Monoisotopic: 475.1907701
Chemical Formula
C21H34ClN3O5S
InChI Key
UHPXMYLONAGUPC-WKLLBTDKSA-N
InChI
InChI=1S/C21H33N3O5S.ClH/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;1H/t14-,15+,17-;/m1./s1
IUPAC Name
[(2S,5R,6R)-6-{[(azepan-1-yl)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate hydrochloride
SMILES
Cl.[H][C@]12SC(C)(C)[C@@]([H])(N1C(=O)[C@@]2([H])N=CN1CCCCCC1)C(=O)OCOC(=O)C(C)(C)C
KEGG Drug
D01499
ChemSpider
19978599
ChEBI
51213
ChEMBL
CHEMBL1355196
Predicted Properties
PropertyValueSource
Water Solubility0.0526 mg/mLALOGPS
logP3.23ALOGPS
logP2.91Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.66Chemaxon
pKa (Strongest Basic)7.91Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area88.51 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity113.03 m3·mol-1Chemaxon
Polarizability47.75 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon