Hetacillin potassiumProduct ingredient for Hetacillin

Name
Hetacillin potassium
Drug Entry
Hetacillin

Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs). Hetacillin has been withdrawn from the market since it has been discovered that it has no therapeutic advantage compared to non-ester derivatives like ampicillin.

Accession Number
DBSALT000966
Structure
Synonyms
Not Available
UNII
95PFX5932Y
CAS Number
5321-32-4
Weight
Average: 427.56
Monoisotopic: 427.09680886
Chemical Formula
C19H22KN3O4S
InChI Key
QRSPJBLLJXVPDD-XFAPPKAWSA-M
InChI
InChI=1S/C19H23N3O4S.K/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10;/h5-9,11-13,16,20H,1-4H3,(H,25,26);/q;+1/p-1/t11-,12-,13+,16-;/m1./s1
IUPAC Name
potassium (2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
SMILES
[K+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C([O-])=O
KEGG Drug
D02203
KEGG Compound
C13980
ChemSpider
391615
BindingDB
50103615
ChEBI
34789
ChEMBL
CHEMBL1201121
Wikipedia
Hetacillin
Predicted Properties
PropertyValueSource
Water Solubility1.12 mg/mLALOGPS
logP1.35ALOGPS
logP0.056Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.33Chemaxon
pKa (Strongest Basic)4.79Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area92.78 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity110.74 m3·mol-1Chemaxon
Polarizability39.24 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon