(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-carboxylic acid

• ChemBase ID: 619
• Molecular Formular: C19H23N3O4S
• Molecular Mass: 389.46862
• Monoisotopic Mass: 389.14092723
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2N1C(N[C@@H](C1=O)c1ccccc1)(C)C
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N1C(=O)[C@H](NC1(C)C)c1ccccc1
• InChI: InChI=1S/C19H23N3O4S/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)/t11-,12-,13+,16-/m1/s1
• InChIKey: DXVUYOAEDJXBPY-NFFDBFGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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-carboxylic acid
• IUPAC Traditional name: hetacillin
• Brand Name: Hetacillin potassium; Versapen; Versapen-k
• Synonyms: Hetacillin

Database IDs

• CAS Number: 3511-16-8
• PubChem SID: 46504545; 160964082
• PubChem CID: 443387

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.602319
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.5889088
• LogD (pH = 7.4): -1.9940143
• Log P: -0.015010228
• Molar Refractivity: 99.8994 cm^3
• Polarizability: 39.65442 Å^3
• Polar Surface Area: 89.95 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.85
• LOG S: -2.88
• Solubility (Water): 5.12e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.3

DETAILS

DrugBank - DB00739

• Drug Groups: approved
• Description: 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).
• Indication: Hetacillin is a beta-lactam antibiotic prodrug used to treat bacterial infections. In the body it gets converted to ampicillin.
• Pharmacology: 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).
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hydrolyzed to active ampicillin via esterases
• External Links: Wikipedia