2-{[(5-carboxypentyl)carbamoyl](2-phenylacetamido)methyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 771
• Molecular Formular: C22H31N3O6S
• Molecular Mass: 465.56304
• Monoisotopic Mass: 465.19335673
• SMILES: S1C(C(NC1C(NC(=O)Cc1ccccc1)C(=O)NCCCCCC(=O)O)C(=O)O)(C)C
• Canonical SMILES: O=C(NC(C1NC(C(S1)(C)C)C(=O)O)C(=O)NCCCCCC(=O)O)Cc1ccccc1
• InChI: InChI=1S/C22H31N3O6S/c1-22(2)18(21(30)31)25-20(32-22)17(19(29)23-12-8-4-7-11-16(27)28)24-15(26)13-14-9-5-3-6-10-14/h3,5-6,9-10,17-18,20,25H,4,7-8,11-13H2,1-2H3,(H,23,29)(H,24,26)(H,27,28)(H,30,31)
• InChIKey: KJABUVRFCPPJPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(5-carboxypentyl)carbamoyl](2-phenylacetamido)methyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: benzylpenicilloyl G
• Brand Name: Pre-pen
• Synonyms: Benzylpenicilloyl Polylysine

Database IDs

• CAS Number: 2642-55-9
• PubChem SID: 160964234
• PubChem CID: 119212

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.9344923
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.7996843
• LogD (pH = 7.4): -4.5027285
• Log P: -0.7185573
• Molar Refractivity: 119.0655 cm^3
• Polarizability: 47.182297 Å^3
• Polar Surface Area: 144.83 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.44
• LOG S: -4.17
• Solubility (Water): 3.16e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.8

DETAILS

DrugBank - DB00895

• Drug Groups: approved
• Description: Benzylpenicilloyl Polylysine is used as a skin-testing reagent to detect immunoglobulin E antibodies in people with a history of penicillin allergy. The quantitation of in vitro IgE antibodies to the benzylpenicilloyl determinant is a useful tool for evaluating allergic subjects.
• Indication: For use as a adjunct in assessing the risk of administering penicillin (benzylpenicillin or penicillin G).
• Pharmacology: Benylpenicilloyl polylysine is penicilloyl bound to polylysine and is considered to be the major determinant of penicillin metabolism; it is used as a skin-testing reagent to detect immunoglobulin E antibodies in people with a history of penicillin allergy. If skin testing using benzylpenicilloyl and penicillin G (as the sole source of minor determinants) is negative, approximately 97% of patients with a negative skin test will tolerate penicillin.
• Toxicity: Symptoms of overdose include urticaria, generalized pruritus, local swelling, generalized flushing, anaphylaxis, bronchospasm, fainting and maculopapular eruption.
• Affected Organisms: Humans and other mammals
• References: [Link]

REFERENCES

• Link