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targets (2)
for drugs
Identification
Name Benzylpenicilloyl Polylysine
Accession Number DB00895 (APRD00822)
Type small molecule
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Pre-pen
Brand name mixtures Not Available
Categories Not Available
CAS number 2642-55-9
Weight Average: 465.563
Monoisotopic: 465.193356429
Chemical Formula C22H31N3O6S
InChI Key InChIKey=KJABUVRFCPPJPD-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
2-{[(5-carboxypentyl)carbamoyl](2-phenylacetamido)methyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
SMILES
CC1(C)SC(NC1C(O)=O)C(NC(=O)CC1=CC=CC=C1)C(=O)NCCCCCC(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Polypeptides
Substructures
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Thiazoles
  • Phenethylamines
  • Polypeptides
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Amino Acids
  • Thiazolidines
Pharmacology
Indication For use as a adjunct in assessing the risk of administering penicillin (benzylpenicillin or penicillin G).
Pharmacodynamics 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.
Mechanism of action The skin test for penicillin demonstrates the presence or absence of specific IgE antibodies to major and minor penicillin determinants. IgE antibodies to major determinants can be detected by using benzylpenicilloyl polylysine. A penicillin skin test predicts only the presence of IgE antibodies for the major or minor penicillin determinants at the time of application and does not predict the future development of IgE-mediated reactions during subsequent courses of penicillin. Benzylpenicilloyl polylysine reacts specifically with penicilloyl skin sensitizing antibodies (reagins) to produce immediate wheal and flare reactions which may reflect increased risk of allergic reactions to subsequent penicillin therapy.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Symptoms of overdose include urticaria, generalized pruritus, local swelling, generalized flushing, anaphylaxis, bronchospasm, fainting and maculopapular eruption.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Allerquest llc
Packagers
Dosage forms
Form Route Strength
Liquid Intradermal
Prices
Unit description Cost Unit
Pre-pen ampul 72.0 USD ampul
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP -0.8 PhysProp
Predicted Properties
Property Value Source
water solubility 3.16e-02 g/l ALOGPS
logP 0.44 ALOGPS
logP -0.78 ChemAxon Molconvert
logS -4.17 ALOGPS
pKa 4.32 ChemAxon Molconvert
hydrogen acceptor count 7 ChemAxon Molconvert
hydrogen donor count 5 ChemAxon Molconvert
polar surface area 144.83 ChemAxon Molconvert
rotatable bond count 12 ChemAxon Molconvert
refractivity 119.07 ChemAxon Molconvert
polarizability 49.25 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Link
External Links
Resource Link
PubChem Compound 119212 Link_out
PubChem Substance 46505002 Link_out
ChemSpider 106497 Link_out
ChEBI 59297 Link_out
ChEMBL 59297 Link_out
Therapeutic Targets Database DAP001314 Link_out
Drug Product Database 0 Link_out
ATC Codes Not Available
AHFS Codes
  • 36:30.00
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. High affinity immunoglobulin epsilon receptor gamma-subunit

Pharmacological action: yes
Actions: agonist

The gamma subunit has a critical role in allowing the IgE Fc receptor to reach the cell surface

Organism class: human
UniProt ID: P30273 Link_out
Gene: FCER1G Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chandra RK, Joglekar SA, Tomas E: Penicillin allergy: anti-penicillin IgE antibodies and immediate hypersensitivity skin reactions employing major and minor determinants of penicillin. Arch Dis Child. 1980 Nov;55(11):857-60. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. High affinity immunoglobulin epsilon receptor subunit alpha

Pharmacological action: yes
Actions: agonist

Binds to the Fc region of immunoglobulins epsilon. High affinity receptor. Responsible for initiating the allergic response. Binding of allergen to receptor-bound IgE leads to cell activation and the release of mediators (such as histamine) responsible for the manifestations of allergy. The same receptor also induces the secretion of important lymphokines

Organism class: human
UniProt ID: P12319 Link_out
Gene: FCER1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chandra RK, Joglekar SA, Tomas E: Penicillin allergy: anti-penicillin IgE antibodies and immediate hypersensitivity skin reactions employing major and minor determinants of penicillin. Arch Dis Child. 1980 Nov;55(11):857-60. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:07

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.