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Showing drug card for Benzylpenicilloyl Polylysine (DB00895)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:02
Primary Accession Number DB00895
Secondary Accession Number
  • APRD00822
Name Benzylpenicilloyl Polylysine
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms Not Available
Brand Names
  1. Pre-pen
Brand Mixtures Not Available
Chemical IUPAC Name 2-[2-[(6-hydroxy-6-oxohexyl)amino]-2-oxo-1-[(2-phenylacetyl)amino]ethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
Chemical Formula C22H31N3O6S
Chemical Structure Structure
CAS Registry Number 2642-55-9
InChI Identifier InChI=1/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)/f/h23-24,27,30H
InChI Key KJABUVRFCPPJPD-KDAFFUTBCU
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 119212 Link Image
PubChem Substance 695873 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 465.5630
Monoisotopic Molecular Weight 465.1934
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 3.16e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -0.8 Source: PhysProp
Predicted LogP 0.45 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.17 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC1(C)S[C@@H](N[C@@H]1C(O)=O)[C@H](NC(=O)CC1=CC=CC=C1)C(=O)NCCCCCC(O)=O
Canonical SMILES CC1(C)SC(NC1C(O)=O)C(NC(=O)CC1=CC=CC=C1)C(=O)NCCCCCC(O)=O
Drug Category Not Available
ATC Codes Not Available
AHFS Codes
  • 36:30.00
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.
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
Toxicity Symptoms of overdose include urticaria, generalized pruritus, local swelling, generalized flushing, anaphylaxis, bronchospasm, fainting and maculopapular eruption.
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Liquid Intradermal
Patient Information Not Available
Contraindications Show Link Image
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. [PubMed Link Image]
Organisms Affected
  • Humans and other mammals
Targets
  1. High affinity immunoglobulin epsilon receptor subunit alpha
  2. High affinity immunoglobulin epsilon receptor gamma-subunit
Drug Target 1 [top]
Target 1 ID 18
Target 1 Name High affinity immunoglobulin epsilon receptor subunit alpha
Target 1 Synonyms
  1. Fc-epsilon RI-alpha
  2. FcERI
  3. High affinity immunoglobulin epsilon receptor subunit alpha precursor
  4. IgE Fc receptor, alpha-subunit
Target 1 Gene Name FCER1A
Target 1 Protein Sequence >High affinity immunoglobulin epsilon receptor alpha-subunit precursor 
MAPAMESPTLLCVALLFFAPDGVLAVPQKPKVSLNPPWNRIFKGENVTLTCNGNNFFEVS
STKWFHNGSLSEETNSSLNIVNAKFEDSGEYKCQHQQVNESEPVYLEVFSDWLLLQASAE
VVMEGQPLFLRCHGWRNWDVYKVIYYKDGEALKYWYENHNISITNATVEDSGTYYCTGKV
WQLDYESEPLNITVIKAPREKYWLQFFIPLLVVILFAVDTGLFISTQQQVTFLLKIKRTR
KGFRLLNPHPKPNPKNN
Target 1 Number of Residues 261
Target 1 Molecular Weight 29596
Target 1 Theoretical pI 6.67
Target 1 GO Classification Not Available
Target 1 General Function Not Available
Target 1 Specific Function 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-25
Target 1 Transmembrane Regions
  • 206-224
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 31318 Link Image
Target 1 UniProtKB/Swiss-Prot ID P12319 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name FCERA_HUMAN Link Image
Target 1 PDB ID 1RPQ Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Membrane
  • single-pass type I membrane protein
Target 1 Gene Sequence >774 bp 
ATGGCTCCTGCCATGGAATCCCCTACTCTACTGTGTGTAGCCTTACTGTTCTTCGCTCCA
GATGGCGTGTTAGCAGTCCCTCAGAAACCTAAGGTCTCCTTGAACCCTCCATGGAATAGA
ATATTTAAAGGAGAGAATGTGACTCTTACATGTAATGGGAACAATTTCTTTGAAGTCAGT
TCCACCAAATGGTTCCACAATGGCAGCCTTTCAGAAGAGACAAATTCAAGTTTGAATATT
GTGAATGCCAAATTTGAAGACAGTGGAGAATACAAATGTCAGCACCAACAAGTTAATGAG
AGTGAACCTGTGTACCTGGAAGTCTTCAGTGACTGGCTGCTCCTTCAGGCCTCTGCTGAG
GTGGTGATGGAGGGCCAGCCCCTCTTCCTCAGGTGCCATGGTTGGAGGAACTGGGATGTG
TACAAGGTGATCTATTATAAGGATGGTGAAGCTCTCAAGTACTGGTATGAGAACCACAAC
ATCTCCATTACAAATGCCACAGTTGAAGACAGTGGAACCTACTACTGTACGGGCAAAGTG
TGGCAGCTGGACTATGAGTCTGAGCCCCTCAACATTACTGTAATAAAAGCTCCGCGTGAG
AAGTACTGGCTACAATTTTTTATCCCATTGTTGGTGGTGATTCTGTTTGCTGTGGACACA
GGATTATTTATCTCAACTCAGCAGCAGGTCACATTTCTCTTGAAGATTAAGAGAACCAGG
AAAGGCTTCAGACTTCTGAACCCACATCCTAAGCCAAACCCCAAAAACAACTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID FCER1A Link Image
Target 1 GenAtlas ID FCER1A Link Image
Target 1 HGNC ID HGNC:3609 Link Image
Target 1 Chromosome Location 1
Target 1 Locus 1q23
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Padlan EA, Helm BA: A modeling study of the alpha-subunit of human high-affinity receptor for immunoglobulin-E. Receptor. 1992 Summer;2(2):129-44. [PubMed Link Image]
  2. Shimizu A, Tepler I, Benfey PN, Berenstein EH, Siraganian RP, Leder P: Human and rat mast cell high-affinity immunoglobulin E receptors: characterization of putative alpha-chain gene products. Proc Natl Acad Sci U S A. 1988 Mar;85(6):1907-11. [PubMed Link Image]
  3. Kochan J, Pettine LF, Hakimi J, Kishi K, Kinet JP: Isolation of the gene coding for the alpha subunit of the human high affinity IgE receptor. Nucleic Acids Res. 1988 Apr 25;16(8):3584. [PubMed Link Image]
  4. Yagi S, Yanagida M, Tanida I, Hasegawa A, Okumura K, Ra C: High-level expression of the truncated alpha chain of human high-affinity receptor for IgE as a soluble form by baculovirus-infected insect cells. Biochemical characterization of the recombinant product. Eur J Biochem. 1994 Mar 1;220(2):593-8. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 55
Target 2 Name High affinity immunoglobulin epsilon receptor gamma-subunit
Target 2 Synonyms
  1. Fc-epsilon RI-gamma
  2. FceRI gamma
  3. High affinity immunoglobulin epsilon receptor gamma-subunit precursor
  4. IgE Fc receptor gamma-subunit
Target 2 Gene Name FCER1G
Target 2 Protein Sequence >High affinity immunoglobulin epsilon receptor gamma-subunit precursor 
MIPAVVLLLLLLVEQAAALGEPQLCYILDAILFLYGIVLTLLYCRLKIQVRKAAITSYEK
SDGVYTGLSTRNQETYETLKHEKPPQ
Target 2 Number of Residues 87
Target 2 Molecular Weight 9668
Target 2 Theoretical pI 7.24
Target 2 GO Classification
Function
signal transducer activity
receptor activity
transmembrane receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
Component
cell
membrane
Target 2 General Function Involved in immune function
Target 2 Specific Function The gamma subunit has a critical role in allowing the IgE Fc receptor to reach the cell surface
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • 1-18
Target 2 Transmembrane Regions
  • 24-44
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 182488 Link Image
Target 2 UniProtKB/Swiss-Prot ID P30273 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name FCERG_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Membrane
  • single-pass type I membrane protein
Target 2 Gene Sequence >261 bp 
ATGATTCCAGCAGTGGTCTTGCTCTTACTCCTTTTGGTTGAACAAGCAGCGGCCCTGGGA
GAGCCTCAGCTCTGCTATATCCTGGATGCCATCCTGTTTCTGTATGGAATTGTCCTCACC
CTCCTCTACTGTCGACTGAAGATCCAAGTGCGAAAGGCAGCTATAACCAGCTATGAGAAA
TCAGATGGTGTTTACACGGGCCTGAGCACCAGGAACCAGGAGACTTACGAGACTCTGAAG
CATGAGAAACCACCACAGTAG
Target 2 GenBank Gene ID
Target 2 GeneCard ID FCER1G Link Image
Target 2 GenAtlas ID FCER1G Link Image
Target 2 HGNC ID HGNC:3611 Link Image
Target 2 Chromosome Location 1
Target 2 Locus 1q23
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Kuster H, Thompson H, Kinet JP: Characterization and expression of the gene for the human Fc receptor gamma subunit. Definition of a new gene family. J Biol Chem. 1990 Apr 15;265(11):6448-52. [PubMed Link Image]
Target 2 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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.