Benzylpenicilloyl Polylysine

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
Synonyms
  • Benzyl penicilloyl-polylysine
  • Benzylpenicilloyl G polylysine
  • Benzylpenicilloyl-polylysine
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pre-penSolution0.000060 mIntradermalAlk Abello, Inc.1975-12-31Not applicableCanada
Pre-penInjection60 umol/0.25mLIntradermal; SubcutaneousAller Quest Llc1974-07-25Not applicableUs
Categories
UNII
76479814OY
CAS number
31855-75-1
Weight
Average: 626.765
Monoisotopic: 626.309783168
Chemical Formula
C28H46N6O8S
InChI Key
IMPVZRLKKKXMKQ-SGDOCVTFSA-N
InChI
InChI=1S/C22H32N4O6S.C6H14N2O2/c1-22(2)17(21(31)32)26-19(33-22)16(25-15(27)12-13-8-4-3-5-9-13)18(28)24-11-7-6-10-14(23)20(29)30;7-4-2-1-3-5(8)6(9)10/h3-5,8-9,14,16-17,19,26H,6-7,10-12,23H2,1-2H3,(H,24,28)(H,25,27)(H,29,30)(H,31,32);5H,1-4,7-8H2,(H,9,10)/t14-,16?,17+,19-;5-/m11/s1
IUPAC Name
SMILES

Pharmacology

Indication

For use as a adjunct in assessing the risk of administering penicillin (benzylpenicillin or penicillin G).

Associated Conditions
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.

TargetActionsOrganism
AHigh affinity immunoglobulin epsilon receptor subunit gamma
agonist
Human
AHigh affinity immunoglobulin epsilon receptor subunit alpha
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinBenzylpenicilloyl Polylysine may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinBenzylpenicilloyl Polylysine may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarinBenzylpenicilloyl Polylysine may increase the anticoagulant activities of 4-hydroxycoumarin.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
AbediterolAbediterol may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
AcemetacinAcemetacin may decrease the excretion rate of Benzylpenicilloyl Polylysine which could result in a higher serum level.
AcenocoumarolBenzylpenicilloyl Polylysine may increase the anticoagulant activities of Acenocoumarol.
AceprometazineAceprometazine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
AcrivastineAcrivastine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
AdrafinilAdrafinil may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015032
PubChem Compound
45266800
PubChem Substance
46505002
ChemSpider
26331550
ChEBI
59297
ChEMBL
CHEMBL1201779
Therapeutic Targets Database
DAP001314
PharmGKB
PA164754810
Wikipedia
Benzylpenicilloyl_polylysine
ATC Codes
J01CR50 — Combinations of penicillins
AHFS Codes
  • 36:30.00 — Drug Hypersensitivity

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedDiagnosticHistory of IgE Dependent Reaction to a Penicillin Product1

Pharmacoeconomics

Manufacturers
  • Allerquest llc
Packagers
  • Allerquest LLC
  • Schwarz Pharma Inc.
  • Taylor Pharmaceuticals
Dosage forms
FormRouteStrength
InjectionIntradermal; Subcutaneous60 umol/0.25mL
SolutionIntradermal0.000060 m
Prices
Unit descriptionCostUnit
Pre-pen ampul72.0USD ampul
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0658 mg/mLALOGPS
logP-0.89ALOGPS
logP-3.8ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)2.04ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area170.85 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity122.22 m3·mol-1ChemAxon
Polarizability50.31 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Igg binding
Specific Function
Associates with a variety of FcR alpha chains to form a functional signaling complex. Regulates several aspects of the immune response. The gamma subunit has a critical role in allowing the IgE Fc ...
Gene Name
FCER1G
Uniprot ID
P30273
Uniprot Name
High affinity immunoglobulin epsilon receptor subunit gamma
Molecular Weight
9667.355 Da
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:17139284]
  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:17016423]
  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:7436456]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Ige receptor activity
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 t...
Gene Name
FCER1A
Uniprot ID
P12319
Uniprot Name
High affinity immunoglobulin epsilon receptor subunit alpha
Molecular Weight
29595.67 Da
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:17139284]
  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:17016423]
  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:7436456]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:32