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-penSolutionIntradermalAlk Abello, Inc.1975-12-31Not applicableCanada
Pre-penInjection60 umol/0.25mLIntradermal; SubcutaneousAllerQuest LLC1974-07-25Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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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
Humans
AHigh affinity immunoglobulin epsilon receptor subunit alpha
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinBenzylpenicilloyl polylysine may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinBenzylpenicilloyl polylysine may increase the anticoagulant activities of (S)-Warfarin.
4-Bromo-2,5-dimethoxyphenethylamine4-Bromo-2,5-dimethoxyphenethylamine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent.
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.
ABT-288ABT-288 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.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015032
PubChem Compound
45266800
PubChem Substance
46505002
ChemSpider
26331550
RxNav
19079
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
SolutionIntradermal
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

Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
Alpha amino acid amides / Beta amino acids and derivatives / Phenylacetamides / D-alpha-amino acids / Medium-chain fatty acids / Heterocyclic fatty acids / Dicarboxylic acids and derivatives / Thiazolidines / Secondary carboxylic acid amides / Amino acids
show 10 more
Substituents
N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Beta amino acid or derivatives / Alpha-amino acid / D-alpha-amino acid / Phenylacetamide / Medium-chain fatty acid / Heterocyclic fatty acid / Monocyclic benzene moiety / Dicarboxylic acid or derivatives
show 27 more
Molecular Framework
Not Available
External Descriptors
amino acid amide, thiazolidinemonocarboxylic acid, polypeptide, random copolymer (CHEBI:59297)

Targets

Kind
Protein
Organism
Humans
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
Humans
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 July 08, 2020 06:59

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