Benzylpenicilloyl polylysine

Identification

Summary

Benzylpenicilloyl polylysine is a penicillin derivative used to determine penicillin allergies.

Brand Names
Pre-pen
Generic Name
Benzylpenicilloyl polylysine
DrugBank Accession Number
DB00895
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 626.765
Monoisotopic: 626.309783168
Chemical Formula
C28H46N6O8S
Synonyms
  • Benzyl penicilloyl-polylysine
  • Benzylpenicilloyl G polylysine
  • Benzylpenicilloyl polylysine
  • Benzylpenicilloyl-polylysine

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Diagnostic agentPenicillin allergy••••••••••••
Diagnostic agentBeta-lactam antibiotic allergy••• •••••
Contraindications & Blackbox Warnings
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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
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

Adverse Effects
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Toxicity

Symptoms of overdose include urticaria, generalized pruritus, local swelling, generalized flushing, anaphylaxis, bronchospasm, fainting and maculopapular eruption.

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
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.
AcrivastineAcrivastine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent.
AlimemazineAlimemazine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Benzylpenicilloyl polylysine is combined with Ambroxol.
Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Pre-penInjection60 umol/0.25mLIntradermal; SubcutaneousAllerQuest LLC1974-07-25Not applicableUS flag
Pre-penSolution28.8348 mg/1IntradermalAlk Abello, Inc.1975-12-31Not applicableCanada flag

Categories

ATC Codes
J01CR50 — Combinations of penicillins
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alpha-amino acid / Alpha-amino acid amide / Amine / Amino acid / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Beta amino acid or derivatives / Carbonyl group / Carboxamide group
show 27 more
Molecular Framework
Not Available
External Descriptors
amino acid amide, thiazolidinemonocarboxylic acid, polypeptide, random copolymer (CHEBI:59297)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
76479814OY
CAS number
31855-75-1
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

References

General References
Not Available
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

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
SolutionIntradermal28.8348 mg/1
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
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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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. [Article]
  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. [Article]
  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. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 19, 2024 11:06