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

Similar Structures

Synonyms

Benzyl penicilloyl-polylysine
Benzylpenicilloyl G polylysine
Benzylpenicilloyl-polylysine

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Pre-pen	Solution	28.8348 mg/1	Intradermal	Alk Abello, Inc.	1975-12-31	Not applicable
Pre-pen	Injection	60 umol/0.25mL	Intradermal; Subcutaneous	AllerQuest LLC	1974-07-25	Not applicable

Additional Data Available

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

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.

Target	Actions	Organism
AHigh affinity immunoglobulin epsilon receptor subunit gamma	agonist	Humans
AHigh affinity immunoglobulin epsilon receptor subunit alpha	agonist	Humans

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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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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.

Drug	Interaction
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(R)-warfarin	Benzylpenicilloyl polylysine may increase the anticoagulant activities of (R)-warfarin.
(S)-Warfarin	Benzylpenicilloyl polylysine may increase the anticoagulant activities of (S)-Warfarin.
4-Bromo-2,5-dimethoxyphenethylamine	4-Bromo-2,5-dimethoxyphenethylamine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent.
4-hydroxycoumarin	Benzylpenicilloyl polylysine may increase the anticoagulant activities of 4-hydroxycoumarin.
4-Methoxyamphetamine	4-Methoxyamphetamine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent.
Abediterol	Abediterol may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent.
ABT-288	ABT-288 may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent.
Acemetacin	Acemetacin may decrease the excretion rate of Benzylpenicilloyl polylysine which could result in a higher serum level.
Acenocoumarol	Benzylpenicilloyl polylysine may increase the anticoagulant activities of Acenocoumarol.
Aceprometazine	Aceprometazine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent.

Additional Data Available

Extended Description

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

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Severity

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

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

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

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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

Phase	Status	Purpose	Conditions	Count
3	Completed	Diagnostic	History of IgE Dependent Reaction to a Penicillin Product	1

Pharmacoeconomics

Manufacturers

Allerquest llc

Packagers

Allerquest LLC
Schwarz Pharma Inc.
Taylor Pharmaceuticals

Dosage forms

Form	Route	Strength
Injection	Intradermal; Subcutaneous	60 umol/0.25mL
Solution	Intradermal	28.8348 mg/1

Prices

Unit description	Cost	Unit
Pre-pen ampul	72.0USD	ampul

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	-0.8	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0658 mg/mL	ALOGPS
logP	-0.89	ALOGPS
logP	-3.8	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	2.04	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	170.85 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	122.22 m³·mol^-1	ChemAxon
Polarizability	50.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Classification: Not classified

Targets

Details1. High affinity immunoglobulin epsilon receptor subunit gamma

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

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]
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]
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]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Details2. High affinity immunoglobulin epsilon receptor subunit alpha

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

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]
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]
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]
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 January 18, 2020 13:29

Benzylpenicilloyl polylysine

Identification

Structure for Benzylpenicilloyl polylysine (DB00895)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References