Patent Blue

Identification

Summary

Patent Blue is a dye used to label lymphatic vessels, arterial territories, and lymph nodes prior to biopsy in some cancers.

Generic Name

Patent Blue

DrugBank Accession Number

DB13967

Background

Patent blue is aniline dye and it is one of the most common dyes used.¹ It is a sodium or calcium salt of diethylammonium hydroxide inner salt.² It has the chemical designation of (4-(alpha-(p-(diethylamino)phenyl)-2,4-disulfobenzylidene)-2,5-cyclohexadiene-1-ylidene)diethylammonium hydroxide. Patent blue was developed by Guerbet and approved by Health Canada on December 31, 1979.⁵ The isomer isosulphan is used in the United States for the same indications than patent blue.²

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 561.69
Monoisotopic: 561.172370179
Chemical Formula: C₂₇H₃₃N₂O₇S₂

Synonyms

patent blue violet

Pharmacology

Indication

Patent blue is used for marking lymphatic vessels and arterial territories as well as for sentinel lymph node prior to biopsy in patients with operable breast cancer and clinically negative lymph nodes in combination with a radiotracer.³

Patent blue is also used in the textile, paper, agriculture and cosmetic industry.²

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Associated Conditions

Circulatory Disorders

Contraindications & Blackbox Warnings

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Pharmacodynamics

Administration of patent blue has been reported to cause hypersensitivity reactions in approximately 1% of the patients. It also presents a localized blue coloration which has made patent blue a sensitive and specific option for the detection of micrometastatic cancer in lymph nodes.⁴

Mechanism of action

The specific binding of patent blue allows it to freely travel in the breast lymphatics and allows staging with a less invasive alternative. Patent blue will form a complex with albumin which will be picked up by regional afferent lymphatics to identify sentinel lymph nodes.³ A sentinel lymph node is the first lymph node in a chain or group of lymph nodes that cancer is most likely to spread to. The determination of the sentinel lymph node allows the physician to stage cancer by observing if cancer has spread to the near lymph nodes.⁶

Target	Actions	Organism
ASerum albumin	binder	Humans

Absorption

Patent blue is selectively absorbed in the lymphatics.² When administered orally, patent blue has a very low absorption and limited systemic availability.⁸

Volume of distribution

This pharmacokinetic parameter has not been studied.

Protein binding

Patent blue gets specifically bound to albumin which allows it to travel through the breast lymphatics.³

Metabolism

In vitro studies have shown that patent blue is not metabolized.⁸

Route of elimination

Patent blue is excreted into the urine and bile.²The excretion is more significant in the urine which after the administration of patent blue intravenously can even change to a blue coloration.⁷ When administered orally, patent blue is excreted unchanged in feces.⁸

Half-life

The elimination half-life is of about 24-48 hours.⁷

Clearance

This pharmacokinetic property has nos been fully studied.

Adverse Effects

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Toxicity

Overdose studies have not been performed but major cases of hypersensitivity have been reported.⁷

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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Abacavir	Abacavir may decrease the excretion rate of Patent Blue which could result in a higher serum level.
Acebutolol	The risk or severity of hypersensitivity reaction can be increased when Patent Blue is combined with Acebutolol.
Aceclofenac	Aceclofenac may decrease the excretion rate of Patent Blue which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Patent Blue which could result in a higher serum level.
Acetaminophen	Acetaminophen may decrease the excretion rate of Patent Blue which could result in a higher serum level.
Acetazolamide	Acetazolamide may increase the excretion rate of Patent Blue which could result in a lower serum level and potentially a reduction in efficacy.
Acetylcholine	The therapeutic efficacy of Acetylcholine can be decreased when used in combination with Patent Blue.
Acetylsalicylic acid	Acetylsalicylic acid may decrease the excretion rate of Patent Blue which could result in a higher serum level.
Aclidinium	Aclidinium may decrease the excretion rate of Patent Blue which could result in a higher serum level.
Acrivastine	Acrivastine may decrease the excretion rate of Patent Blue which could result in a higher serum level.

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Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Patent Blue V calcium	8QE473DV1Z	3536-49-0	RTMBGDBBDQKNNZ-UHFFFAOYSA-L
Patent Blue V sodium	9ZL680Q9Z5	20262-76-4	PMLFOMWMYRKZRF-UHFFFAOYSA-M

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Patent Blue Sodium Injection	Solution	50 mg / 2 mL	Intravenous; Subcutaneous	Guerbet	1979-12-31	Not applicable

Chemical Identifiers

UNII: D4RJJ6R97N
CAS number: 25305-77-5
InChI Key: DHAHKSQXIXFZJB-UHFFFAOYSA-O
InChI: InChI=1S/C27H32N2O7S2/c1-5-28(6-2)21-13-9-19(10-14-21)27(20-11-15-22(16-12-20)29(7-3)8-4)23-17-24(30)26(38(34,35)36)18-25(23)37(31,32)33/h9-18H,5-8H2,1-4H3,(H2-,30,31,32,33,34,35,36)/p+1
IUPAC Name: 4-{[4-(diethylamino)phenyl](5-hydroxy-2,4-disulfophenyl)methylidene}-N,N-diethylcyclohexa-2,5-dien-1-iminium
SMILES: CCN(CC)C1=CC=C(C=C1)C(=C1C=CC(C=C1)=[N+](CC)CC)C1=C(C=C(C(O)=C1)S(O)(=O)=O)S(O)(=O)=O

References

General References

Iqbal FM, Basit A, Salem F, Vidya R: Feeling blue, going green and finding other attractive alternatives: a case of biphasic anaphylaxis to patent blue and a literature review of alternative sentinel node localisation methods. BMJ Case Rep. 2015 Dec 15;2015. pii: bcr-2015-213107. doi: 10.1136/bcr-2015-213107. [Article]
Tripathy S, Nair PV: Adverse drug reaction, patent blue V dye and anaesthesia. Indian J Anaesth. 2012 Nov;56(6):563-6. doi: 10.4103/0019-5049.104576. [Article]
Gumus M, Gumus H, Jones SE, Jones PA, Sever AR, Weeks J: How long will I be blue? Prolonged skin staining following sentinel lymph node biopsy using intradermal patent blue dye. Breast Care (Basel). 2013 Jun;8(3):199-202. doi: 10.1159/000352092. [Article]
Joshi M, Hart M, Ahmed F, McPherson S: Adverse reaction; patent blue turning patient blue. BMJ Case Rep. 2012 Nov 30;2012. pii: bcr-2012-007339. doi: 10.1136/bcr-2012-007339. [Article]
Health Canada [Link]
Canadian Cancer Society [Link]
Patent blue V monograph [Link]
European Food Safety Authority [Link]

External Links

ChemSpider: 69520
RxNav: 32950
ChEBI: 59601
ZINC: ZINC000004365621
Wikipedia: Patent_Blue_V

FDA label

Download (343 KB)

MSDS

Download (47.5 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Unknown Status	Treatment	Breast Cancer	1
Not Available	Completed	Diagnostic	Breast Cancer	1
Not Available	Terminated	Diagnostic	Breast Cancer	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Solution	Intravenous; Subcutaneous	50 mg / 2 mL
Solution	Intravenous; Subcutaneous	25 mg/1ml

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	200 ºC	'MSDS'
boiling point (°C)	Decomposes	'MSDS'
water solubility	Soluble	'MSDS'
logP	-1.82	'MSDS'
pKa	7.63	Nollet L. and Toldra F. Handbook of food analysis. (2015)

Predicted Properties

Property	Value	Source
Water Solubility	0.00268 mg/mL	ALOGPS
logP	-0.5	ALOGPS
logP	2.4	Chemaxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	-2.6	Chemaxon
pKa (Strongest Basic)	5.33	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	8	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	135.22 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	173.8 m³·mol^-1	Chemaxon
Polarizability	59.14 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST): Not Available
Spectra: Not Available

Targets

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Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Gumus M, Gumus H, Jones SE, Jones PA, Sever AR, Weeks J: How long will I be blue? Prolonged skin staining following sentinel lymph node biopsy using intradermal patent blue dye. Breast Care (Basel). 2013 Jun;8(3):199-202. doi: 10.1159/000352092. [Article]

Drug created at January 17, 2018 21:10 / Updated at September 21, 2023 08:43

Patent Blue

Identification

Structure for Patent Blue (DB13967)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References