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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
Structure for Patent Blue (DB13967)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Circulatory disorders •••••••••••• •••••••••• •••••••• - Contraindications & Blackbox Warnings
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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 AAlbumin binderHumans - 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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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 Integrate drug-drug
interactions in your softwareAbacavir 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. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 Canada 
Categories
- ATC Codes
- V04CX09 — Patent blue
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
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
- 32950
- ChEBI
- 59601
- ZINC
- ZINC000004365621
- Wikipedia
- Patent_Blue_V
- FDA label
- Download (343 KB)
- MSDS
- Download (47.5 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Terminated Diagnostic Breast Cancer 1 somestatus stop reason just information to hide 2 Unknown Status Treatment Breast Cancer 1 somestatus stop reason just information to hide Not Available Completed Diagnostic Breast Cancer 1 somestatus stop reason just information to hide
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
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- Antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- 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 15, 2024 01:12