Identification
- Summary
Isosulfan blue is a visual lymphatic imaging agent used during lymphography as an adjunct.
- Brand Names
- Lymphazurin
- Generic Name
- Isosulfan blue
- DrugBank Accession Number
- DB09136
- Background
Not Available
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Isosulfan blue (DB09136)
- Weight
- Average: 545.69
Monoisotopic: 545.177455559 - Chemical Formula
- C27H33N2O6S2
- Synonyms
- Isosulfan blue inner salt
Pharmacology
- Indication
Isosulfan Blue is a synthetic visual lymphatic imaging agent. Isosulfan blue upon subcutaneous administration, delineates the lymphatic vessels draining the region of injection. It is an adjunct to lymphography in: primary and secondary lymphedema of the extremities; chyluria, chylous ascites or chylothorax; lymph node involvement by primary or secondary neoplasm; lymph node response to therapeutic modalities.
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- Contraindications & Blackbox Warnings
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Following subcutaneous administration, Lymphazurin 1% binds to serum proteins and is picked up by the lymphatic vessels. Thus, the lymphatic vessels are delineated by the blue dye.
- Mechanism of action
Isosulfan Blue is injected into the periphery of the tumor site, it localizes to the lymphatic system and aids in the surgical identification of tumor sentinel nodes which stain blue.
- Absorption
Intradermal and parenchymal injections of vital blue dyes, such as isosulfan blue, can lead to systemic absorption through lymphatic channels and vascular beds near tumor sites.
- Volume of distribution
Not available
- Protein binding
1% binds to serum proteins
- Metabolism
- Not Available
- Route of elimination
Excreted unchanged in the urine
- Half-life
Slow release of the dye from the subcutaneous tissue or the lymphatic tissue and the half-life of the dye in the body of several hours.
- Clearance
Up to 10% of the subcutaneously administered dose of isosulfan blue 1% is excreted in 24 hours in human.
- Adverse Effects
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LD50 greater than 150 mg/kg in the rat.
- 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 Isosulfan blue which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Isosulfan blue which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Isosulfan blue which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Isosulfan blue which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Isosulfan blue which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Isosulfan blue which could result in a higher serum level. Aclidinium Aclidinium may decrease the excretion rate of Isosulfan blue which could result in a higher serum level. Acrivastine Isosulfan blue may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Isosulfan blue which could result in a higher serum level. Adefovir dipivoxil Adefovir dipivoxil may decrease the excretion rate of Isosulfan blue which could result in a higher serum level. 
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- 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 Isosulfan blue 39N9K8S2A4 68238-36-8 NLUFDZBOHMOBOE-UHFFFAOYSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Isosulfan Blue Solution 10 mg/1mL Subcutaneous Anazao Health Corporation 2012-06-19 Not applicable US 
Lymphazurin Injection, solution 10 mg/1mL Subcutaneous United States Surgical Corporation 2012-01-12 Not applicable US Lymphazurin 1% Solution 10 mg / mL Subcutaneous Tyco Healthcare 1983-12-31 2010-01-07 Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Isosulfan Blue Injection, solution 10 mg/1mL Subcutaneous Mylan Institutional LLC 2015-03-26 2017-08-31 US Isosulfan Blue Injection, solution 10 mg/1mL Subcutaneous Somerset Therapeutics, Llc 2019-07-23 Not applicable US Isosulfan Blue Injection, solution 50 mg/5mL Subcutaneous AuroMedics Pharma LLC 2016-02-02 Not applicable US Isosulfan Blue Injection, solution 10 mg/1mL Subcutaneous Mylan Institutional LLC 2013-03-14 Not applicable US Isosulfan Blue Injection, solution 10 mg/1mL Subcutaneous Meitheal Pharmaceuticals Inc. 2021-11-03 Not applicable US Isosulfan Blue Injection, solution 10 mg/1mL Subcutaneous Bioniche Pharma USA LLC 2011-09-27 2010-08-15 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Isosulfan Blue Isosulfan blue (10 mg/1mL) Solution Subcutaneous Anazao Health Corporation 2012-06-19 Not applicable US
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- NS6Q291771
- CAS number
- 748080-29-7
- InChI Key
- YFKDCGWIINMRQY-UHFFFAOYSA-O
- InChI
- InChI=1S/C27H32N2O6S2/c1-5-28(6-2)22-13-9-20(10-14-22)27(21-11-15-23(16-12-21)29(7-3)8-4)25-19-24(36(30,31)32)17-18-26(25)37(33,34)35/h9-19H,5-8H2,1-4H3,(H-,30,31,32,33,34,35)/p+1
- IUPAC Name
- 4-{[4-(diethylamino)phenyl](2,5-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=CC(=CC=C1S(O)(=O)=O)S(O)(=O)=O
References
- General References
- Vokach-Brodsky L, Jeffrey SS, Lemmens HJ, Brock-Utne JG: Isosulfan blue affects pulse oximetry. Anesthesiology. 2000 Oct;93(4):1002-3. [Article]
- Daley MD, Norman PH, Leak JA, Nguyen DT, Bui TP, Kowalski AM, Srejic U, Popat K, Arens JF, Gershenwald JE, Hunt KK, Kuerer HM: Adverse events associated with the intraoperative injection of isosulfan blue. J Clin Anesth. 2004 Aug;16(5):332-41. [Article]
- Scherer K, Studer W, Figueiredo V, Bircher AJ: Anaphylaxis to isosulfan blue and cross-reactivity to patent blue V: case report and review of the nomenclature of vital blue dyes. Ann Allergy Asthma Immunol. 2006 Mar;96(3):497-500. [Article]
- Blass N, Fung D: Dyed but not dead--methylene blue overdose. Anesthesiology. 1976 Oct;45(4):458-9. [Article]
- Hirsch JI, Tisnado J, Cho SR, Beachley MC: Use of isosulfan blue for identification of lymphatic vessels: experimental and clinical evaluation. AJR Am J Roentgenol. 1982 Dec;139(6):1061-4. [Article]
- FDA label [Link]
- Drugs.com [Link]
- External Links
- PubChem Compound
- 50108
- PubChem Substance
- 310265051
- ChemSpider
- 4533
- 1546453
- ChEMBL
- CHEMBL1615783
- ZINC
- ZINC000003873832
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Active Not Recruiting Prevention Breast Cancer, Stage II / Breast Cancer, Stage III / Stage I Breast Cancer 1 2 Completed Diagnostic Breast Cancer 1 2 Completed Diagnostic Melanoma / Rhabdomyosarcomas 1 2 Unknown Status Diagnostic Colorectal Cancer 1 1 Terminated Treatment Endometrial Cancer 1 1, 2 Terminated Supportive Care Breast Cancer 1 0 Recruiting Treatment Breast Cancer 1 Not Available Completed Diagnostic Breast Cancer 3 Not Available Completed Diagnostic Colorectal Cancer / Metastatic Cancer 1 Not Available Completed Diagnostic Endometrial Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Subcutaneous 50 mg/5mL Solution Subcutaneous 10 mg/1mL Injection, solution Subcutaneous 10 mg/1mL Solution Subcutaneous 10 mg / mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00094 mg/mL ALOGPS logP -0.65 ALOGPS logP 2.05 Chemaxon logS -5.8 ALOGPS pKa (Strongest Acidic) -2.5 Chemaxon pKa (Strongest Basic) 5.33 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 114.99 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 171.81 m3·mol-1 Chemaxon Polarizability 58.06 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
Drug created at September 29, 2015 22:19 / Updated at January 09, 2021 18:39