Isosulfan blue

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
Thumb
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.

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

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
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Isosulfan blue which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
AcrivastineIsosulfan blue may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
Adefovir dipivoxilAdefovir dipivoxil may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
No interactions found.

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Isosulfan blue39N9K8S2A468238-36-8NLUFDZBOHMOBOE-UHFFFAOYSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Isosulfan BlueSolution10 mg/1mLSubcutaneousAnazao Health Corporation2012-06-19Not applicableUS flag
LymphazurinInjection, solution10 mg/1mLSubcutaneousUnited States Surgical Corporation2012-01-12Not applicableUS flag
Lymphazurin 1%Solution10 mg / mLSubcutaneousTyco Healthcare1983-12-312010-01-07Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Isosulfan BlueInjection, solution10 mg/1mLSubcutaneousMylan Institutional LLC2015-03-262017-08-31US flag
Isosulfan BlueInjection, solution10 mg/1mLSubcutaneousMylan Institutional LLC2013-03-14Not applicableUS flag
Isosulfan BlueInjection, solution50 mg/5mLSubcutaneousAuroMedics Pharma LLC2016-02-02Not applicableUS flag
Isosulfan BlueInjection, solution10 mg/1mLSubcutaneousBioniche Pharma USA LLC2011-09-272010-08-15US flag
Isosulfan BlueInjection, solution10 mg/1mLSubcutaneousSomerset Therapeutics, Llc2019-07-23Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Isosulfan BlueIsosulfan blue (10 mg/1mL)SolutionSubcutaneousAnazao Health Corporation2012-06-19Not applicableUS flag

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
  1. Vokach-Brodsky L, Jeffrey SS, Lemmens HJ, Brock-Utne JG: Isosulfan blue affects pulse oximetry. Anesthesiology. 2000 Oct;93(4):1002-3. [Article]
  2. 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]
  3. 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]
  4. Blass N, Fung D: Dyed but not dead--methylene blue overdose. Anesthesiology. 1976 Oct;45(4):458-9. [Article]
  5. 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]
  6. FDA label [Link]
  7. Drugs.com [Link]
PubChem Compound
50108
PubChem Substance
310265051
ChemSpider
4533
RxNav
1546453
ChEMBL
CHEMBL1615783
ZINC
ZINC000003873832

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingPreventionBreast Cancer, Stage II / Breast Cancer, Stage III / Early Breast Cancer1
2CompletedDiagnosticBreast Cancer1
2CompletedDiagnosticMalignant Melanoma of Skin / Rhabdomyosarcomas1
2Unknown StatusDiagnosticColorectal Carcinoma (CRC)1
1TerminatedTreatmentEndometrial Cancer1
1, 2TerminatedSupportive CareBreast Cancer1
Not AvailableCompletedDiagnosticBreast Cancer3
Not AvailableCompletedDiagnosticColorectal Carcinoma (CRC) / Metastatic Cancers1
Not AvailableCompletedDiagnosticEndometrial Cancer1
Not AvailableCompletedDiagnosticHead and Neck Carcinoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionSubcutaneous50 mg/5mL
SolutionSubcutaneous10 mg/1mL
Injection, solutionSubcutaneous10 mg/1mL
SolutionSubcutaneous10 mg / mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00094 mg/mLALOGPS
logP-0.65ALOGPS
logP2.05ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)-2.5ChemAxon
pKa (Strongest Basic)5.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area114.99 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity171.81 m3·mol-1ChemAxon
Polarizability58.06 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created on September 29, 2015 22:19 / Updated on January 09, 2021 18:39