Isosulfan blue

Identification

Name
Isosulfan blue
Accession Number
DB09136
Type
Small Molecule
Groups
Approved
Description
Not Available
Structure
Thumb
Synonyms
  • Isosulfan blue inner salt
Product Ingredients
IngredientUNIICASInChI Key
Isosulfan blue39N9K8S2A468238-36-8NLUFDZBOHMOBOE-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LymphazurinInjection, solution10 mg/1mLSubcutaneousUnited States Surgical Corporation2012-01-12Not applicableUs
Lymphazurin 1%Solution10 mgSubcutaneousTyco Healthcare1983-12-312010-01-07Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Isosulfan BlueInjection, solution10 mg/1mLSubcutaneousBioniche Pharma USA LLC2011-09-272010-08-15Us
Isosulfan BlueInjection, solution10 mg/1mLSubcutaneousMylan Institutional2013-03-14Not applicableUs
Isosulfan BlueInjection, solution50 mg/5mLSubcutaneousAuro Medics Pharma Llc2016-02-02Not applicableUs
Isosulfan BlueInjection, solution10 mg/1mLSubcutaneousMylan Institutional2015-03-26Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Isosulfan BlueIsosulfan blue (10 mg/1mL)SolutionSubcutaneousAnazao Health Corporation2012-06-19Not applicableUs
Categories
UNII
NS6Q291771
CAS number
748080-29-7
Weight
Average: 545.69
Monoisotopic: 545.177455559
Chemical Formula
C27H33N2O6S2
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

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.

Associated Conditions
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.

Toxicity

LD50 greater than 150 mg/kg in the rat.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
AcarboseAcarbose 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.
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.
AdefovirAdefovir may decrease the excretion rate of Isosulfan blue which could result in a higher serum level.
Food Interactions
Not Available

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. [PubMed:11020754]
  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. [PubMed:15374553]
  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. [PubMed:16597088]
  4. Blass N, Fung D: Dyed but not dead--methylene blue overdose. Anesthesiology. 1976 Oct;45(4):458-9. [PubMed:973698]
  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. [PubMed:6983249]
  6. FDA label [Link]
  7. Drugs.com [Link]
External Links
PubChem Compound
50108
PubChem Substance
310265051
ChemSpider
4533
ChEMBL
CHEMBL1615783

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentEndometrial Cancers1
2CompletedDiagnosticCancer, Breast1
2RecruitingDiagnosticMelanoma / Rhabdomyosarcomas1
2Unknown StatusDiagnosticColorectal Cancers1
Not AvailableCompletedDiagnosticCancer, Breast2
Not AvailableCompletedDiagnosticColorectal Cancers / Metastatic Cancers1
Not AvailableCompletedDiagnosticEndometrial Cancers1
Not AvailableCompletedDiagnosticHead and Neck Carcinoma1
Not AvailableTerminatedDiagnosticAdenocarcinoma of the Cervix / Adenosquamous carcinoma of the cervix / Cervical Squamous Cell Carcinoma / Stage I Cervical Cancer1
Not AvailableTerminatedDiagnosticStage I Endometrial Carcinoma / Stage II Endometrial Carcinoma / Stage III Endometrial Carcinoma / Stage IV Endometrial Carcinoma1
Not AvailableUnknown StatusDiagnosticRecurrent Melanoma / Stage IA Melanoma / Stage IB Melanoma / Stage IIA Melanoma / Stage IIB Melanoma / Stage IIC Melanoma / Stage IIIA Melanoma / Stage IIIB Melanoma / Stage IIIc Melanoma / Stage IV Melanoma1

Pharmacoeconomics

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

Taxonomy

Classification
Not classified

Drug created on September 29, 2015 16:19 / Updated on November 02, 2018 09:15