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Isosulfan blue

Cat No.:V22738 Purity: ≥98%
Isosulfan blue is a blue dye used for lymphatic vessel identification in lymphangiography.
Isosulfan blue
Isosulfan blue Chemical Structure CAS No.: 68238-36-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
100mg
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Product Description
Isosulfan blue is a blue dye used for lymphatic vessel identification in lymphangiography. Isosulfan blue for sentinel lymph node biopsy in breast cancer. Isosulfan blue may cause allergic reactions during breast cancer surgery.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Lymphoid tissue can absorb isosulfan blue quickly, and it rarely spreads to other nearby tissues [1].
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Intradermal and intracellular injections of reactive blue dyes (e.g., isosulfan) allow for systemic absorption via lymphatic vessels and the vascular bed near the tumor site. Excretion in Urine Unchanged No data available. In humans, up to 10% of a 1% isosulfan injection is excreted within 24 hours. Following subcutaneous injection, the 1% isosulfan solution binds to serum proteins and is absorbed by the lymphatic vessels. Therefore, the lymphatic vessels are outlined by the blue dye. It is currently unknown whether this drug is secreted into human breast milk. In humans, up to 10% of a 1% isosulfan injection is excreted unchanged in the urine within 24 hours. Biological Half-Life The dye is slowly released from subcutaneous or lymphatic tissues, with a half-life of several hours in the body.
Toxicity/Toxicokinetics
Protein Binding
1% bound to serum proteins
References

[1]. Anaphylactic reaction to isosulfan blue used for sentinel node biopsy: case report and literature review. Breast J. 2002 Nov-Dec;8(6):396-9.

[2]. Anaphylaxis to isosulfan blue. Ann Allergy Asthma Immunol. 2002 Jan;88(1):64-6.

Additional Infomation
Isosulfan blue is a synthetic lymphoimaging agent. When injected around the tumor site, isosulfan blue localizes to the lymphatic system and aids in surgical identification of tumor sentinel lymph nodes stained blue. (NCI04)
See also: Isosulfan inner salt (containing the active fraction).
Pharmaceutical Indications
Isosulfan blue is a synthetic lymphoimaging agent. Subcutaneous injection of isosulfan blue visualizes the lymphatic vessels draining from the injection area. It can be used as an adjunct to lymphography for: primary and secondary lymphedema of the extremities; chyluria, chylous ascites, or chylothorax; primary or secondary tumors involving lymph nodes; lymph node response to treatment.
Mechanism of Action
Isosulfan blue, when injected around the tumor site, localizes to the lymphatic system and aids in surgical identification of tumor sentinel lymph nodes stained blue.
Therapeutic Use
1% isosulfan subcutaneous injection can visualize lymphatic drainage at the injection site. It can be used as an adjunct to lymphography for: primary and secondary lymphedema of the extremities; chyluria, chylous ascites, or chylothorax; primary or secondary tumors involving lymph nodes; and lymph node response to treatment. /US Product Label Content/
Drug Warnings
1% isosulfan injection is contraindicated in patients with known hypersensitivity to triphenylmethane or related compounds.
Life-threatening anaphylactic reactions (respiratory distress, shock, angioedema) have occurred after injection of 1% isosulfan. Patients with bronchial asthma, a history of allergies, a history of drug reactions, or a history of reactions to triphenylmethane dyes are more susceptible to such reactions. Patients should be closely monitored for at least 60 minutes after injection of 1% isosulfan. Trained personnel should be available to provide emergency care, including resuscitation.
1% isosulfan blue injection may interfere with pulse oximetry measurements of peripheral blood oxygen saturation and may cause falsely low readings. The interference reaches its maximum 30 minutes after administration and typically reaches its minimum 4 hours after administration. Arterial blood gas analysis may be necessary to verify the decrease in arterial oxygen partial pressure.
1% isosulfan blue injection may also cause a falsely elevated methemoglobin reading on arterial blood gas analyzers. Therefore, blood oxygen saturation monitoring may be necessary to verify methemoglobin levels.
For more complete data on drug warnings for isosulfan blue (10 in total), please visit the HSDB record page.
Pharmacodynamics
After subcutaneous injection, 1% lymphosulfan blue binds to serum proteins and is absorbed by lymphatic vessels. Therefore, lymphatic vessels will be visualized by the blue dye.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H31N2O6S2-.NA+
Molecular Weight
566.66464
Exact Mass
569.176
CAS #
68238-36-8
PubChem CID
50108
Appearance
Light green to green solid powder
LogP
6.212
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
7
Heavy Atom Count
38
Complexity
1040
Defined Atom Stereocenter Count
0
InChi Key
NLUFDZBOHMOBOE-UHFFFAOYSA-M
InChi Code
InChI=1S/C27H32N2O6S2.Na/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);/q;+1/p-1
Chemical Name
sodium;2-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]benzene-1,4-disulfonate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~83.33 mg/mL (~147.05 mM)
H2O : ≥ 7.69 mg/mL (~13.57 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.67 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (3.67 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.7647 mL 8.8236 mL 17.6473 mL
5 mM 0.3529 mL 1.7647 mL 3.5295 mL
10 mM 0.1765 mL 0.8824 mL 1.7647 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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