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Isosulfan Blue

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Also known as: 68238-36-8, Sulphan blue, Isosulfan blue [usan], Iso-sulfan blue, Patentblueviolet, Sulphan blue 2,5-disulfophenyl isomer

Molecular Formula

C₂₇H₃₁N₂NaO₆S₂

Molecular Weight

566.7 g/mol

InChI Key

NLUFDZBOHMOBOE-UHFFFAOYSA-M

FDA UNII

39N9K8S2A4

Isosulfan Blue is a synthetic visual lymphatic imaging agent. Injected into the periphery of the tumor site, isosulfan blue localizes to the lymphatic system and aids in the surgical identification of tumor sentinel nodes which stain blue. (NCI04)

1 2D Structure

Isosulfan Blue

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;2-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]benzene-1,4-disulfonate

2.1.2 InChI

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

2.1.3 InChI Key

NLUFDZBOHMOBOE-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CCN(CC)C1=CC=C(C=C1)C(=C2C=CC(=[N+](CC)CC)C=C2)C3=C(C=CC(=C3)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+]

2.2 Other Identifiers

2.2.1 UNII

39N9K8S2A4

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(alpha-(p-(diethylamino)phenyl)-(2,5-disulfobenzylidene)-2,5-cyclohexadien-1-ylidene)diethylammonium Hydroxide Inner Salt, Sodium Salt

2. Iso-sulfan Blue

3. Iso-sulphan Blue

4. Lymphazurin

5. Lymphazurin Blue

2.3.2 Depositor-Supplied Synonyms

1. 68238-36-8

2. Sulphan Blue

3. Isosulfan Blue [usan]

4. Iso-sulfan Blue

5. Patentblueviolet

6. Sulphan Blue 2,5-disulfophenyl Isomer

7. Lymphazurin

8. Sodium 2-((4-(diethylamino)phenyl)(4-(diethyliminio)cyclohexa-2,5-dien-1-ylidene)methyl)benzene-1,4-disulfonate

9. P-1888

10. P-4125

11. 39n9k8s2a4

12. Mfcd00867653

13. Nsc-734902

14. Ethanaminium, N-(4-((4-(diethylamino)phenyl)(2,5-disulfophenyl)methylene)-2,5-cyclohexadien-1-ylidene)-n-ethyl-, Hydroxide, Inner Salt, Sodium Salt

15. Sulfanblau

16. Isosulfan Blue (usan)

17. Disulphin Blau

18. Patent Blau V

19. Azul Isosulfano

20. Bleu Isosulfan

21. Blu Isosulfan

22. Unii-39n9k8s2a4

23. Hsdb 8071

24. Azul De Isosulfan

25. P 1888

26. P 4125

27. Lymphazurin (tn)

28. Dsstox_cid_31594

29. Dsstox_rid_97478

30. Dsstox_gsid_57805

31. (4-(alpha-(p-(diethylamino)phenyl)-2,5-disulfobenzylidene)-2,5-cyclohexadien-1-ylidene)diethylammonium Hydroxide, Inner Salt, Sodium Salt

32. Isosulfan Blue [vandf]

33. Schembl3324345

34. Chembl1200859

35. Dtxsid8057805

36. Isosulfan Blue [who-dd]

37. Tox21_113733

38. Isosulfan Blue [orange Book]

39. Akos015904521

40. Fd10698

41. Nsc 734902

42. Ncgc00253597-01

43. Sy238240

44. Cas-68238-36-8

45. D04634

46. Sulphan Blue 2,5-disulfophenyl Isomer [mi]

47. (4-(.alpha.-(p-(diethylamino)phenyl)-2,5-disulfobenzylidene)-2,5-cyclohexadien-1-ylidene)diethylammonium Hydroxide, Inner Salt, Sodium Salt

48. Ethanaminium, N-(4-((4-(diethylamino)phenyl)(2,5-disulfophenyl)methylene)-2,5-cyclohexadien-1-ylidene)-n-ethyl-, Inner Salt, Sodium Salt

49. Sodium 2-((4-(diethylamino)phenyl)(4-(diethyliminio)cyclohexa-2,5-dien-1-ylidene)methyl)benzene-1,4-disulphonate

50. Sodium;2-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]benzene-1,4-disulfonate

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₁N₂NaO₆S₂
Molecular Weight	566.7 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	7
Exact Mass	566.15212334 g/mol
Monoisotopic Mass	566.15212334 g/mol
Topological Polar Surface Area	137 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	1040
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Isosulfan blue
PubMed Health	Isosulfan Blue (Injection)
Drug Classes	Diagnostic Agent, Lymphatic Visualization
Drug Label	The chemical name of isosulfan blue injection 1% is N-[4- [[4-(diethylamino)phenyl] (2,5-disulfophenyl) methylene]-2,5-cyclohexadien-1-ylidene]-N-ethylethanaminium hydroxide, inner salt, sodium salt. Its structural formula is:ISOSULFAN BLUEIsosulfan...
Active Ingredient	Isosulfan blue
Dosage Form	Injectable
Route	Injection
Strength	1%
Market Status	Prescription
Company	Mylan Institutional

2 of 2
Drug Name	Isosulfan blue
PubMed Health	Isosulfan Blue (Injection)
Drug Classes	Diagnostic Agent, Lymphatic Visualization
Drug Label	The chemical name of isosulfan blue injection 1% is N-[4- [[4-(diethylamino)phenyl] (2,5-disulfophenyl) methylene]-2,5-cyclohexadien-1-ylidene]-N-ethylethanaminium hydroxide, inner salt, sodium salt. Its structural formula is:ISOSULFAN BLUEIsosulfan...
Active Ingredient	Isosulfan blue
Dosage Form	Injectable
Route	Injection
Strength	1%
Market Status	Prescription
Company	Mylan Institutional

4.2 Therapeutic Uses

Isosulfan blue injection 1% upon subcutaneous administration, delineates 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; and lymph node response to therapeutic modalities. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for ISOSULFAN BLUE injection, solution (August 2010). Available from, as of June 8, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=1878964e-5220-48c8-a872-dcadbc451aff

4.3 Drug Warning

Isosulfan blue injection 1% is contraindicated in those individuals with known hypersensitivity to triphenylmethane or related compounds.

Life-threatening anaphylactic reactions (respiratory distress, shock, angioedema) have occurred after isosulfan blue injection 1% administration. Reactions are more likely to occur in patients with a history of bronchial asthma, allergies, drug reactions or previous reactions to triphenylmethane dyes. Monitor patients closely for at least 60 minutes after administration of isosulfan blue injection 1%. Trained personnel should be available to administer emergency care including resuscitation.

Isosulfan blue injection 1% interferes with measurements of oxygen saturation in peripheral blood by pulse oximetry and can cause falsely low readings. The interference effect is maximal at 30 minutes and minimal generally by four hours after administration. Arterial blood gas analysis may be needed to verify decreased arterial partial pressure of oxygen.

Isosulfan blue injection 1% may also cause falsely elevated readings of methemoglobin by arterial blood gas analyzer. Therefore, co-oximetry may be needed to verify methemoglobin level.

For more Drug Warnings (Complete) data for Isosulfan blue (10 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Coloring Agents

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)

5.2 Absorption, Distribution and Excretion

Following subcutaneous administration, isosulfan blue injection 1% binds to serum proteins and is picked up by the lymphatic vessels. Thus, the lymphatic vessels are delineated by the blue dye.

It is not known whether this drug is excreted in human milk.

Up to 10% of the subcutaneously administered dose of isosulfan blue injection 1% is excreted unchanged in the urine in 24 hours in humans.

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