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Talaporfin

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Chemistry

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Also known as: Laserphyrin, 220201-34-3, Taporfin sodium, Mono-l-aspartyl chlorin e6, Npe6, Ls-11

Molecular Formula

C₃₈H₃₇N₅Na₄O₉

Molecular Weight

799.7 g/mol

InChI Key

JLWROAPZCOJYGT-OBJGRMLXSA-J

FDA UNII

L63605PZ70

Talaporfin Sodium is an agent consisting of chlorin e6, derived from chlorophyll, and L-aspartic acid with photosensitizing activity. After intratumoral activation by light emitting diodes, taporfin sodium forms an extended high energy conformational state that generates singlet oxygen, resulting in free radical-mediated cell death. (NCI04)

1 2D Structure

Talaporfin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

tetrasodium;(2S)-2-[[2-[(2S,3S)-7-carboxylato-3-(2-carboxylatoethyl)-17-ethenyl-12-ethyl-2,8,13,18-tetramethyl-2,3,23,24-tetrahydroporphyrin-5-yl]acetyl]amino]butanedioate

2.1.2 InChI

InChI=1S/C38H41N5O9.4Na/c1-7-20-16(3)24-12-26-18(5)22(9-10-32(45)46)35(42-26)23(11-31(44)41-30(37(49)50)15-33(47)48)36-34(38(51)52)19(6)27(43-36)14-29-21(8-2)17(4)25(40-29)13-28(20)39-24;;;;/h7,12-14,18,22,30,39-40H,1,8-11,15H2,2-6H3,(H,41,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52);;;;/q;4*+1/p-4/t18-,22-,30-;;;;/m0..../s1

2.1.3 InChI Key

JLWROAPZCOJYGT-OBJGRMLXSA-J

2.1.4 Canonical SMILES

CCC1=C(C2=CC3=C(C(=C(N3)C=C4C(C(C(=N4)C(=C5C(=C(C(=N5)C=C1N2)C)C(=O)[O-])CC(=O)NC(CC(=O)[O-])C(=O)[O-])CCC(=O)[O-])C)C)C=C)C.[Na+].[Na+].[Na+].[Na+]

2.1.5 Isomeric SMILES

CCC1=C(C2=CC3=C(C(=C(N3)C=C4[C@H]([C@@H](C(=N4)C(=C5C(=C(C(=N5)C=C1N2)C)C(=O)[O-])CC(=O)N[C@@H](CC(=O)[O-])C(=O)[O-])CCC(=O)[O-])C)C)C=C)C.[Na+].[Na+].[Na+].[Na+]

2.2 Other Identifiers

2.2.1 UNII

L63605PZ70

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Laserphyrin

2. Mono-l-aspartyl Chlorin E6

3. Monoaspartyl Chlorin E6

4. N-aspartyl Chlorin E6

5. N-aspartylchlorin E6

6. Npe6

7. Talaporfin

2.3.2 Depositor-Supplied Synonyms

1. Laserphyrin

2. 220201-34-3

3. Taporfin Sodium

4. Mono-l-aspartyl Chlorin E6

5. Npe6

6. Ls-11

7. Talaporfin Sodium [usan]

8. Talaporfin Tetrasodium Salt

9. Me-2906

10. L63605pz70

11. Me 2906

12. Tetrasodium (2s)-2-((((7s,8s)-3-carboxylato-7-(2-carboxylatoethyl)-13-ethenyl-18-ethyl-2,8,12,17-tetramethyl-7,8-dihydroporphyrin-5-yl)acetyl)amino)butanedioate

13. Tetrasodium;(2s)-2-[[2-[(2s,3s)-7-carboxylato-3-(2-carboxylatoethyl)-17-ethenyl-12-ethyl-2,8,13,18-tetramethyl-2,3,23,24-tetrahydroporphyrin-5-yl]acetyl]amino]butanedioate

14. Aptocine

15. L-aspartic Acid, N-(((7s,8s)-3-carboxy-7-(2-carboxyethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-21h,23h-porphin-5-yl)acetyl)-, Tetrasodium Salt

16. Talaporfinsodium

17. Laserphyrin (tn)

18. Ls 11 (photosensitizer)

19. Ls11

20. Talaporfin Sodium (jan/usan)

21. Talaporfin Sodium [jan]

22. Chembl2107806

23. Unii-l63605pz70

24. Dtxsid70420519

25. Talaporfin Sodium [mart.]

26. Talaporfin Sodium [who-dd]

27. Me2906

28. At34139

29. Talaporfin Tetrasodium Salt [mi]

30. D01985

31. Q27282754

32. 220680-62-6

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₃₈H₃₇N₅Na₄O₉
Molecular Weight	799.7 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	8
Exact Mass	799.21820490 g/mol
Monoisotopic Mass	799.21820490 g/mol
Topological Polar Surface Area	247 Å²
Heavy Atom Count	56
Formal Charge	0
Complexity	1340
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	5

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in macular degeneration.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Photosensitizing Agents

Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)

5.2 Mechanism of Action

Light Sciences Oncology (LSO) aims to en-light-en cancer patients. Light Sciences has developed Light Infusion Therapy (Litx) which is a novel treatment for solid tumors. The therapy involves inserting a flexible light-emitting diode (LED) into a tumor, followed by an injection of LS11 (talaporfin sodium), a light-activated drug. Once the LED activates LS11, molecular oxygen is converted into singlet oxygen, killing tissue within the LED's scope and shutting down the blood supply to the area. The treatment is designed for use on three types of cancers: hepatoma (liver cancer), metastatic colorectal cancer, and Gioma (brain tumor).

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