Tezampanel

Synopsis, Chemistry

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Also known as: 154652-83-2, Tezampanel (anhydrous), Ly-293558, Ly293558, 150131-78-5, Tezampanel [inn]

Molecular Formula

C₁₃H₂₁N₅O₂

Molecular Weight

279.34 g/mol

InChI Key

ZXFRFPSZAKNPQQ-YTWAJWBKSA-N

FDA UNII

GA36S2O9C2

Tezampanel is an AMPA receptor antagonist.

1 2D Structure

Tezampanel

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,4aR,6R,8aR)-6-[2-(2H-tetrazol-5-yl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid

2.1.2 InChI

InChI=1S/C13H21N5O2/c19-13(20)11-6-10-5-8(1-3-9(10)7-14-11)2-4-12-15-17-18-16-12/h8-11,14H,1-7H2,(H,19,20)(H,15,16,17,18)/t8-,9+,10-,11+/m1/s1

2.1.3 InChI Key

ZXFRFPSZAKNPQQ-YTWAJWBKSA-N

2.1.4 Canonical SMILES

C1CC2CNC(CC2CC1CCC3=NNN=N3)C(=O)O

2.1.5 Isomeric SMILES

C1C[C@H]2CN[C@@H](C[C@H]2C[C@H]1CCC3=NNN=N3)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

GA36S2O9C2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (3s,4ar,6r,8ar)-6-(2-(1(2)h-tetrazole-5yl)ethyl)decahydroisoquinoline-3carboxylic Acid

2. 6-(2-(1h-tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic Acid

3. Ly 215490

4. Ly 293558

5. Ly 326325

6. Ly-215490

7. Ly-293558

8. Ly-326325

9. Ly293558

10. Ngx424

2.3.2 Depositor-Supplied Synonyms

1. 154652-83-2

2. Tezampanel (anhydrous)

3. Ly-293558

4. Ly293558

5. 150131-78-5

6. Tezampanel [inn]

7. Tezampanel, Anhydrous

8. Ly 293558

9. Ngx-424

10. Ly-293,558

11. 6-(2-(1h-tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic Acid

12. Chembl14935

13. Ga36s2o9c2

14. (3s,4ar,6r,8ar)-6-[2-(2h-tetrazol-5-yl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic Acid

15. 154652-83-2 (anhydrous)

16. (3s,4ar,6r,8ar)-6-(2-(1h-tetrazol-5-yl)ethyl)decahydroisoquinoline-3-carboxylic Acid

17. Ted-isoquinoline-3-cooh

18. Unii-ga36s2o9c2

19. Ly215490

20. Decahydro-6-(2-(1h-tetrazol-5-yl)ethyl)-3-isoquinolinecarboxylic Acid

21. Tezampanel Anhydrous

22. Gtpl4245

23. Schembl1649338

24. Bdbm86751

25. Zinc5134714

26. Bdbm50494341

27. Cs-0821

28. Db06354

29. 3-isoquinolinecarboxylic Acid, Decahydro-6-(2-(1h-tetrazol-5-yl)ethyl)-, (3s,4ar,6r,8ar)-

30. Ncgc00378884-01

31. 3-isoquinolinecarboxylic Acid, Decahydro-6-(2-(1h-tetrazol-5-yl)ethyl)-, (3s-(3alpha,4aalpha,6beta,8aalpha))-

32. Hy-75704

33. Q7708612

34. (3s,4ar,6r,8ar)-6-[2-(1h-1,2,3,4-tetrazol-5-yl)ethyl]-decahydroisoquinoline-3-carboxylic Acid

35. (3s,4ar,6r,8ar)-6-[2-(2h-1,2,3,4-tetrazol-5-yl)ethyl]-decahydroisoquinoline-3-carboxylic Acid

36. (3s,4as,6r,8as)-6-(2-(1h-tetrazol-5-yl)ethyl)decahydroisoquinoline-3-carboxylic Acid

37. 3-isoquinolinecarboxylic Acid, Decahydro-6-(2-(1h-tetrazol-5-yl)ethyl)-, (3s,4as,6r,8as)-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₂₁N₅O₂
Molecular Weight	279.34 g/mol
XLogP3	-0.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	279.16952493 g/mol
Monoisotopic Mass	279.16952493 g/mol
Topological Polar Surface Area	104 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	354
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in pain (acute or chronic) and migraine and cluster headaches.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

NGX426 is a prodrug of tezampanel (NGX424). Tezampanel is an antagonist that binds to glutamate kainate (Glu K5) receptors, inhibiting excitatory synapases the brain.