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R 115866

R 115866

Synopsis, Chemistry

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Also known as: 201410-53-9, Rambazole, R115866, R-115866, N-(4-(2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl)phenyl)benzo[d]thiazol-2-amine, Talarozole (r enantiomer)

Molecular Formula

C₂₁H₂₃N₅S

Molecular Weight

377.5 g/mol

InChI Key

SNFYYXUGUBUECJ-UHFFFAOYSA-N

FDA UNII

XKD9N5CJ6W

Talarozole has been investigated for the treatment of Psoriasis and Cutaneous Inflammation.

1 2D Structure

R 115866

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[4-[2-ethyl-1-(1,2,4-triazol-1-yl)butyl]phenyl]-1,3-benzothiazol-2-amine

2.1.2 InChI

InChI=1S/C21H23N5S/c1-3-15(4-2)20(26-14-22-13-23-26)16-9-11-17(12-10-16)24-21-25-18-7-5-6-8-19(18)27-21/h5-15,20H,3-4H2,1-2H3,(H,24,25)

2.1.3 InChI Key

SNFYYXUGUBUECJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCC(CC)C(C1=CC=C(C=C1)NC2=NC3=CC=CC=C3S2)N4C=NC=N4

2.2 Other Identifiers

2.2.1 UNII

XKD9N5CJ6W

2.3 Synonyms

2.3.1 MeSH Synonyms

1. N-(4-(2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl)phenyl)-2-benzothiazolamine

2. R 115866

3. R-115866

4. R115866

5. Rambazole

2.3.2 Depositor-Supplied Synonyms

1. 201410-53-9

2. Rambazole

3. R115866

4. R-115866

5. N-(4-(2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl)phenyl)benzo[d]thiazol-2-amine

6. Talarozole (r Enantiomer)

7. Xkd9n5cj6w

8. 201410-66-4

9. N-[4-[2-ethyl-1-(1,2,4-triazol-1-yl)butyl]phenyl]-1,3-benzothiazol-2-amine

10. Chembl459505

11. (+)-n-[4-[2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl]phenyl]-2-benzothiazolamine

12. 2-benzothiazolamine, N-[4-[2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl]phenyl]-

13. N-(4-((1rs)-2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl)phenyl)benzothiazol-2-amine

14. Rambazole (tn)

15. Talarozole [usan]

16. Talarozole (usan/inn)

17. Talarozole [usan:inn]

18. Unii-xkd9n5cj6w

19. 2-benzothiazolamine, N-(4-(2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl)phenyl)-

20. N-{4-[2-ethyl-1-(1,2,4-triazol-1-yl)butyl]phenyl}-1,3-benzothiazol-2-amine

21. R 115866

22. N-(4-(2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl)phenyl)-2-benzothiazolamine

23. Talarozole [inn]

24. Talarozole [who-dd]

25. Schembl721201

26. Schembl21020998

27. Gtpl11381

28. Dtxsid70942185

29. Chebi:102167

30. Bcp21218

31. Bcp28256

32. Bia41053

33. Bdbm50253810

34. Akos005067289

35. Cs-1343

36. Db13083

37. Ncgc00378894-01

38. Ncgc00378894-02

39. Hy-14531

40. Ws-02133

41. D09385

42. D85497

43. A926099

44. Q15410180

45. Rambazole; R115866; R-115866; R 115866

46. Talarozole R Enantiomer;r115866;r 115866;r-115866

47. R115866;r-115866;r 115866

48. (+/-)-n-[4-[2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl]phenyl]-2-benzothiazol-amine

49. (+/-)-n-[4-[2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl]phenyl]-2-benzothiazolamine

50. N-{4-[2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl]phenyl}-1,3-benzothi Azol-2-amine

51. N-{4-[2-ethyl-1-(1h-1,2,4-triazol-1-yl)butyl]phenyl}-1,3-benzothiazol-2-amine

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₃N₅S
Molecular Weight	377.5 g/mol
XLogP3	6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	377.16741693 g/mol
Monoisotopic Mass	377.16741693 g/mol
Topological Polar Surface Area	83.9 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	452
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Cytochrome P-450 Enzyme Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 ENZYMES. (See all compounds classified as Cytochrome P-450 Enzyme Inhibitors.)

4.2 Mechanism of Action

Rambazole is a new generation all-trans retinoic acid metabolism blocking agent, highly specific against the retinoic acid 4-hydroxylase. The drug alleviates hyperproliferation and normalizes differentiation of the epidermis in animal models of psoriasis. All-trans-retinoic acid (RA) regulates epithelial differentiation and growth through activation of specific nuclear RA receptors (RARs). Rambazole acts by inhibiting the metabolic breakdown of the retinoid, increasing the biological efficacy of RA.