Lestaurtinib

Synopsis, Chemistry

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Also known as: 111358-88-4, Cep-701, Kt-5555, Spm-924, Kt5555, Cep 701

Molecular Formula

C₂₆H₂₁N₃O₄

Molecular Weight

439.5 g/mol

InChI Key

UIARLYUEJFELEN-LROUJFHJSA-N

FDA UNII

DO989GC5D1

Lestaurtinib is an orally bioavailable indolocarbazole derivative with antineoplastic properties. Lestaurtinib inhibits autophosphorylation of FMS-like tyrosine kinase 3 (FLT3), resulting in inhibition of FLT3 activity and induction of apoptosis in tumor cells that overexpress FLT3. (NCI05)

1 2D Structure

Lestaurtinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(15S,16S,18R)-16-hydroxy-16-(hydroxymethyl)-15-methyl-28-oxa-4,14,19-triazaoctacyclo[12.11.2.115,18.02,6.07,27.08,13.019,26.020,25]octacosa-1,6,8,10,12,20,22,24,26-nonaen-3-one

2.1.2 InChI

InChI=1S/C26H21N3O4/c1-25-26(32,12-30)10-18(33-25)28-16-8-4-2-6-13(16)20-21-15(11-27-24(21)31)19-14-7-3-5-9-17(14)29(25)23(19)22(20)28/h2-9,18,30,32H,10-12H2,1H3,(H,27,31)/t18-,25+,26+/m1/s1

2.1.3 InChI Key

UIARLYUEJFELEN-LROUJFHJSA-N

2.1.4 Canonical SMILES

CC12C(CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)(CO)O

2.1.5 Isomeric SMILES

C[C@@]12[C@](C[C@@H](O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)(CO)O

2.2 Other Identifiers

2.2.1 UNII

DO989GC5D1

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cep 701

2. Cep-701

3. Cep701

4. Kt-555

5. Kt-5555

6. Kt5555

7. Sp-924

8. Sp924

9. Spm-924

2.3.2 Depositor-Supplied Synonyms

1. 111358-88-4

2. Cep-701

3. Kt-5555

4. Spm-924

5. Kt5555

6. Cep 701

7. Sp924

8. Sp 924

9. Sp-924

10. Kt 5555

11. Kt-555

12. Cep701

13. C26h21n3o4

14. Chembl603469

15. Do989gc5d1

16. A-154475.0

17. (9s,10s,12r)-2,3,9,10,11,12-hexahydro-10-hydroxy-10-(hydroxymethyl)-9-methyl-9,12-epoxy-1h-diindolo[1,2,3-fg:3',2',1'-kl]pyrrolo[3,4-i][1,6]benzodiazocin-1-one

18. Ncgc00168772-01

19. (5s,6s,8r)-6-hydroxy-6-(hydroxymethyl)-5-methyl-7,8,14,15-tetrahydro-5h-16-oxa-4b,8a,14-triaza-5,8-methanodibenzo[b,h]cycloocta[jkl]cyclopenta[e]-as-indacen-13(6h)-one

20. A-154475

21. Lestaurtinib [usan]

22. Lestaurtinib (usan/inn)

23. Lestaurtinib [usan:inn]

24. Unii-do989gc5d1

25. 4otg

26. A 1544750

27. Cep-701 Hydrate

28. Lestaurtinib; Cep701

29. Lestaurtinib [inn]

30. Dsstox_cid_26778

31. Dsstox_rid_81897

32. Dsstox_gsid_46778

33. Lestaurtinib [mart.]

34. Lestaurtinib [who-dd]

35. A 154475.0

36. Gtpl5672

37. Schembl1649693

38. Dtxsid5046778

39. Chebi:91471

40. 9,12-epoxy-1h-diindolo(1,2,3-fg:3',2',1'-kl)pyrrolo(3,4-i)(1,6)benzodiazocin-1-one, 2,3,9,10,11,12-hexahydro-10-hydroxy-10-(hydroxymethyl)-9-methyl-, (9s,10s,12r)-

41. 9,12-epoxy-1h-diindolo[1,2,3-fg:3',2',1'-kl]pyrrolo[3,4-i][1,6]benzodiazocin-1-one, 2,3,9,10,11,12-hexahydro-10-hydroxy-10-(hydroxymethyl)-9-methyl-, (9s,10s,12r)-

42. Bcp06977

43. Zinc3781738

44. Tox21_112633

45. Bdbm50308060

46. Mfcd09840836

47. Nsc772196

48. Nsc800782

49. Akos024457603

50. Ac-5243

51. Am81228

52. Db06469

53. Nsc-772196

54. Nsc-800782

55. Ncgc00168772-02

56. Ncgc00168772-03

57. Ncgc00168772-04

58. Hy-50867

59. Cas-111358-88-4

60. Cs-0004336

61. D04696

62. J-002567

63. Q6531771

64. Brd-k23192422-001-01-1

65. (15s,16s,18r)-16-hydroxy-16-(hydroxymethyl)-15-methyl-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1^{15,18}.0^{2,6}.0^{7,27}.0^{8,13}.0^{19,26}.0^{20,25}]octacosa-1(26),2(6),7(27),8,10,12,20,22,24-nonaen-3-one

66. (15s,16s,18r)-16-hydroxy-16-(hydroxymethyl)-15-methyl-28-oxa-4,14,19-triazaoctacyclo[12.11.2.115,18.02,6.07,27.08,13.019,26.020,25]octacosa-1,6,8(13),9,11,20(25),21,23,26-nonaen-3-one

67. (15s,16s,18r)-16-hydroxy-16-(hydroxymethyl)-15-methyl-28-oxa-4,14,19-triazaoctacyclo[12.11.2.115,18.02,6.07,27.08,13.019,26.020,25]octacosa-1,6,8,10,12,20,22,24,26-nonaen-3-one

68. (9s,10s,12r)-10-hydroxy-10-(hydroxymethyl)-9-methyl-2,3,9,10,11,12-hexahydro-9,12-epoxy-1h-diindolo(1,2,3-fg:3',2',1'-kl)pyrrolo(3,4-i)(1,6)benzodiazocin-1-one

69. (9s,10s,12r)-2,3,9,10,11,12-hexahyd Ro-10-hydroxy-10-(hydroxymethyl)-9-methyl-9,12-epo Xy-1h-diindolo[1,2,3-fg:3',2',1'-kl]pyrrolo[3,4-i][1, 6]benzodiazocin-1-one

70. 16-hydroxy-16-(hydroxymethyl)-15-methyl-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1^{15,18}.0^{2,6}.0^{7,27}.0^{8,13}.0^{19,26}.0^{20,25}]octacosa-1(26),2(6),7(27),8(13),9,11,20(25),21,23-nonaen-3-one

71. 9,12-epoxy-1h-diindolo(1,2,3-fg:3',2',1'-kl)pyrrolo(3,4-i)(1,6)benzodiazocin-1-one, 2,3,9,10,11,12-hexahydro-10-hydroxy-10-(hydroxymethyl)-9-methyl-, (9s-(9alpha,10beta,12alpha))-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₁N₃O₄
Molecular Weight	439.5 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	439.15320616 g/mol
Monoisotopic Mass	439.15320616 g/mol
Topological Polar Surface Area	88.6 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	886
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	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in pancreatic cancer, prostate cancer, and leukemia (myeloid).

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

Lestaurtinib inhibits autophosphorylation of FMS-like tyrosine kinase 3 (FLT3), resulting in inhibition of FLT3 activity and induction of apoptosis in tumor cells that overexpress FLT3.