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Nelarabine

Synopsis, Chemistry

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Also known as: Nelzarabine, 121032-29-9, Arranon, Atriance, 506u78, Gw-506u78

Molecular Formula

C₁₁H₁₅N₅O₅

Molecular Weight

297.27 g/mol

InChI Key

IXOXBSCIXZEQEQ-UHTZMRCNSA-N

FDA UNII

60158CV180

Nelarabine is an arabinonucleoside antimetabolite with antineoplastic activity. Nelarabine is demethoxylated by adenosine deaminase to become biologically active 9-beta-D-arabinosylguanine (ara-G); ara-G incorporates into DNA, thereby inhibiting DNA synthesis and inducing an S phase-dependent apoptosis of tumor cells. (NCI04)

Nelarabine is a Nucleoside Metabolic Inhibitor. The mechanism of action of nelarabine is as a Nucleic Acid Synthesis Inhibitor.

1 2D Structure

Nelarabine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4S,5R)-2-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

2.1.2 InChI

InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1

2.1.3 InChI Key

IXOXBSCIXZEQEQ-UHTZMRCNSA-N

2.1.4 Canonical SMILES

COC1=NC(=NC2=C1N=CN2C3C(C(C(O3)CO)O)O)N

2.1.5 Isomeric SMILES

COC1=NC(=NC2=C1N=CN2[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N

2.2 Other Identifiers

2.2.1 UNII

60158CV180

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-amino-6-methoxypurine Arabinoside

2. 2-amino-9-beta-d-arabinofuranosyl-6-methoxy-9h-purine

3. 506u78

4. Arranon

5. Compound 506u78

6. Gw506u78

2.3.2 Depositor-Supplied Synonyms

1. Nelzarabine

2. 121032-29-9

3. Arranon

4. Atriance

5. 506u78

6. Gw-506u78

7. 506u

8. Gw 506u78

9. Attriance

10. Nsc-686673

11. 2-amino-9-beta-d-arabinofuranosyl-6-methoxy-9h-purine

12. (2r,3s,4s,5r)-2-(2-amino-6-methoxy-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

13. Nelarabine (arranon)

14. Chebi:63612

15. Nsc-755985

16. (2r,3s,4s,5r)-2-(2-amino-6-methoxy-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

17. May

18. 2-amino-6-methoxypurine Arabinoside

19. Nsc-759876

20. Ncgc00181098-01

21. 60158cv180

22. S1213

23. Dsstox_cid_26842

24. Dsstox_rid_81952

25. Dsstox_gsid_46842

26. Nelarabine [usan]

27. Arranong

28. Gw506u78

29. Smr002544682

30. Arranon (tn)

31. Nelzarabine (usan)

32. Cas-121032-29-9

33. Compound 506u78

34. 9-beta-d-arabinofuranosyl-6-methoxy-9h-purin-2-amine

35. Nelarabine [usan:inn:ban]

36. Gw-506u

37. Unii-60158cv180

38. Nelarabine [inn]

39. 9beta-d-arabinofuranosyl-6-methoxy-9h-purin-2-amine

40. Nsc 686673

41. Nelarabine [mi]

42. Nelarabine [jan]

43. Nelarabine [vandf]

44. Nelarabine [mart.]

45. Nelarabine [who-dd]

46. Schembl18820

47. Mls003915614

48. Mls004774135

49. Mls006010906

50. Nelarabine (jan/usan/inn)

51. Nelarabine [ema Epar]

52. Gtpl7090

53. Chembl1201112

54. Dtxsid6046842

55. Nelarabine [orange Book]

56. Bcpp000392

57. Hms3715i16

58. Zinc3823492

59. Tox21_112714

60. Bdbm50247985

61. Mfcd00871078

62. Nsc755985

63. 2-(2-amino-6-methoxy-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

64. Akos015852325

65. Akos015920191

66. Tox21_112714_1

67. Bcp9000318

68. Ccg-267441

69. Cs-1607

70. Db01280

71. Ncgc00274059-01

72. Ncgc00274059-02

73. As-47664

74. Hy-13701

75. N1144

76. Sw218086-2

77. D05134

78. F15095

79. Ab01274773-01

80. Ab01274773_02

81. 032n299

82. A804639

83. A935144

84. Sr-01000931847

85. 9-?-d-arabinofuranosyl-6-methoxy-9h-purin-2-amine

86. Q1216264

87. Sr-01000931847-3

88. 2-amino-6-methoxy-9-b-d-arabinofuranosyl-9 H-purine

89. 2-amino-6-methoxy-9-b-d-arabinofuranosyl-9h-purine

90. 9h-purin-2-amine, 9-b-d-arabinofuranosyl-6-methoxy-

91. Brd-k84466663-001-01-3

92. 2-amino-6-methoxy-9-beta-d-arabinofuranosyl-9h-purine

93. 9-(beta-d-arabinofuranosyl)-6-methoxy-9h-purin-2-amine

94. 9-beta -d-arabinofuranosyl-2-amino-6-methoxy-9h-purine

95. 9-beta-d-arabinofuranosyl-2-amino-6-methoxy-9 H-purine

96. 9h-purin-2-amine, 9beta-d-arabinofuranosyl-6-methyl-

97. 2-amino-6-methoxy-9-(beta-d-arabinofuranosyl)-9h-purine

98. 2-amino-9-.beta.-d-arabinofuranosyl-6-methoxy-9h-purine

99. 9-.beta.-d-arabinofuranosyl-6-methoxy-9h-purin-2-amine

100. 9h-purin-2-amine, 9-.beta.-d-arabinofuranosyl-6-methoxy-

101. (2r,3s,4s,5r)-2-(2-amino-6-methoxy-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol

102. (2r,3s,4s,5r)-2-(2-amino-6-methoxy-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

103. (2r,3s,4s,5r)-2-(2-azanyl-6-methoxy-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

104. (2r,3s,4s,5r)-2-(hydroxymethyl)-5-(2-imino-6-methoxy-3,9-dihydro-2h-purin-9-yl)oxolane-3,4-diol

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₅N₅O₅
Molecular Weight	297.27 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Exact Mass	297.10731860 g/mol
Monoisotopic Mass	297.10731860 g/mol
Topological Polar Surface Area	149 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	377
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 Information

1 of 2
Drug Name	Arranon
PubMed Health	Nelarabine (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	ARRANON (nelarabine) is a pro-drug of the cytotoxic deoxyguanosine analogue, 9--D-arabinofuranosylguanine (ara-G). The chemical name for nelarabine is 2-amino-9--D-arabinofuranosyl-6-methoxy-9H-purine. It has the molecular formula C11H15N5O5 and...
Active Ingredient	Nelarabine
Dosage Form	Injectable
Route	Iv (infusion)
Strength	250mg/50ml (5mg/ml)
Market Status	Prescription
Company	Smithkline Beecham

2 of 2
Drug Name	Arranon
PubMed Health	Nelarabine (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	ARRANON (nelarabine) is a pro-drug of the cytotoxic deoxyguanosine analogue, 9--D-arabinofuranosylguanine (ara-G). The chemical name for nelarabine is 2-amino-9--D-arabinofuranosyl-6-methoxy-9H-purine. It has the molecular formula C11H15N5O5 and...
Active Ingredient	Nelarabine
Dosage Form	Injectable
Route	Iv (infusion)
Strength	250mg/50ml (5mg/ml)
Market Status	Prescription
Company	Smithkline Beecham

4.2 Drug Indication

For the treatment of pediatric and adult patients with acute T-cell lymphoblastic leukemia and T-cell lymphoblastic lymphoma whose disease has not responded to or has relapsed following treatment with at least two chemotherapy regimens.

FDA Label

Nelarabine is indicated for the treatment of patients with T-cell acute lymphoblastic leukaemia (T-ALL) and T-cell lymphoblastic lymphoma (T-LBL) whose disease has not responded to or has relapsed following treatment with at least two chemotherapy regimens.

Due to the small patient populations in these disease settings, the information to support these indications is based on limited data.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nelarabine is a prodrug of the cytotoxic deoxyguanosine analogue 9-ß-D-arabinofuranosylguanine (ara-G). Nelarabine is demethylated by adenosine deaminase (ADA) to ara-G. Ara-G is then transported into cells, where it undergoes three phosphorylation steps, resulting in the formation of ara-G triphosphate (ara-GTP). In the first phosphorylation step, ara-G is converted to ara-G monophosphate (ara-GMP). Ara-GMP is then monophosphorylated by deoxyguanosine kinase and deoxycytidine kinase to ara-G diphosphate, and then subsequently to the active ara-G triphosphate (ara-GTP). Ara-GTP is the one that exerts the pharmacological effect. Pre-clinical studies have demonstrated that targeted T-cells possess marked sensitivity to the agent.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

NELARABINE

5.2.2 FDA UNII

60158CV180

5.2.3 Pharmacological Classes

Nucleoside Metabolic Inhibitor [EPC]; Nucleic Acid Synthesis Inhibitors [MoA]

5.3 ATC Code

L01BB07

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01B - Antimetabolites

L01BB - Purine analogues

L01BB07 - Nelarabine

5.4 Absorption, Distribution and Excretion

Route of Elimination

Excretion: Nelarabine and ara-G are partially eliminated by the kidneys.

Clearance

197 +/- 189 L/h/m2 [Adult patients with refractory leukemia or lymphoma receiving doses of 199 to 2,900 mg/m2]

259 +/- 409 L/h/m2 [Pediatric patients with refractory leukemia or lymphoma receiving doses of 104 to 2,900 mg/m2]

5.5 Metabolism/Metabolites

The principal route of metabolism for nelarabine is O-demethylation by adenosine deaminase to form ara-G, which undergoes hydrolysis to form guanine. In addition, some nelarabine is hydrolyzed to form methylguanine, which is O-demethylated to form guanine. Guanine is N-deaminated to form xanthine, which is further oxidized to yield uric acid. Ring opening of uric acid followed by further oxidation results in the formation of allantoin.

5.6 Biological Half-Life

Nelarabine and ara-G are rapidly eliminated from plasma with a half-life of approximately 30 minutes and 3 hours.

5.7 Mechanism of Action

Once nelarabine is metabolized into ara-GTP, the metabolite accumulates in leukemic blasts and incorporates into DNA to exert its S phase-specific cytotoxic effects, leading to the induction of fragmentation and apoptosis. Ara-GTP competes with endogenous deoxyGTP (dGTP) for incorporation into DNA. Once ara-GTP is incorporated at the 3' end of DNA, further DNA elongation is inhibited, which signals apoptosis and leads to cellular destruction. Additional cytotoxic activities may exist, but these are not fully understood.