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Clofarabine

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Chemistry

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Also known as: 123318-82-1, Clolar, Evoltra, Clofarex, Cafda, Cl-f-ara-a

Molecular Formula

C₁₀H₁₁ClFN₅O₃

Molecular Weight

303.68 g/mol

InChI Key

WDDPHFBMKLOVOX-AYQXTPAHSA-N

FDA UNII

762RDY0Y2H

An adenine arabinonucleoside derivative that acts as an antineoplastic antimetabolite. It is used in the treatment of ACUTE LYMPHOID LEUKEMIA in pediatric patients who have relapsed.

Clofarabine is a Nucleoside Metabolic Inhibitor. The mechanism of action of clofarabine is as a Nucleic Acid Synthesis Inhibitor.

1 2D Structure

Clofarabine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R,4S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

2.1.2 InChI

InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4+,6-,9-/m1/s1

2.1.3 InChI Key

WDDPHFBMKLOVOX-AYQXTPAHSA-N

2.1.4 Canonical SMILES

C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)CO)O)F)Cl)N

2.1.5 Isomeric SMILES

C1=NC2=C(N=C(N=C2N1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)F)Cl)N

2.2 Other Identifiers

2.2.1 UNII

762RDY0Y2H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2 Chloro 2' Arabino Fluoro 2' Deoxyadenosine

2. 2 Chloro 2' Fluoroarabino 2' Deoxyadenosine

3. 2-chloro-2'-arabino-fluoro-2'-deoxyadenosine

4. 2-chloro-2'-fluoroarabino-2'-deoxyadenosine

5. 2-chloro-9-(2-deoxy-2-fluoro-beta-d-arbinofuranosyl)adenine

6. 2-chloro-9-(2-deoxy-2-fluoroarabinofuranosyl)adenine

7. 9h-purin-6-amine, 2-chloro-9-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-

8. Cl-f-ara-a

9. Clofarex

10. Clolar

11. Evoltra

2.3.2 Depositor-Supplied Synonyms

1. 123318-82-1

2. Clolar

3. Evoltra

4. Clofarex

5. Cafda

6. Cl-f-ara-a

7. C1-f-ara-a

8. (2r,3r,4s,5r)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

9. 2-chloro-9-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-9h-purin-6-amine

10. 2-chloro-9-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)adenine

11. Chebi:681569

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

13. 762rdy0y2h

14. 9h-purin-6-amine, 2-chloro-9-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-

15. (2r,3r,4s,5r)-5-(6-amino-2-chloro-9h-purin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

16. Nsc-759857

17. Clofarabine [usan]

18. 2-chloro-9-(2'-deoxy-2'-fluoro-beta-d-arabinofuranosyl)adenine

19. Dsstox_cid_26437

20. Dsstox_rid_81613

21. Dsstox_gsid_46437

22. Cfb

23. Clofarabina

24. Clofarabinum

25. Cl-f-araa

26. Mfcd00871077

27. 2-chloro-9-(2-deoxy-2-fluoro-b -d-arabinofuranosyl)-9h-purin-6-amine

28. (2r,3r,4s,5r)-5-(6-amino-2-chloro-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol

29. Clolar (tn)

30. Cas-123318-82-1

31. 2-cl-2'-f-araa

32. Unii-762rdy0y2h

33. Clofarabine [usan:inn:ban]

34. Ncgc00164553-01

35. Clofarabine [mi]

36. Clofarabine [inn]

37. Clofarabine [jan]

38. 2-chloro-9-(2-deoxy-2-fluoro-b-d-arabinofuranosyl)-9h-purin-6-amine

39. 2-chloro-2'-arabino-fluoro-2'-deoxyadenosine

40. Clofarabine [vandf]

41. Clofarabine,clolar, Evoltra

42. Schembl9040

43. Chembl1750

44. Clofarabine [mart.]

45. Clofarabine [who-dd]

46. Mls003915615

47. Clofarabine (jan/usan/inn)

48. Clofarabine [ema Epar]

49. Gtpl6802

50. Dtxsid5046437

51. Clofarabine, >=98% (hplc)

52. Clofarabine [orange Book]

53. Hms2090a07

54. Hms3413j15

55. Hms3677j15

56. Act05522

57. Bcp23422

58. Hy-a0005

59. Zinc3798247

60. Tox21_112182

61. Ac-274

62. Bdbm50247921

63. S1218

64. Akos005063562

65. Akos015919355

66. Tox21_112182_1

67. Bcp9000540

68. Ccg-264865

69. Cs-0373

70. Db00631

71. Nsc 759857

72. Sar-393590

73. Ncgc00164553-02

74. Ncgc00164553-05

75. As-12958

76. Smr002530055

77. Bcp0726000280

78. Sw218080-2

79. D03546

80. Ab00430247-03

81. Ab00430247-04

82. Ab00430247_06

83. 318c821

84. Sr-01000930565

85. Q5134875

86. Sr-01000930565-3

87. Z1557400138

88. 2-chloro-9-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-adenine

89. 2-chloro-9-(2-deoxy-2-fluoro-?-d-arabinofuranosyl)-9h-purin-6-amine

90. 9h-purine-6-amine,2-chloro-9-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-

91. 2-chloro-9-(2-deoxy-2-fluoro-.beta.-d-arabinofuranosyl)-9h-purin-6-amine

92. 9h-purin-6-amine, 2-chloro-9-(2-deoxy-2-fluoro-.beta.-d-arabinofuranosyl)

93. (2r,3r,4s,5r)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol 2-chloro-2''-arabino-fluoro-2''-deoxyadenosine

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₁ClFN₅O₃
Molecular Weight	303.68 g/mol
XLogP3	0.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	2
Exact Mass	303.0534451 g/mol
Monoisotopic Mass	303.0534451 g/mol
Topological Polar Surface Area	119 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	370
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	Clolar
PubMed Health	Clofarabine (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	Clolar (clofarabine) Injection contains clofarabine, a purine nucleoside metabolic inhibitor. Clolar (1 mg/mL) is supplied in a 20 mL, single-use vial. The 20 mL vial contains 20 mg clofarabine formulated in 20 mL unbuffered normal saline (comprised...
Active Ingredient	Clofarabine
Dosage Form	Injectable
Route	Iv (infusion)
Strength	20mg/20ml (1mg/ml)
Market Status	Prescription
Company	Genzyme

2 of 2
Drug Name	Clolar
PubMed Health	Clofarabine (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	Clolar (clofarabine) Injection contains clofarabine, a purine nucleoside metabolic inhibitor. Clolar (1 mg/mL) is supplied in a 20 mL, single-use vial. The 20 mL vial contains 20 mg clofarabine formulated in 20 mL unbuffered normal saline (comprised...
Active Ingredient	Clofarabine
Dosage Form	Injectable
Route	Iv (infusion)
Strength	20mg/20ml (1mg/ml)
Market Status	Prescription
Company	Genzyme

4.2 Drug Indication

For the treatment of pediatric patients 1 to 21 years old with relapsed or refractory acute lymphocytic (lymphoblastic) leukemia after at least two prior regimens. It is designated as an orphan drug by the FDA for this use.

FDA Label

Treatment of acute lymphoblastic leukaemia (ALL) in paediatric patients who have relapsed or are refractory after receiving at least two prior regimens and where there is no other treatment option anticipated to result in a durable response. Safety and efficacy have been assessed in studies of patients 21 years old at initial diagnosis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Clofarabine is a purine nucleoside antimetabolite that differs from other puring nucleoside analogs by the presence of a chlorine in the purine ring and a flourine in the ribose moiety. Clofarabine seems to interfere with the growth of cancer cells, which are eventually destroyed. Since the growth of normal body cells may also be affected by clofarabine, other effects also occur. Clofarabine prevents cells from making DNA and RNA by interfering with the synthesis of nucleic acids, thus stopping the growth of cancer cells.

5.2 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CLOFARABINE

5.3.2 FDA UNII

762RDY0Y2H

5.3.3 Pharmacological Classes

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

5.4 ATC Code

L01BB06

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01B - Antimetabolites

L01BB - Purine analogues

L01BB06 - Clofarabine

5.5 Absorption, Distribution and Excretion

Route of Elimination

Based on 24-hour urine collections in the pediatric studies, 49 - 60% of the dose is excreted in the urine unchanged.

Volume of Distribution

172 L/m2

Clearance

28.8 L/h/m2 [Pediatric patients (2 - 19 years old) with relapsed or refractory acute lymphoblastic leukemia (ALL) or acute myelogenous leukemia (AML) receiving 52 mg/m2 dose]

5.6 Metabolism/Metabolites

Clofarabine is sequentially metabolized intracellularly to the 5’-monophosphate metabolite by deoxycytidine kinase and mono- and di-phosphokinases to the active 5’-triphosphate metabolite. Clofarabine has high affinity for the activating phosphorylating enzyme, deoxycytidine kinase, equal to or greater than that of the natural substrate, deoxycytidine.

5.7 Biological Half-Life

The terminal half-life is estimated to be 5.2 hours.

5.8 Mechanism of Action

Clofarabine is metabolized intracellularly to the active 5'-monophosphate metabolite by deoxycytidine kinase and 5'-triphosphate metabolite by mono- and di-phospho-kinases. This metabolite inhibits DNA synthesis through an inhibitory action on ribonucleotide reductase, and by terminating DNA chain elongation and inhibiting repair through competitive inhibition of DNA polymerases. This leads to the depletion of the intracellular deoxynucleotide triphosphate pool and the self-potentiation of clofarabine triphosphate incorporation into DNA, thereby intensifying the effectiveness of DNA synthesis inhibition. The affinity of clofarabine triphosphate for these enzymes is similar to or greater than that of deoxyadenosine triphosphate. In preclinical models, clofarabine has demonstrated the ability to inhibit DNA repair by incorporation into the DNA chain during the repair process. Clofarabine 5'-triphosphate also disrupts the integrity of mitochondrial membrane, leading to the release of the pro-apoptotic mitochondrial proteins, cytochrome C and apoptosis-inducing factor, leading to programmed cell death.

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