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Troxacitabine

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Also known as: Troxacitabine, 145918-75-8, Bch-4556, (-)-oddc, 4-amino-1-((2s,4s)-2-(hydroxymethyl)-1,3-dioxolan-4-yl)pyrimidin-2(1h)-one, 60kqz0388y

Molecular Formula

C₈H₁₁N₃O₄

Molecular Weight

213.19 g/mol

InChI Key

RXRGZNYSEHTMHC-BQBZGAKWSA-N

FDA UNII

60KQZ0388Y

Troxacitabine is a dioxolane derivative and a novel L-configuration deoxycytidine analogue with potent antineoplastic activity. When incorporated into growing chain during DNA replication, troxacitabine stops DNA polymerization due to its unnatural L-configuration, in contrast to the normal nucleotides with D-configuration. As a result, this agent terminates DNA synthesis upon incorporated into DNA molecules, and consequently interrupts tumor cell proliferation.

1 2D Structure

Troxacitabine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-1-[(2S,4S)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]pyrimidin-2-one

2.1.2 InChI

InChI=1S/C8H11N3O4/c9-5-1-2-11(8(13)10-5)6-4-14-7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m0/s1

2.1.3 InChI Key

RXRGZNYSEHTMHC-BQBZGAKWSA-N

2.1.4 Canonical SMILES

C1C(OC(O1)CO)N2C=CC(=NC2=O)N

2.1.5 Isomeric SMILES

C1[C@H](O[C@H](O1)CO)N2C=CC(=NC2=O)N

2.2 Other Identifiers

2.2.1 UNII

60KQZ0388Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2s-cis)-4-amino-1-(2-(hydroxymethyl)-1,3-dioxolan-4-yl)-2(1h)-pyrimidinone

2. 1-(2-(hydroxymethyl)-1,3-dioxolan-4-yl)cytosine

3. 2r(-)-cis-hmd-cytosine

4. 2r(-)-trans-hmd-cytosine

5. 2s(-)-cis-hmd-cytosine

6. Bch 4556

7. Bch-4556

8. Beta-l-dioxolane-cytidine

9. Hmd-cytosine

10. Troxacitabine

11. Troxacitabine, 2r(-)-cis-isomer

12. Troxacitabine, 2r(-)-trans-isomer

13. Troxacitabine, 2s(-)-trans-isomer

14. Troxacitabine, Cis-(+-)-isomer

15. Troxacitabine, Trans-(+-)-isomer

2.3.2 Depositor-Supplied Synonyms

1. Troxacitabine

2. 145918-75-8

3. Bch-4556

4. (-)-oddc

5. 4-amino-1-((2s,4s)-2-(hydroxymethyl)-1,3-dioxolan-4-yl)pyrimidin-2(1h)-one

6. 60kqz0388y

7. Cis-dioxolane-c

8. (-)-1-((2s,4s)-2-(hydroxymethyl)-1,3-dioxolan-4-yl)cytosine

9. (2s-cis)-4-amino-1-(2-(hydroxymethyl)-1,3-dioxolan-4-yl)-2(1h)-pyrimidinone

10. 4-amino-1-[(2s,4s)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]pyrimidin-2(1h)-one

11. L-oddc

12. (-)-occc

13. Troxacitabine [usan:inn]

14. Unii-60kqz0388y

15. Nsc668281

16. Lamivudine Impurity I

17. (-)-bch 204

18. Lamivudine Impurity I Rs

19. Troxacitabine [mi]

20. (-)-l-.b.-dioxolanec

21. 4-amino-1-[(2s,4s)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]pyrimidin-2-one

22. Troxacitabine [inn]

23. Troxacitabine (usan/inn)

24. Troxacitabine [usan]

25. Schembl18548

26. ((-))-oddc

27. Troxacitabine [who-dd]

28. Chembl359164

29. Chebi:134886

30. Bcpp000031

31. (-)-l-.beta.-dioxolane-cytosine

32. Zinc1642845

33. Akos015967351

34. Db04961

35. Hy-13770

36. Lamivudine Impurity I [ep Impurity]

37. Cs-0007785

38. Lamivudine Impurity I [usp Impurity]

39. D06255

40. 918t758

41. Lamivudine Related Compound (alpha-troxacitabine)

42. J-525143

43. Q7846702

44. (-)-(2s,4s)-1-[2-hydroxymethyl)-1,3-dioxolan-4-yl]cytosine

45. (-)-l-2',3'-dideoxy-3'-oxacytidine; Troxacitabine; Troxatyl

46. 2(1h)-pyrimidinone, 4-amino-1-((2s,4s)-2-(hydroxymethyl)-1,3-dioxolan-4-yl)-

47. 2(1h)-pyrimidinone, 4-amino-1-(-2-(hydroxymethyl)-1,3-dioxolan-4-yl)-, (2s-cis)-

48. 4-amino-1-[(2s,4s)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]-1,2-dihydropyrimidin-2-one

49. Ltt

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₈H₁₁N₃O₄
Molecular Weight	213.19 g/mol
XLogP3	-1.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	213.07495584 g/mol
Monoisotopic Mass	213.07495584 g/mol
Topological Polar Surface Area	97.4 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	328
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 leukemia (myeloid).

5 Pharmacology and Biochemistry

5.1 Pharmacology

Troxacitabine is a beta-L-nucleoside analog, which has shown preclinical antitumor activity in human xenograft tumor models and antileukemic response in patients with relapsed myeloid leukemia.

5.2 MeSH Pharmacological Classification

Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

5.3 Mechanism of Action

Troxacitabine is activated by cellular kinases and incorporated into DNA, inhibiting its replication. In contrast to other cytosine nucleoside analogs, troxacitabine is resistant to inactivation by cytidine deaminase (CD).