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Elvucitabine

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Synopsis

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Chemistry

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Also known as: 181785-84-2, Beta-l-fd4c, L-fd4c, .beta.-l-fd4c, Ach-126,443, L-f-d4c

Molecular Formula

C₉H₁₀FN₃O₃

Molecular Weight

227.19 g/mol

InChI Key

HSBKFSPNDWWPSL-VDTYLAMSSA-N

FDA UNII

M09BUF90C0

Elvucitabine is a nucleoside reverse transcriptase inhibitor analog of cytosine. Elvucitabine has activity against HIV and chronic hepatitis B.

1 2D Structure

Elvucitabine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one

2.1.2 InChI

InChI=1S/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m1/s1

2.1.3 InChI Key

HSBKFSPNDWWPSL-VDTYLAMSSA-N

2.1.4 Canonical SMILES

C1=CC(OC1CO)N2C=C(C(=NC2=O)N)F

2.1.5 Isomeric SMILES

C1=C[C@H](O[C@H]1CO)N2C=C(C(=NC2=O)N)F

2.2 Other Identifiers

2.2.1 UNII

M09BUF90C0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine

2. 2',3'-dideoxy-2',3'-didehydro-beta-d-5-fluorocytidine

3. 2',3'-dideoxy-2',3'-didehydro-beta-l-5-fluorocytidine

4. 2(1h)-pyrimidinone, 4-amino-1-((2s,5r)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl)-5-fluoro-

5. 4-amino-5-fluoro-1-((2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidin-2(1h)-one

6. Ach-126-443

7. Beta-d-d4fc

8. Beta-l-fd4c

9. D-d4fc

10. Dexelvucitabine

11. Dpc 817

12. Dpc-817

13. Dpc817

14. Incb-8721

15. L-d4fc

16. Reverset

2.3.2 Depositor-Supplied Synonyms

1. 181785-84-2

2. Beta-l-fd4c

3. L-fd4c

4. .beta.-l-fd4c

5. Ach-126,443

6. L-f-d4c

7. Ach-126443

8. L-d4fc

9. 4-amino-5-fluoro-1-((2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidin-2(1h)-one

10. 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one

11. M09buf90c0

12. 2(1h)-pyrimidinone, 4-amino-1-((2s,5r)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl)-5-fluoro-

13. 2(1h)-pyrimidinone, 4-amino-1-[(2s,5r)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-5-fluoro-

14. Elvucitabine [usan]

15. Elvucitabine [usan:inn]

16. Unii-m09buf90c0

17. Ach 126443

18. Ach 126,443

19. B-l-fd4c

20. Elvucitabine (usan/inn)

21. Elvucitabine [inn]

22. Chembl38700

23. (-)fd4c

24. Schembl1649928

25. Zinc7048

26. Beta-l-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine

27. Dtxsid20171185

28. Bdbm50421604

29. Db06236

30. Hy-117582

31. Cs-0066557

32. A14435

33. D03981

34. J-011630

35. Q1334337

36. .beta.-l-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine

37. 2(1h)-pyrimidinone, 4-amino-1-(2,5-dihydro-5-(hydroxymethyl)-2-furanyl)-5-fluoro-, (2s-cis)-

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₀FN₃O₃
Molecular Weight	227.19 g/mol
XLogP3	-1.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	227.07061935 g/mol
Monoisotopic Mass	227.07061935 g/mol
Topological Polar Surface Area	88.2 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	405
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 hepatitis (viral, B) and HIV infection.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Reverse Transcriptase Inhibitors

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

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.)

5.2 Mechanism of Action

Elvucitabine is a L-cytosine Nucleoside analog Reverse Transcriptase Inhibitor (NRTIs) anti-HIV drug. NRTI's inhibit the activity of viral RNA-directed DNA polymerase (i.e., reverse transcriptase). It is believed that inhibition of reverse transcriptase interferes with the generation of DNA copies of viral RNA, which, in turn, are necessary for synthesis of new virions. Intracellular enzymes subsequently eliminate the HIV particle that previously had been uncoated, and left unprotected, during entry into the host cell. Thus, reverse transcriptase inhibitors are virustatic and do not eliminate HIV from the body.

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