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Merimepodib

Merimepodib

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Also known as: 198821-22-6, Vx-497, Mmpd, Vi-21497, 2zl2ba06fu, (s)-tetrahydrofuran-3-yl 3-(3-(3-methoxy-4-(oxazol-5-yl)phenyl)ureido)benzylcarbamate

Molecular Formula

C₂₃H₂₄N₄O₆

Molecular Weight

452.5 g/mol

InChI Key

JBPUGFODGPKTDW-SFHVURJKSA-N

FDA UNII

2ZL2BA06FU

Merimepodib is an inosine monophosphate dehydrogenase (IMPDH) inhibitor with activity against hepatitis C virus (HCV). IMPDH catalyzes the rate-limiting step in the de novo synthesis of guanine nucleotides, and treatment with merimepodib reduces the intracellular guanine nucleotide levels that are required for RNA and DNA synthesis, resulting in antiproliferative and antiviral effect.

1 2D Structure

Merimepodib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(3S)-oxolan-3-yl] N-[[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]methyl]carbamate

2.1.2 InChI

InChI=1S/C23H24N4O6/c1-30-20-10-17(5-6-19(20)21-12-24-14-32-21)27-22(28)26-16-4-2-3-15(9-16)11-25-23(29)33-18-7-8-31-13-18/h2-6,9-10,12,14,18H,7-8,11,13H2,1H3,(H,25,29)(H2,26,27,28)/t18-/m0/s1

2.1.3 InChI Key

JBPUGFODGPKTDW-SFHVURJKSA-N

2.1.4 Canonical SMILES

COC1=C(C=CC(=C1)NC(=O)NC2=CC=CC(=C2)CNC(=O)OC3CCOC3)C4=CN=CO4

2.1.5 Isomeric SMILES

COC1=C(C=CC(=C1)NC(=O)NC2=CC=CC(=C2)CNC(=O)O[C@H]3CCOC3)C4=CN=CO4

2.2 Other Identifiers

2.2.1 UNII

2ZL2BA06FU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. N-3-(3-(3-methoxy-4-oxazol-5-ylphenyl)ureido)benzylcarbamic Acid Tetrahydrofuran-3-yl Ester

2. Vx 497

3. Vx-497

2.3.2 Depositor-Supplied Synonyms

1. 198821-22-6

2. Vx-497

3. Mmpd

4. Vi-21497

5. 2zl2ba06fu

6. (s)-tetrahydrofuran-3-yl 3-(3-(3-methoxy-4-(oxazol-5-yl)phenyl)ureido)benzylcarbamate

7. Vi-21,497

8. Chembl304087

9. [(3s)-oxolan-3-yl] N-[[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]methyl]carbamate

10. Vx497

11. Merimepodib, Vi-21497, Vx-497

12. (s)-tetrahydro-3-furyl (m-(3-(3-methoxy-4-(5-oxazolyl)phenyl)ureido)benzyl)carbamate

13. Carbamic Acid, ((3-((((3-methoxy-4-(5-oxazolyl)phenyl)amino)carbonyl)amino)phenyl)methyl)-, (3s)-tetrahydro-3-furanyl Ester

14. Vx 497

15. Merimepodib [usan:inn]

16. Unii-2zl2ba06fu

17. Merimebodib

18. Carbamic Acid, [[3-[[[[3-methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]methyl]-, (3s)-tetrahydro-3-furanyl Ester

19. Merimepodib [usan]

20. Merimepodib [mi]

21. Merimepodib [inn]

22. Merimepodib (usan/inn)

23. Merimepodib [who-dd]

24. Schembl329922

25. Gtpl10741

26. Dtxsid70173639

27. [[3-[[[[3-methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]methyl]carbamic Acid (3s)-tetrahydro-3-furanyl Ester

28. Bcp28336

29. Ex-a1201

30. Yha82122

31. Zinc3975663

32. Bdbm50102249

33. Fd5020

34. Mfcd09837807

35. S6689

36. Db04862

37. N-3-(3-(3-methoxy-4-oxazol-5-ylphenyl)ureido)benzylcarbamic Acid Tetrahydrofuran-3-yl Ester

38. Ncgc00378589-01

39. Ac-35396

40. As-75124

41. Hy-13986

42. D04936

43. A919457

44. Q1727082

45. (3s)-oxolan-3-yl N-{[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]methyl}carbamate

46. [(3s)-tetrahydrofuran-3-yl] N-[[3-[(3-methoxy-4-oxazol-5-yl-phenyl)carbamoylamino]phenyl]methyl]carbamate

47. {3-[3-(3-methoxy-4-oxazol-5-yl-phenyl)-ureido]-benzyl}-carbamic Acid (s)-(tetrahydro-furan-3-yl) Ester

48. {3-[3-(3-methoxy-4-oxazol-5-yl-phenyl)-ureido]-benzyl}-carbamic Acid Tetrahydro-furan-3-yl Ester

49. Carbamic Acid, N-[[3-[[[[3-methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]methyl]-, (3s)-tetrahydro-3-furanyl Ester

50. N-[3-3-[3-methoxy-4-(5-oxazolyl)phenyl]ureido]benzyl]carbamic Acid Tetrahydrofuran-3-(s)-yl Ester

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₄N₄O₆
Molecular Weight	452.5 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	8
Exact Mass	452.16958450 g/mol
Monoisotopic Mass	452.16958450 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	652
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

For the treatment of hepatitis C virus (HCV) infection.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Merimepodib, an oral drug, contains a novel inhibitor of inosine monophosphate dehydrogenase (IMPDH), an enzyme responsible for stimulating the production of lymphocytes. Merimepodib has the potential to exert direct antiviral activity, as well as affect the immune response by acting on lymphocyte migration and proliferation. Consequently, merimepodib may be an effective treatment for hepatitis C virus (HCV) infection, as the disease involves both viral proliferation and liver inflammation.

5.2 Mechanism of Action

Merimepodib is a orally active inhibitor of inosine monophospate dehydrogenase (IMPDH). IMPDH inhibition leads to a reduction in intracellular guanosine triphosphate (GTP), a molecule required for DNA and RNA synthesis.