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EIDD 2801

EIDD 2801

Synopsis, Chemistry

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Also known as: Eidd 2801, Eidd2801, Molnupiravir, 2349386-89-4, Mk-4482, Molnupiravir [inn]

Molecular Formula

C₁₃H₁₉N₃O₇

Molecular Weight

329.31 g/mol

InChI Key

HTNPEHXGEKVIHG-QCNRFFRDSA-N

FDA UNII

YA84KI1VEW

Molnupiravir is an orally bioavailable prodrug of EIDD-1931, the synthetic ribonucleoside derivative N4-hydroxycytidine and ribonucleoside analog, with potential antiviral activity against a variety of RNA viruses. Upon oral administration, molnupiravir, being a prodrug, is metabolized into its active form EIDD-1931 and converted into its triphosphate (TP) form. The TP form of EIDD-1931 is incorporated into RNA and inhibits the action of viral RNA-dependent RNA polymerase. This results in the termination of RNA transcription and decreases viral RNA production, and viral RNA replication.

1 2D Structure

EIDD 2801

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 2-methylpropanoate

2.1.2 InChI

InChI=1S/C13H19N3O7/c1-6(2)12(19)22-5-7-9(17)10(18)11(23-7)16-4-3-8(15-21)14-13(16)20/h3-4,6-7,9-11,17-18,21H,5H2,1-2H3,(H,14,15,20)/t7-,9-,10-,11-/m1/s1

2.1.3 InChI Key

HTNPEHXGEKVIHG-QCNRFFRDSA-N

2.1.4 Canonical SMILES

CC(C)C(=O)OCC1C(C(C(O1)N2C=CC(=NC2=O)NO)O)O

2.1.5 Isomeric SMILES

CC(C)C(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)NO)O)O

2.2 Other Identifiers

2.2.1 UNII

YA84KI1VEW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. ((2r,3s,4r,5r)-3,4-dihydroxy-5-((4z)-4-(hydroxyimino)-2-oxo-3,4- Dihydropyrimidin-1(2h)-yl)oxolan-2-yl)methyl 2-methylpropanoate

2. Lagevrio

3. Mk-4482

4. Molnupiravir

2.3.2 Depositor-Supplied Synonyms

1. Eidd 2801

2. Eidd2801

3. Molnupiravir

4. 2349386-89-4

5. Mk-4482

6. Molnupiravir [inn]

7. 2492423-29-5

8. Molnupiravir [usan]

9. Molnupiravir [who-dd]

10. Ya84ki1vew

11. Eidd 1931-isopropyl Ester

12. Uridine, 4-oxime, 5'-(2-methylpropanoate), (4z)-

13. N4-hydroxycytidine, 5'-isopropyl Ester

14. ((2r,3s,4r,5r)-3,4-dihydroxy-5-((4z)-4-(hydroxyimino)-2-oxo-3,4- Dihydropyrimidin-1(2h)-yl)oxolan-2-yl)methyl 2-methylpropanoate

15. ((2r,3s,4r,5r)-3,4-dihydroxy-5-(4-(hydroxyamino)-2-oxopyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl Isobutyrate

16. [(2r,3s,4r,5r)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 2-methylpropanoate

17. Lagevrio

18. Who 11853

19. ((2r,3s,4r,5r)-3,4-dihydroxy-5-(4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl Isobutyrate

20. Molnupiravirum

21. Unii-ya84ki1vew

22. Pro-eidd-1931

23. Molnupiravir [jan]

24. Eidd-2801(molnupiravir)

25. Chembl4650320

26. Eidd 1931 5'-isopropylester

27. Gtpl10737

28. Med.21724, Compound 182

29. Chebi:180653

30. Bdbm429508

31. Dtxsid501028058

32. Bcp32744

33. Eidd-1931 Isopropyl Ester

34. Ex-a3432

35. Mfcd32663515

36. Mk4482

37. S8969

38. At13078

39. N(4)-hydroxycytidine 5'-isopropylester

40. Ac-35171

41. As-84465

42. Beta-d-n4 Hydroxycytidine-5'-isopropyl Ester

43. Beta-d-n(4)-hydroxycytidine-5'-isopropyl Ester

44. A936190

45. .beta.-d-n4 Hydroxycytidine-5'-isopropyl Ester

46. N-hydroxy-5'-o-(2-methylpropanoyl)-3,4-dihydrocytidine

47. Eidd 2801; Eidd2801; Uridine, 4-oxime, 5'-(2-methylpropanoate

48. ((2r,3s,4r,5r)-3,4-dihydroxy-5-((e)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl Isobutyrate

49. ((2r,3s,4r,5r)-3,4-dihydroxy-5-((z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl Isobutyrate

50. [(2r,3s,4r,5r)-3,4-dihydroxy-5-[(4e)-4-(hydroxyimino)-2-oxo-1,2,3,4-tetrahydropyrimidin-1-yl]oxolan-2-yl]methyl 2-methylpropanoate

51. {(2r,3s,4r,5r)-3,4-dihydroxy-5-[4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2h)-yl]tetrahydrofuran-2-yl}methyl 2-methylpropanoate

2.4 Create Date

2020-03-16

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₉N₃O₇
Molecular Weight	329.31 g/mol
XLogP3	-0.8
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Exact Mass	329.12229995 g/mol
Monoisotopic Mass	329.12229995 g/mol
Topological Polar Surface Area	141 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	534
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 Indication

[N4-hydroxycytidine] and its prodrug molnupiravir are being studied for its activity against a number of viral infections including influenza, MERS-CoV, and SARS-CoV-2. Molnupiravir is approved in the UK for reducing the risk of hospitalization and death in mild to moderate COVID-19 cases for patients at increased risk of severe disease (eg. with obesity, diabetes mellitus, heart disease, or are over 60 years old).

Treatment of Coronavirus disease 2019 (COVID-19)

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

5.2 Absorption, Distribution and Excretion

Absorption

After an 800 mg oral dose of molnupiravir every 12 hours, the active compound (N4-hydroxycytidine) reaches a C_max of 2970 ng/mL, with a T_max of 1.5 hours, and an AUC_0-12h of 8360 h\*ng/mL.

Route of Elimination

3% of an oral molnupiravir dose is eliminated in the urine as the active metabolite N4-hydroxycytidine.

5.3 Metabolism/Metabolites

Molnupiravir is hydrolyzed to [N4-hydroxycytidine], which distributes into tissues. Once inside cells, N4-hydroxycytidine is phosphorylated to the 5'-triphosphate form.

5.4 Biological Half-Life

The half life of the active metabolite, N4-hydroxycytidine, is 3.3 hours.

5.5 Mechanism of Action

Molnupiravir is hydrolyzed _in vivo_ to N4-hydroxycytidine, which is phosphorylated in tissue to the active 5-triphosphate form, and incorporated into the genome of new virions, resulting in the accumulation of inactivating mutations, known as viral error catastrophe. A [remdesivir] resistant mutant mouse hepatitis virus has also been shown to have increased sensitivity to N4-hydroxycytidine.