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Naproxcinod

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Chemistry

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Also known as: 163133-43-5, Nitronaproxen, Naproxen-n-butyl nitrate, Hct 3012, Azd3582, No-naproxen

Molecular Formula

C₁₈H₂₁NO₆

Molecular Weight

347.4 g/mol

InChI Key

AKFJWRDCWYYTIG-ZDUSSCGKSA-N

FDA UNII

V24GR4LI3I

1 2D Structure

Naproxcinod

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate

2.1.2 InChI

InChI=1S/C18H21NO6/c1-13(18(20)24-9-3-4-10-25-19(21)22)14-5-6-16-12-17(23-2)8-7-15(16)11-14/h5-8,11-13H,3-4,9-10H2,1-2H3/t13-/m0/s1

2.1.3 InChI Key

AKFJWRDCWYYTIG-ZDUSSCGKSA-N

2.1.4 Canonical SMILES

CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)OCCCCO[N+](=O)[O-]

2.1.5 Isomeric SMILES

C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)OCCCCO[N+](=O)[O-]

2.2 Other Identifiers

2.2.1 UNII

V24GR4LI3I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(nitrooxy)butyl-(2s)-2-(6-methoxy-2-naphthyl)propanoate

2. Azd 3582

3. Azd-3582

4. Azd3582

5. Naproxen-n-butyl Nitrate

6. Nicox

7. Nitric Oxide Naproxen

8. Nitric Oxide-releasing Naproxen

9. No-naproxen

2.3.2 Depositor-Supplied Synonyms

1. 163133-43-5

2. Nitronaproxen

3. Naproxen-n-butyl Nitrate

4. Hct 3012

5. Azd3582

6. No-naproxen

7. Azd-3582

8. Hct-3012

9. Ar-p900758xx

10. Azd 3582

11. V24gr4li3i

12. Chebi:76254

13. (s)-2-(6-methoxy-2-naphthyl)propanoic Acid 4-nitrooxybutyl Ester

14. 2-naphthaleneacetic Acid, 6-methoxy-alpha-methyl-, 4-(nitrooxy)butyl Ester, (alphas)-

15. 4-nitrooxybutyl (2s)-2-(6-methoxynaphthalen-2-yl)propanoate

16. 4-(nitrooxy)butyl (2s)-2-(6-methoxynaphthalen-2-yl)propanoate

17. 4-(nitrooxy)butyl (s)-2-(6-methoxynaphthalen-2-yl)propanoate

18. 4-(nitrooxy)butyl (2s)-2-(6-methoxy-2-naphthyl)propanoate

19. Naproxcinod [usan]

20. Naproxcinod [usan:inn]

21. Unii-v24gr4li3i

22. Naproxcinodum

23. Naproxcinod [mi]

24. Naproxcinod [inn]

25. Naproxcinod (usan/inn)

26. Naproxen Nitroxybutyl Ester

27. Naproxcinod [who-dd]

28. Gtpl9551

29. Schembl1170879

30. Chembl2103831

31. Dtxsid20167523

32. Zinc1541804

33. Akos015914063

34. Db06682

35. Me-0138

36. Zd-3582

37. Ac-23946

38. Hy-14931

39. Cs-0003642

40. D09568

41. E87348

42. Q3335996

43. 4-(nitrooxy)butyl(2s)-2-(6-methoxy-2-naphthyl)propanoate

44. 4-(nitrooxy)butyl-(2s)-2-(6-methoxy-2 Naphthyl)propanoate

45. (s)-2-(6-methoxy-2-naphtyl) Propionic Acid 4-nitrooxybutyl Ester

46. 2-naphthaleneacetic Acid, 6-methoxy-alpha-methyl-, 4-(nitrooxy)butyl Ester, (s)-

47. 2-naphthaleneacetic Acid, 6-methoxy-.alpha.-methyl-, 4-(nitrooxy)butyl Ester, (.alpha.s)-

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₁NO₆
Molecular Weight	347.4 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Exact Mass	347.13688739 g/mol
Monoisotopic Mass	347.13688739 g/mol
Topological Polar Surface Area	90.6 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	438
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

Investigated for use/treatment in pain (acute or chronic), inflammatory disorders (unspecified), osteoarthritis, and arthritis and arthritic pain.

Primary osteoarthritis

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Nitric Oxide Donors

A diverse group of agents, with unique chemical structures and biochemical requirements, which generate NITRIC OXIDE. These compounds have been used in the treatment of cardiovascular diseases and the management of acute myocardial infarction, acute and chronic congestive heart failure, and surgical control of blood pressure. (Adv Pharmacol 1995;34:361-81) (See all compounds classified as Nitric Oxide Donors.)

5.2 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AE - Propionic acid derivatives

M01AE18 - Naproxcinod

Drugs in Development