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Also known as: 38520-57-9, (r)-2-acetamido-3-mercaptopropanamide, Acetylcysteine amide, Nac amide, N-acetyl-l-cysteinamide, Naca

Molecular Formula

C₅H₁₀N₂O₂S

Molecular Weight

162.21 g/mol

InChI Key

UJCHIZDEQZMODR-BYPYZUCNSA-N

FDA UNII

4N69717RKW

N-Acetylcysteine Amide is the amide form of N-acetylcysteine (NAC), a synthetic N-acetyl derivative and prodrug of the endogenous amino acid and antioxidant glutathione (GSH) precursor L-cysteine, with potential antioxidant and anti-inflammatory activities. Upon administration, N-acetylcysteine amide (NACA) increases GSH levels. GSH scavenges reactive oxygen species (ROS), reduces oxidative stress and prevents ROS-mediated cell damage and apoptosis. NACA has enhanced lipophilicity and membrane permeability compared with NAC.

1 2D Structure

N-Acetylcysteine Amide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-acetamido-3-sulfanylpropanamide

2.1.2 InChI

InChI=1S/C5H10N2O2S/c1-3(8)7-4(2-10)5(6)9/h4,10H,2H2,1H3,(H2,6,9)(H,7,8)/t4-/m0/s1

2.1.3 InChI Key

UJCHIZDEQZMODR-BYPYZUCNSA-N

2.2 Other Identifiers

2.2.1 UNII

4N69717RKW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-acetamido-3-mercapto-l-propionamide

2. N-acetylcysteinamide

2.3.2 Depositor-Supplied Synonyms

1. 38520-57-9

2. (r)-2-acetamido-3-mercaptopropanamide

3. Acetylcysteine Amide

4. Nac Amide

5. N-acetyl-l-cysteinamide

6. Naca

7. Acetylcysteinamide

8. N-acetyl-l-cysteine Amide

9. N-acetyl Cysteine Amide

10. N-acetyl-cysteine-amide

11. N-acetylcysteinamide

12. Propanamide, 2-(acetylamino)-3-mercapto-, (2r)-

13. Mfcd01696115

14. 4n69717rkw

15. Propanamide, 2-(acetylamino)-3-mercapto-, (r)-

16. (2r)-2-acetamido-3-sulfanylpropanamide

17. (2r)-2-(acetylamino)-3-mercaptopropanamide;

18. Unii-4n69717rkw

19. N-acetylcysteine Amide [who-dd]

20. Ac-cys-nh2

21. (r)- 2-(acetylamino)-3-mercapto-propanamide

22. N-acetylcysteine Amide;(r)-2-acetamido-3-mercaptopropanamide

23. Schembl377413

24. Dtxsid30436398

25. Chebi:231847

26. Ujchizdeqzmodr-bypyzucnsa-n

27. Hms3886b05

28. S5804

29. Akos006373417

30. Db14480

31. Da-55966

32. N-acetylcysteine Amide, >=98% (hplc)

33. Hy-110256

34. Cs-0033121

35. Q15408428

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₅H₁₀N₂O₂S
Molecular Weight	162.21 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	73.2
Heavy Atom Count	10
Formal Charge	0
Complexity	149
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