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Also known as: 69819-86-9, Zinapar, Zio-101, Dmas(iii)g, Sp-02l, Zio 101

Molecular Formula

C₁₂H₂₂AsN₃O₆S

Molecular Weight

411.31 g/mol

InChI Key

JGDXFQORBMPJGR-YUMQZZPRSA-N

FDA UNII

9XX54M675G

Darinaparsin is a small-molecule organic arsenical with potential antineoplastic activity. Although the exact mechanism of action is unclear, darinaparsin, a highly toxic metabolic intermediate of inorganic arsenicals (iAs) that occurs in vivo, appears to generate volatile cytotoxic arsenic compounds when glutathione (GSH) concentrations are low. The arsenic compounds generated from darinaparsin disrupt mitochondrial bioenergetics, producing reactive oxygen species (ROS) and inducing ROS-mediated tumor cell apoptosis; in addition, this agent or its byproducts may initiate cell death by interrupting the G2/M phase of the cell cycle and may exhibit antiangiogenic effects. Compared to inorganic arsenic compounds such as arsenic trioxide (As2O3), darinaparsin appears to exhibit a wide therapeutic window.

1 2D Structure

Darinaparsin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-dimethylarsanylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

2.1.2 InChI

InChI=1S/C12H22AsN3O6S/c1-13(2)23-6-8(11(20)15-5-10(18)19)16-9(17)4-3-7(14)12(21)22/h7-8H,3-6,14H2,1-2H3,(H,15,20)(H,16,17)(H,18,19)(H,21,22)/t7-,8-/m0/s1

2.1.3 InChI Key

JGDXFQORBMPJGR-YUMQZZPRSA-N

2.1.4 Canonical SMILES

C[As](C)SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N

2.1.5 Isomeric SMILES

C[As](C)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

9XX54M675G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Clarinaparsin

2. Dimethylarsinous Glutathione

3. Dmas(iii)g

4. Dmas(iii)sg

5. S-(dimethylarsino)-glutathione

6. S-(dimethylarsino)glutathione

7. S-dimethylarsino-glutathione

8. Zio 101

9. Zio-101

10. Zio101

2.3.2 Depositor-Supplied Synonyms

1. 69819-86-9

2. Zinapar

3. Zio-101

4. Dmas(iii)g

5. Sp-02l

6. Zio 101

7. 9xx54m675g

8. Glycine, L-gamma-glutamyl-s-(dimethylarsino)-l-cysteinyl-

9. Clarinaparsin

10. (s)-2-amino-5-(((r)-1-((carboxymethyl)amino)-3-((dimethylarsino)thio)-1-oxopropan-2-yl)amino)-5-oxopentanoic Acid

11. Darinaparsin [usan]

12. Dmas(iii)sg

13. Darinaparsin [usan:inn]

14. Dimethylarsinous Glutathione

15. S-dimethylarsino-glutathione

16. S-(dimethylarsino)glutathione

17. S-(dimethylarsino)-glutathione

18. Unii-9xx54m675g

19. Zio101

20. Sglu1

21. Darinaparsin [mi]

22. S-dimethylarsinoglutathione

23. Darinaparsin (jan/usan)

24. Darinaparsin [inn]

25. Darinaparsin [jan]

26. S-dimethylarsino Glutathione

27. Darinaparsin [who-dd]

28. Schembl411358

29. Sp02

30. Chembl3247378

31. Chebi:94295

32. Zio-101-c

33. Dtxsid80220108

34. Bcp15637

35. Db06179

36. Hy-14943

37. Zio 101; Zio101; Zio-101

38. D08898

39. Brd-k35723520-001-01-0

40. Q27166111

41. Glycine, L-gamma-glutamyl-s-(dimethylarsino)-l-cysteinyl

42. L-gamma-glutamyl-s-(dimethylarsanyl)-l-cysteinylglycine

43. L-gamma-glutamyl-s-(dimethylarsino)-l-cysteinyl-glycine

44. Glycine, L-.gamma.-glutamyl-s-(dimethylarsino)-l-cysteinyl-

45. (2s)-2-amino-5-[[(2r)-1-(carboxymethylamino)-3-dimethylarsanylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic Acid

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₂₂AsN₃O₆S
Molecular Weight	411.31 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	11
Exact Mass	411.044526 g/mol
Monoisotopic Mass	411.044526 g/mol
Topological Polar Surface Area	184 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	449
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 blood (blood forming organ disorders, unspecified), cancer/tumors (unspecified), solid tumors, multiple myeloma, and liver cancer.