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2D Structure
Also known as: 23696-28-8, Bayernox, Bisergon, Bayonox, 2-((2-hydroxyethyl)carbamoyl)-3-methylquinoxaline 1,4-dioxide, Bay va 9391
Molecular Formula
C12H13N3O4
Molecular Weight
263.25  g/mol
InChI Key
TURHTASYUMWZCC-UHFFFAOYSA-N
FDA UNII
G3LAW9U88T

1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-(2-hydroxyethyl)-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carboxamide
2.1.2 InChI
InChI=1S/C12H13N3O4/c1-8-11(12(17)13-6-7-16)15(19)10-5-3-2-4-9(10)14(8)18/h2-5,16H,6-7H2,1H3,(H,13,17)
2.1.3 InChI Key
TURHTASYUMWZCC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C([N+](=O)C2=CC=CC=C2N1[O-])C(=O)NCCO
2.2 Other Identifiers
2.2.1 UNII
G3LAW9U88T
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(n-2'-hydroxyethylcarbamoyl)-3-methylquinoxaline- Di-n-oxide

2. Bay Va 9391

3. Bayo-n-ox

4. Bisergon

5. Olanquindox

2.3.2 Depositor-Supplied Synonyms

1. 23696-28-8

2. Bayernox

3. Bisergon

4. Bayonox

5. 2-((2-hydroxyethyl)carbamoyl)-3-methylquinoxaline 1,4-dioxide

6. Bay Va 9391

7. N-(2-hydroxyethyl)-3-methyl-2-quinoxalinecarboxamide 1,4-dioxide

8. 2-quinoxalinecarboxamide, N-(2-hydroxyethyl)-3-methyl-, 1,4-dioxide

9. Olachindox

10. Bay-va-9391

11. Olaquindox (inn)

12. Nsc634933

13. Ncgc00164265-01

14. Olaquindox [inn]

15. N-(2-hydroxyethyl)-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carboxamide

16. Dsstox_cid_20726

17. Dsstox_rid_79573

18. Dsstox_gsid_40726

19. Olaquindox [ban:inn]

20. Cas-23696-28-8

21. N-(2-hydroxyethyl)-3-methyl-1,4-dioxidoquinoxaline-1,4-diium-2-carboxamide

22. Olaquindox [mi]

23. Olaquindox [hsdb]

24. Olaquindox-(ethylene-d4)

25. Olaquindox [mart.]

26. G3law9u88t

27. Schembl557579

28. Olaquindox [veterinary] (tn)

29. Chembl1649716

30. Dtxsid3040726

31. Chebi:177538

32. Act06680

33. Hy-n0465

34. Zinc1624227

35. Tox21_112095

36. Mfcd00210341

37. Akos015895584

38. Akos037514759

39. Olaquindox 100 Microg/ml In Methanol

40. Tox21_112095_1

41. Nsc-634933

42. Ncgc00164265-02

43. Ac-13888

44. As-12544

45. Olaquindox 100 Microg/ml In Acetonitrile

46. Db-046225

47. Cs-0008992

48. Ft-0630505

49. Ft-0673254

50. N2086

51. A14807

52. D08292

53. Olaquindox, Vetranal(tm), Analytical Standard

54. J-015187

55. Q27278699

56. 2-(2-hydroxyethylcarbamoyl)-3-methylquinoxaline 1,4-dioxide

57. 2-(n-(2-hydroxyethyl)carbamoyl)-3-methylquinoxaline1,4-dioxide

58. 2-[(2-hydroxyethyl)carbamoyl]-3-methyl-1-oxo-1,4-dihydro-1

59. E?-quinoxalin-1-ylium-4-olate

60. N-(2-hydroxyethyl)-3-methyl-1,4-dioxido-quinoxaline-1,4-diium-2-carboxamide

61. 1,4-dihydroxy-n-(2-hydroxyethyl)-3-methyl-1.lambda.~5~,4.lambda.~5~-quinoxaline-2-carboxamide

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 263.25 g/mol
Molecular Formula C12H13N3O4
XLogP3-0.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass263.09060590 g/mol
Monoisotopic Mass263.09060590 g/mol
Topological Polar Surface Area95.7 Ų
Heavy Atom Count19
Formal Charge0
Complexity421
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

The compound /olaquindox/ is used as a growth promoter in pigs.

WHO/FAO; Joint Meeting on Food Additives; Toxicological Evaluation of Certain Veterinary Drug Residues in Food, WHO Food Additive Series 27: Olaquindox (1991). Available from, as of November 5, 2015: https://www.inchem.org/pages/jecfa.html


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Experiments with (3-1)4C-olaquindox intraduodenally administered to rats with bile duct fistulas suggested that around 18% of the dose was excreted in the bile. Similar findings were made after intravenous dosing. Distribution occurred in a generalized manner throughout the body after oral dosing and most of the radioactivity had disappeared by 24 hours. Autoradiography revealed the highest amount in the rat kidney at 4 hours, indicative of the extent of urinary excretion already noted. Slightly elevated concentrations were also observed in liver, testes, adrenals and hair follicles.

WHO/FAO; Joint Meeting on Food Additives; Toxicological Evaluation of Certain Veterinary Drug Residues in Food, WHO Food Additive Series 27: Olaquindox (1991). Available from, as of November 5, 2015: https://www.inchem.org/pages/jecfa.html


After pigs were given diets containing up to 45 ppm olaquindox for the duration of the fattening period, the highest levels were found in the liver (0.14 ppm) and kidney (0.28 ppm) 6 hours after withdrawal. By 24 hours the levels were below the limit of detection (0.1 ppm). Similar results were noted when pigs were given diets containing 10 ppm olaquindox.

WHO/FAO; Joint Meeting on Food Additives; Toxicological Evaluation of Certain Veterinary Drug Residues in Food, WHO Food Additive Series 27: Olaquindox (1991). Available from, as of November 5, 2015: https://www.inchem.org/pages/jecfa.html


When pigs were dosed at levels in the range of those recommended in use (up to 100 ppm in the diet) for up to 20 weeks, relatively high levels were found in the kidney (around 2000 ppb) with relatively moderate levels in the liver (300 ppb) when the animals were killed six hours after drug withdrawal. When killed 2 days after withdrawal, levels had fallen to below the limits of detection (50 ppb) in liver, kidney and muscle. Pigs given diets containing olaquindox at levels in excess of those recommended (160 or 250 ppm) for up to 4 weeks also had high initial levels in kidney, liver and muscle but these had fallen to below the limits of detection by day 2 after withdrawal.

WHO/FAO; Joint Meeting on Food Additives; Toxicological Evaluation of Certain Veterinary Drug Residues in Food, WHO Food Additive Series 27: Olaquindox (1991). Available from, as of November 5, 2015: https://www.inchem.org/pages/jecfa.html


Olaquindox was rapidly absorbed when given orally to pigs. Over 90% of an oral dose of 2 mg/kg bw was eliminated in the urine within 24 hours, which is indicative of rapid and extensive absorption. The remainder was excreted in the feces. Maximum plasma levels were attained within 1-2 hours of dosing (1-2 ppm). This was followed by a rapid decline in plasma levels reaching around 0.03 ppm by 24 hours and 0.005-0.01 ppm by 48 hours. Radioactivity was present in all tissues when examined 2 days after dosing, but the levels were extremely low. In the kidney and liver, levels of 110 and 52 ppb were found, while levels in muscle were only 9 ppb. After 8 days, levels in liver and kidney had fallen to 27 and 12 ppb, respectively, while those in muscle were in the range of 2.5 ppb. By 28 days after dosing only low levels were found in kidney and muscle (0.9 and 0.5-0.8 ppb, respectively) with slightly higher concentrations in the liver (2 ppb).

WHO/FAO; Joint Meeting on Food Additives; Toxicological Evaluation of Certain Veterinary Drug Residues in Food, WHO Food Additive Series 27: Olaquindox (1991). Available from, as of November 5, 2015: https://www.inchem.org/pages/jecfa.html


For more Absorption, Distribution and Excretion (Complete) data for OLAQUINDOX (6 total), please visit the HSDB record page.


5.2 Metabolism/Metabolites

The biotransformation of olaquindox has been investigated only in the pig. The majority of an oral dose of olaquindox (70%) was excreted in the urine unchanged. The major metabolites appeared to be the reduced compounds, the 1- or 4-mono-N-oxides (16%). Three other compounds thought to be carboxylic acid derivatives made up the remainder. Later work led to the elucidation of the structures of these metabolites in the pig. Again the major urinary component after oral dosing was olaquindox with about 7% present as the 4-mono-N-oxide. Omega oxidation produced the 2-carboxymethylaminocarbonyl compound and its 4-mono-N-oxide derivative (6%). Some of the corresponding 1-mono-N-oxide moiety of the 2-carboxymethylaminocarbonyl was also noted (1%). The remaining metabolite was the di-desoxy derivative of 2-carboxymethylaminocarbonyl compound, 2-carboxymethylaminocarbonyl-3- methyl quinoxaline (>1%).

WHO/FAO; Joint Meeting on Food Additives; Toxicological Evaluation of Certain Veterinary Drug Residues in Food, WHO Food Additive Series 27: Olaquindox (1991). Available from, as of November 5, 2015: https://www.inchem.org/pages/jecfa.html