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Sodium Arsanilate

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Chemistry

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Also known as: Atoxyl, 127-85-5, Sodium aminarsonate, Sodium anilarsonate, Arsamin, Soamin

Molecular Formula

C₆H₇AsNNaO₃

Molecular Weight

239.04 g/mol

InChI Key

OUFRIWNNMFWZTM-UHFFFAOYSA-M

FDA UNII

UC2409302Q

An arsenical which has been used as a feed additive for enteric conditions in pigs and poultry. It causes blindness and is ototoxic and nephrotoxic in animals.

1 2D Structure

Sodium Arsanilate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(4-aminophenyl)-hydroxyarsinate

2.1.2 InChI

InChI=1S/C6H8AsNO3.Na/c8-6-3-1-5(2-4-6)7(9,10)11;/h1-4H,8H2,(H2,9,10,11);/q;+1/p-1

2.1.3 InChI Key

OUFRIWNNMFWZTM-UHFFFAOYSA-M

2.1.4 Canonical SMILES

C1=CC(=CC=C1N)[As](=O)(O)[O-].[Na+]

2.2 Other Identifiers

2.2.1 UNII

UC2409302Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4 Aminobenzenearsonic Acid

2. 4-aminobenzenearsonic Acid

3. Acid, 4-aminobenzenearsonic

4. Acid, Arsanilic

5. Acid, P-aminophenylarsonic

6. Arsanilate, Sodium

7. Arsanilic Acid

8. Arsenilate, Sodium

9. Atoxyl

10. P Aminophenylarsonic Acid

11. P-aminophenylarsonic Acid

12. Sodium Arsenilate

2.3.2 Depositor-Supplied Synonyms

1. Atoxyl

2. 127-85-5

3. Sodium Aminarsonate

4. Sodium Anilarsonate

5. Arsamin

6. Soamin

7. Sodium Hydrogen 4-aminophenylarsonate

8. Arsanilic Acid Sodium Salt

9. Sodium P-aminophenylarsonate

10. Monosodium (4-aminophenyl)arsonate

11. Sodium 4-aminophenylarsonate

12. 4-aminophenylarsonic Acid Sodium Salt

13. (4-aminophenyl)arsonic Acid Sodium Salt

14. Sodium;(4-aminophenyl)-hydroxyarsinate

15. Chebi:36049

16. Uc2409302q

17. 4-aminobenzenearsonic Acid Sodium Salt

18. Arsinosolvin

19. Nuarsol

20. Protoxyl

21. Trypoxyl

22. Sonate

23. Pro-gen Sodium

24. Sodium Arsonilate

25. Piglet Pro-gen V

26. Sodium P-arsanilate

27. Sodium Aniline-arsonate

28. Sodium-analine Arsonate

29. Sodium Aminophenylarsonate

30. Sodium Arsenilate

31. Anhydrous Sodium Arsanilate

32. Sodium Aminophenol Arsonate

33. Sodium P-aminobenzenearsonate

34. Ccris 4715

35. Hsdb 5189

36. Nci-c61176

37. Einecs 204-869-9

38. Nci-61176

39. Un2473

40. Ai3-29289-x

41. Natriumarsanilat

42. Unii-uc2409302q

43. Arsonic Acid, (4-aminophenyl)-, Monosodium Salt

44. Dsstox_cid_6022

45. Dsstox_rid_77986

46. Dsstox_gsid_26022

47. P-arsanilic Acid Sodium Salt

48. Sodium Arsanilate [mi]

49. Schembl1649934

50. Chembl3188525

51. Dtxsid2026022

52. Sodium Arsanilate [hsdb]

53. Sodium Arsanilate [mart.]

54. Sodium Arsanilate [who-dd]

55. Tox21_202893

56. Mfcd00067431

57. Sodium Hydrogen (4-aminophenyl)arsonate

58. Ncgc00260439-01

59. Sodium Arsanilate [un2473] [poison]

60. Cas-127-85-5

61. A0531

62. D88275

63. As-(4-aminophenyl)arsonic Acid Sodium Salt

64. Q2864363

65. 10361-33-8

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₆H₇AsNNaO₃
Molecular Weight	239.04 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	238.953957 g/mol
Monoisotopic Mass	238.953957 g/mol
Topological Polar Surface Area	86.4 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	182
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Therapeutic Uses

MEDICATION (VET): ALTHOUGH ONE OF THE MOST EFFECTIVE AGENTS FOR BLOODY ENTERITIS IN SWINE, ITS USE IS OFTEN ASSOCIATED WITH NUMEROUS RELAPSES AND STUNTING WHICH CAN LARGELY BE AVOIDED BY CONCURRENT USE AND FOLLOW UP USE OF BACITRACIN METHYLENE DISALICYLATE (QV). HERD BENEFITS SHOULD BE NOTICED WITHIN TWO-THREE DAYS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 531

MEDICATION (VET): LITTLE BENEFIT HAS BEEN NOTED IN CATTLE TRIALS EXCEPT WITH SCOURING CALVES.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 531

MEDICATION (VET): HAS BEEN USED AS ANTHELMINTIC IN SWINE DYSENTERY & OTHER ENTERIC CONDITIONS OF PIGS & POULTRY

The Merck Index. 10th ed. Rahway, New Jersey: Merck Co., Inc., 1983., p. 1230

MEDICATION (VET): PROTOZOASTAT, GROWTH PROMOTER, ALTERATIVE

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 530

MEDICATION (VET): GROWTH PROMOTION AGENT, ESP FOR SWINE & POULTRY; VET ANTIINFECTIVE, ESP FOR SWINE & POULTRY; CHEM INT FOR MELARSEN & CARBARSONE, ANTIPROTOZOAL DRUGS; ANTHELMINTIC & ANTISYPHILITIC FOR HUMANS (POSSIBLE USE)

SRI

4.2 Drug Warning

SODIUM ARSANILATE WAS FORMERLY USED IN TREATMENT OF SYPHILIS AND TRYPANOSOMIASIS ... THERE HAVE BEEN AT LEAST 50 REPORTS IN THE LITERATURE ON DISTURBANCES OF VISION. BY 1932 SODIUM ARSANILATE WAS KNOWN TO HAVE CAUSED MORE THAN 80 CASES OF BLINDNESS AND WAS NO LONGER USED.

Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 114

VET: POISON. BE CERTAIN THAT NO OTHER FEED OR WATER SOURCE OF ARSENIC IS GIVEN AT THE SAME TIME. DO NOT FEED TO EGG LAYING BIRDS OR ADMINISTER TO DUCKS OR GEESE. AVOID CONTAMINATION WITH ANY OTHER LIVESTOCK OR HUMAN FEEDS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 531

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

ATOXYL (100 MG/KG) ADMIN SC TO GUINEA PIGS WAS ELIMINATED MUCH MORE SLOWLY BY THE COCHLEAE THAN BY BLOOD & MUSCLE. ATOXYL WAS EXCRETED VIA KIDNEYS. BLOOD ATOXYL CONCN REACHED A MAXIMUM WITHIN 1/2 HR AFTER INJECTION & THEN DECREASED RAPIDLY.

ANNIKO M, PLANTIN LO; ARCH OTO-RHINO-LARYNGOL 215 (1): 81 (1977)

/Arsanilic/ acid and its sodium salt, both poorly absorbed from the digestive tract ... Sodium arsanilate may be absorbed through intact skin.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-130

5.2 Metabolism/Metabolites

QUAL & QUANT ANALYSIS OF 24-HR URINE AFTER PARENTERAL ADMIN OF SODIUM P-ARSANILATE (15 MG ARSENIC/KG) TO RATS & GUINEA PIGS FAILED TO DETECT THE PRESENCE OF ANY ARSENIC-CONTAINING MATERIAL OTHER THAN UNCHANGED SODIUM P-ARSANILATE.

PMID:1147529 CRISTAU B ET AL; ANN PHARM FR 33 (1): 37 (1975)

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