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Sulfinpyrazone

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Chemistry

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Also known as: 57-96-5, Sulphinpyrazone, Anturane, (+/-)-sulfinpyrazone, Sulfinpyrazon, Anturan

Molecular Formula

C₂₃H₂₀N₂O₃S

Molecular Weight

404.5 g/mol

InChI Key

MBGGBVCUIVRRBF-UHFFFAOYSA-N

FDA UNII

V6OFU47K3W

A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.

1 2D Structure

Sulfinpyrazone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione

2.1.2 InChI

InChI=1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2

2.1.3 InChI Key

MBGGBVCUIVRRBF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)N2C(=O)C(C(=O)N2C3=CC=CC=C3)CCS(=O)C4=CC=CC=C4

2.2 Other Identifiers

2.2.1 UNII

V6OFU47K3W

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Anturan

2. Anturane

3. Apo Sulfinpyrazone

4. Apo-sulfinpyrazone

5. Nu Sulfinpyrazone

6. Nu-sulfinpyrazone

7. Sulfoxyphenylpyrazolidin

8. Sulphinpyrazone

2.3.2 Depositor-Supplied Synonyms

1. 57-96-5

2. Sulphinpyrazone

3. Anturane

4. (+/-)-sulfinpyrazone

5. Sulfinpyrazon

6. Anturan

7. Diphenylpyrazone

8. Sulfoxyphenylpyrazolidine

9. Anturanil

10. Anturidin

11. Enturen

12. Anturano

13. Sulfinpyrazine

14. Usaf Ge-13

15. 1,2-diphenyl-4-(2-(phenylsulfinyl)ethyl)pyrazolidine-3,5-dione

16. Sulfinpyrazonum

17. Anturen

18. Enturan

19. Nsc 75925

20. 4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione

21. Anturane (tn)

22. G 28315

23. 4-(phenylsulfoxyethyl)-1,2-diphenyl-3,5-pyrazolidinedione

24. 1,2-diphenyl-4-(2'-phenylsulfinethyl)-3,5-pyrazolidinedione

25. Chebi:9342

26. 1,2-diphenyl-3,5-dioxo-4-(2-phenylsulfinylethyl)pyrazolidine

27. 4-(2-benzenesulfinylethyl)-1,2-diphenylpyrazolidine-3,5-dione

28. 3,5-pyrazolidinedione, 1,2-diphenyl-4-(2-(phenylsulfinyl)ethyl)-

29. Nsc-75925

30. 1,2-diphenyl-4-(2-(phenylsulfinyl)ethyl)-3,5-pyrazolidinedione

31. G-28315

32. Diphenylpyrazone;g-28315

33. V6ofu47k3w

34. ( Inverted Exclamation Marka)-sulfinpyrazone

35. 1,2-diphenyl-4-[2-(phenylsulfinyl)ethyl]-3,5-pyrazolidinedione

36. 1,2-diphenyl-3,5-dioxo-4-(2'-phenyl-sulfinyl-aethyl)-pyrazolidin

37. 3,5-pyrazolidinedione, 1,2-diphenyl-4-[2-(phenylsulfinyl)ethyl]-

38. Nsc75925

39. Apo-sulfinpyrazone

40. Cas-57-96-5

41. Ncgc00016255-01

42. Sulfinpirazona

43. 1,2-diphenyl-4-[2-(phenylsulfinyl)ethyl]pyrazolidine-3,5-dione

44. Dsstox_cid_3618

45. Dsstox_rid_77113

46. Dsstox_gsid_23618

47. Sulfinpyrazonum [inn-latin]

48. Sulfinpirazona [inn-spanish]

49. Smr000058991

50. Sulfinpyrazone (spz)

51. Hsdb 3396

52. Sr-01000003152

53. Einecs 200-357-4

54. Unii-v6ofu47k3w

55. Brn 0713597

56. G 28,315

57. Sufinpyrazone

58. Suphinpyrazone

59. Sulphinepyrazolone

60. Prestwick_455

61. 1,2-diphenyl-3,5-dioxo-4-(2'-phenyl-sulfinyl-aethyl)-pyrazolidin [german]

62. Sulfinpyrazone [usp:inn:ban:jan]

63. (-+)-sulfinpyrazone

64. Spectrum_001022

65. Prestwick0_000290

66. Prestwick1_000290

67. Prestwick2_000290

68. Prestwick3_000290

69. Spectrum2_001324

70. Spectrum3_000590

71. Spectrum4_000845

72. Spectrum5_000984

73. Sulfinpyrazone [mi]

74. Sulfinpyrazone [inn]

75. Sulfinpyrazone [jan]

76. Bidd:pxr0096

77. Schembl34421

78. Bspbio_000200

79. Bspbio_002040

80. Kbiogr_001449

81. Kbioss_001502

82. Mls000028565

83. Mls001074941

84. Divk1c_000090

85. Spectrum1500554

86. Sulfinpyrazone [vandf]

87. Spbio_001447

88. Spbio_002419

89. Sulfinpyrazone [mart.]

90. Bpbio1_000220

91. Gtpl5826

92. Sulfinpyrazone (jan/usp/inn)

93. Sulfinpyrazone [usp-rs]

94. Sulfinpyrazone [who-dd]

95. Dtxsid0023618

96. Hms500e12

97. Kbio1_000090

98. Kbio2_001502

99. Kbio2_004070

100. Kbio2_006638

101. Kbio3_001540

102. Ninds_000090

103. 1,2-diphenyl-4-(phenylsulfinylethyl)-3,5-pyrazolidinedione

104. Hms1568j22

105. Hms1921c09

106. Hms2092k11

107. Hms2095j22

108. Hms2233h11

109. Hms3259i06

110. Hms3371b22

111. Hms3712j22

112. Hms3885f12

113. Pharmakon1600-01500554

114. Bcp05344

115. Hy-b1271

116. Sulfinpyrazone [ep Impurity]

117. Sulfinpyrazone [orange Book]

118. Sulfinpyrazone For System Suitability

119. Tox21_110331

120. 4-[2-(benzenesulfinyl)ethyl]-1,2-diphenyl-pyrazolidine-3,5-dione

121. Bdbm50237626

122. Ccg-39262

123. Mfcd00057279

124. Nsc757332

125. S4628

126. Sulfinpyrazone [ep Monograph]

127. Sulfinpyrazone [usp Impurity]

128. Akos015913283

129. Tox21_110331_1

130. Db01138

131. Ds-6609

132. Nc00539

133. Nsc-757332

134. Idi1_000090

135. (invertedexclamationmarka)-sulfinpyrazone

136. Ncgc00016255-02

137. Ncgc00016255-03

138. Ncgc00016255-04

139. Ncgc00016255-05

140. Ncgc00016255-06

141. Ncgc00016255-07

142. Ncgc00016255-10

143. Ncgc00018267-01

144. Ncgc00023932-03

145. Ncgc00023932-04

146. Ac-13602

147. Ac-32767

148. (+/-)-sulfinpyrazone, Analytical Standard

149. Sbi-0051528.p003

150. Wln: T5vnnv Ehj Br& Cr& E2so&r

151. Db-053135

152. Ab00052103

153. Cs-0013052

154. Ft-0603240

155. U0114

156. 4-(phenylsulfoxyethyl)-1,5-pyrazolidinedione

157. C07317

158. D00449

159. H10364

160. 3, 1,2-diphenyl-4-[2-(phenylsulfinyl)ethyl]-

161. Ab00052103_13

162. A869550

163. Q3790542

164. Sr-01000003152-2

165. Sr-01000003152-4

166. W-105427

167. Brd-a36217750-001-05-6

168. Brd-a36217750-001-09-8

169. Z1565440323

170. Sulfinpyrazone, European Pharmacopoeia (ep) Reference Standard

171. 1,2-di(phenyl)-4-(2-phenylsulfinylethyl)pyrazolidine-3,5-dione

172. 1,2-diphenyl-4-[2-(phenylsulfinyl)-ethyl]-pyrazolidine-3,5-dione

173. Sulfinpyrazone, United States Pharmacopeia (usp) Reference Standard

174. Sulfinpyrazone For System Suitability, European Pharmacopoeia (ep) Reference Standard

175. Sulfinpyrazone; 1,2-diphenyl-4-(2-phenylsulphinylethyl)pyrazolidine-3,5-dione;(+/-)-sulfinpyrazone

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₀N₂O₃S
Molecular Weight	404.5 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	404.11946368 g/mol
Monoisotopic Mass	404.11946368 g/mol
Topological Polar Surface Area	76.9 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	571
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Uricosuric Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

EXPTL USE: SULFINPYRAZONE...PROLONGS PLATELET SURVIVAL IN MAN. ...BLOCK PLATELET AGGREGATION IN RESPONSE TO COLLAGEN & ANTIGEN-ANTIBODY COMPLEXES BUT NOT IN RESPONSE TO ADP OR THROMBIN...APPEARS RELATED TO DIMINISHED RELEASE OF ADP & 5-HYDROXYTRYPTAMINE. ...BEING STUDIED FOR...PROPHYLACTIVE VALUE IN THROMBOEMBOLIC DISORDERS

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1365

SULFINPYRAZONE USP...AS OFFICIAL 100-MG TABLETS & 200 MG CAPSULES. FOR... CHRONIC GOUT, INITIAL DOSAGE IS 100-200 MG/DAY. AFTER 1ST WK, DOSE...GRADUALLY INCR UNTIL SATISFACTORY LOWERING OF PLASMA URIC ACID IS ACHIEVED & MAINTAINED...MAY REQUIRE FROM 100-400 MG/DAY, DIVIDED INTO 2-4 DOSES & PREFERABLY GIVEN WITH MEALS.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 864

OCCASIONAL RESISTANT PT HAVE BEEN TREATED SUCCESSFULLY WITH DOSES AS HIGH AS 800 MG/DAY. LARGER DOSES ARE POORLY TOLERATED & UNLIKELY TO PRODUCE FURTHER URICOSURIC EFFECT IN RESISTANT PT. IN RESPONSIVE PT...SINGLE DAILY DOSE OF 100 MG IS SOMETIMES SATISFACTORY FOR MAINTENANCE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 864

For more Therapeutic Uses (Complete) data for SULFINPYRAZONE (10 total), please visit the HSDB record page.

4.2 Drug Warning

SULFINPYRAZONE LACKS CLINICALLY-STRIKING ANTI-INFLAMMATORY & ANALGESIC PROPERTIES OF ITS CONGENER, PHENYLBUTAZONE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 864

GI IRRITATION OCCURS IN 10-15% OF ALL PT...AN OCCASIONAL PT MAY REQUIRE DISCONTINUANCE OF ITS USE. FREQUENCY & SEVERITY INCR WITH DOSAGE...DISTRESS IS LESSENED WHEN DRUG IS TAKEN IN DIVIDED DOSES WITH MEALS. ...GIVEN TO PT WITH HISTORY OF PEPTIC ULCER ONLY WITH GREATEST CAUTION & CAREFUL OBSERVATION.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 864

...ABILITY OF DRUG TO DEPRESS HEMATOPOIESIS HAS BEEN DEMONSTRATED...PERIODIC BLOOD-CELL COUNTS ARE THEREFORE ADVISED DURING PROLONGED THERAPY. ADEQUATE PRECAUTIONS MUST ALSO BE TAKEN TO PREVENT INTRARENAL PPTN OF URATES...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 864

IN CLINICAL USE OF...URICOSURIC DRUGS, IT MUST BE KEPT IN MIND THAT THEY CAN ALTER PLASMA BINDING, DISTRIBUTION, & RENAL EXCRETION OF OTHER ORG ACIDS... WHETHER THESE BE NATURALLY OCCURRING...OR DRUGS & DRUG METABOLITES. /URICOSURICS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 865

For more Drug Warnings (Complete) data for SULFINPYRAZONE (8 total), please visit the HSDB record page.

4.3 Drug Indication

For the treatment of gout and gouty arthritis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Sulfinpyrazone's pharmacologic activity is the potentiation of the urinary excretion of uric acid. It is useful for reducing the blood urate levels in patients with chronic tophaceous gout and acute intermittent gout, and for promoting the resorption of tophi.

5.2 MeSH Pharmacological Classification

Uricosuric Agents

Gout suppressants that act directly on the renal tubule to increase the excretion of uric acid, thus reducing its concentrations in plasma. (See all compounds classified as Uricosuric Agents.)

5.3 ATC Code

M - Musculo-skeletal system

M04 - Antigout preparations

M04A - Antigout preparations

M04AB - Preparations increasing uric acid excretion

M04AB02 - Sulfinpyrazone

5.4 Absorption, Distribution and Excretion

...WELL ABSORBED AFTER ORAL ADMIN. ...BOUND TO PLASMA PROTEINS...98-99%. T/2... IN PLASMA AFTER IV INJECTION IS ABOUT 3 HR. AFTER ORAL ADMIN...URICOSURIC EFFECT MAY PERSIST FOR...10 HR. ALTHOUGH LITTLE...IS AVAILABLE FOR FILTRATION @ GLOMERULUS, IT IS SECRETED BY PROXIMAL TUBULE & UNDERGOES LITTLE PASSIVE BACK DIFFUSION...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 864

APPROX HALF OF ORALLY ADMIN DOSE APPEARS IN URINE WITHIN 24 HR. MOST OF DRUG (90%) IN URINE IS UNCHANGED; REMAINDER IS ELIMINATED AS...METABOLITE...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 864

...RAPIDLY EXCRETED IN MAN, TOGETHER WITH P-HYDROXYLATED METABOLITE. PLASMA T/2...IN RATS...16.2 HR, &...18% OF IP DOSE...WAS EXCRETED INTO URINE. PLASMA T/2 IN MAN...BETWEEN 1 & 3 HR. MAIN ROUTE OF ELIMINATION IN RAT...FECES (68% OF DOSE)...CONSIDERABLE PORTION...EXCRETED IN BILE WAS REABSORBED FROM INTESTINAL TRACT.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 578

...SULFINPYRAZONE...IS EXCRETED IN URINE OF RATS TO ONLY A SMALL EXTENT. ... CLEARED FROM CIRCULATION MAINLY THROUGH BILE...NO EVIDENCE OF ENTERO-HEPATIC CIRCULATION MECHANISM.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 133

UNCHANGED DRUG /IN RAT/ WAS PRINCIPAL EXCRETION PRODUCT & ONLY 28%...IN URINE & 24%...IN FECES & BILE WAS FOUND AS P-HYDROXYSULFINPYRAZOLE. FAILURE OF RAT TO EXCRETE A HIGH PROPORTION OF THE DRUG IN URINE MAY BE RELATED TO ITS LACK OF URICOSURIC PROPERTIES IN THIS SPECIES.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 578

5.5 Metabolism/Metabolites

MOST OF DRUG (90%) IN URINE IS UNCHANGED; REMAINDER IS ELIMINATED AS N1-P-HYDROXYPHENYL METABOLITE...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 864

.../IN RAT/ 28%...IN URINE & 24%...IN FECES & BILE WAS FOUND AS P-HYDROXYSULFINPYRAZOLE.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 578

Sulfinpyrazone has known human metabolites that include Sulfinpyrazone sulfone.

Sulfinpyrazone is a known human metabolite of sulfinpyrazone_sulfide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.6 Biological Half-Life

Approximately 4-6 hours

5.7 Mechanism of Action

Sulfinpyrazone is an oral uricosuric agent (pyrazolone derivative) used to treat chronic or intermittent gouty arthritis. Sulfinpyrazone competitively inhibits the reabsorption of uric acid at the proximal convoluted tubule, thereby facilitating urinary excretion of uric acid and decreasing plasma urate concentrations. This is likely done through inhibition of the urate anion transporter (hURAT1) as well as the human organic anion transporter 4 (hOAT4). Sulfinpyrazone is not intended for the treatment of acute attacks because it lacks therapeutically useful analgesic and anti-inflammatory effects. Sulfinpyrazone and its sulfide metabolite possess COX inhibitory effects. Sulfinpyrazone has also been shown to be a UDP-glucuronsyltransferase inhibitor and a very potent CYP2C9 inhibitor. Sulfinpyrazone is also known to be a cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor as well as an inhibitor of several multridrug resistance proteins (MRPs).

...IN SUFFICIENT DOSAGE IS POTENT INHIBITOR OF RENAL TUBULAR REABSORPTION OF URIC ACID. ...SMALL DOSES MAY REDUCE EXCRETION...PRESUMABLY BY INHIBITING SECRETORY BUT NOT REABSORPTIVE TRANSPORT. BY COMPETITIVE INHIBITION...REDUCES RENAL TUBULAR SECRETION OF OTHER ORG ANIONS...AS PAH /PARA-AMINOHIPPURIC/ & SALICYLIC ACID.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 864

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