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Chemistry

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Also known as: 110-17-8, Trans-butenedioic acid, Allomaleic acid, Fumarate, Lichenic acid, Boletic acid

Molecular Formula

C₄H₄O₄

Molecular Weight

116.07 g/mol

InChI Key

VZCYOOQTPOCHFL-OWOJBTEDSA-N

FDA UNII

88XHZ13131

Fumaric acid is a metabolite found in the aging mouse brain.

1 2D Structure

Fumaric Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-but-2-enedioic acid

2.1.2 InChI

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

2.1.3 InChI Key

VZCYOOQTPOCHFL-OWOJBTEDSA-N

2.1.4 Canonical SMILES

C(=CC(=O)O)C(=O)O

2.1.5 Isomeric SMILES

C(=C/C(=O)O)\C(=O)O

2.2 Other Identifiers

2.2.1 UNII

88XHZ13131

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (e)-2-butenedioic Acid

2. 2-butenedioic Acid

3. Ammonium Fumarate

4. Fumarate Dianion

5. Fumarate(2-)

6. Furamag

7. Mafusol

8. Magnesium Fumarate

9. Sodium Fumarate

2.3.2 Depositor-Supplied Synonyms

1. 110-17-8

2. Trans-butenedioic Acid

3. Allomaleic Acid

4. Fumarate

5. Lichenic Acid

6. Boletic Acid

7. (2e)-but-2-enedioic Acid

8. 2-butenedioic Acid

9. Tumaric Acid

10. Trans-1,2-ethylenedicarboxylic Acid

11. But-2-enedioic Acid

12. Allomalenic Acid

13. Trans-2-butenedioic Acid

14. (e)-2-butenedioic Acid

15. 2-butenedioic Acid, (e)-

16. Fumaricum Acidum

17. 2-butenedioic Acid (e)-

18. Kyselina Fumarova

19. Usaf Ek-p-583

20. Fema No. 2488

21. Butenedioic Acid

22. Butenedioic Acid, (e)-

23. (2e)-2-butenedioic Acid

24. (e)-but-2-enedioic Acid

25. 2-butenedioic Acid (2e)-

26. Caswell No. 465e

27. Nsc-2752

28. Fema Number 2488

29. 2-(e)-butenedioic Acid

30. 1,2-ethylenedicarboxylic Acid, (e)

31. Ccris 1039

32. Hsdb 710

33. Allomaleic-acid

34. U-1149

35. Boletic-acid

36. Trans-but-2-enedioic Acid

37. 1,2-ethenedicarboxylic Acid, Trans-

38. Epa Pesticide Chemical Code 051201

39. Fumaric Acid (nf)

40. Fumaric Acid [nf]

41. (e)-butenedioic Acid

42. Ai3-24236

43. 6915-18-0

44. Ins No.297

45. Chebi:18012

46. Ins-297

47. Nsc2752

48. Fc 33

49. 88xhz13131

50. Fum

51. 2-butenedioic Acid (2e)-, Homopolymer

52. E297

53. Lichenic Acid (van)

54. E-297

55. Dsstox_cid_1518

56. (e)-2-butenedioate

57. Dsstox_rid_76195

58. Dsstox_gsid_21518

59. Fumaric Acid 1000 Microg/ml In Acetonitrile:water

60. Kyselina Fumarova [czech]

61. (2e)-but-2-enedioate

62. Fumarsaeure

63. Donitic Acid

64. But-2-enedioicacid

65. 9003-16-1

66. Cas-110-17-8

67. Fumarate, 10

68. E-2-butenedioic Acid

69. Fumaric Acid (8ci)

70. Einecs 203-743-0

71. Fc 33 (acid)

72. Futrans-2-butenedioic Acid

73. Brn 0605763

74. Allomaleate

75. Boletate

76. Lichenate

77. Fumeric Acid

78. Unii-88xhz13131

79. Modified Gumrosin

80. Trans-butenedioate

81. Ncgc00091192-02

82. Fumaric Acid,(s)

83. Maleic Acid (ma)

84. Mfcd00002700

85. Fumaric Acid Solution

86. Trans-2-butenedioate

87. Fumaric Acid (fa)

88. 2-(e)-butenedioate

89. Fumaric Acid, 99%

90. Ethylenedicarboxylic Acid

91. (trans)-butenedioic Acid

92. F0067

93. Fumaric Acid, >=99%

94. Bmse000083

95. Fumaric Acid [ii]

96. Fumaric Acid [mi]

97. Ec 203-743-0

98. Wln: Qv1u1vq-t

99. Fumaric Acid [fcc]

100. Schembl1177

101. Fumaric Acid [fhfi]

102. Fumaric Acid [hsdb]

103. Fumaric Acid [inci]

104. Fumaric Acid [vandf]

105. 4-02-00-02202 (beilstein Handbook Reference)

106. Mls002454406

107. 2-butenedioic Acid, (2e)-

108. Fumaric Acid [mart.]

109. (2e)-2-butenedioic Acid #

110. Fumaric Acid [usp-rs]

111. Fumaric Acid [who-dd]

112. Chembl503160

113. Fumaric Acid (fragrance Grade)

114. Fumaricum Acidum [hpus]

115. Trans-1,2-ethylenedicarboxylate

116. Dtxsid3021518

117. Bdbm26122

118. Chebi:22958

119. 2(trans)-butenedioic Acid

120. Hms2270c12

121. Pharmakon1600-01301022

122. Fumaric Acid, >=99.0% (t)

123. Amy30339

124. Fumaric Acid [usp Impurity]

125. Str02646

126. Zinc3860193

127. Tox21_201769

128. Tox21_302826

129. 2-butenedioic Acid (2e)- (9ci)

130. Fumaric Acid, >=99%, Fcc, Fg

131. Nsc760395

132. S4952

133. Akos000118896

134. Fumaric Acid, Qnmr Standard For Dmso

135. Ccg-266065

136. Cs-w016599

137. Db01677

138. Hy-w015883

139. Nsc-760395

140. Ncgc00091192-01

141. Ncgc00091192-03

142. Ncgc00256360-01

143. Ncgc00259318-01

144. Bp-13087

145. Fumaric Acid, Tested According To Usp/nf

146. Ls-12976

147. Smr000112117

148. Fumaric Acid, Puriss., >=99.5% (t)

149. Fumaric Acid 100 Microg/ml In Acetonitrile

150. Malic Acid Impurity A [ep Impurity]

151. Fumaric Acid, Vetec(tm) Reagent Grade, 99%

152. 1, (e)

153. C00122

154. D02308

155. D85166

156. Q139857

157. Fumaric Acid, Bioreagent, Suitable For Cell Culture

158. J-002389

159. Fumarate; 2-butenedioic Acid; Trans-butenedioic Acid

160. Sodium Aurothiomalate Impurity B [ep Impurity]

161. F8886-8257

162. Fumaric Acid, Certified Reference Material, Tracecert(r)

163. 26b3632d-e93f-4655-90b0-3c17855294ba

164. Fumaric Acid, Anhydrous, Free-flowing, Redi-dri(tm), >=99%

165. Fumaric Acid, European Pharmacopoeia (ep) Reference Standard

166. Fumaric Acid, United States Pharmacopeia (usp) Reference Standard

167. Fumaric Acid Solution, Tracecert(r), 1h-qnmr Standard, 1 Mg/g In D2o

168. Fumaric Acid, Pharmaceutical Secondary Standard; Certified Reference Material

169. Fumaric Acid, Pharmagrade, Usp/nf, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production.

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₄H₄O₄
Molecular Weight	116.07 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	116.01095860 g/mol
Monoisotopic Mass	116.01095860 g/mol
Topological Polar Surface Area	74.6 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	119
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Fumaric acid is used in oral pharmaceutical formulations and food products, and is generally regarded as a relatively nontoxic and nonirritant material.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 277

Fumaric acid preparations are used as long term and effective treatment of psoriasis. /Fumaric acid preparation/

PMID:10627662 Raschka C, Koch Hj; Hum Exp Toxicol 18 (12): 738-9 (1999).

/EXPERIMENTAL THERAPY/ Fumaric acid and its esters (FAE) ... are already in use for treatment of psoriasis and are known to have an immunomodulatory effect ... A phase II clinical study in relapsing-remitting multiple sclerosis (RRMS) patients with the modified fumaric acid ester BG-12 showed as "proof of principle" in a frequent MRI design that FAE significantly reduce the number of gadolinium-enhancing lesions after 24 weeks of treatment. Further phase III studies have been started to explore the long-term efficacy of this substance ...

PMID:18210050 Stangel M et al; Nervenarzt 79 (2): 212-7 (2008).

/EXPERIMENTAL THERAPY/ Oral treatment of psoriasis on an outpatient basis, using a preparation containing fumaric acid derivatives, was evaluated as initial monotherapy (3 months) and as long-term basic therapy (12-14 months) in 13 and 11 patients, respectively. The course of the disease was analysed in each individual case. After completion of both parts of the trial, half of the patients that had only responded poorly to conventional antipsoriatic therapy showed a significant improvement which occurred after several weeks of treatment. In 4 patients the medication had to be stopped because of abdominal pain. No severe side effects, particularly of renal, hepatic or hematological nature, could be established. Studies in mice and rats disclosed only a low acute toxicity of the fumaric acid derivatives used. In additional analyses, hypotheses were dealt with concerning the mechanism of action of fumaric acid in psoriasis. To establish fumaric acid derivatives in the treatment of psoriasis, studies on chronic toxicity and pharmacokinetics will have to be conducted. Further clinical trials should evaluate a single fumaric acid derivative instead of mixtures. /Fumaric acid derivatives/

Bayard W et al; Hautarz (5): 279-85 (1987)

4.2 Drug Warning

Fumaric acid ...is generally regarded as a relatively nontoxic and nonirritant material. However, acute renal falure and other adverse reactions have occurred following the topical and systemic therapeutic use of fumaric acid and fumaric acid derivatives in the treatment of psoriasis or other skin disorders. Other adverse effects of oral therapy have included disturbances of liver function, gastrointestinal effects, and flushing.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 277

Two patients who developed acute renal failure during therapy with fumaric acid esters /are discussed/. Histologic findings after renal biopsy in one patient were compatible with the diagnosis of acute tubular necrosis, and renal function was restored after cessation of the medication. The histologic diagnosis in the other patient was tubulo-interstitial nephritis, possibly reactive to acute tubular necrosis. The recovery of renal function was incomplete after 9 months. Two other patients had deterioration of renal function and proteinuria during therapy with fumaric acid-esters. The symptoms were completely reversible in one patient after discontinuation of the medication, and incompletely reversible in the other.

PMID:2772586 Roodnat JI et al; Schweiz Med Wochenschr 119 (23): 826-30 (1989).

24 days after starting treatment of psoriasis with fumaric acid derivatives (0.8-1.0 g orally, plus unknown quantities locally) a 21-year-old woman developed acute oliguric renal failure with a rise of serum creatinine levels to 1094 mmol/L (12.4 mg/dL). Deterioration of renal function had been preceded by severe abdominal symptoms with nausea, vomiting and colicky pain. On admission to hospital she was dehydrated with hyponatremia and hypokalemia. There was glomerular microhematuria, increased excretion of renal epithelia, and tubular proteinuria. Renal biopsy demonstrated acute tubular damage with vacuolization of proximal epithelia, dilated tubules and scattered necroses. After intermittent hemodialysis (13 courses over two weeks) renal function gradually recovered, as demonstrated at a follow-up examination four months after discharge. /Fumaric acid derivatives/

PMID:2361438 Dalhoff K et al; Dtsch Med Wochenschr 115 (26): 1014-7 (1990).

Apart from gastrointestinal, dermatological and hematological side-effects, transient renal damage was observed during treatment with fumaric acid. The case of a 38 year old woman who was treated with fumaric acid (420 mg bid) for 5 years before she complained of fatigue and weakness. According to clinical laboratory she had developed severe proximal tubular damage. Hypophosphatemia, glycosuria and proteinuria persisted although medication was stopped immediately. /Fumaric acid preparation/

PMID:10627662 Raschka C, Koch Hj; Hum Exp Toxicol 18 (12): 738-9 (1999).

5 Pharmacology and Biochemistry

5.1 ATC Code

D - Dermatologicals

D05 - Antipsoriatics

D05A - Antipsoriatics for topical use

D05AX - Other antipsoriatics for topical use

D05AX01 - Fumaric acid

5.2 Absorption, Distribution and Excretion

The total activity of labeled carbon dioxide in the blood entering and leaving the brain was determined following a single injection of fumarate-2-(14)C in four normal human subjects. Blood samples were drawn simultaneously from the femoral artery and the superior bulb of the internal jugular vein. Also, cerebrospinal fluid specimens were collected. Evidence from the experiments indicates that there was an immmediate formation of (14)CO2 by the brain after injection of the isotope. It suggests that fumarate penetrates the blood-brain barrier with little difficulty.

European Commission, ESIS; IUCLID Dataset, Fumaric acid (110-17-8) pp.39-40 (2000 CD-ROM edition). Available from, as of February 25, 2010: https://esis.jrc.ec.europa.eu/

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SHANGHAI COVAN CHEMICAL CO., LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"UNIFORM SYNTHETICS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"23000.00","actualQuantity":"23000","unit":"KGS","unitRateFc":"1","totalValueFC":"23033.7","currency":"USD","unitRateINR":"84","date":"28-Aug-2024","totalValueINR":"1932034.5","totalValueInUsd":"23033.7","indian_port":"JNPT","hs_no":"29171950","bill_no":"5294599","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"3RD FLOOR, NO.1990 LONGYANG ROAD, PUDONG NEW DISTRICT, SHANGHAI, 201204, CN","customerAddress":"413, GOYAL TRADE CENTRE"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1725042600,"product":"FUMARIC ACID 99.5% MIN TECH GRADE","address":"304, SHYAM KAMAL, A WEST WING,","city":"MUMBAI ,MAHARASHTRA","supplier":"SNOWHITE CHEMICAL CO ","supplierCountry":"CHINA","foreign_port":"QINGDAO","customer":"JAYDIP AGENCIES","customerCountry":"INDIA","quantity":"28000.00","actualQuantity":"28000","unit":"KGS","unitRateFc":"1","totalValueFC":"26908.1","currency":"USD","unitRateINR":"80.6","date":"31-Aug-2024","totalValueINR":"2257010","totalValueInUsd":"26908.1","indian_port":"JNPT","hs_no":"29171950","bill_no":"5357234","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"QINGDAO","supplierAddress":"NO.9 BAIXIA ROAD BAIXIA DISTRICT NANJING CHINA Nanjing, CHINASDNF CHINA","customerAddress":"304, SHYAM KAMAL, A WEST WING,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1725301800,"product":"FUMARIC ACID 99.5%MIN (TECHNICAL GRADE)","address":"B\/10, KANMOOR HOUSE,","city":"MUMBAI .MAHARASHTRA","supplier":"RELYBO PHARMACHEMICAL CO ","supplierCountry":"CHINA","foreign_port":"NINGBO","customer":"R.R.INNOVATIVE PRIVATE LIMITED","customerCountry":"INDIA","quantity":"54000.00","actualQuantity":"54000","unit":"KGS","unitRateFc":"1","totalValueFC":"53308.9","currency":"USD","unitRateINR":"82.7","date":"03-Sep-2024","totalValueINR":"4467352.5","totalValueInUsd":"53308.9","indian_port":"JNPT","hs_no":"29171950","bill_no":"5400403","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Technical Grade","supplierPort":"NINGBO","supplierAddress":"NO.1 CHUANGZHI ROAD, NANJING(210019 ), JIANGSU, ., , China SDNF China China","customerAddress":"B\/10, KANMOOR HOUSE,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1725474600,"product":"FUMARIC ACID","address":"Plot no 564-A-22, Road No 92 ,? 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