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
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.
| Molecular Weight | 116.07 g/mol |
|---|---|
| Molecular Formula | C4H4O4 |
| 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 Ų |
| 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 |
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)
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).
D - Dermatologicals
D05 - Antipsoriatics
D05A - Antipsoriatics for topical use
D05AX - Other antipsoriatics for topical use
D05AX01 - Fumaric acid
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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