General Description
Nonproprietary Names
USP-NF: Fumaric Acid
Synonyms
Allomaleic acid; allomalenic acid; boletic acid; butenedioic
acid; E297; 1,2-ethenedicarboxylic acid; lichenic acid; trans-butenedioic acid;
NSC-2752; trans-1,2-ethylenedicarboxylic acid; U-1149; USAF EK-P-583.
Description
Fumaric acid occurs as white, odorless or nearly odorless, granules or as a crystalline powder that is virtually nonhygroscopic.
Chemical Name: (E)-2-Butenedioic acid
CAS Registry Number: [110-17-8]
Empirical Formula: C4H4O4
Molecular Weight: 116.07
Uses
Fumaric acid is used primarily in liquid pharmaceutical preparations as an acidulant and flavouring agent. Fumaric acid may be included as the acid part of effervescent tablet formulations, although this use is limited as the compound has an extremely low solubility in water. It is also used as a chelating agent which exhibits synergism when used in combination with other true antioxidants.
In the design of novel pelletized formulations manufactured by extrusion–spheronization, fumaric acid was used to aid spheronization, favoring the production of fine pellets. It has also been investigated as an alternative filler to lactose in pellets.
Fumaric acid has been investigated as a lubricant for effervescent tablets, and copolymers of fumaric acid and sebacic acid have been investigated as bioadhesive microspheres. It has been used in film-coated pellet formulations as an acidifying agent and also to increase drug solubility.
Fumaric acid is also used as a food additive at concentrations up to 3600 ppm, and as a therapeutic agent in the treatment of psoriasis and other skin disorders.
Incompatibilities
Fumaric acid undergoes reactions typical of an organic acid.
Safety
Fumaric acid is used in oral pharmaceutical formulations and food products, and is generally regarded as a relatively nontoxic and nonirritant material. However, acute renal failure 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.
Handling Precautions
Observe normal precautions appropriate to the circumstances and quantity of material handled. Fumaric acid may be irritating to the skin, eyes, and respiratory system, and should be handled in a well-ventilated environment. Gloves and eye protection are recommended.
Related Substances
Citric acid monohydrate; malic acid; tartaric acid.