3-isobutylglutaric acid

Pale Brown Solid

An impurity of Pregabalin (P704800) with anticonvulsant properties.

3-Butylglutaric acid is an intermediate in the synthesis of pregabalin.Pregabalin is approved by the United States Food and Drug Administration (FDA) to treat neuropathic pain associated with diabetic peripheral neuropathy, spinal cord injury, and postherpetic neuralgia. Pregabalin is FDA-approved for the treatment of fibromyalgia. Pregabalin also has FDA approval as adjunctive therapy for partial-onset seizures in adults with epilepsy.

3-isobutylglutaric acid, a potential impurity which is base hydrolyzed product during Hofmann reaction, was synthesized by the reaction of (R)-(-)-3-carbamoylmethyl-5-methylhexanoic acid with excess of sodium hydroxide at elevated temperature^[1].

[1] Sripathi, S., Somesetti, N. R., Veeramalla, R., Challa, N. R., Peddi, S., Karnati, V. R. (2010). Synthesis and characterization of impurities of an anticonvulsant drug, Pregabalin. Arkivoc, 2010 1. https://doi.org/10.3998/ARK.5550190.0011.A22