Picamilon

Picamilon
Clinical data
Trade names	НПК ЭХО
Other names	nicotinoyl-GABA
Routes of; administration	Oral
ATC code	N02CX (WHO) ;
Legal status
Legal status	US: Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled.; RU: OTC;
Pharmacokinetic data
Bioavailability	50%–88%
Elimination half-life	1.5 hours
Excretion	Renal
Identifiers
	IUPAC name 4-(Pyridine-3-carbonylamino)butanoic acid;
CAS Number	34562-97-5 ;
PubChem CID	60608;
ChemSpider	54634 ;
UNII	0S5N9SEK4N;
CompTox Dashboard (EPA)	DTXSID40188098 ;
ECHA InfoCard	100.118.799
Chemical and physical data
Formula	C10H12N2O3
Molar mass	208.217 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(NCCCC(=O)O)c1cccnc1;
	InChI InChI=1S/C10H12N2O3/c13-9(14)4-2-6-12-10(15)8-3-1-5-11-7-8/h1,3,5,7H,2,4,6H2,(H,12,15)(H,13,14) ; Key:NAJVRARAUNYNDX-UHFFFAOYSA-N ;
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Picamilon (also known as N-nicotinoyl-GABA, pycamilon, and pikamilon) is a drug formed by a synthetic combination of niacin and γ-aminobutyric acid (GABA). It was developed in the Soviet Union in 1969^[3] and further studied in both Russia^[4] and Japan as a prodrug of GABA.^[5]

In Russia, picamilon is sold as a prescription drug. The rights to the drug belong to the Russian pharmaceutical company NPK ECHO ("НПК ЭХО"). It is not approved for sale in the United States and has been deemed an adulterating agent in dietary supplements,^[6] with five American companies required to remove their picamilon products from the market in November 2015.^[7] However, as recently as 2020, picamilon has been found in pharmaceutical dosages in over-the-counter supplements in the US.^[8]

^ "Picamilon in Dietary Supplements". FDA. November 29, 2017. Retrieved June 9, 2023.
^ ^a ^b Cite error: The named reference cui was invoked but never defined (see the help page).
^ Kopelevich VM, Gunar VI (April 1999). "Some approaches to the directed search for new drugs based on nicotinic acid". Pharmaceutical Chemistry Journal. 33 (4): 177–187. doi:10.1007/BF02509934. S2CID 36930437.
^ Mirzoian RS, Gan'shina TS (1989). "[The new cerebrovascular preparation pikamilon]". Farmakologiia i Toksikologiia (in Russian). 52 (1): 23–6. PMID 2707413.
^ Matsuyama K, Yamashita C, Noda A, Goto S, Noda H, Ichimaru Y, et al. (October 1984). "Evaluation of isonicotinoyl-gamma-aminobutyric acid (GABA) and nicotinoyl-GABA as pro-drugs of GABA". Chemical & Pharmaceutical Bulletin. 32 (10): 4089–95. doi:10.1248/cpb.32.4089. PMID 6529802.
^ Avula B, Chittiboyina AG, Sagi S, Wang YH, Wang M, Khan IA, et al. (March 2016). "Identification and quantification of vinpocetine and picamilon in dietary supplements sold in the United States". Drug Testing and Analysis. 8 (3–4): 334–43. doi:10.1002/dta.1853. PMID 26426301.
^ "FDA sends five warning letters over supplements containing picamilon". NutraIngredients-USA.com, William Reed Business Media. 2 December 2015. Retrieved 3 December 2015.
^ Cohen PA, Avula B, Wang YH, Zakharevich I, Khan I (June 2021). "Five Unapproved Drugs Found in Cognitive Enhancement Supplements". Neurology. Clinical Practice. 11 (3): e303–e307. doi:10.1212/CPJ.0000000000000960. PMC 8382366. PMID 34484905.

[1] "Picamilon in Dietary Supplements". FDA. November 29, 2017. Retrieved June 9, 2023.

[cui-2] Cite error: The named reference cui was invoked but never defined (see the help page).

[Some_approaches_to_the_directed_search_for_new_drugs_based_on_nicotinic_acid-3] Kopelevich VM, Gunar VI (April 1999). "Some approaches to the directed search for new drugs based on nicotinic acid". Pharmaceutical Chemistry Journal. 33 (4): 177–187. doi:10.1007/BF02509934. S2CID 36930437.

[pmid2707413-4] Mirzoian RS, Gan'shina TS (1989). "[The new cerebrovascular preparation pikamilon]". Farmakologiia i Toksikologiia (in Russian). 52 (1): 23–6. PMID 2707413.

[pmid6529802-5] Matsuyama K, Yamashita C, Noda A, Goto S, Noda H, Ichimaru Y, et al. (October 1984). "Evaluation of isonicotinoyl-gamma-aminobutyric acid (GABA) and nicotinoyl-GABA as pro-drugs of GABA". Chemical & Pharmaceutical Bulletin. 32 (10): 4089–95. doi:10.1248/cpb.32.4089. PMID 6529802.

[DTA2015-6] Avula B, Chittiboyina AG, Sagi S, Wang YH, Wang M, Khan IA, et al. (March 2016). "Identification and quantification of vinpocetine and picamilon in dietary supplements sold in the United States". Drug Testing and Analysis. 8 (3–4): 334–43. doi:10.1002/dta.1853. PMID 26426301.

[nutra-7] "FDA sends five warning letters over supplements containing picamilon". NutraIngredients-USA.com, William Reed Business Media. 2 December 2015. Retrieved 3 December 2015.

[neuro-8] Cohen PA, Avula B, Wang YH, Zakharevich I, Khan I (June 2021). "Five Unapproved Drugs Found in Cognitive Enhancement Supplements". Neurology. Clinical Practice. 11 (3): e303–e307. doi:10.1212/CPJ.0000000000000960. PMC 8382366. PMID 34484905.

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