Sodium phenylbutyrate

Sodium phenylbutyrate
Clinical data
Trade names	Buphenyl, Pheburane, Ammonaps, others
AHFS/Drugs.com	Micromedex Detailed Consumer Information
License data	US DailyMed: Sodium phenylbutyrate;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth
ATC code	A16AX03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Liver and kidney to phenylacetic acid
Elimination half-life	0.8 hours (phenylbutyrate), 1.15-1.29 hours (phenylacetate)
Excretion	Urine (80-100% as phenylacetylglutamine)
Identifiers
	IUPAC name Sodium 4-phenylbutanoate;
CAS Number	1716-12-7 ;
PubChem CID	5258;
DrugBank	DBSALT002404 ;
ChemSpider	5068 ;
UNII	NT6K61736T;
KEGG	D05868;
ChEBI	CHEBI:75316 ;
ChEMBL	ChEMBL1746 ;
CompTox Dashboard (EPA)	DTXSID7040948 ;
ECHA InfoCard	100.130.318
Chemical and physical data
Formula	C10H11NaO2
Molar mass	186.186 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [Na+].[O-]C(=O)CCCC1=CC=CC=C1;
	InChI InChI=1S/C10H12O2.Na/c11-10(12)8-4-7-9-5-2-1-3-6-9;/h1-3,5-6H,4,7-8H2,(H,11,12);/q;+1/p-1 ; Key:VPZRWNZGLKXFOE-UHFFFAOYSA-M ;
	(what is this?) (verify)

Sodium phenylbutyrate, sold under the brand name Buphenyl among others, is a salt of an aromatic fatty acid, 4-phenylbutyrate (4-PBA) or 4-phenylbutyric acid.^[7] The compound is used to treat urea cycle disorders, because its metabolites offer an alternative pathway to the urea cycle to allow excretion of excess nitrogen.^[8]^[9]

Sodium phenylbutyrate is also a histone deacetylase inhibitor and chemical chaperone, leading respectively to research into its use as an anti-cancer agent and in protein misfolding diseases such as cystic fibrosis.^[7]

^ "Prescription medicines: registration of new chemical entities in Australia, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 9 April 2023.
^ "Prescription medicines and biologicals: TGA annual summary 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 31 March 2024.
^ "Health Canada New Drug Authorizations: 2015 Highlights". Health Canada. 4 May 2016. Retrieved 7 April 2024.
^ Cite error: The named reference Buphenyl FDA label was invoked but never defined (see the help page).
^ "Olpruva - sodium phenylbutyrate kit". DailyMed. 22 December 2022. Retrieved 21 January 2023.
^ "Ammonaps EPAR". European Medicines Agency. 17 September 2018. Retrieved 3 January 2023.
^ ^a ^b Iannitti T, Palmieri B (September 2011). "Clinical and experimental applications of sodium phenylbutyrate". Drugs in R&D. 11 (3): 227–249. doi:10.2165/11591280-000000000-00000. PMC 3586072. PMID 21902286.
^ Batshaw ML, MacArthur RB, Tuchman M (January 2001). "Alternative pathway therapy for urea cycle disorders: twenty years later". The Journal of Pediatrics. 138 (1 Suppl): S46–S54, discussion S54–S55. doi:10.1067/mpd.2001.111836. PMID 11148549.
^ Walker V (September 2009). "Ammonia toxicity and its prevention in inherited defects of the urea cycle". Diabetes, Obesity & Metabolism. 11 (9): 823–835. doi:10.1111/j.1463-1326.2009.01054.x. PMID 19531057. S2CID 25998574.

[1] "Prescription medicines: registration of new chemical entities in Australia, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 9 April 2023.

[2] "Prescription medicines and biologicals: TGA annual summary 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 31 March 2024.

[3] "Health Canada New Drug Authorizations: 2015 Highlights". Health Canada. 4 May 2016. Retrieved 7 April 2024.

[Buphenyl_FDA_label-4] Cite error: The named reference Buphenyl FDA label was invoked but never defined (see the help page).

[Olpruva_FDA_label-5] "Olpruva - sodium phenylbutyrate kit". DailyMed. 22 December 2022. Retrieved 21 January 2023.

[Ammonaps_EPAR-6] "Ammonaps EPAR". European Medicines Agency. 17 September 2018. Retrieved 3 January 2023.

[r&d-7] Iannitti T, Palmieri B (September 2011). "Clinical and experimental applications of sodium phenylbutyrate". Drugs in R&D. 11 (3): 227–249. doi:10.2165/11591280-000000000-00000. PMC 3586072. PMID 21902286.

[batshaw-8] Batshaw ML, MacArthur RB, Tuchman M (January 2001). "Alternative pathway therapy for urea cycle disorders: twenty years later". The Journal of Pediatrics. 138 (1 Suppl): S46–S54, discussion S54–S55. doi:10.1067/mpd.2001.111836. PMID 11148549.

[9] Walker V (September 2009). "Ammonia toxicity and its prevention in inherited defects of the urea cycle". Diabetes, Obesity & Metabolism. 11 (9): 823–835. doi:10.1111/j.1463-1326.2009.01054.x. PMID 19531057. S2CID 25998574.

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