Details of the Drug

General Information of Drug (ID: DMXLBCQ)

Drug Name

Sodium phenylbutyrate

Synonyms

Ammonaps; Buphenyl; EL-532; Sodium 4-phenylbutyrate; Sodium phenylbutyrate, Elan; Sodium phenylbutyrate, Medicis; Sodium phenylbutyrate, Ucyclyd; VP-101; Sodium 4-phenylbutyrate, Elan; Sodium 4-phenylbutyrate, Ucyclyd; Sodium phenylbutyrate (cancer), MacroChem/Access; Sodium phenylbutyrate (cancer), Virium/ Somanta; Sodium phenylbutyrate (cancer), Virium/Access Pharmaceuticals; Sodium 4-phenyibutyrate (cancer), MacroChem/Access; Sodium 4-phenylbutyrate (cancer), Virium/ Somanta; Sodium 4-phenylbutyrate (cancer), Virium/Access Pharmaceuticals

Indication

Disease Entry	ICD 11	Status	REF
Spinal muscular atrophy	8B61	Approved	[1]
Spinal muscular atrophy, type II	N.A.	Approved	[2]
Urea cycle disorder	5C50.A	Approved	[2]
Citrullinemia	N.A.	Investigative	[2]
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ATC Code

A16AX03: Sodium phenylbutyrate

A16AX: Various alimentary tract and metabolism products

A16A: OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS

A16: OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS

A: ALIMENTARY TRACT AND METABOLISM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski):
0

Molecular Weight

186.18

Logarithm of the Partition Coefficient

Not Available

Rotatable Bond Count

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Chemical Identifiers

Formula: C10H11NaO2
IUPAC Name: sodium;4-phenylbutanoate
Canonical SMILES: C1=CC=C(C=C1)CCCC(=O)[O-].[Na+]
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
InChIKey: VPZRWNZGLKXFOE-UHFFFAOYSA-M

Cross-matching ID

PubChem CID: 5258
ChEBI ID: CHEBI:75316
CAS Number: 1716-12-7
TTD ID: D0P2GK
ACDINA ID: D00633

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Histone deacetylase (HDAC)	TTBH0VX	NOUNIPROTAC	Inhibitor	[3]
Protein kinase C alpha (PRKCA)	TTFJ8Q1	KPCA_HUMAN	Modulator	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
116 kDa U5 small nuclear ribonucleoprotein component (EFTUD2)	OT3X7QG2	U5S1_HUMAN	Gene/Protein Processing	[5]
Actin, aortic smooth muscle (ACTA2)	OTEDLG8E	ACTA_HUMAN	Gene/Protein Processing	[6]
Activator of 90 kDa heat shock protein ATPase homolog 1 (AHSA1)	OTC7AFHT	AHSA1_HUMAN	Gene/Protein Processing	[5]
Alanine--tRNA ligase, cytoplasmic (AARS1)	OTW8D813	SYAC_HUMAN	Gene/Protein Processing	[5]
Aldo-keto reductase family 1 member C1 (AKR1C1)	OTQKR4CM	AK1C1_HUMAN	Gene/Protein Processing	[5]
ATP-dependent RNA helicase DDX55 (DDX55)	OTH8ZBPA	DDX55_HUMAN	Gene/Protein Processing	[5]
B-cell lymphoma 6 protein (BCL6)	OTQAWWO1	BCL6_HUMAN	Gene/Protein Processing	[5]
Baculoviral IAP repeat-containing protein 5 (BIRC5)	OTILXZYL	BIRC5_HUMAN	Gene/Protein Processing	[6]
Cbp/p300-interacting transactivator 2 (CITED2)	OT812TV7	CITE2_HUMAN	Gene/Protein Processing	[5]
CCR4-NOT transcription complex subunit 2 (CNOT2)	OT98OJ42	CNOT2_HUMAN	Gene/Protein Processing	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Calcium stearate	E00244	15324	lubricant
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Sodium phenylbutyrate 500 mg tablet	500 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	ClinicalTrials.gov (NCT00533559) Mechanism of Fatty Acid-induced Impairment of Glucose-simulated Insulin Secretion - Effect of Buphenyl. U.S. National Institutes of Health.
2	Sodium phenylbutyrate FDA Label
3	Histone Deacetylase inhibitors: new promise in the treatment of immune and inflammatory diseases. Curr Drug Targets. 2010 Nov;11(11):1430-8.
4	Polo-like kinase inhibitor Ro5203280 has potent antitumor activity in nasopharyngeal carcinoma.Mol Cancer Ther. 2013 Aug;12(8):1393-401.
5	Gene expression profile analysis of 4-phenylbutyrate treatment of IB3-1 bronchial epithelial cell line demonstrates a major influence on heat-shock proteins. Physiol Genomics. 2004 Jan 15;16(2):204-11.
6	Comparison of the antifibrotic effects of the pan-histone deacetylase-inhibitor panobinostat versus the IPF-drug pirfenidone in fibroblasts from patients with idiopathic pulmonary fibrosis. PLoS One. 2018 Nov 27;13(11):e0207915. doi: 10.1371/journal.pone.0207915. eCollection 2018.