phenylbutanoic acid 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	24	1821-12-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: phenylbutyrate sodium 4-phenylbutanoate sodium 4-phenylbutyrate phenylbutanoic acid buphenyl pheburane benzenebutyric acid 4-Phenylbutanoic acid 4-Phenylbutyric acid gamma-Phenylbutanoic acid sodium phenylbutyrate relyvrio	Approved in combination with taurursodiol, as relyvrio, for the treatment of amyotrophic lateral sclerosis (ALS) in adults.The mechanism by which relyvrio exerts its therapeutic effects in patients with ALS is unknown. Molecular weight: 164.20 Formula: C10H12O2 CLOGP: 2.28 LIPINSKI: 0 HAC: 2 HDO: 1 TPSA: 37.30 ALOGS: -2.51 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

phenylbutyrate
sodium 4-phenylbutanoate
sodium 4-phenylbutyrate
phenylbutanoic acid
buphenyl
pheburane
benzenebutyric acid
4-Phenylbutanoic acid
4-Phenylbutyric acid
gamma-Phenylbutanoic acid
sodium phenylbutyrate
relyvrio

Approved in combination with taurursodiol, as relyvrio, for the treatment of amyotrophic lateral sclerosis (ALS) in adults.The mechanism by which relyvrio exerts its therapeutic effects in patients with ALS is unknown.

Molecular weight: 164.20
Formula: C10H12O2
CLOGP: 2.28
LIPINSKI: 0
HAC: 2
HDO: 1
TPSA: 37.30
ALOGS: -2.51
ROTB: 4

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
20	g	O

ADMET properties:

Property	Value	Reference
BA (Bioavailability)	78 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
April 30, 1996	FDA	HYPERION THERAPS INC

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hyperammonaemia	116.85	50.12	18	113	5214	63483677

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hyperammonaemic crisis	66.09	47.33	7	110	56	34956758

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hyperammonaemia	113.92	53.76	20	168	11073	79733127
Hyperammonaemic crisis	85.56	53.76	9	179	98	79744102

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A16AX03	ALIMENTARY TRACT AND METABOLISM OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS Various alimentary tract and metabolism products
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:50266	Prodrugs
CHEBI has role	CHEBI:61115	histone deacetylase inhibitors
CHEBI has role	CHEBI:68495	Type I cell-death inducers
CHEBI has role	CHEBI:63726	neuroprotective agents
CHEBI has role	CHEBI:71031	orphan drugs
CHEBI has role	CHEBI:176497	geroprotectors
MeSH PA	D000970	Antineoplastic Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Disorder of the urea cycle metabolism	indication	36444000	DOID:9267
Congenital hyperammonemia, type I	indication	62522004
Ornithine Carbamyltransferase Deficiency	indication	80908008	DOID:9271
Amyotrophic lateral sclerosis	indication	86044005	DOID:332
Citrullinemia	indication	398680004	DOID:9273
Deficiency of carbamylphosphate synthetase (CPS)	indication	765329008	DOID:9280
Hyperammonemia	off-label use	9360008
Arginase deficiency	off-label use	23501004	DOID:9278
Arginosuccinate Lyase Deficiency	off-label use	41013004	DOID:14755
Isovaleryl-CoA dehydrogenase deficiency	off-label use	87827003	DOID:14753

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.65	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
2GM/PACKET	OLPRUVA	ACER	N214860	Dec. 22, 2022	RX	FOR SUSPENSION	ORAL	11202767	Oct. 17, 2036	TREATMENT OF A UREA CYCLE DISORDER INVOLVING DEFICIENCIES OF CARBAMYLPHOSPHATE SYNTHETASE, ORNITHINE TRANSCARBAMYLASE, OR ARGININOSUCCINIC ACID SYNTHETASE
3GM/PACKET	OLPRUVA	ACER	N214860	Dec. 22, 2022	RX	FOR SUSPENSION	ORAL	11202767	Oct. 17, 2036	TREATMENT OF A UREA CYCLE DISORDER INVOLVING DEFICIENCIES OF CARBAMYLPHOSPHATE SYNTHETASE, ORNITHINE TRANSCARBAMYLASE, OR ARGININOSUCCINIC ACID SYNTHETASE
3GM/PACKET; 1GM/PACKET	RELYVRIO	AMYLYX	N216660	Sept. 29, 2022	RX	FOR SUSPENSION	ORAL	10251896	Dec. 24, 2033	TREATMENT OF AMYOTROPHIC LATERAL SCLEROSIS (ALS) IN ADULTS
3GM/PACKET; 1GM/PACKET	RELYVRIO	AMYLYX	N216660	Sept. 29, 2022	RX	FOR SUSPENSION	ORAL	10857162	Dec. 24, 2033	TREATMENT OF AMYOTROPHIC LATERAL SCLEROSIS (ALS) IN ADULTS
3GM/PACKET; 1GM/PACKET	RELYVRIO	AMYLYX	N216660	Sept. 29, 2022	RX	FOR SUSPENSION	ORAL	9872865	Dec. 24, 2033	TREATMENT OF AMYOTROPHIC LATERAL SCLEROSIS (ALS) IN ADULTS
4GM/PACKET	OLPRUVA	ACER	N214860	Dec. 22, 2022	RX	FOR SUSPENSION	ORAL	11202767	Oct. 17, 2036	TREATMENT OF A UREA CYCLE DISORDER INVOLVING DEFICIENCIES OF CARBAMYLPHOSPHATE SYNTHETASE, ORNITHINE TRANSCARBAMYLASE, OR ARGININOSUCCINIC ACID SYNTHETASE
5GM/PACKET	OLPRUVA	ACER	N214860	Dec. 22, 2022	RX	FOR SUSPENSION	ORAL	11202767	Oct. 17, 2036	TREATMENT OF A UREA CYCLE DISORDER INVOLVING DEFICIENCIES OF CARBAMYLPHOSPHATE SYNTHETASE, ORNITHINE TRANSCARBAMYLASE, OR ARGININOSUCCINIC ACID SYNTHETASE
6.67GM/PACKET	OLPRUVA	ACER	N214860	Dec. 22, 2022	RX	FOR SUSPENSION	ORAL	11202767	Oct. 17, 2036	TREATMENT OF A UREA CYCLE DISORDER INVOLVING DEFICIENCIES OF CARBAMYLPHOSPHATE SYNTHETASE, ORNITHINE TRANSCARBAMYLASE, OR ARGININOSUCCINIC ACID SYNTHETASE
6GM/PACKET	OLPRUVA	ACER	N214860	Dec. 22, 2022	RX	FOR SUSPENSION	ORAL	11202767	Oct. 17, 2036	TREATMENT OF A UREA CYCLE DISORDER INVOLVING DEFICIENCIES OF CARBAMYLPHOSPHATE SYNTHETASE, ORNITHINE TRANSCARBAMYLASE, OR ARGININOSUCCINIC ACID SYNTHETASE

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
3GM/PACKET; 1GM/PACKET	RELYVRIO	AMYLYX	N216660	Sept. 29, 2022	RX	FOR SUSPENSION	ORAL	Sept. 29, 2027	NEW CHEMICAL ENTITY
3GM/PACKET; 1GM/PACKET	RELYVRIO	AMYLYX	N216660	Sept. 29, 2022	RX	FOR SUSPENSION	ORAL	Sept. 29, 2029	TREATMENT OF AMYOTROPHIC LATERAL SCLEROSIS (ALS) IN ADULTS

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Type	Activity value (-log[M])	Bioact source
Aldose reductase	Enzyme	P15121	ALDR_HUMAN	IC50	4.02	CHEMBL
Histone deacetylase 2	Enzyme	Q92769	HDAC2_HUMAN	IC50	4.19	CHEMBL
Histone deacetylase 1	Enzyme	Q13547	HDAC1_HUMAN	IC50	4.19	CHEMBL
Histone deacetylase 8	Enzyme	Q9BY41	HDAC8_HUMAN	IC50	4.03	CHEMBL

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External reference:

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ID	Source
CLT	PDB_CHEM_ID
005954	NDDF
005955	NDDF
11518	MMSL
1545685	RXNORM
1716-12-7	SECONDARY_CAS_RN
205556	MMSL
361870	MMSL
387058003	SNOMEDCT_US
4021030	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
BUPHENYL	HUMAN PRESCRIPTION DRUG LABEL	1	75987-060	TABLET	500 mg	ORAL	NDA	22 sections
BUPHENYL	HUMAN PRESCRIPTION DRUG LABEL	1	75987-060	TABLET	500 mg	ORAL	NDA	22 sections
BUPHENYL	HUMAN PRESCRIPTION DRUG LABEL	1	75987-060	TABLET	500 mg	ORAL	NDA	22 sections
Buphenyl	HUMAN PRESCRIPTION DRUG LABEL	1	75987-070	POWDER	0.94 g	ORAL	NDA	22 sections
Buphenyl	HUMAN PRESCRIPTION DRUG LABEL	1	75987-070	POWDER	0.94 g	ORAL	NDA	22 sections
Buphenyl	HUMAN PRESCRIPTION DRUG LABEL	1	75987-070	POWDER	0.94 g	ORAL	NDA	22 sections
PHEBURANE	HUMAN PRESCRIPTION DRUG LABEL	1	71770-210	PELLET	483 mg	ORAL	NDA	28 sections
PHEBURANE	HUMAN PRESCRIPTION DRUG LABEL	1	71770-210	PELLET	483 mg	ORAL	NDA	28 sections
RELYVRIO	HUMAN PRESCRIPTION DRUG LABEL	2	73063-035	POWDER, FOR SUSPENSION	3 g	ORAL	NDA	27 sections
RELYVRIO	HUMAN PRESCRIPTION DRUG LABEL	2	73063-035	POWDER, FOR SUSPENSION	3 g	ORAL	NDA	27 sections

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