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Sodium phenylbutyrate

Sodium phenylbutyrate structure

CAS No:
1716-12-7
Formula:
C10H12O2.Na
Chemical Name:
Sodium phenylbutyrate
Synonyms:
Benzenebutanoic acid,sodium salt (1:1);Butyric acid,4-phenyl-,sodium salt;Benzenebutanoic acid,sodium salt;Sodium phenylbutyrate;Sodium 4-phenylbutyrate;Sodium γ-phenylbutyrate;TriButyrate;Buphenyl;NSC 657802;Pheburane;Ammonaps
Categories:
Biochemical Engineering > Inhibitors

Description

Sodium phenylbutyrate is an inhibitor of HDAC and endoplasmic reticulum (ER) stress, used in cancer and infection research.

Sodium phenylbutyrate is the organic sodium salt of 4-phenylbutyric acid. A prodrug for phenylacetate, it is used to treat urea cycle disorders. It has a role as a prodrug, an EC 3.5.1.98 (histone deacetylase) inhibitor, a neuroprotective agent, an orphan drug and a geroprotector. It contains a 4-phenylbutyrate.|Phenylbutyrate and sodium benzoate are orphan drugs approved for the treatment of hyperammonemia in patients with urea cycle disorders, a series of at least 8 rare genetic enzyme deficiencies. The urea cycle is the major pathway of elimination of excess nitrogen including ammonia, and absence of one of the urea cycle enzymes often causes elevations in serum ammonia which can be severe, life-threatening and result in permanent neurologic damage and cognitive deficiencies. Both phenylbutyrate and sodium benzoate act by promoting an alternative pathway of nitrogen elimination. Neither phenylbutyrate nor sodium benzoate have been linked to cases of liver injury either in the form of serum enzyme elevations during therapy or clinically apparent acute liver injury.|Sodium Phenylbutyrate is the sodium salt of phenylbutyrate, a derivative of the short-chain fatty acid butyrate, with potential antineoplastic activity. Phenylbutyrate reversibly inhibits class I and II histone deacetylases (HDACs), which may result in a global increase in gene expression, decreased cellular proliferation, increased cell differentiation, and the induction of apoptosis in susceptible tumor cell populations.

Sodium phenylbutyrate Basic Attributes

Molecular Weight：

186.18300

Exact Mass：

186.06600

EC Number：

605-612-7

UNII：

NT6K61736T

DSSTox ID：

DTXSID7040948

NCI Thesaurus Code：

C1440

ATC Code：

A16AX03|A - Alimentary tract and metabolism

HScode：

2916399090

Characteristics

PSA：

40.13000

XLogP3：

0.75920

Density：

1.095g/cm3

Melting Point：

207 °C (dec.)(lit.)

Boiling Point：

290.7ºC at 760mmHg

Flash Point：

187.9ºC

Storage Conditions：

Desiccate at -20ºC

Vapor Pressure：

0.00288mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S26; S36

RTECS Number：

XJ1921000

Marks：

Precautionary statement(s)：

P305 + P351 + P338

Hazard Statements：

H319

GHS Classification：

|Warning|H319 (97.62%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 43 companies from 5 notifications to the ECHA C&L Inventory.

Toxicity

Hepatotoxicity：

While the urea cycle disorders are caused by deficiencies of hepatic enzymes responsible for the elimination of nitrogen, patients generally present with hyperammonemia without other features or biochemical evidence of hepatic injury. Thus, serum aminotransferase, alkaline phosphatase and bilirubin levels are generally normal or only mildly elevated. Newborns presenting with hyperammonemia may have hepatomegaly but other, non-urea cycle, liver function is normal as is hepatic histology. Phenylbutyrate can help to lower ammonia levels acutely and manage to keep them in the normal or near normal range, but generally does not affect other liver functions. In open label studies, a small proportion of patients (particularly with ornithine transcarbamylase [OTC] deficiency) have had ALT or AST elevations, but these have generally been attributed to the underlying condition or its complications. Phenylbutyrate has not been linked to instances of clinically apparent liver injury with jaundice.

Drug Information

Drug Indication：

Treatment of chronic management of urea-cycle disorders.|Ammonaps is indicated as adjunctive therapy in the chronic management of urea cycle disorders, involving deficiencies of carbamylphosphate synthetase, ornithine transcarbamylase orargininosuccinate synthetase.It is indicated in all patients with neonatal-onset presentation (complete enzyme deficiencies, presenting within the first 28 days of life). It is also indicated in patients with late-onset disease(partial enzyme deficiencies, presenting after the first month of life) who have a history of hyperammonaemic encephalopathy.|Treatment of amyotrophic lateral sclerosis

LiverTox Summary：

Phenylbutyrate and sodium benzoate are orphan drugs approved for the treatment of hyperammonemia in patients with urea cycle disorders, a series of at least 8 rare genetic enzyme deficiencies. The urea cycle is the major pathway of elimination of excess nitrogen including ammonia, and absence of one of the urea cycle enzymes often causes elevations in serum ammonia which can be severe, life-threatening and result in permanent neurologic damage and cognitive deficiencies. Both phenylbutyrate and sodium benzoate act by promoting an alternative pathway of nitrogen elimination. Neither phenylbutyrate nor sodium benzoate have been linked to cases of liver injury either in the form of serum enzyme elevations during therapy or clinically apparent acute liver injury.

Drug Classes：

Urea Cycle Disorder Agents

MeSH：

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

MeSH Entry Terms：

4-phenylbutyrate

Sodium phenylbutyrate Use and Manufacturing

Uses

ACE inhibitor, antihypertensive

Use Classification：

Human drugs -> Pheburane -> EMA Drug Category|Various alimentary tract and metabolism products -> Human pharmacotherapeutic group|Human drugs -> Ammonaps -> EMA Drug Category|Other alimentary tract and metabolism products -> Human pharmacotherapeutic group|Human drugs -> Rare disease (orphan)|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:186.18
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:186.06567387
Monoisotopic Mass:186.06567387
Topological Polar Surface Area:40.1
Heavy Atom Count:13
Complexity:142
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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