PHENACEMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10N2O2
Molecular Weight	178.1879
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)NC(=O)CC1=CC=CC=C1

InChI

InChIKey=XPFRXWCVYUEORT-UHFFFAOYSA-N

InChI=1S/C9H10N2O2/c10-9(13)11-8(12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22512548

Phenacemide, also known as phenylacetylurea, is an anticonvulsant of the ureide (acetylurea) class. Phenacemide was introduced in 1949 for the treatment of epilepsy, but was eventually withdrawn from the market because of its severe side effects, which includes personality changes, blood, renal and skin disorders.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunit 72 Target ID: CHEMBL2331043 Sources: https://www.drugbank.ca/drugs/DB01121	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13451900	Primary		Approved 8583	PHENURONE Approved Use Phenacemide, also known as phenylacetylurea, is an anticonvulsant of the ureide (acetylurea) class. Launch Date 1951

Doses

Dose	Population	Adverse events
1.5 g 1 times / day steady, oral Dose: 1.5 g, 1 times / day Route: oral Route: steady Dose: 1.5 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/	unhealthy, 16 years Health Status: unhealthy Age Group: 16 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/	Other AEs: Creatinine serum increased... Other AEs: Creatinine serum increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/
2 g 1 times / day steady, oral Dose: 2 g, 1 times / day Route: oral Route: steady Dose: 2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/630790/	unhealthy, 16 years Health Status: unhealthy Age Group: 16 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/630790/	Other AEs: Creatinine increased... Other AEs: Creatinine increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/630790/
3.5 g 1 times / day steady, oral Dose: 3.5 g, 1 times / day Route: oral Route: steady Dose: 3.5 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/630790/	unhealthy, 16 years Health Status: unhealthy Age Group: 16 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/630790/	Other AEs: Creatinine increased... Other AEs: Creatinine increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/630790/
2 g 1 times / day steady, oral Dose: 2 g, 1 times / day Route: oral Route: steady Dose: 2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/	unhealthy, 18 years Health Status: unhealthy Age Group: 18 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/	Other AEs: Creatinine serum increased... Other AEs: Creatinine serum increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/
2.5 g 1 times / day steady, oral Dose: 2.5 g, 1 times / day Route: oral Route: steady Dose: 2.5 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/	unhealthy, 18 years Health Status: unhealthy Age Group: 18 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/	Other AEs: Creatinine serum increased... Other AEs: Creatinine serum increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/
4 g 1 times / day steady, oral Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/630790/	unhealthy, 23 years Health Status: unhealthy Age Group: 23 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/630790/	Other AEs: Creatinine increased... Other AEs: Creatinine increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/630790/
52 ug/mL steady, oral Dose: 52 ug/mL Route: oral Route: steady Dose: 52 ug/mL Sources: https://pubmed.ncbi.nlm.nih.gov/3683877/	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/3683877/	Sources: https://pubmed.ncbi.nlm.nih.gov/3683877/

AEs

AE	Significance	Dose	Population
Creatinine serum increased	1 patient	1.5 g 1 times / day steady, oral Dose: 1.5 g, 1 times / day Route: oral Route: steady Dose: 1.5 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/	unhealthy, 16 years Health Status: unhealthy Age Group: 16 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/
Creatinine increased	1 patient	2 g 1 times / day steady, oral Dose: 2 g, 1 times / day Route: oral Route: steady Dose: 2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/630790/	unhealthy, 16 years Health Status: unhealthy Age Group: 16 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/630790/
Creatinine increased	1 patient	3.5 g 1 times / day steady, oral Dose: 3.5 g, 1 times / day Route: oral Route: steady Dose: 3.5 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/630790/	unhealthy, 16 years Health Status: unhealthy Age Group: 16 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/630790/
Creatinine serum increased	1 patient	2 g 1 times / day steady, oral Dose: 2 g, 1 times / day Route: oral Route: steady Dose: 2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/	unhealthy, 18 years Health Status: unhealthy Age Group: 18 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/
Creatinine serum increased	1 patient	2.5 g 1 times / day steady, oral Dose: 2.5 g, 1 times / day Route: oral Route: steady Dose: 2.5 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/	unhealthy, 18 years Health Status: unhealthy Age Group: 18 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3956382/
Creatinine increased	1 patient	4 g 1 times / day steady, oral Dose: 4 g, 1 times / day Route: oral Route: steady Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/630790/	unhealthy, 23 years Health Status: unhealthy Age Group: 23 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/630790/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 116		CYP450 32

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 41	inducer 1966 Sources: https://www.sciencedirect.com/science/article/abs/pii/089669749190075T Page: 2.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 119	inhibitor 2237 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3174407/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY564374	https://www.001chemical.com/chem/63-98-9
3B Scientific (Wuhan) Corp	3B3-030387	http://www.3bsc.com/index/pro_info.php?id=51651
abcr GmbH	AB125035	http://www.abcr.com/shop/en/AB125035
AHH Chemical co.,ltd	MT-20981	http://www.ahhchemical.com/product/MT-20981.html
Alichem	19113419	http://www.alichem.com/en/products/63-98-9.html
BLD Pharm	BD147626	http://www.bldpharm.com/products/63-98-9.html
ChemMol	99117864	http://www.chemmol.com/chemmol/99117864.html
Debye Scientific	DB-054589	http://www.debyesci.com/cas_63-98-9.html
Finetech	FT-0631283	http://www.finetechnology-ind.com/prod/detail/pub/63-98-9.html
LGC Standards	LGCFOR1431.00	https://www.lgcstandards.com/US/en/p/LGCFOR1431.00
mcule	MCULE-7359277785	https://mcule.com/MCULE-7359277785/
Molcore	MC564374	https://www.molcore.com/product/63-98-9
OChem	30685	http://www.ocheminc.com/index.php?act=psearch&pid=063P989
Sigma-Aldrich	T332364_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/t332364
Smolecule	S575045	https://www.smolecule.com/products/s575045
THE BioTek	bt-364982	https://www.thebiotek.com/product/others/bt-364982

PubMed

Title	Date	PubMed
The effect of acyclovir on the tubular secretion of creatinine in vitro.	2010-12-30	21192814
Phenacemide therapy of complex partial epilepsy in children: determination of plasma drug concentrations.	1987-12	3683877
The use of phenacemide for intractable partial complex epilepsy in children.	1986-07-01	3508693
Ouabain induced seizures: site of production and response to anticonvulsants.	1978-11	743650

Patents

Sample Use Guides

In Vivo Use Guide

Phenacemide was administered orally at 500-5000 mg daily dose

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

PHENURONE

Preferred Name

English

PHENACEMIDE

Official Name

English

(Phenylacetyl)urea

Systematic Name

English

PHENACEMIDE [VANDF]

Common Name

English

BENZENEACETAMIDE, N-(AMINOCARBONYL)-

Systematic Name

English

PHENACEMIDE [MI]

Common Name

English

PHENACEMIDE [MART.]

Common Name

English

phenacemide [INN]

Common Name

English

Phenacemide [WHO-DD]

Common Name

English

NSC-39458

Code

English

PHENACEMIDE [HSDB]

Common Name

English

PHENACEMIDE [ORANGE BOOK]

Common Name

English

PHENACEMIDE [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C264