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 Phenacemide was introduced in 1949 for the treatment of epilepsy, but was eventually withdrawn from the market because of its severe side effects, which includes personality changes, blood, renal and skin disorders.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 76 Target ID: CHEMBL2331043 Sources: https://www.drugbank.ca/drugs/DB01121	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13451900	Primary		Approved 8429	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 n = 1 Health Status: unhealthy Condition: psychomotor retardation Age Group: 16 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: uncontrollable psychomotor epilepsy Age Group: 16 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: uncontrollable psychomotor epilepsy Age Group: 16 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: psychomotor retardation Age Group: 18 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: psychomotor seizures Age Group: 18 years Sex: F Population Size: 1 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 n = 1 Health Status: unhealthy Condition: uncontrollable psychomotor epilepsy Age Group: 23 years Sex: M Population Size: 1 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 n = 13 Health Status: unhealthy Condition: complex partial seizures Age Group: children Sex: unknown Population Size: 13 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 n = 1 Health Status: unhealthy Condition: psychomotor retardation Age Group: 16 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: uncontrollable psychomotor epilepsy Age Group: 16 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: uncontrollable psychomotor epilepsy Age Group: 16 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: psychomotor retardation Age Group: 18 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: psychomotor seizures Age Group: 18 years Sex: F Population Size: 1 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 n = 1 Health Status: unhealthy Condition: uncontrollable psychomotor epilepsy Age Group: 23 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/630790/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 97		CYP450 32

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 41	inducer 1573 Sources: https://www.sciencedirect.com/science/article/abs/pii/089669749190075T Page: 2.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 100	inhibitor 1626 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
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
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
abcr GmbH	AB125035	http://www.abcr.com/shop/en/AB125035
mcule	MCULE-7359277785	https://mcule.com/MCULE-7359277785/

PubMed

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

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

PHENACEMIDE

Official Name

English

(Phenylacetyl)urea

Systematic Name

English

PHENACEMIDE [VANDF]

Common Name

English

PHENURONE

Brand 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