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HCID 4753Erstellt: 4. November 2026

Phenacemid

Efron · A-1348 · Eferon · Epheron · Felurea · Fenilep · Fenised · Fenural

https://huagongshe.com/de/chemical/4753

Molekülstruktur von Phenacemid

Identifikatoren & physikalische Daten

CAS No.63-98-9
SummenformelC9H10N2O2
Durchschnittliche Molmasse178,19 g/mol
Monoisotopische Masse178,07422757 g/mol
SMILESNC(=O)NC(=O)Cc1ccccc1
InChIKeyXPFRXWCVYUEORT-UHFFFAOYSA-N
PubChem CID4753
ChEMBLCHEMBL918
ChEBICHEBI:8049
EC No.200-570-2
DTXSIDDTXSID6023442
Lokaler NamePhenacemid

Chemische & physikalische Eigenschaften

XLogP0,9
Polarare Oberfläche (TPSA)72,2
H-Brücken-Donoren2
H-Brücken-Akzeptoren2
Frei drehbare Bindungen2
Schwere Atome13
Formalladung0
Komplexität198
ArzneimittelPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antiepileptics
LogP (Verteilungskoeffizient)Log Kow = 0.870.66
GeruchODORLESS, OR PRACTICALLY SO
GeschmackTASTELESS
Color/FormCRYSTALS FROM ALCOHOLWHITE TO PRACTICALLY WHITE, FINE, CRYSTALLINE POWDERWHITE TO CREAMY WHITE CRYSTALLINE SOLID
LöslichkeitVERY SLIGHTLY SOL IN WATERSLIGHTLY SOL IN ALC, BENZENE, CHLOROFORM, ETHERSLIGHTLY SOL IN ACETONE1.06e+00 g/L182mg/L(temperature not stated)
Human DrugsFDA approved drugs -> Active ingredientPharmaceuticals
DecompositionWhen heated to decomposition it emits toxic fumes of NOx.
Schmelzpunkt212-216 °C215 °C214-216 °C
Physical DescriptionSolid
Stability/Shelf LifeCommercially available phenacemide tablets have an expiration date of 5 years following the data of manufacture.
Collision Cross Section148.19 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]128.3 Ų [M+H]+ [CCS Type: TW
Siedepunkt310.41°C (rough estimate)
Dichte1.2221 (rough estimate)
Brechungsindex1.5600 (estimate)
pKa (Säurekonstante)12.38±0.70(Predicted)
FarbeCrystals from EtOH
CAS Datenbank63-98-9
EPA chemische InformationenPhenacemide (63-98-9)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Regulatorische InformationenHazard Traits - Developmental Toxicity
FDA-AnforderungenManufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).
Special ReportsTroupin ASDrug Saf 14: 299-328 (1996). Dose related adverse effects of anticonvulsants.Badalian LO, et alZh Nevropatol Psikhiatr Im S S Korsakova 93 (1): 90-3 (1993). Epilepsy and pregnancy a review.Dostert P, Benedetti MSEncephale 10 (5): 199-209 (1984). The first part of this article presents the mechanisms for the hepatotoxicity of xenobiotics known to date, in particular the interference with the metabolism of bilirubin, hepatotoxicity arising from the metabolism of drugs as well as hepatotoxicity due to immunological factors. In the second part, the classification of the diverse hepatic diseases due to drugs is presented: acute injury (cytotoxic, cholestatic, mixed) and chronic damage. The extrahepatic manifestations of drug induced hepatic injury are also mentioned. Finally, in the third part, ... the principal cases of hepatotoxicity caused by psychotropic drugs /is presented/: antidepressants (MAOIs and tricyclics), neuroleptics, phenothiazines, thioxanthenes, butyrophenones and benzamides) and anxiolytics, and ... the anticonvulsants (phenytoin, phenacemide, oxazolidinediones, carbamazepine and valproic acid). ...
Hazard Classes and CategoriesAcute Tox. 4 (100%)
LagerbedingungenStore below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by manufacturer. Store in a well-closed container. /Phenacemide Tablets USP/
WechselwirkungenConcurrent use of alcohol or CNS depression-producing medications with phenacemide may enhance CNS depression.

Anwendungen & Verwendung

Verwenden

Anticonvulsant.

There is a risk of additive toxicity when other anticonvulsants (especially ethotoin) are used concurrently with phenacemide. Concurrent use of ethotoin with phenacemide has been reported to cause paranoid symptoms. Extreme caution is recommended during concurrent use of phenacemide with other anticonvulsants.
Gesundheitliche AuswirkungenMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
ExpositionspfadeAlmost completely absorbed.
ToxizitätsübersichtPhenacemide binds to and blocks neuronal sodium channels or voltage sensitive calcium channels. This blocks or suppresses neuronal depolarization and hypersynchronization. Hypersynchronization is what often causes seizures.
Human Toxicity ExcerptsOverdosage of phenacemide produces excitement or mania followed by drowsiness, ataxia, and coma which has persisted for nearly 24 hours.Clinical effects of overdose /of phenacemide/ include excitement or mania (unusual nervousness or irritability), ataxia (clumsiness or unsteadiness), and severe drowsiness.OBJECTIVE: To report two cases of incr true serum creatinine (Scr) without renal failure caused by an anticonvulsant drug, phenacemide, and to discuss the possible mechanisms. CASE SUMMARY: Two patients treated with phenacemide were investigated for markedly incr Scr and decr creatinine clearance (Clcr) values. Glomerular filtration rates, as determined by (125)I-iothlalamate clearance, were normal in both patients and analytical interferences with the Jaffe reaction were excluded. After discontinuation of the drug, phenacemide concn became undetectable within 2 days but it took 7-14 days for Scr and Clcr to return to normal values. DISCUSSION: The Scr increase with phenacemide (120-170 percent) was higher than that reported with cimetidine or trimethoprim (10-40%) and could not be explained solely by inhibition of the tubular secretion of creatinine. The hypothesis of an overproduction of creatinine caused by phenacemide was ruled out by experimental studies in rats. Creatinine incr in tissues was lower than that in the serum of rats given phenacemide. In vitro creatinine influx into red blood cells was inhibited in a dose dependent way by phenacemide. CONCLUSIONS: Incr Scr concn in these patients could be related to an inhibition of transport and a decr in creatinine volume of distribution. Creatinine concn should not be considered when dosage adjustments of renally eliminated drugs are being calculated for patients with such metabolic interferences.Three adolescent patients with severe seizure disorders were treated with phenacemide. All three patients showed elevated serum creatinine and normal blood urea nitrogen values while on phenacemide. Simultaneous urea and creatinine clearance studies performed on each patient demonstrated normal urea clearances and decr creatinine clearances. Inulin clearance performed in one patient was normal. The medication was discontinued in two of the patients because of co-existing neutropenia. Serum creatinine values returned to normal after phenacemide treatment was terminated. The elevation in serum creatinine values with phenacemide appears to be dose related, reversible, and unrelated to impairment of glomerular filtration.The Hungarian Case-Control Surveillance of Congenital Anomalies from 1980-1987, involved 10,698 malformed cases and 21,546 non-malformed controls. Ninety-five pregnant women were treated by 144 anticonvulsants excluding diazepam and barbiturates. The rate of anticonvulsant use was 2.9 times higher in pregnant women having malformed offspring than in control mothers and this difference was greater in polytherapy than in monotherapy.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity ExcerptsHIGH DOSES OF PHENACEMIDE IN ANIMALS CAUSE CNS DEPRESSION.... In this paper the ... parameters for the description of teratogenic potency and hazard in quantitative terms /is detailed/.. Derivation and calculation of the parameters are illustrated by the analysis of adult lethality and teratogenicity data of eight structurally related anhydrides and imides, following testing in the CD-1 mouse. Teratogenicity was evaluated following treatment on Days 8-10 of gestation, using an average of four dose groups per compound and at least 10 dams per group. Adult lethality was estimated following a similar 3 day dosage schedule with an average of 6 dose groups per compound and at least 8 animals per group. Dose response relationships of teratogenicity were fitted to a probit model from which tD50 (median effective dose), and other effective doses were computed. It is proposed that tD05, as a minimum teratogenic dose, best represents teratogenic potency. In this study, potency ranged from 0.17 mmol/kg/day for phenytoin to 5.2 mmol/kg/day for ethosuximide. In order to measure teratogenic hazard a ratio between adult toxic (lethality was chosen as the most appropriate measure) and teratogenic responses was made. Since the dose response slopes of lethality and teratogenicity were different, a simple ratio between median effective doses could not be used. It is shown that a ratio of LDOl to tD05 provides a Relative Teratogenic Index (RTI) which reflects the teratogenic hazard of a test agent. The following RTI values (LDOl/tD05) were computed in this study: phthalic anhydride, 0.9phensuximide, 1.0succinic anhydride, 1.0ethosuximide, 1.2phenytoin, 1.6phenacemide, 3.3trimethadione, 4.0and sodium valproate, 4.1. For these data, tD05 and RTI clearly represent the differing teratogenic potencies and hazards of the tested compounds. it is suggested that these parameters may be useful in comparative teratogenicity studies and may be valuable components of developmental toxicity risk assessment.Human lymphocytes incubated with a mouse hepatic microsomal drug metabolizing system were used to study the cytotoxicity of four anticonvulsants. In vitro toxicity assessed by trypan blue dye exclusion was significantly greater for compounds with relatively high clinical toxicity (mephenytoin and phenacemide) than those with only rare cytotoxic complications (phenytoin and phenobarbital). No toxicity occurred in the absence of microsomes and toxicity was enhanced by inhibitors of epoxide hydrolase suggesting that the cytotoxicity of the drugs may result from arene oxide metabolites. In vivo, the covalent binding of such metabolites to cell macromolecules could lead to cell death and, by acting as haptens, to secondary hypersensitivity reactions. The method may be useful in assessing the potential of a drug for toxicity, the mechanism of cell damage and individual differences in cell defenses within the human population.
Antidote and Emergency TreatmentInitial treatment should include gastric lavage and/or induction of emesis and general supportive measures. The patient's renal, hepatic, and hematologic status, and mental state should be carefully evaluated following recovery from acute overdosage.There is no specific antidote for phenacemide overdose. Recommended treatment consists of the following. To decrease absorption - evacuation of stomach by induction of emesis or lavage. Supportive care - patients in whom intentional overdose is confirmed or suspected should be referred for psychiatric consultation. Following recovery, evaluation of hepatic and renal function, mental state, and blood-forming organs should be performed.
Toxicity DataLD50: 987 mg/kg (Oral, Mouse) (A308) LD50: 2500 mg/kg (Oral, Rabbit) (A308) LD50: 1600 mg/kg (Oral, Rat) (A308)
Non-Human Toxicity ValuesOral LD50 mice = 5.54 mmol/kgOral LD50 rat = >10 mmol/kg
Zollcode29242998
R-Sätze (R)22
ToxizitätLD50 in mice, rats (mmol/kg): 5.54, >10 orally (Nakamura)
GefahrensymboleXn
Gefahrstoffdaten63-98-9(Hazardous Substances Data)