Etiracetam, (R)-

HCID 441341

基本情報

CAS
102767-28-2
標準SMILES
CC[C@H](C(N)=O)N1CCCC1=O
InChIKey
HPHUVLMMVZITSG-ZCFIWIBFSA-N
分子式
C8H14N2O2
平均分子量
170.21 g/mol
単同位体質量
170.10552769

名称と識別子

優先名称
Etiracetam, (R)-
IUPAC
(2R)-2-(2-oxopyrrolidin-1-yl)butanamide
英語名
(R)-2-(2-Oxo-pyrrolidin-1-yl)-butyramide
分子式
C8H14N2O2
分子量
170.21

名称と別名

103765-01-1(2R)-2-(2-oxopyrrolidin-1-yl)butanamideUCB-L 060Etiracetam, (R)-etiracetam, R-isomer(R)-Etiracetam(alphaR)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide(R)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide73HC18Y1LW1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-, (R)-UCB-L-060DTXSID10146044
名称をさらに表示
Levetiracetam EP Impurity DLevetiracetaM IMpurity DLevetiracetam-4R-(+)-ETIRACETAMR-(+)-LevetiracetaMLEVETIRACETAM EP IMP Dlevetiraccetam R-isomerLevetiracetam EnantiomerLevetiracetam impurities519
LEVETIRACETAM IMPURITY D [EP IMPURITY](2R)-2-(2-OXO-PYRROLIDIN-1-YL)BUTANAMIDE1-PYRROLIDINEACETAMIDE, .ALPHA.-ETHYL-2-OXO-, (R)-(.ALPHA.R)-.ALPHA.-ETHYL-2-OXO-1-PYRROLIDINEACETAMIDE1-PYRROLIDINEACETAMIDE, .ALPHA.-ETHYL-2-OXO-, (.ALPHA.R)-LEVETIRACETAM IMPURITY D (EP IMPURITY)RefChem:596840DTXCID4068535

データベース識別子

CAS
102767-28-2、103765-01-1
PubChem CID
441341
DTXSID
DTXSID10146044
ChEMBL
CHEMBL150361
UNII
73HC18Y1LW
EC Number
642-991-8
Nikkaji
J1.380.981J

物性

構造計算による物性

XLogP
-0.3
極性表面積
63.4 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
3
重原子数
12

実験および物理化学的性質

LogP-0.6
Solubility2.98e+02 g/L
Physical DescriptionSolid

物理化学的性質

融点
114 · 114-116 °C(Solv: acetone (67-64-1))
沸点
395.9 · 395.9±25.0 °C(Predicted)
比重(密度)
1.168 · 1.168±0.06 g/cm3(Predicted)
貯蔵温度
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
溶解性
アセトン(少量、超音波処理)、クロロホルム(微量)、メタノール(微量)
酸解離定数(Pka)
15.74 · 15.74±0.50(Predicted)

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 25% (1 of 4) of reports.

Warning

H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral];H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (75%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (25%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H411 (25%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 4 reports by companies.;There are 3 notifications provided by 3 of 4 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (25%);Skin Irrit. 2 (25%);Eye Irrit. 2 (75%);STOT SE 3 (25%);Aquatic Chronic 2 (25%)

毒性情報

Treatment · 1 件

There is no specific antidote for overdose with Levetiracetam. If indicated, elimination of unabsorbed drug should be attempted by emesis or gastric lavage; usual precautions should be observed to maintain airway. General supportive care of the patient is indicated including monitoring of vital signs and observation of the patient's clinical status.

Health EffectsMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
Exposure RoutesRapidly and almost completely absorbed after oral administration (99%). Peak plasma concentrations occurring in about an hour following oral administration in fasted subjects.
Toxicity Summary · 1 件

The precise mechanism(s) by which levetiracetam exerts its antiepileptic effect is unknown. The antiepileptic activity of levetiracetam was assessed in a number of animal models of epileptic seizures. Levetiracetam did not inhibit single seizures induced by maximal stimulation with electrical current or different chemoconvulsants and showed only minimal activity in submaximal stimulation and in threshold tests. Protection was observed, however, against secondarily generalized activity from focal seizures induced by pilocarpine and kainic acid, two chemoconvulsants that induce seizures that mimic some features of human complex partial seizures with secondary generalization. Levetiracetam also displayed inhibitory properties in the kindling model in rats, another model of human complex partial seizures, both during kindling development and in the fully kindled state. The predictive value of these animal models for specific types of human epilepsy is uncertain. Levetiracetam is thought to stimulate synaptic vesicle protein 2A (SV2A), inhibiting neurotransmitter release.

Signs and SymptomsSide effects include aggression, agitation, coma, drowsiness, reduced consciousness, slowed breathing.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

wgk
WGK 3
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

The major metabolic pathway of levetiracetam (24% of dose) is an enzymatic hydrolysis of the acetamide group. No CYP450 metabolism detected. Route of Elimination: Sixty-six percent (66%) of the dose is renally excreted unchanged. The metabolites have no known pharmacological activity and are renally excreted. The mechanism of excretion is glomerular filtration with subsequent partial tubular reabsorption. Half Life: 6-8 hours

MeSH Pharmacological Classification · 2 件

Drugs used to prevent SEIZURES or reduce their severity.

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms.

Cellular LocationsCytoplasm;Membrane

用途と製造

UsesUsed as adjunctive therapy in the treatment of partial onset seizures in adults and children 4 years of age and older with epilepsy.
応用分野 · 1 件

使用(R)-Levetiracetam [REV] (Levetiracetam EP Impurity D), is the enantiomer to Levetiracetam [LEV] (L331500), the antiepileptic drug that is highly enantioselective. It is apparent that [LEV] is more potent than [REV] in terms of antiepileptic potency.

サプライヤー75 社

济南百隆化学有限公司[email protected] · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
怀化元研达生物技术有限责任公司18711085600 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
北京科迈启医药科技有限公司15910349257 15910349257 · [email protected]

関連反応

4 件

化合物ノート

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