Etiracetam, (R)-
Grundinformationen
- CAS
102767-28-2- Standard-SMILES
CC[C@H](C(N)=O)N1CCCC1=O- InChIKey
HPHUVLMMVZITSG-ZCFIWIBFSA-N- Summenformel
- C8H14N2O2
- Durchschnittliche Molmasse
- 170,21 g/mol
- Monoisotopische Masse
- 170,10552769
Namen und Bezeichner
- Bevorzugter Name
- Etiracetam, (R)-
- IUPAC
- (2R)-2-(2-oxopyrrolidin-1-yl)butanamide
- Englischer Name
- (R)-2-(2-Oxo-pyrrolidin-1-yl)-butyramide
- Summenformel
- C8H14N2O2
- Molmasse
- 170.21
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,3
- Polarare Oberfläche (TPSA)
- 63,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 203
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 114 · 114-116 °C(Solv: acetone (67-64-1))
- Siedepunkt
- 395.9 · 395.9±25.0 °C(Predicted)
- Dichte
- 1.168 · 1.168±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- Löslichkeit
- Acetone (Sparingly, Sonicated), Chloroform (Slightly), Methanol (Slightly)
- pka
- 15.74 · 15.74±0.50(Predicted)
- Farbe
- White to Off-White
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m1/s1
- InChIKey
- HPHUVLMMVZITSG-ZCFIWIBFSA-N
- SMILES
- N1(CCCC1=O)[C@H](CC)C(=O)N
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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.
Gefahrenhinweise
Toxikologische Informationen
Treatment
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.
Toxicity Summary
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.
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
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
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.
Verwendung und Herstellung
Anwendungen
Verwenden(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.
Anbieter75 Anbieter
Zugehörige Reaktionen
Notizen zur Verbindung
Wird geladen…