Basic information
- CAS
102767-28-2- Standard SMILES
CC[C@H](C(N)=O)N1CCCC1=O- InChIKey
HPHUVLMMVZITSG-ZCFIWIBFSA-N- Molecular formula
- C8H14N2O2
- Average molar mass
- 170.21 g/mol
- Monoisotopic mass
- 170.10552769
Names & identifiers
- Preferred name
- Etiracetam, (R)-
- IUPAC
- (2R)-2-(2-oxopyrrolidin-1-yl)butanamide
- English name
- (R)-2-(2-Oxo-pyrrolidin-1-yl)-butyramide
- Molecular formula
- C8H14N2O2
- Molecular weight
- 170.21
Names & synonyms
Show more names
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 63.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 203
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 114 · 114-116 °C(Solv: acetone (67-64-1))
- Boiling point
- 395.9 · 395.9±25.0 °C(Predicted)
- Density
- 1.168 · 1.168±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- Acetone (Sparingly, Sonicated), Chloroform (Slightly), Methanol (Slightly)
- pka
- 15.74 · 15.74±0.50(Predicted)
- color
- 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
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 73 HC18Y1LW · 73HC18Y1LW
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 302 · H302-H319-H411
- Precautionary statements
- 264 · P264-P270-P273-P280-P301+P312-P305+P351+P338
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2
Safety & regulation
GHS classification
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.
Hazard information
Toxicology
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.
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H319-H411
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2
- Precautionary statements
- P264-P270-P273-P280-P301+P312-P305+P351+P338
Chemistry & industry
Pharmacology
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.
Uses & manufacturing
Applications
Uses(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.
Suppliers75 total
Related reactions
Compound notes
Loading…