Etiracetam, (R)-

HCID 441341

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

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
Show more names
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

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

Experimental & physicochemical properties

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

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)

Safety & regulation

GHS classification

GHS Classification · 6 items

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

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

Toxicology

Treatment · 1 item

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 item

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).

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

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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 items

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

Uses & manufacturing

UsesUsed as adjunctive therapy in the treatment of partial onset seizures in adults and children 4 years of age and older with epilepsy.
Applications · 1 item

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

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]

Related reactions

4 records

Compound notes

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CAS 102767-28-2 Etiracetam, (R)- (HCID 441341)|Huagongshe