Oxcarbazepine

Names

[ Name ]:
Oxcarbazepine

[Synonym ]:
10,11-Dihydro-10-oxo-5h-dibenz[b,f]azepine-5-carboxamide,Oxacarbazepine
10,11-Dihydro-10-oxo-5h-dibenz[b,f]azepine-5-carboxamide Oxacarbazepine
Oxecarb
OXCARBAMAZEPINE
Trileptal
Oxcarbapezine
Ocarbazepine
Oxetol
Aurene
Oxcarbazepine
10-Oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide
10,11-Dihydro-10-oxo-5H-dibenzo[b,f]azepine-5-carboxamide
10,11-Dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carboxamide
10-Oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide
5H-Dibenz[b,f]azepine-5-carboxamide, 10,11-dihydro-10-oxo-
EINECS 249-188-8
OXACARBAZEPINE
MFCD00865307

Biological Activity

[Description]:

Oxcarbazepine inhibits the binding of [3H]BTX to sodium channels with IC50 of 160 μM and also inhibits the influx of 22Na+ into rat brain synaptosomes with IC50 about 100 μM.Target: Sodium ChannelOxcarbazepine is an antiepileptic drug with a chemical structure similar to carbamazepine, but with different metabolism. Oxcarbazepine is rapidly reduced to 10,11-dihydro-10-hydroxy-carbazepine (monohydroxy derivative, MHD), the clinically relevant metabolite of oxcarbazepine. MHD has (S)-(+)- and the (R)-(-)-enantiomer [1]. Oxcarbazepine (oxcarb) 600 and 900 mg (2360 and 3540 mumol) was taken by 3 volunteers (2 female, 1 male; 45-67 kg; age 22-34 years) after an overnight fast. Blood, saliva and urine were collected for the next 72 h for assay of oxcarb, 10,11-dihydro-10-hydroxy-carbamazepine (OHcarb), and 10,11-dihydro-trans-10,11-dihydroxy-carbamazepine (diol). Oxcarb reached a maximum level of about 1 microgram/ml (3.93 mumol/l) within 1 h and dropped below the detection limit (0.1 microgram/ml = 0.39 mumol/l) within 3 h. The active metabolite OHcarb appeared in the blood before oxcarb and reached the higher maximum level of 7.4 microgram/ml (29 mumol/l) after 7 h [2]. Clinical indications: EpilepsyToxicity: Isolated cases of overdose with oxcarbazepine have been reported. The maximum dose taken was approximately 24,000 mg. All patients recovered with symptomatic treatment.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Natural Products >> Alkaloid

Research Areas >> Neurological Disease

[References]

[1]. May, T.W., E. Korn-Merker, and B. Rambeck, Clinical pharmacokinetics of oxcarbazepine. Clin Pharmacokinet, 2003. 42(12): p. 1023-42.

[2]. Theisohn, M. and G. Heimann, Disposition of the antiepileptic oxcarbazepine and its metabolites in healthy volunteers. Eur J Clin Pharmacol, 1982. 22(6): p. 545-51.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
457.2±55.0 °C at 760 mmHg

[ Melting Point ]:
215-216°C

[ Molecular Formula ]:
C₁₅H₁₂N₂O₂

[ Molecular Weight ]:
252.268

[ Flash Point ]:
230.3±31.5 °C

[ Exact Mass ]:
252.089874

[ PSA ]:
63.40000

[ LogP ]:
1.44

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.662

[ Storage condition ]:
Store at RT

[ Water Solubility ]:
DMSO: ~9 mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HN8445000

CHEMICAL NAME :: 5H-Dibenz(b,f)azepine-5-carboxamide, 10,11-dihydro-10-oxo-

CAS REGISTRY NUMBER :: 28721-07-5

LAST UPDATED :: 199806

DATA ITEMS CITED :: 1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 14300 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 279,1237,1996

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn,F

[ Risk Phrases ]:
22-36-20/21/22-11

[ Safety Phrases ]:
16-36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
HN8445000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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