Oxcarbazepine

Modify Date: 2024-01-02 07:09:59

Oxcarbazepine Structure
Oxcarbazepine structure
 Common Name Oxcarbazepine
CAS Number 28721-07-5 Molecular Weight 252.268
Density 1.3±0.1 g/cm3 Boiling Point 457.2±55.0 °C at 760 mmHg
Molecular Formula C15H12N2O2 Melting Point 215-216°C
MSDS Chinese USA Flash Point 230.3±31.5 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Oxcarbazepine


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.

 Names

Name oxcarbazepine
Synonym More Synonyms

 Oxcarbazepine 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
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.

 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

 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
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

 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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 Synonyms

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
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