CAS 28721-07-5|Oxcarbazepine

Introduction：Basic information about CAS 28721-07-5|Oxcarbazepine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Oxcarbazepine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles36
8. Synonyms

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	ChineseUSA	Flash Point	230.3±31.5 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	oxcarbazepine
Synonym	More Synonyms

Oxcarbazepine BiologicalActivity

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 ChannelNatural Products >>AlkaloidResearch 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.

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 ChannelNatural Products >>AlkaloidResearch 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.

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
InChIKey	CTRLABGOLIVAIY-UHFFFAOYSA-N
SMILES	NC(=O)N1c2ccccc2CC(=O)c2ccccc21
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
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

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%

Articles36

Functionalized nanocarrier combined seizure-specific vector with P-glycoprotein modulation property for antiepileptic drug delivery.

Biomaterials 74 , 64-76, (2015)

Despite optimal therapeutic regimen with currently available antiepileptic drugs (AEDs), approximately a third of epilepsy patients remain drug refractory. Region-specific overexpression of multidrug ...

Development of a SPE-HPLC-MS/MS method for the determination of most prescribed pharmaceuticals and related metabolites in urban sewage samples.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 990 , 23-30, (2015)

Based on regional prescription data several pharmaceuticals with variable amounts of prescription and corresponding metabolites were selected and analyzed in influent and effluent samples of the sewag...

Enhanced brain delivery of lamotrigine with Pluronic(®) P123-based nanocarrier.

Int. J. Nanomedicine 9 , 3923-35, (2014)

P-glycoprotein (P-gp) mediated drug efflux across the blood-brain barrier (BBB) is an important mechanism underlying poor brain penetration of certain antiepileptic drugs (AEDs). Nanomaterials, as dru...

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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