Oxcarbazepine

Iupac Name：5-oxo-6H-benzo[b][1]benzazepine-11-carboxamide

Molecular Weight：252.273

Modify Date.: 2022-10-31 22:38

Introduction: Oxcarbazepine is a new antiepileptic carbamazepine derivative, reportedly bettertolerated than carbamazepine. It appears to be most effective in partial epilepsy withcomplex seizures. View more+

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1. Names and Identifiers

1.1 Name: Oxcarbazepine
1.2 Synonyms: 10,11-DIHDYRO-10-OXO-5H-DIBENZ[B,F]AZEPINE-5-CARBOXAMIDE 10,11-DIHYDRO-10-OXO-5H-DIBENZ[B,F]AZEPINE-5-CARBOXAMIDE 10,11-Dihydro-10-oxo-5H-dibenzo[b,f]azepine-5-carboxamide 10-Oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide 10-Oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide 5H-DIBENZ[B,F]AZEPINE-5-CARBOXAMIDE, 10,11-DIHYDRO-10-OXO- Aurene GP 47680 Oxacarbazepine Oxcarbazepine 10,11-Dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide Oxecarb Oxetol Oxtellar Timox Tolep TRILEPTAL

1.3 CAS No.: 28721-07-5

1.4 CID: 34312

1.5 EINECS(EC#): 249-188-8

1.6 Molecular Formula: C15H12N2O2 (isomer)

1.7 Inchi: InChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)

1.8 InChkey: CTRLABGOLIVAIY-UHFFFAOYSA-N

1.9 Canonical Smiles: C1C2=CC=CC=C2N(C3=CC=CC=C3C1=O)C(=O)N

1.10 Isomers Smiles: C1C2=CC=CC=C2N(C3=CC=CC=C3C1=O)C(=O)N

2. Properties

2.1 Density: 1.329

2.1 Melting point: 218 - 224 C

2.1 Boiling point: 457

2.1 Refractive index: 1.661

2.1 Flash Point: 230

2.1 Precise Quality: 252.09000

2.1 PSA: 63.40000

2.1 logP: 3.40750

2.1 Solubility: DMSO: ~9?mg/mL

2.2 Appearance: White to off-white crystalline powder

2.3 Storage: Store at RT

2.4 Chemical Properties: Oxcarbazepine is the 10-keto analogue of carbamazepine. It is a neutral lipophilic compound, and, like carbamazepine, very insoluble in water. It is not clear whether it is as unstable in humid conditions as is carbamazepine. The antiepileptic action of carbamazepine is, like carbamazepine[3–6], thought to be due primarily to blockage of voltage sensitive sodium channels, resulting in stabilization of hyper-excited neural membranes, inhibition of repetitive neuronal firing and inhibition of the spread of discharges. It also increases potassium conductance, reduces glutaminergic transmission and modulates calcium channel function. The rationale behind its original development was to use the parent molecule carbamazepine as a template, and to produce a drug as effective as carbamazepine, but with an improved side-effect profile. A key difference between the two drugs is that oxcarbazepine unlike carbamazepine is not metabolized to an epoxide derivative[7]. As the epoxide is responsible for some of the toxic effects of carbamazepine, the lack of epoxidation of Oxcarbazepine is probably one reason for its better side effect profile. Its biotransformation is largely by hydroxylation, to an active non-toxic 10-monohydroxy metabolite(MHD: 10,11 dihydro-10-hydroxy-5Hdibenzol[b,f]azepine-5-carboxamide)[7]. The pharmacological action of the drug is exerted primarily though this metabolite, and oxcarbazepine is in essence a prodrug of MHD.

2.5 Color/Form: white

2.6 Physical: Solid

2.7 pKa: 13.73±0.20(Predicted)

2.8 Water Solubility: DMSO: ~9?mg/mL

2.9 StorageTemp: Store at RT

3. Use and Manufacturing

3.1 Definition: ChEBI: A dibenzoazepine derivative, having a carbamoyl group at the ring nitrogen, substituted with an oxo group at C-4 of the azepeine ring which is also hydrogenated at C-4 and C-5. It is a anticholinergic anticonvulsant and mood stabilizing drug, used primaril in the treatment of epilepsy.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 66 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 4 of 66 companies. For more detailed information, please visit ECHA C&L website

Of the 4 notification(s) provided by 62 of 66 companies with hazard statement code(s):

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (58.06%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (58.06%): Harmful if inhaled [Warning Acute toxicity, inhalation]

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.

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501

3.3 Methods of Manufacturing: Reaction of 10-methoxy-5H-dibenz(b,f)azepine; with phosgene; gives the 5-chlorocarbonyl compound, treatment with NH3 affords 10-methoxy-5H-dibenz(b,f)azepine-5-carboxamide;, which is hydrolyzed with diluted HCl to oxcarbazepine;.

3.4 Usage: A metabolite of Eslicarbazepine acetate, (BIA 2-093), a novel central nervous system drug.

4. Safety and Handling

4.1 Risk Statements: 22-36-20/21/22-11

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl oxcarbazepine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

4.2 Octanol/Water Partition Coefficient: log Kow = 1.11 (est)

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.4 RIDADR: 20kgs

4.4 Formulations/Preparations: Oral: Suspension: 300 mg/5 mL Trileptal (with alcohol and propylene glycol), (Novartis). Tablets, film-coated: 150 mg Trileptal (scored), (Novartis), 300 mg Trileptal (scored), (Novartis), 600 mg Trileptal (scored), (Novartis).

4.5 WGK Germany: 3

4.5 RTECS: HN8445000

4.5 Toxicity

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

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Acute toxicity - Inhalation, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H312 Harmful in contact with skin H332 Harmful if inhaled
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

28721-07-5Total: 45 Synthesis Route

95-53-4 120 Suppliers

28721-07-5 259 Suppliers

Literatures:
Lohse, Olivier; Beutler, Ulrich; Fuenfschilling, Peter; Furet, Pascal; France, Julien; Kaufmann, Daniel; Penn, Gerhard; Zaugg, Werner Tetrahedron Letters, 2001 , vol. 42, # 3 p. 385 - 389
Yield: null

298-46-4 488 Suppliers

28721-07-5 259 Suppliers

Literatures:
Tian, Maoqun; Abdelrahman, Aliaa; Weinhausen, Stephanie; Hinz, Sonja; Weyer, Stefanie; Dosa, Stefan; El-Tayeb, Ali; Mueller, Christa E. Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 3 p. 1077 - 1088
Yield: null

551-93-9 199 Suppliers

28721-07-5 259 Suppliers

Literatures:
Carril, Monica; SanMartin, Raul; Churruca, Fatima; Tellitu, Imanol; Dominguez, Esther Organic Letters, 2005 , vol. 7, # 22 p. 4787 - 4789
Yield: null

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7. Precursor and Product

precursor:

332081-60-4

76041-86-6

869668-71-3

29331-92-8

332081-68-2

332081-64-8

731851-94-8

95-53-4

3335-98-6

39507-06-7

1859-70-7

54616-47-6

36507-30-9

78880-65-6

10464-31-0

28721-09-7

353497-37-7

332081-70-6

731851-85-7

3564-73-6

731851-81-3

551-93-9

298-46-4

353497-31-1

4698-11-7

View all

product :

21737-58-6

19579-83-0

29331-92-8

104746-04-5

113952-21-9

104746-03-4

8. Other Information

8.0 Usage: Oxcarbazepine is a sodium channel protein inhibitor. It is an anticonvulsant and mood-stab.

9. Computational chemical data

Molecular Weight: 252.273g/mol
Molecular Formula: C₁₅H₁₂N₂O₂
Compound Is Canonicalized: True
XLogP3-AA: 1.7
Exact Mass: 252.089877630
Monoisotopic Mass: 252.089877630
Complexity: 382
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 63.4
Heavy Atom Count: 19
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzMAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAABYAAAAABQAAAHgAQAAAADAyBmAAxwINAAACIAqRSUACCAAAlAgAIiAEAZMiIIHrAlZGEIYhghALIyecciMCOAAAAAAACAAAAAAAAAAQAAAAAAAAAAA==

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Oxcarbazepine

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Time: 2023/06/06

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Oxcarbazepine CAS 28721-07-5