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Substance Name: Carbamazepine [USAN:USP:INN:BAN:JAN]
RN: 298-46-4
UNII: 33CM23913M
InChIKey: FFGPTBGBLSHEPO-UHFFFAOYSA-N

Note

  • A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.

Molecular Formula

  • C15-H12-N2-O

Molecular Weight

  • 236.273
 

Classification Codes

  • Analgesic
  • Analgesics
  • Analgesics, Non-Narcotic
  • Anticonvulsant
  • Anticonvulsants
  • Antimanic Agents
  • Cardiovascular Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Cytochrome P-450 CYP3A Inducers
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Metabolic Side Effects of Drugs and Substances
  • Mutation Data
  • Peripheral Nervous System Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Sensory System Agents
  • Sodium Channel Blockers
  • Tranquilizing Agents

Names and Synonyms

Name of Substance

  • Carbamazepine
  • Carbamazepine [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Carbamazepine

Synonyms

  • 5-20-08-00247 (Beilstein Handbook Reference)
  • 5-Carbamoyl-5H-dibenz(b,f)azepine
  • 5-Carbamoyl-5H-dibenzo(b,f)azepine
  • 5-Carbamyl-5H-dibenzo(b,f)azepine
  • 5H-Dibenz(b,f)azepine-5-carboxamide
  • Amizepin
  • Bipotrol
  • Biston
  • BRN 1246090
  • Carbamazepen
  • Carbamazepina
  • Carbamazepina [INN-Spanish]
  • Carbamazepine
  • Carbamazepinum
  • Carbamazepinum [INN-Latin]
  • Carbamezepine
  • Carbatrol
  • Carbatrol extended-release
  • Carbazepine
  • Carnexiv
  • EINECS 206-062-7
  • Epitol
  • Equetro
  • Finlepsin
  • G 32883
  • G-32883
  • Geigy 32883
  • HSDB 3019
  • Karbamazepin
  • Lexin
  • Neurotol
  • NSC 169864
  • Stazepine
  • Tegretal
  • Tegretol
  • Tegretol-XR
  • Telesmin
  • Teril
  • Timonil
  • UNII-33CM23913M

Systematic Names

  • 5H-Dibenz(b,f)azepine-5-carboxamide
  • Carbamazepine

Superlist Name

  • Carbamazepine

Registry Numbers

CAS Registry Number

  • 298-46-4

FDA UNII

  • 33CM23913M

Related Registry Number

  • 85756-57-6 (di-hydrate)

System Generated Number

  • 0000298464

Structure Descriptors

InChI

InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)

InChIKey

FFGPTBGBLSHEPO-UHFFFAOYSA-N

Smiles

NC(=O)N1c2ccccc2C=Cc3ccccc13

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 19mg/kg/4W-I (19mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS Pediatrics. Vol. 73, Pg. 841, 1984.
child TDLo oral 25926ug/kg (25.926mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 320, 1993.
child TDLo oral 55mg/kg (55mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA
Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 323, 2000.
child TDLo oral 65mg/kg (65mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: COMA
Journal of Pediatrics. Vol. 121, Pg. 295, 1992.
child TDLo oral 420mg/kg/3W-I (420mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: TREMOR

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Journal of Toxicology, Clinical Toxicology. Vol. 36, Pg. 109, 1998.
child TDLo oral 1050mg/kg/6W- (1050mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) American Journal of Psychiatry. Vol. 143, Pg. 1176, 1985.
dog LD50 oral 5620mg/kg (5620mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 63, 1972.
guinea pig LD50 oral 920mg/kg (920mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 63, 1972.
human TDLo oral 43mg/kg (43mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: NAUSEA OR VOMITING
British Medical Journal. Vol. 1, Pg. 754, 1977.
man LDLo oral 54mg/kg/9D-I (54mg/kg) BLOOD: AGRANULOCYTOSIS

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

BEHAVIORAL: ATAXIA
Canadian Medical Association Journal. Vol. 132, Pg. 1040, 1985.
man TDLo oral 94mg/kg/11D-I (94mg/kg) BLOOD: THROMBOCYTOPENIA Journal of Clinical Pyschopharmacology. Vol. 10, Pg. 305, 1990.
man TDLo oral 160mg/kg/3W-I (160mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Journal of Clinical Pyschopharmacology. Vol. 5, Pg. 185, 1985.
man TDLo oral 253mg/kg/6W-I (253mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: LIVER FUNCTION TESTS IMPAIRED
Journal of Clinical Pyschopharmacology. Vol. 6, Pg. 251, 1986.
mouse LD50 intraperitoneal 114mg/kg (114mg/kg)   Farmakologiya i Toksikologiya Vol. 53(4), Pg. 19, 1990.
mouse LD50 oral 529mg/kg (529mg/kg)   Farmaco. Vol. 44, Pg. 595, 1989.
mouse LD50 subcutaneous > 1gm/kg (1000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 477, 1980.
rabbit LD50 oral 2680mg/kg (2680mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 63, 1972.
rat LD50 intraperitoneal 158mg/kg (158mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 202, Pg. 106, 1973.
rat LD50 oral 1957mg/kg (1957mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Japanese Kokai Tokyo Koho Patents. Vol. #79-163823,
rat LD50 subcutaneous > 1500mg/kg (1500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 477, 1980.
women LDLo oral 1920mg/kg/17W (1920mg/kg) BLOOD: APLASTIC ANEMIA American Journal of Psychiatry. Vol. 142, Pg. 974, 1985.
women TDLo oral 28mg/kg/4D-I (28mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING
American Journal of Psychiatry. Vol. 143, Pg. 1328, 1986.
women TDLo oral 112mg/kg/2W-I (112mg/kg) BLOOD: THROMBOCYTOPENIA

GASTROINTESTINAL: NAUSEA OR VOMITING
American Journal of Psychiatry. Vol. 150, Pg. 1750, 1993.
women TDLo oral 144mg/kg/2W-I (144mg/kg) BLOOD: THROMBOCYTOPENIA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
Journal of Clinical Psychiatry. Vol. 53, Pg. 378, 1992.
women TDLo oral 560mg/kg/4W-I (560mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE British Journal of Clinical Practice. Vol. 43, Pg. 302, 1989.
women TDLo oral 7604mg/kg/69W (7604mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

BEHAVIORAL: GENERAL ANESTHETIC
Japanese Heart Journal. Vol. 39, Pg. 469, 1998.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 190.2 deg C   EXP
log P (octanol-water) 2.45 (none)   EXP
Water Solubility 17.7 mg/L 25 EST
Vapor Pressure 1.84E-07 mm Hg 25 EST
Henry's Law Constant 1.08E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.07E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.