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

Note

  • An anticonvulsant used to control grand mal and psychomotor or focal seizures. Its mode of action is not fully understood, but some of its actions resemble those of PHENYTOIN; although there is little chemical resemblance between the two compounds, their three-dimensional structure is similar.

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.