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Basic information

  • Name:

  • Carbamazepine

  • CAS No.:

  • 298-46-4

  • Molecular Structure:
  • Formula:
  • C15H12N2O
  • Molecular Weight:
  • 236.27 .
  • Synonyms:
  • Geigy 32883;Carbamazepine BP;Carbamazepine Bromine Free;5-Carbamyl-5H-dibenzo(b,f)azepine;Amizepin;Tegretal;Carbamazepine (JP14/USP);G 32883;Lexin;Karbamazepin;G-32883;Neurotol;Finlepsin;5-Carbamoyldibenzo(b,f)azepine;Carbamazepen;Tegretol (TN);5-Carbamoyl-5H-dibenzo(b,f)azepine;Carbazepine;Stazepine;Biston;5H-Dibenz[b,f]azepine-5-carboxamide;
  • EINECS:
  • 206-062-7
  • Density:
  • 1.266 g/cm3
  • Melting Point:
  • 189-192 °C
  • Boiling Point:
  • 410.984 °C at 760 mmHg
  • Flash Point:
  • 202.356 °C
  • Solubility:
  • insoluble in water
  • Appearance:
  • white solid
  • Hazard Symbols:
  • HarmfulXn
  • Risk Codes:
  • 42/43-22-20/21/22
  • Safety Description:
  • 37-24-22-36/37/39-36 Details
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Chemistry

IUPAC Name: Benzo[b][1]benzazepine-11-carboxamide
Molecular Formula: C15H12N2O
Molar mass: 236.27 g/mol
EINECS: 206-062-7
Density: 1.266 g/cm3
Flash Point: 202.4 °C
Index of Refraction: 1.669
Boiling Point: 411 °C at 760 mmHg
Vapour Pressure: 5.78E-07 mmHg at 25 °C
Melting point: 189-192 °C
Storage temp: 2-8 °C
Appearance: White Solid
Solubility: Soluble in Ethanol , Acetone , Propylene glycol , insoluble in water. Odorless, tasteless
Product categories: Acids and Derivatives;Active Pharmaceutical Ingredients;APIs;Intermediates & Fine Chemicals;Heterocycles
Structure of Carbamazepine (CAS NO.298-46-4):
                        
XLogP3-AA: 2.5
H-Bond Donor: 1
H-Bond Acceptor: 1
Canonical SMILES: C1=CC=C2C(=C1)C=CC3=CC=CC=C3N2C(=O)N
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) 

History

 Carbamazepine (CAS NO.298-46-4) was discovered by chemist Walter Schindler at J.R. Geigy AG (now part of Novartis) in Basel, Switzerland, in 1953, and was first marketed as a drug to treat trigeminal neuralgia (formerly known as tic douloureux) in 1962. It has been approved in the U.S. since 1974. Carbamazepine would be studied for bipolar disorder throughout the 1970s.

Uses

 Carbamazepine (CAS NO.298-46-4) is an anticonvulsant and mood stabilizing drug used primarily in the treatment of epilepsy and bipolar disorder, as well as trigeminal neuralgia. It is also used off-label for a variety of indications, including schizophrenia, attention-deficit hyperactivity disorder (ADHD), paroxysmal extreme pain disorder, phantom limb syndrome, and post-traumatic stress disorder.

Production

Toxicity Data With Reference

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: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 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
BEHAVIORAL: COMA
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Journal of Pediatrics. Vol. 121, Pg. 295, 1992.
child TDLo oral 420mg/kg/3W-I (420mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
BEHAVIORAL: TREMOR
BEHAVIORAL: GENERAL ANESTHETIC		 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) BEHAVIORAL: ATAXIA

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
BLOOD: AGRANULOCYTOSIS		 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) GASTROINTESTINAL: NAUSEA OR VOMITING
BLOOD: THROMBOCYTOPENIA		 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) BEHAVIORAL: GENERAL ANESTHETIC

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE		 Japanese Heart Journal. Vol. 39, Pg. 469, 1998.
 

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 42/43-22-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R22:Harmful if swallowed. 
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements: 37-24-22-36/37/39-36
S22:Do not breathe dust. 
S24:Avoid contact with skin. 
S36:Wear suitable protective clothing. 
S37:Wear suitable gloves. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 

Specification

 Carbamazepine ,its cas register number is 298-46-4. It can be called Finlepsin and Tegretol . And it has been sold under the names Biston, Tegretol, Calepsin, Equetro, Finlepsin, Sirtal, Carbatrol, Epitol, Stazepine, Telesmin, Teril, Trimonil, Timonil, Epimaz, Amizepin (Poland), Hermolepsin (Sweden), Carbama/Carbamaze (New Zealand), and Degranol (South Africa).

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