File:Carbamazepine.svg · Wikimedia Commons · See Wikimedia Commons
carbamazepin
Sign in to saveAlso known as TEG111, 5-carbamoyl-5H-dibenz[b,f]azepine, CBZ, 5H-dibenz[b,f]azepine-5-carboxamide, 5-carbamyl-5H-dibenzo[b,f]azepine, 5-carbamoyl-5H-dibenzo[b,f]azepine
Carbamazepine, sold under the brand name Tegretol among others, is an anticonvulsant medication used in the treatment of epilepsy and neuropathic pain. It is used as an adjunctive treatment in schizophrenia along with other medications and as a second-line agent in bipolar disorder. Carbamazepine appears to work as well as phenytoin and valproate for focal and generalized seizures. It is not effective for absence or myoclonic seizures.
OverviewAI-generated
Carbamazepine, also stylized as carBAMazepine or TEGretol, is a chemical compound with the formula C₁₅H₁₂N₂O. Its IUPAC name is benzo[b][1]benzazepine-11-carboxamide. The substance has a melting point of 191.5 and a mass of 236.094963.
Chemical properties include an xlogp of 2.5 and a topological polar surface area of 46.3. The molecule features one hydrogen bond donor and one hydrogen bond acceptor, with a charge of 0. Its canonical SMILES representation is C1=CC=C2C(=C1)C=CC3=CC=CC=C3N2C(=O)N.
The compound is associated with the MCN code 2933.99.32. It has been the subject of 21,589 publications in PubMed and is referenced by 1,942 other encyclopedia articles.
Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
In the Vinony graph
Vinony's link graph records 1,942 inbound references to carbamazepin, and connects out to valproic acid, benzodiazepine drug and voltage-gated sodium channel.
It sits within the topics Anticonvulsants, Antidiuretics and CYP3A4 inducers.
Vinony links it to 43 Wikipedia language editions.
Key facts
- Drug.KEGG
- D00252
- Drug.ChEMBL
- 108
- Drug.synonyms
- CBZ
- Drug.verifiedrevid
- 451682337
- Drug.image
- Carbamazepine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 175
- Drug.image2
- Carbamazepine-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 175
- Drug.tradename
- Tegretol, others
- Drug.MedlinePlus
- a682237
- Drug.DailyMedID
- Carbamazepine
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- Oral, Intravenous
- Drug.class
- Anticonvulsant
- Drug.ATC_prefix
- N03
- Drug.ATC_suffix
- AF01
via Wikipedia infobox
Chemical data
- Formula
- C15H12N2O
- Molecular weight
- 236.27 g/mol
- IUPAC name
- benzo[b][1]benzazepine-11-carboxamide
- SMILES
- C1=CC=C2C(=C1)C=CC3=CC=CC=C3N2C(=O)N
- InChIKey
- FFGPTBGBLSHEPO-UHFFFAOYSA-N
- XLogP
- 2.5
- Polar surface area
- 46.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1968
- Admin. routes
- oral, parenteral
- Indications
- epilepsy, partial epilepsy, trigeminal neuralgia, HIV infection
via ChEMBL · EBI
Research
21,589 papers- Association of Prenatal Exposure to Antiseizure Medication With Risk of Autism and Intellectual Disability.JAMA neurology · 2022
- Oxcarbazepine.Epilepsy research. Supplement · 1991
- Oxcarbazepine: a review.Seizure · 2000
- Oxcarbazepine.Lancet (London, England) · 1989
- [Carbamazepine].Deutsche medizinische Wochenschrift (1946) · 2004
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 236.094963
- Has use
- medication
Show 11 more facts
- MCN code
- 2933.99.32
- Commons category
- Carbamazepine
- chemical formula
- C₁₅H₁₂N₂O
- melting point
- 191.5
- medical condition treated
- epilepsy
- World Health Organisation international non-proprietary name
- carbamazepine
- canonical SMILES
- C1=CC=C2C(=C1)C=CC3=CC=CC=C3N2C(=O)N
- different from
- diethylcarbamazine
- stylized name
- TEGretol
- legal status (medicine)
- boxed warning
- significant drug interaction
- danazol
Sources (11)
via Wikidata · CC0
~12 min read
Encyclopedic overview
14 sectionsContents
- Medical uses
- Adverse effects
- Pharmacogenetics
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- History
- Society and culture
- Environmental impact
- Brand names
- References
- Further reading
- External links
Carbamazepine, sold under the brand name Tegretol among others, is an anticonvulsant medication used in the treatment of epilepsy and neuropathic pain. It is used as an adjunctive treatment in schizophrenia along with other medications and as a second-line agent in bipolar disorder. Carbamazepine appears to work as well as phenytoin and valproate for focal and generalized seizures. It is not effective for absence or myoclonic seizures.
Carbamazepine was discovered in 1953 by Swiss chemist Walter Schindler. It was first marketed in 1962. It is available as a generic medication. It is on the World Health Organization's List of Essential Medicines. In 2023, it was the 185th most commonly prescribed medication in the United States, with more than 2million prescriptions.
Excerpted from Wikipedia’s “carbamazepin” article, available under the CC BY-SA 4.0 licence.