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Details

Stereochemistry ACHIRAL
Molecular Formula C15H12N2O.2H2O
Molecular Weight 272.2997
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBAMAZEPINE DIHYDRATE

SMILES

c1ccc2c(c1)C=Cc3ccccc3N2C(=N)O.O.O

InChI

InChIKey=UPTJXAHTRRBMJE-UHFFFAOYSA-N
InChI=1S/C15H12N2O.2H2O/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);2*1H2

HIDE SMILES / InChI

Molecular Formula C15H12N2O
Molecular Weight 236.2691
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including: https://www.drugs.com/carbamazepine.html http://www.rxlist.com/carnexiv-drug.htm http://www.wikidoc.org/index.php/Carbamazepine

Carbamazepine is an analgesic, anti-epileptic agent that is FDA approved for the treatment of epilepsy, trigeminal neuralgia. It appears to act by reducing polysynaptic responses and blocking the post-tetanic potentiation. It depresses thalamic potential and bulbar and polysynaptic reflexes, including the linguomandibular reflex in cats. Commonly reported side effects of carbamazepine include: dizziness, drowsiness, nausea, ataxia, and vomiting. Carbamazepine is a potent inducer of hepatic CYP1A2, 2B6, 2C9/19, and 3A4 and may reduce plasma concentrations of concomitant medications mainly metabolized by CYP1A2, 2B6, 2C9/19, and 3A4 through induction of their metabolism, like Boceprevir, Cyclophosphamide, Aripiprazole, Tacrolimus, Temsirolimus and others.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
152.0 µM [IC50]
25.0 µM [Ki]
Target ID: Q9NY46|||Q9Y6P4
Gene ID: 6328.0
Gene Symbol: SCN3A
Target Organism: Homo sapiens (Human)
16.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TEGRETOL

Approved Use

Epilepsy Carbamazepine is indicated for use as an anticonvulsant drug. Evidence supporting efficacy of carbamazepine as an anticonvulsant was derived from active drug-controlled studies that enrolled patients with the following seizure types: 1. Partial seizures with complex symptomatology (psychomotor, temporal lobe). Patients with these seizures appear to show greater improvement than those with other types. 2. Generalized tonic-clonic seizures (grand mal). 3. Mixed seizure patterns which include the above, or other partial or generalized seizures. Absence seizures (petit mal) do not appear to be controlled by carbamazepine (see PRECAUTIONS, General). Trigeminal Neuralgia Carbamazepine is indicated in the treatment of the pain associated with true trigeminal neuralgia. Beneficial results have also been reported in glossopharyngeal neuralgia. This drug is not a simple analgesic and should not be used for the relief of trivial aches or pains.

Launch Date

-5.7110401E10
Primary
TEGRETOL

Approved Use

Epilepsy Carbamazepine is indicated for use as an anticonvulsant drug. Evidence supporting efficacy of carbamazepine as an anticonvulsant was derived from active drug-controlled studies that enrolled patients with the following seizure types: 1. Partial seizures with complex symptomatology (psychomotor, temporal lobe). Patients with these seizures appear to show greater improvement than those with other types. 2. Generalized tonic-clonic seizures (grand mal). 3. Mixed seizure patterns which include the above, or other partial or generalized seizures. Absence seizures (petit mal) do not appear to be controlled by carbamazepine (see PRECAUTIONS, General). Trigeminal Neuralgia Carbamazepine is indicated in the treatment of the pain associated with true trigeminal neuralgia. Beneficial results have also been reported in glossopharyngeal neuralgia. This drug is not a simple analgesic and should not be used for the relief of trivial aches or pains.

Launch Date

-5.7110401E10
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.2 μg/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAMAZEPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
1.9 μg/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAMAZEPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
11 μg/mL
800 mg 2 times / day multiple, oral
dose: 800 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CARBAMAZEPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
4.3 μg/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAMAZEPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: HIGH-FAT
3.2 μg/mL
1600 mg 1 times / day multiple, oral
dose: 1600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CARBAMAZEPINE-10,11-EPOXIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1.5 μg/mL
800 mg 1 times / day multiple, oral
dose: 800 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CARBAMAZEPINE-10,11-EPOXIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
0.11 μg/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAMAZEPINE-10,11-EPOXIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
2.2 μg/mL
800 mg 2 times / day multiple, oral
dose: 800 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CARBAMAZEPINE-10,11-EPOXIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
32.6 μg × h/mL
1600 mg 1 times / day multiple, oral
dose: 1600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CARBAMAZEPINE-10,11-EPOXIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
15.7 μg × h/mL
800 mg 1 times / day multiple, oral
dose: 800 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CARBAMAZEPINE-10,11-EPOXIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
37.5 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAMAZEPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
14.5 h
800 mg 2 times / day multiple, oral
dose: 800 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CARBAMAZEPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
34 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAMAZEPINE-10,11-EPOXIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
24%
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAMAZEPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
50%
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBAMAZEPINE-10,11-EPOXIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1000 mg 2 times / day multiple, oral
Highest studied dose
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Sources: Page: p.1297
unhealthy, 73.1 ± 5.5
n = 91
Health Status: unhealthy
Condition: Epilepsy
Age Group: 73.1 ± 5.5
Sex: M+F
Population Size: 91
Sources: Page: p.1297
Disc. AE: Skin and subcutaneous conditions NEC, Fatigue...
AEs leading to
discontinuation/dose reduction:
Skin and subcutaneous conditions NEC (8.8%)
Fatigue
Somnolence
Sources: Page: p.1297
AEs

AEs

AESignificanceDosePopulation
Skin and subcutaneous conditions NEC 8.8%
Disc. AE
1000 mg 2 times / day multiple, oral
Highest studied dose
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Sources: Page: p.1297
unhealthy, 73.1 ± 5.5
n = 91
Health Status: unhealthy
Condition: Epilepsy
Age Group: 73.1 ± 5.5
Sex: M+F
Population Size: 91
Sources: Page: p.1297
Fatigue Disc. AE
1000 mg 2 times / day multiple, oral
Highest studied dose
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Sources: Page: p.1297
unhealthy, 73.1 ± 5.5
n = 91
Health Status: unhealthy
Condition: Epilepsy
Age Group: 73.1 ± 5.5
Sex: M+F
Population Size: 91
Sources: Page: p.1297
Somnolence Disc. AE
1000 mg 2 times / day multiple, oral
Highest studied dose
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Sources: Page: p.1297
unhealthy, 73.1 ± 5.5
n = 91
Health Status: unhealthy
Condition: Epilepsy
Age Group: 73.1 ± 5.5
Sex: M+F
Population Size: 91
Sources: Page: p.1297
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
strong
yes (co-administration study)
Comment: Midazolam plasma concentrations reduced dramatically in patients treated with carbamazepine and phenytoin; The CYP3A4-mediated metabolism of cyclosporin is markedly accelerated by carbamazepine comedication; Many other likely DDIs with carbamazepine. See https://pubmed.ncbi.nlm.nih.gov/8877250/
Page: 12.0
yes
yes
yes
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Assessment of colour vision in epileptic patients exposed to single-drug therapy.
1999
N-acetyl-beta-glucosaminidase and beta-galactosidase activity in children receiving antiepileptic drugs.
1999 Jan
Potential fluconazole-induced carbamazepine toxicity.
1999 Jul-Aug
Carbamazepine-induced hepatorenal failure in a child.
1999 May
Radial microbrain form of micrencephaly: possible association with carbamazepine.
1999 Oct
Epileptic negative myoclonus induced by carbamazepine in a child with BECTS. Benign childhood epilepsy with centrotemporal spikes.
1999 Sep
Lithium-treated mood disorders, paroxysmal rhinorrhea, and mesial temporal lobe epilepsy.
1999 Summer
Carbamazepine-associated severe left ventricular dysfunction.
2000
Carbamazepine induced bradycardia.
2000 Dec
A multicenter randomized controlled trial on the clinical impact of therapeutic drug monitoring in patients with newly diagnosed epilepsy. The Italian TDM Study Group in Epilepsy.
2000 Feb
Carbamazepine-induced systemic lupus erythematosus presenting as cardiac tamponade.
2000 Feb
Gabapentin prophylaxis of clozapine-induced seizures.
2000 Mar
[Carbamazepine-induced hepatitis].
2000 Oct 10
[Two cases of auditory disturbance caused by carbamazepine].
2000 Sep
Novel treatments for bipolar disorder.
2001 Apr
Relation between dosage of carbamazepine and concentration in hair and plasma samples from a compliant inpatient epileptic population.
2001 Feb
Rufinamide: a double-blind, placebo-controlled proof of principle trial in patients with epilepsy.
2001 Feb
The response of neuropathic pain and pain in complex regional pain syndrome I to carbamazepine and sustained-release morphine in patients pretreated with spinal cord stimulation: a double-blinded randomized study.
2001 Feb
[Maintenance dose requirement for phenytoin is lowered in genetically impaired drug metabolism independent of concommitant use of other antiepileptics].
2001 Feb 17
Acute intermittent porphyria, seizures, and antiepileptic drugs: a report on a 3-year-old Nigerian boy.
2001 Jan
Effect of drugs used for neuropathic pain management on tetrodotoxin-resistant Na(+) currents in rat sensory neurons.
2001 Jan
Additional educational needs in children born to mothers with epilepsy.
2001 Jan
Treatment of bipolar affective disorder in clinical practice.
2001 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: The total daily dose of CARNEXIV is 70% of the total daily oral carbamazepine dose from which patients are being switched. The total daily dose of CARNEXIV should be equally divided in four 30-minute infusions, separated by 6 hours.
Initial Dose: 400 mg per day. Subsequent Dose: add up to 200 mg per day at weekly intervals. Maximum daily dose is 1600 mg
Route of Administration: Other
Human liver microsomes (HLMs) converted carbamazepine (30-300 microM) to 3-hydroxycarbamazepine at rates >25 times those of 2-hydroxycarbamazepine. Rates of carbamazepine 2- and 3-hydroxylation correlated strongly with CYP2B6 activity (r >or= 0.757) in a panel of HLMs (n = 8). Carbamazepine 3-hydroxylation also correlated significantly with CYP2C8 activity at a carbamazepine concentration of 30 microM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:15:23 UTC 2021
Edited
by admin
on Sat Jun 26 02:15:23 UTC 2021
Record UNII
78M1RMW7Q8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBAMAZEPINE DIHYDRATE
Common Name English
5H-DIBENZ(B,F)AZEPINE-5-CARBOXAMIDE, HYDRATE (1:2)
Systematic Name English
Code System Code Type Description
PUBCHEM
158856
Created by admin on Sat Jun 26 02:15:23 UTC 2021 , Edited by admin on Sat Jun 26 02:15:23 UTC 2021
PRIMARY
CAS
85756-57-6
Created by admin on Sat Jun 26 02:15:23 UTC 2021 , Edited by admin on Sat Jun 26 02:15:23 UTC 2021
PRIMARY
EPA CompTox
85756-57-6
Created by admin on Sat Jun 26 02:15:23 UTC 2021 , Edited by admin on Sat Jun 26 02:15:23 UTC 2021
PRIMARY
FDA UNII
78M1RMW7Q8
Created by admin on Sat Jun 26 02:15:23 UTC 2021 , Edited by admin on Sat Jun 26 02:15:23 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE