carbamazepine indications/contra

Stem definitionDrug idCAS RN
tricyclic compounds 489 298-46-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • carbamazepine
  • carbamazepen
  • carbamazepin
  • carbazepine
  • carbamazepine dihydrate
  • carbamazepine hydrate
  • carbamazepine hydrochloride
  • carbamazepine sulfate
  • carbamazepine anhydrous
  • carbamazepine phosphate
  • carbamazepine tartrate
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 weight: 236.27
  • Formula: C15H12N2O
  • CLOGP: 2.38
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 46.33
  • ALOGS: -3.19
  • ROTB: 0

Drug dosage:

DoseUnitRoute
1 g O
1 g R

Approvals:

DateAgencyCompanyOrphan
March 11, 1968 FDA NOVARTIS

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Seizure 3056.89 29.92 1043 11220 39357 3334239
Drug reaction with eosinophilia and systemic symptoms 2322.72 29.92 587 11676 7308 3366288
Pyrexia 1877.03 29.92 894 11369 80221 3293375
Toxicity to various agents 1666.02 29.92 700 11563 46354 3327242
Hyponatraemia 1425.28 29.92 486 11777 17873 3355723
Maternal exposure during pregnancy 1384.19 29.92 414 11849 9857 3363739
Foetal exposure during pregnancy 1350.33 29.92 448 11815 15103 3358493
Drug interaction 1253.41 29.92 573 11690 46239 3327357
Epilepsy 1102.03 29.92 318 11945 6627 3366969
Somnolence 1032.87 29.92 448 11815 31756 3341840
Rash 1017.57 29.92 569 11694 70252 3303344
Stevens-Johnson syndrome 994.29 29.92 292 11971 6480 3367116
Abortion spontaneous 919.99 29.92 307 11956 10478 3363118
Completed suicide 887.93 29.92 399 11864 30715 3342881
Drug eruption 885.86 29.92 251 12012 4874 3368722
Exposure during pregnancy 881.63 29.92 383 11880 27180 3346416
Generalised tonic-clonic seizure 852.52 29.92 270 11993 7772 3365824
Overdose 844.97 29.92 396 11867 33582 3340014
Anticonvulsant drug level increased 841.04 29.92 166 12097 554 3373042
Gamma-glutamyltransferase increased 814.86 29.92 269 11994 8859 3364737
Dizziness 704.81 29.92 463 11800 76049 3297547
Alanine aminotransferase increased 698.68 29.92 311 11952 23329 3350267
Suicide attempt 694.41 29.92 276 11987 15571 3358025
Intentional overdose 691.01 29.92 272 11991 14953 3358643
Drug level increased 657.88 29.92 194 12069 4351 3369245
Status epilepticus 637.14 29.92 179 12084 3356 3370240
Toxic epidermal necrolysis 636.01 29.92 189 12074 4356 3369240
Aspartate aminotransferase increased 634.09 29.92 281 11982 20832 3352764
Lymphadenopathy 625.32 29.92 213 12050 7719 3365877
Coma 625.25 29.92 240 12023 12312 3361284

Pharmacologic Action:

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SourceCodeDescription
ATC N03AF01 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Carboxamide derivatives
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35477 antimanic drug
CHEBI has role CHEBI:35623 anticonvulsant
CHEBI has role CHEBI:64370 glutamate transporter activator
MeSH PA D000927 Anticonvulsants
MeSH PA D018692 Antimanic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D065701 Cytochrome P-450 CYP3A Inducers
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
FDA PE N0000008486 Decreased Central Nervous System Disorganized Electrical Activity
FDA EPC N0000175751 Mood Stabilizer
FDA MoA N0000185506 Cytochrome P450 3A4 Inducers
FDA MoA N0000191266 Cytochrome P450 1A2 Inducers
FDA MoA N0000187064 Cytochrome P450 2B6 Inducers
FDA MoA N0000185507 Cytochrome P450 2C9 Inducers
FDA MoA N0000185607 Cytochrome P450 2C19 Inducers
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018689 Sensory System Agents
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Mixed bipolar I disorder indication 16506000 DOID:3312
Trigeminal neuralgia indication 31681005 DOID:12098
Glossopharyngeal neuralgia indication 43763009 DOID:14423
Tonic-clonic seizure indication 54200006
Epilepsy indication 84757009 DOID:1826
Bipolar disorder in remission indication 85248005
Bipolar affective disorder, current episode manic indication 191618007
Localization-related epilepsy indication 230381009 DOID:2234
Lennox-Gastaut syndrome indication 230418006
Tonic-clonic epilepsy indication 352818000 DOID:7725
Epilepsy characterized by intractable complex partial seizures indication 442481002
Simple partial seizure indication 117891000119100
Mixed Epilepsy indication
Ocular hypertension contraindication 4210003 DOID:9282
Suicidal thoughts contraindication 6471006
Hypercholesterolemia contraindication 13644009
Agranulocytosis contraindication 17182001 DOID:12987
Mood swings contraindication 18963009
Glaucoma contraindication 23986001 DOID:1686
Complete atrioventricular block contraindication 27885002
Depressive disorder contraindication 35489007 DOID:2848
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Syndrome of inappropriate vasopressin secretion contraindication 55004003 DOID:3401
Acute nephropathy contraindication 58574008
Absence seizure contraindication 79631006 DOID:1825
Hyponatremia contraindication 89627008
Kidney disease contraindication 90708001 DOID:2527
Pancytopenia contraindication 127034005 DOID:12450
Impaired renal function disorder contraindication 197663003
Non-infective meningitis contraindication 230155003
Acute intermittent porphyria contraindication 234422006 DOID:3890
Disease of liver contraindication 235856003 DOID:409
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Aplastic anemia contraindication 306058006 DOID:12449
Bone marrow depression contraindication 307762000
Disorder of coronary artery contraindication 414024009
HLA-B 1502 Positive Status contraindication
Carbamazepine Toxicity contraindication
Neurohypophyseal diabetes insipidus off-label use 45369008 DOID:12388
Bipolar affective disorder, current episode depression off-label use 191627008 DOID:3312
Neuropathic pain off-label use 247398009
Attention deficit hyperactivity disorder off-label use 406506008
Rapid Cycling Bipolar Affective Disorder off-label use
Prevention of Seizures following Cranial Trauma or Surgery off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.13 acidic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
100MG EQUETRO VALIDUS PHARMS N021710 Dec. 10, 2004 RX CAPSULE, EXTENDED RELEASE ORAL 6977253 May 19, 2024 THE RECOMMENDED INITIAL DOSE OF EQUETRO IS 400MG/DAY GIVEN IN DIVIDED DOSES, TWICE DAILY. THE DOSE SHOULD BE ADJUSTED IN 200MG DAILY INCREMENTS TO ACHIEVE OPTIMAL CLINICAL RESPONSE.
200MG EQUETRO VALIDUS PHARMS N021710 Dec. 10, 2004 RX CAPSULE, EXTENDED RELEASE ORAL 6977253 May 19, 2024 THE RECOMMENDED INITIAL DOSE OF EQUETRO IS 400MG/DAY GIVEN IN DIVIDED DOSES, TWICE DAILY. THE DOSE SHOULD BE ADJUSTED IN 200MG DAILY INCREMENTS TO ACHIEVE OPTIMAL CLINICAL RESPONSE.
300MG EQUETRO VALIDUS PHARMS N021710 Dec. 10, 2004 RX CAPSULE, EXTENDED RELEASE ORAL 6977253 May 19, 2024 THE RECOMMENDED INITIAL DOSE OF EQUETRO IS 400MG/DAY GIVEN IN DIVIDED DOSES, TWICE DAILY. THE DOSE SHOULD BE ADJUSTED IN 200MG DAILY INCREMENTS TO ACHIEVE OPTIMAL CLINICAL RESPONSE.
200MG/20ML (10MG/ML) CARNEXIV LUNDBECK PHARMS LLC N206030 Oct. 7, 2016 RX SOLUTION IV (INFUSION) 9629797 Nov. 10, 2028 REPLACEMENT THERAPY FOR ORAL CARBAMAZEPINE IN ADULTS WITH GENERALIZED TONIC-CLONIC SEIZURES
200MG/20ML (10MG/ML) CARNEXIV LUNDBECK PHARMS LLC N206030 Oct. 7, 2016 RX SOLUTION IV (INFUSION) 9629797 Nov. 10, 2028 REPLACEMENT THERAPY FOR ORAL CARBAMAZEPINE IN ADULTS WITH MIXED SEIZURE PATTERNS THAT INCLUDE PARTIAL SEIZURES WITH COMPLEX SYMPTOMATOLOGY, GENERALIZED TONIC-CLONIC SEIZURES, OR OTHER PARTIAL OR GENERALIZED SEIZURES
200MG/20ML (10MG/ML) CARNEXIV LUNDBECK PHARMS LLC N206030 Oct. 7, 2016 RX SOLUTION IV (INFUSION) 9629797 Nov. 10, 2028 REPLACEMENT THERAPY FOR ORAL CARBAMAZEPINE IN ADULTS WITH PARTIAL SEIZURES WITH COMPLEX SYMPTOMATOLOGY

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
200MG/20ML (10MG/ML) CARNEXIV LUNDBECK PHARMS LLC N206030 Oct. 7, 2016 RX SOLUTION IV (INFUSION) Oct. 7, 2023 REPLACEMENT THERAPY FOR ORAL CARBAMAZEPINE FORMULATIONS, WHEN ORAL ADMINISTRATION IS TEMPORARILY NOT FEASIBLE, IN ADULTS WITH THE FOLLOWING SEIZURE TYPES: PARTIAL WITH COMPLEX SYMPTOMOLOGY, GENERALIZED CLONIC-TONIC, AND MIXED

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium channel protein type 9 subunit alpha Ion channel BLOCKER IC50 4.66 CHEMBL CHEMBL
Sodium channel protein type 4 subunit alpha Ion channel BLOCKER Ki 4.28 CHEMBL CHEMBL
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Histamine H1 receptor GPCR Ki 4.13 WOMBAT-PK
Neuronal acetylcholine receptor; alpha2/beta4 Ion channel IC50 4.31 WOMBAT-PK
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor WOMBAT-PK
Sodium-dependent serotonin transporter Transporter Kd 4.49 WOMBAT-PK
GABA-A receptor alpha-1/beta-2/gamma-2 Ion channel WOMBAT-PK

External reference:

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IDSource
DB00564 DRUGBANK_ID
5339 IUPHAR_LIGAND_ID
4017873 VUID
N0000146226 NUI
C0006949 UMLSCUI
D00252 KEGG_DRUG
CHEMBL108 ChEMBL_ID
33CM23913M UNII
1836 INN_ID
85756-57-6 SECONDARY_CAS_RN
2554 PUBCHEM_CID
4017873 VANDF
N0000007470 NDFRT
N0000146226 NDFRT
001634 NDDF
2002 RXNORM
513 MMSL
d00058 MMSL
387222003 SNOMEDCT_US
40820003 SNOMEDCT_US
4350 MMSL
CHEBI:3387 CHEBI
D002220 MESH_DESCRIPTOR_UI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Tegretol HUMAN PRESCRIPTION DRUG LABEL 1 0078-0508 SUSPENSION 100 mg ORAL NDA 24 sections
Tegretol HUMAN PRESCRIPTION DRUG LABEL 1 0078-0509 TABLET 200 mg ORAL NDA 24 sections
Tegretol HUMAN PRESCRIPTION DRUG LABEL 1 0078-0510 TABLET, EXTENDED RELEASE 100 mg ORAL NDA 24 sections
Tegretol HUMAN PRESCRIPTION DRUG LABEL 1 0078-0511 TABLET, EXTENDED RELEASE 200 mg ORAL NDA 24 sections
Tegretol HUMAN PRESCRIPTION DRUG LABEL 1 0078-0512 TABLET, EXTENDED RELEASE 400 mg ORAL NDA 24 sections
Epitol HUMAN PRESCRIPTION DRUG LABEL 1 0093-0090 TABLET 200 mg ORAL ANDA 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 0093-0109 TABLET 200 mg ORAL ANDA 14 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 0093-0778 TABLET, CHEWABLE 100 mg ORAL ANDA 14 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 0093-5512 CAPSULE, EXTENDED RELEASE 100 mg ORAL ANDA 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 0093-5513 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 0093-5514 CAPSULE, EXTENDED RELEASE 300 mg ORAL ANDA 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 0615-3505 TABLET 200 mg ORAL ANDA 13 sections
CARBAMAZEPINE HUMAN PRESCRIPTION DRUG LABEL 1 0615-4515 TABLET 100 mg ORAL ANDA 14 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 0781-5986 TABLET, EXTENDED RELEASE 100 mg ORAL NDA AUTHORIZED GENERIC 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 0781-5987 TABLET, EXTENDED RELEASE 200 mg ORAL NDA AUTHORIZED GENERIC 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 0781-5988 TABLET, EXTENDED RELEASE 400 mg ORAL NDA AUTHORIZED GENERIC 15 sections
CARBAMAZEPINE HUMAN PRESCRIPTION DRUG LABEL 1 0904-3854 TABLET, CHEWABLE 100 mg ORAL ANDA 14 sections
CARBAMAZEPINE HUMAN PRESCRIPTION DRUG LABEL 1 0904-6172 TABLET 200 mg ORAL ANDA 14 sections
CARBAMAZEPINE HUMAN PRESCRIPTION DRUG LABEL 1 13668-271 TABLET, CHEWABLE 100 mg ORAL ANDA 14 sections
CARBAMAZEPINE HUMAN PRESCRIPTION DRUG LABEL 1 16590-475 TABLET 200 mg ORAL ANDA 14 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 17856-4047 SUSPENSION 100 mg ORAL ANDA 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 21695-724 TABLET 200 mg ORAL ANDA 13 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 24236-024 TABLET 200 mg ORAL ANDA 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 24236-025 TABLET, CHEWABLE 100 mg ORAL ANDA 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 29033-004 CAPSULE, EXTENDED RELEASE 300 mg ORAL ANDA 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 29033-019 CAPSULE, EXTENDED RELEASE 100 mg ORAL ANDA 15 sections
Carbamazepine HUMAN PRESCRIPTION DRUG LABEL 1 29033-020 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 15 sections
EQUETRO HUMAN PRESCRIPTION DRUG LABEL 1 30698-419 CAPSULE, EXTENDED RELEASE 100 mg ORAL NDA 19 sections
EQUETRO HUMAN PRESCRIPTION DRUG LABEL 1 30698-421 CAPSULE, EXTENDED RELEASE 200 mg ORAL NDA 19 sections
EQUETRO HUMAN PRESCRIPTION DRUG LABEL 1 30698-423 CAPSULE, EXTENDED RELEASE 300 mg ORAL NDA 19 sections