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carbamazepine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
tricyclic compounds	489	298-46-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: carbamazepine carbamazepen carbamazepin carbazepine carbamazepine dihydrate carbamazepine hydrate carbamazepine hydrochloride carbamazepine sulfate carbamazepine anhydrous carbamazepine phosphate carbamazepine tartrate	A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties. Molecular weight: 236.27 Formula: C15H12N2O CLOGP: 2.24 LIPINSKI: 0 HAC: 3 HDO: 1 TPSA: 46.33 ALOGS: -3.19 ROTB: 0 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

carbamazepine
carbamazepen
carbamazepin
carbazepine
carbamazepine dihydrate
carbamazepine hydrate
carbamazepine hydrochloride
carbamazepine sulfate
carbamazepine anhydrous
carbamazepine phosphate
carbamazepine tartrate

A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.

Molecular weight: 236.27
Formula: C15H12N2O
CLOGP: 2.24
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 46.33
ALOGS: -3.19
ROTB: 0

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
1	g	O
1	g	R

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	70 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	113.00 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.29 %	Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K
S (Water solubility)	0.11 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
March 11, 1968	FDA	NOVARTIS

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Seizure	1358.07	10.78	1241	83606	131393	63272782
Drug reaction with eosinophilia and systemic symptoms	957.04	10.78	584	84263	33252	63370923
Toxicity to various agents	755.31	10.78	1255	83592	245995	63158180
Sedation	663.43	10.78	490	84357	38319	63365856
Cognitive disorder	642.87	10.78	559	84288	55256	63348919
Sedation complication	640.39	10.78	330	84517	13492	63390683
Creatinine renal clearance decreased	600.02	10.78	334	84513	15974	63388201
Balance disorder	573.13	10.78	633	84214	83789	63320386
Abortion spontaneous	572.56	10.78	487	84360	46708	63357467
Orthostatic hypotension	548.18	10.78	425	84422	35735	63368440

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Seizure	1062.52	11.52	1104	60405	103753	34791669
Drug reaction with eosinophilia and systemic symptoms	762.29	11.52	557	60952	32455	34862967
Generalised tonic-clonic seizure	369.89	11.52	303	61206	20871	34874551
Epilepsy	353.44	11.52	297	61212	21198	34874224
Anticonvulsant drug level increased	347.10	11.52	124	61385	1492	34893930
Status epilepticus	297.99	11.52	216	61293	12398	34883024
Stevens-Johnson syndrome	262.88	11.52	236	61273	18403	34877019
Aggression	251.40	11.52	326	61183	38638	34856784
Drug interaction	248.32	11.52	916	60593	225030	34670392
Ataxia	222.70	11.52	189	61320	13664	34881758

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms	1568.00	10.35	1057	119405	63187	79560739
Seizure	1449.75	10.35	1599	118863	187235	79436691
Toxicity to various agents	842.70	10.35	1920	118542	419620	79204306
Generalised tonic-clonic seizure	678.58	10.35	549	119913	43361	79580565
Drug interaction	678.20	10.35	1750	118712	413433	79210493
Sedation complication	630.44	10.35	355	120107	15314	79608612
Cognitive disorder	592.88	10.35	625	119837	69301	79554625
Epilepsy	587.64	10.35	490	119972	40370	79583556
Status epilepticus	572.32	10.35	396	120066	24645	79599281
Balance disorder	571.21	10.35	725	119737	98132	79525794

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N03AF01	NERVOUS SYSTEM ANTIEPILEPTICS ANTIEPILEPTICS Carboxamide derivatives
CHEBI has role	CHEBI:35477	antimanic drugs
CHEBI has role	CHEBI:35623	anticonvulsants
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:38633	sodium channel blockers
CHEBI has role	CHEBI:52290	mitogens
CHEBI has role	CHEBI:61115	histone deacetylase inhibitors
CHEBI has role	CHEBI:64370	glutamate transporter activators
CHEBI has role	CHEBI:78298	environmental contaminants
CHEBI has role	CHEBI:88188	allergenic drug

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.13	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent 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.
200MG/20ML (10MG/ML)	CARNEXIV	LUNDBECK PHARMS LLC	N206030	Oct. 7, 2016	DISCN	SOLUTION	INTRAVENOUS	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	DISCN	SOLUTION	INTRAVENOUS	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	DISCN	SOLUTION	INTRAVENOUS	9629797	Nov. 10, 2028	REPLACEMENT THERAPY FOR ORAL CARBAMAZEPINE IN ADULTS WITH PARTIAL SEIZURES WITH COMPLEX SYMPTOMATOLOGY
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.

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
200MG/20ML (10MG/ML)	CARNEXIV	LUNDBECK PHARMS LLC	N206030	Oct. 7, 2016	DISCN	SOLUTION	INTRAVENOUS	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

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Sodium channel protein type 4 subunit alpha	Ion channel	P35499	SCN4A_HUMAN	BLOCKER	Ki	4.28	CHEMBL	CHEMBL
Sodium channel protein type 9 subunit alpha	Ion channel	Q15858	SCN9A_HUMAN	BLOCKER	IC50	4.66	CHEMBL	CHEMBL
Sodium channel protein type 5 subunit alpha	Ion channel	Q14524	SCN5A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Nuclear receptor subfamily 1 group I member 2	Nuclear hormone receptor	O75469	NR1I2_HUMAN				WOMBAT-PK
GABA-A receptor alpha-1/beta-2/gamma-2	Ion channel	P14867 P18507 P47870	GBRA1_HUMAN GBRG2_HUMAN GBRB2_HUMAN				WOMBAT-PK
Neuronal acetylcholine receptor; alpha2/beta4	Ion channel	P30926 Q15822	ACHB4_HUMAN ACHA2_HUMAN		IC50	4.31	WOMBAT-PK
Frizzled-8	GPCR	Q9H461	FZD8_HUMAN	ALLOSTERIC MODULATOR	Kd	4.77	IUPHAR
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Kd	4.50	WOMBAT-PK
Histamine H1 receptor	GPCR	P35367	HRH1_HUMAN		Ki	4.13	WOMBAT-PK
Frizzled-8	GPCR		FZD8_MOUSE		Kd	4.78	CHEMBL

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External reference:

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ID	Source
001634	NDDF
1836	INN_ID
2002	RXNORM
2554	PUBCHEM_CID
33CM23913M	UNII
387222003	SNOMEDCT_US
4017873	VUID
4017873	VANDF
40820003	SNOMEDCT_US
4350	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-0109	TABLET	200 mg	ORAL	ANDA	27 sections
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-0109	TABLET	200 mg	ORAL	ANDA	27 sections
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-0778	TABLET, CHEWABLE	100 mg	ORAL	ANDA	27 sections
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-0778	TABLET, CHEWABLE	100 mg	ORAL	ANDA	27 sections
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0862	SUSPENSION	100 mg	ORAL	ANDA	28 sections
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0947	SUSPENSION	100 mg	ORAL	ANDA	29 sections
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0947	SUSPENSION	100 mg	ORAL	ANDA	29 sections
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0121-1724	SUSPENSION	200 mg	ORAL	ANDA	28 sections
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0121-1894	SUSPENSION	200 mg	ORAL	ANDA	29 sections
Carbamazepine	HUMAN PRESCRIPTION DRUG LABEL	1	0121-1894	SUSPENSION	200 mg	ORAL	ANDA	29 sections

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