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Drug

D1375 | Carbamazepine

Molecular Formula C15H12N2O
Molecular Weight 236.27
Structure
State solid
Route of elimination 72% of the dose is in the urine while 28% is in the feces. Hydroxylated and conjugated metabolites are largely what was recovered in the urine. 3% of the dose is recovered as unchanged carbamazepine.
Protein binding 76% bound to plasma proteins.
Half life Initial half-life values range from 25-65 hours, decreasing to 12-17 hours on repeated doses.
Absorption In clinical studies, carbamazepine suspension, conventional tablets, and extended-release tablets delivered equivalent amounts of drug to the systemic circulation. However, it has been observed that the suspension is somewhat faster absorbed. Furthermore, the extended-release tablet is slightly slower than the conventional tablet. The bioavailability of the extended-release tablet is 89%, compared to the suspension. Plasma levels of carbamazepine are variable. The time to peak concentration for the different formulations are as follows: Suspension = 1.5 hours; Conventional tablets = 4-5 hours; Extended-release tablets = 3-12 hours.
Trade names Tegretol, Temporol, Neurotol
Description nticonvulsant drug ; analgesic drug

N

N03AF01 Carbamazepine


[N03AF] Carboxamide derivatives


[N03A] ANTIEPILEPTICS


[N03] ANTIEPILEPTICS


[N] Nervous system

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 66.9 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 53.4 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION 170.8 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. increase EC20 36
MITOCHONDRIAL FATTY ACID BETA OXIDATION >400μM 341 mice Lean mice vs Ob/ob mice Measurement of oxygen consumption in the presence of ADP (state 3) and the different substrates was carried out on the Mitologics screening platform EC20 227
SWELLING > 200 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 53.4 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Cytochrome c > 400 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 178 companies from 24 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 1 of 178 companies. For more detailed information, please visit ECHA C&L website


Of the 23 notification(s) provided by 177 of 178 companies with hazard statement code(s):


H302 (96.05%): Harmful if swallowed [Warning Acute toxicity, oral]


H317 (93.79%): May cause an allergic skin reaction [Warning Sensitization, Skin]


H334 (90.96%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]


H361 (13.56%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P261, P264, P270, P272, P280, P281, P285, P301+P312, P302+P352, P304+P341, P308+P313, P321, P330, P333+P313, P342+P311, P363, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
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.
child TDLo oral 1050mg/kg/6W- (1050mg/kg) behavioral: muscle contraction or spasticity) American Journal of Psychiatry. Vol. 143, Pg. 1176, 1985.
child TDLo oral 65mg/kg (65mg/kg) Journal of Pediatrics. Vol. 121, Pg. 295, 1992.
man TDLo oral 94mg/kg/11D-I (94mg/kg) blood: thrombocytopenia Journal of Clinical Pyschopharmacology. Vol. 10, Pg. 305, 1990.
human TDLo oral 43mg/kg (43mg/kg) British Medical Journal. Vol. 1, Pg. 754, 1977.
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.
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.
women TDLo oral 112mg/kg/2W-I (112mg/kg) American Journal of Psychiatry. Vol. 150, Pg. 1750, 1993.
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.
man LDLo oral 54mg/kg/9D-I (54mg/kg) Canadian Medical Association Journal. Vol. 132, Pg. 1040, 1985.
man TDLo oral 253mg/kg/6W-I (253mg/kg) Journal of Clinical Pyschopharmacology. Vol. 6, Pg. 251, 1986.
women TDLo oral 28mg/kg/4D-I (28mg/kg) American Journal of Psychiatry. Vol. 143, Pg. 1328, 1986.
women LDLo oral 1920mg/kg/17W (1920mg/kg) blood: aplastic anemia American Journal of Psychiatry. Vol. 142, Pg. 974, 1985.
child TDLo oral 55mg/kg (55mg/kg) Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 323, 2000.
child TDLo oral 25926ug/kg (25.926mg/kg) Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 320, 1993.
rat LD50 subcutaneous > 1500mg/kg (1500mg/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.
women TDLo oral 7604mg/kg/69W (7604mg/kg) Japanese Heart Journal. Vol. 39, Pg. 469, 1998.
rat LD50 oral 1957mg/kg (1957mg/kg) behavioral: altered sleep time (including change in righting reflex) Japanese Kokai Tokyo Koho Patents. Vol. #79-163823,
child TDLo oral 420mg/kg/3W-I (420mg/kg) Journal of Toxicology, Clinical Toxicology. Vol. 36, Pg. 109, 1998.
women TDLo oral 144mg/kg/2W-I (144mg/kg) Journal of Clinical Psychiatry. Vol. 53, Pg. 378, 1992.
rat LD50 intraperitoneal 158mg/kg (158mg/kg) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 202, Pg. 106, 1973.
child TDLo oral 19mg/kg/4W-I (19mg/kg) peripheral nerve and sensation: fasciculations Pediatrics. Vol. 73, Pg. 841, 1984.
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.
mouse LD50 intraperitoneal 114mg/kg (114mg/kg) Farmakologiya i Toksikologiya Vol. 53(4), Pg. 19, 1990.


  • (z)-5h-dibenzo[b,f]azepine-5-carboxamide 11-benzo[b][1]benzazepinecarboxamide 2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide
    298-46-4 33CM23913M 5-Carbamoyl-5H-dibenz(b,f)azepine
    5-Carbamoyl-5H-dibenz[b,f]azepine 5-Carbamoyl-5H-dibenzo(b,f)azepine 5-Carbamoyldibenzo(b,f)azepine
    5-Carbamyl-5H-dibenzo(b,f)azepine 5-Carbamyldibenzo(b,f)azepine 5-Carbomoyl-5H-dibenzo(b,f)azepine
    5H-Dibenz(b,f)azepine-5-carboxamide 5H-Dibenz(b,f)azepine-5-carboxamide DL-tartaric acid 5H-Dibenz(b,f)azepine-5-carboxamide maleic acid
    5H-Dibenz(b,f)azepine-5-carboxamide oxalic acid 5H-Dibenz[ b, f]azepine-5-carboxamide 5H-Dibenz[b,f]azepine-5-carboxamide
    5H-Dibenz[b,f]azepine-5-carboxamine 5H-Dibenzo[b,f]azepine-5-carboxamide 5H-Dibenzo[b,f]azepine-5-carboxamide #
    5H-dibenzo[b,f]azepine-5-carboxamide;Oxcarbazepine IMpurity A 5H-dibenzo[b,f]azepine-5-carboximidic acid A820074
    AB00051931-17 AB00051931-18 AB00051931_19
    AB00051931_20 AB0070254 AC-9538
    ACT02606 AK116064 AKOS003235644
    AKOS025397243 AOB5783 Amizepin
    Amizepine BBL005372 BCP21380
    BDBM50003659 BG0497 BIDD:GT0479
    BIM-0050280.0001 BPBio1_000225 BRD-K71799949-001-06-7
    BRN 1246090 BSPBio_000203 BSPBio_001929
    Bipotrol Biston C 4024
    C-13993 C06868 CAS-298-46-4
    CBChromo1_000350 CBZ CBZ;NSC 169864
    CC-25382 CC-25383 CCG-38931
    CDS1_002710 CHEBI:3387 CHEMBL108
    CS-2225 Calepsin Carbamazepen
    Carbamazepin Carbamazepina Carbamazepina [INN-Spanish]
    Carbamazepine (Carbatrol) Carbamazepine (JP17/USP/INN) Carbamazepine 1.0 mg/ml in Methanol
    Carbamazepine [USAN:INN:BAN:JAN] Carbamazepine [USAN:USP:INN:BAN:JAN] Carbamazepine solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material
    Carbamazepine(Atretol) Carbamazepine, 98% Carbamazepine, British Pharmacopoeia (BP) Reference Standard
    Carbamazepine, European Pharmacopoeia (EP) Reference Standard Carbamazepine, Pharmaceutical Secondary Standard Carbamazepine, United States Pharmacopeia (USP) Reference Standard
    Carbamazepine, analytical standard Carbamazepine, meets USP testing specifications Carbamazepine, powder
    Carbamazepine_194_ p Carbamazepinum Carbamazepinum [INN-Latin]
    Carbamezepine Carbatrol Carbatrol extended-release
    Carbazepin Carbazepine Carbelan
    Carnexiv Certified Reference Material ChemDiv1_018966
    D00252 DB-047659 DB00564
    DSSTox_CID_2731 DSSTox_GSID_22731 DSSTox_RID_76704
    DTXSID4022731 Dibenzo[b,f]azepine-5-carboxylic acid amide Dibenzo[b,f]azepine-5-carboxylic acid amide(Carbamazepine)
    DivK1c_000388 DivK1c_003750 EINECS 206-062-7
    EN300-21678 EU-0100292 Epitol
    Epitope ID:174842 Equetro Equetro (TN)
    F0348-2551 FT-0602927 FT-0696814
    Finlepsin G 32883 G-32883
    GP8250 GTPL5339 Geigy 32883
    H2605 H495 HMS1568K05
    HMS1920I17 HMS2090M07 HMS2091O19
    HMS2095K05 HMS2233G16 HMS3039K09
    HMS3259B21 HMS3260L06 HMS3372J13
    HMS3657G03 HMS3712K05 HMS3747E03
    HMS501D10 HMS640O02 HSDB 3019
    HY-B0246 IDI1_000388 IMED104589831
    Iminostilbene-N-carboxamide KBio1_000388 KBio2_000516
    KBio2_003084 KBio2_005652 KBio3_001149
    KBioGR_000724 KBioSS_000516 KS-00000KI8
    KS-5146 Karbamazepin LP00292
    LS-60362 Lexin Lopac-C-4024
    Lopac0_000292 MCULE-9121567287 MFCD00005073
    MLS000069652 MLS001055475 MLS001074172
    MLS002548877 N6W NC00679
    NCGC00015234-01 NCGC00015234-02 NCGC00015234-03
    NCGC00015234-04 NCGC00015234-05 NCGC00015234-06
    NCGC00015234-07 NCGC00015234-08 NCGC00015234-09
    NCGC00015234-10 NCGC00015234-11 NCGC00015234-12
    NCGC00015234-13 NCGC00015234-14 NCGC00015234-15
    NCGC00015234-16 NCGC00015234-19 NCGC00023877-03
    NCGC00023877-04 NCGC00023877-05 NCGC00023877-06
    NCGC00023877-07 NCGC00023877-08 NCGC00253982-01
    NCGC00259822-01 NCGC00260977-01 NINDS_000388
    NSC 169864 NSC-169864 NSC-755920
    NSC169864 NSC755920 Neurotol
    Neurotop retard Opera_ID_72 Oprea1_790775
    Pharmakon1600-01500159 Prestwick0_000052 Prestwick1_000052
    Prestwick2_000052 Prestwick3_000052 Prestwick_104
    Q-200792 Q410412 SBI-0050280.P004
    SC-16243 SCHEMBL19838283 SCHEMBL21639
    SDCCGSBI-0050280.P005 SMR000058201 SMR001227191
    SPBio_000170 SPBio_002124 SPD-417
    SPECTRUM1500159 SR-01000000229 SR-01000000229-2
    SR-01000000229-4 SR-01000000229-7 ST075773
    STK177357 STL453548 SW220141-1
    SY002823 Sirtal Spectrum2_000125
    Spectrum3_000325 Spectrum4_000262 Spectrum5_000936
    Spectrum_000096 Stazepin Stazepine
    Tegretal Tegretol Tegretol (TN)
    Tegretol Cr Tegretol,Carbamazepine Tegretol-Xr
    Telesmin Teril Timonil
    Tox21_110104 Tox21_110104_1 Tox21_202273
    Tox21_300195 Tox21_500292 Trimonil
    UNII-33CM23913M WLN: T C676 BNJ BVZ Z2199879032
    ZINC4785 benzo[b][1]benzazepine-11-carboxamide carbamazepine
    carbamazepine (Tegretol) carbamazepine host structure with 4-hydroxybenzoic acid removed carbamazepine host structure with DL-tartaric acid removed
    carbamazepine host structure with maleic acid removed carbamazepine host structure with oxalic acid removed dibenzo[b,f]azepine-5-carboxamide
    s1693

    DrugBank DB00564
    CAS Number 1189902-21-3, 298-46-4, 85756-57-6
    PubChem Compound 2554