1. Amizepine
2. Carbamazepine Acetate
3. Carbamazepine Anhydrous
4. Carbamazepine Dihydrate
5. Carbamazepine Hydrochloride
6. Carbamazepine L-tartrate (4:1)
7. Carbamazepine Phosphate
8. Carbamazepine Sulfate (2:1)
9. Carbazepin
10. Epitol
11. Finlepsin
12. Neurotol
13. Tegretol
1. 298-46-4
2. Tegretol
3. Carbamazepen
4. Finlepsin
5. Biston
6. 5h-dibenzo[b,f]azepine-5-carboxamide
7. Equetro
8. Tegretal
9. 5h-dibenz[b,f]azepine-5-carboxamide
10. Carbazepine
11. Neurotol
12. Epitol
13. Timonil
14. Carbamezepine
15. Carbatrol
16. Karbamazepin
17. Stazepine
18. Telesmin
19. Lexin
20. Tegretol-xr
21. Benzo[b][1]benzazepine-11-carboxamide
22. Carbamazepin
23. Carbamazepinum
24. Teril
25. Geigy 32883
26. 5h-dibenz(b,f)azepine-5-carboxamide
27. Carbamazepina
28. Amizepin
29. Bipotrol
30. Carnexiv
31. Sirtal
32. 5-carbamyl-5h-dibenzo(b,f)azepine
33. 5-carbamoyl-5h-dibenzo(b,f)azepine
34. Calepsin
35. Carbamazepine Anhydrous
36. 5-carbamoyl-5h-dibenz(b,f)azepine
37. 5-carbamoyl-5h-dibenz[b,f]azepine
38. G-32883
39. G 32883
40. Karbelex
41. Neurotop
42. Nsc 169864
43. Mfcd00005073
44. Chebi:3387
45. Chembl108
46. Nsc-169864
47. Carbamazepine Extended Release
48. 5-carbamyldibenzo(b,f)azepine
49. Mls000069652
50. 5-carbamoyldibenzo(b,f)azepine
51. Cbz
52. Nsc169864
53. 33cm23913m
54. Ncgc00015234-11
55. Cas-298-46-4
56. Smr000058201
57. Stazepin
58. Dsstox_cid_2731
59. 2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide
60. Dsstox_rid_76704
61. Dsstox_gsid_22731
62. 5h-dibenzo[b,f]azepine-5-carboxamide;oxcarbazepine Impurity A
63. Carbelan
64. Tegretol Cr
65. Carbamazepinum [inn-latin]
66. Carbamazepina [inn-spanish]
67. Smr001227191
68. Hsdb 3019
69. Sr-01000000229
70. Carbatrol Extended-release
71. Einecs 206-062-7
72. Brn 1246090
73. Trimonil
74. Neurotop Retard
75. Unii-33cm23913m
76. Dibenzo[b,f]azepine-5-carboxamide
77. Tegretol (tn)
78. Prestwick_104
79. Equetro (tn)
80. Carbamazepine-[d2]
81. Carbamazepine, Powder
82. Opera_id_72
83. Spectrum_000096
84. Carbamazepine [usan:usp:inn:ban:jan]
85. Prestwick0_000052
86. Prestwick1_000052
87. Prestwick2_000052
88. Prestwick3_000052
89. Spectrum2_000125
90. Spectrum3_000325
91. Spectrum4_000262
92. Spectrum5_000936
93. Carbamazepine (carbatrol)
94. Lopac-c-4024
95. Chemdiv1_018966
96. Carbamazepine [mi]
97. Cbchromo1_000350
98. Epitope Id:174842
99. Iminostilbene-n-carboxamide
100. Carbamazepine [inn]
101. Carbamazepine [jan]
102. Carbamazepine [hsdb]
103. Carbamazepine [usan]
104. Carbamazepine-[13c,15n]
105. Lopac0_000292
106. Oprea1_790775
107. Schembl21639
108. Bspbio_000203
109. Bspbio_001929
110. Carbamazepine [vandf]
111. Kbiogr_000724
112. Kbioss_000516
113. Mls001055475
114. Mls001074172
115. Mls002548877
116. Bidd:gt0479
117. Carbamazepine [mart.]
118. Divk1c_000388
119. Divk1c_003750
120. Spectrum1500159
121. Spbio_000170
122. Spbio_002124
123. Carbamazepine [usp-rs]
124. Carbamazepine [who-dd]
125. Carbamazepine [who-ip]
126. Bpbio1_000225
127. Gtpl5339
128. Zinc4785
129. Dtxsid4022731
130. Schembl19838283
131. Hms501d10
132. Hms640o02
133. Kbio1_000388
134. Kbio2_000516
135. Kbio2_003084
136. Kbio2_005652
137. Kbio3_001149
138. Wln: T C676 Bnj Bvz
139. Carbamazepine (jp17/usp/inn)
140. Cbz;nsc 169864
141. Spd-417
142. Carbamazepine, Analytical Standard
143. Ninds_000388
144. Hms1568k05
145. Hms1920i17
146. Hms2090m07
147. Hms2091o19
148. Hms2095k05
149. Hms2233g16
150. Hms3039k09
151. Hms3259b21
152. Hms3260l06
153. Hms3372j13
154. Hms3657g03
155. Hms3712k05
156. Hms3747e03
157. Pharmakon1600-01500159
158. Carbamazepine [orange Book]
159. Act02606
160. Bcp21380
161. Hy-b0246
162. 5-carbomoyl-5h-dibenzo(b,f)azepine
163. Carbamazepine [ep Monograph]
164. Carbamazepine [usp Impurity]
165. Tox21_110104
166. Tox21_202273
167. Tox21_300195
168. Tox21_500292
169. Ac2074
170. Bdbm50003659
171. Carbamazepine [usp Monograph]
172. Ccg-38931
173. Nsc755920
174. S1693
175. Stk177357
176. Stl453548
177. 11-benzo[b][1]benzazepinecarboxamide
178. 5h-dibenz[b,f]azepine-5-carboxamine
179. Carbamazepine 1.0 Mg/ml In Methanol
180. Carbamazepinum [who-ip Latin]
181. Akos003235644
182. Akos025397243
183. Tox21_110104_1
184. Ac-9538
185. Db00564
186. Ks-5146
187. Lp00292
188. Nc00679
189. Nsc-755920
190. Sdccgsbi-0050280.p005
191. 5h-dibenz[ B, F]azepine-5-carboxamide
192. Carbamazepin 100 Microg/ml In Methanol
193. Cds1_002710
194. Idi1_000388
195. 5h-dibenzo[b,f]azepine-5-carboxamide #
196. Ncgc00015234-01
197. Ncgc00015234-02
198. Ncgc00015234-03
199. Ncgc00015234-04
200. Ncgc00015234-05
201. Ncgc00015234-06
202. Ncgc00015234-07
203. Ncgc00015234-08
204. Ncgc00015234-09
205. Ncgc00015234-10
206. Ncgc00015234-12
207. Ncgc00015234-13
208. Ncgc00015234-14
209. Ncgc00015234-15
210. Ncgc00015234-16
211. Ncgc00015234-18
212. Ncgc00015234-19
213. Ncgc00015234-33
214. Ncgc00023877-03
215. Ncgc00023877-04
216. Ncgc00023877-05
217. Ncgc00023877-06
218. Ncgc00023877-07
219. Ncgc00023877-08
220. Ncgc00253982-01
221. Ncgc00259822-01
222. Ncgc00260977-01
223. Bc166161
224. Sy002823
225. (z)-5h-dibenzo[b,f]azepine-5-carboxamide
226. Sbi-0050280.p004
227. 5h-dibenzo[b,f]azepine-5-carboximidic Acid
228. Db-047659
229. Dibenzo[b,f]azepine-5-carboxylic Acid Amide
230. Eu-0100292
231. Ft-0602927
232. Ft-0696814
233. Sw220141-1
234. Oxcarbazepine Impurity A [ep Impurity]
235. Bim-0050280.0001
236. C 4024
237. C06868
238. Carbamazepine, Meets Usp Testing Specifications
239. D00252
240. 5h-dibenz(b,f)azepine-5-carboxamide Maleic Acid
241. 5h-dibenz(b,f)azepine-5-carboxamide Oxalic Acid
242. Ab00051931-17
243. Ab00051931-18
244. Ab00051931_19
245. Ab00051931_20
246. A820074
247. Q410412
248. Carbamazepine Host Structure With Maleic Acid Removed
249. Carbamazepine Host Structure With Oxalic Acid Removed
250. Q-200792
251. Sr-01000000229-2
252. Sr-01000000229-4
253. Sr-01000000229-7
254. 5h-dibenz(b,f)azepine-5-carboxamide Dl-tartaric Acid
255. Brd-k71799949-001-06-7
256. F0348-2551
257. Z2199879032
258. Carbamazepine Host Structure With Dl-tartaric Acid Removed
259. Dibenzo[b,f]azepine-5-carboxylic Acid Amide(carbamazepine)
260. Carbamazepine Host Structure With 4-hydroxybenzoic Acid Removed
261. Carbamazepine, British Pharmacopoeia (bp) Reference Standard
262. Carbamazepine, European Pharmacopoeia (ep) Reference Standard
263. Carbamazepine, United States Pharmacopeia (usp) Reference Standard
264. Carbamazepine Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material
265. Carbamazepine, Pharmaceutical Secondary Standard; Certified Reference Material
266. N6w
| Molecular Weight | 236.27 g/mol |
|---|---|
| Molecular Formula | C15H12N2O |
| XLogP3 | 2.5 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Exact Mass | 236.094963011 g/mol |
| Monoisotopic Mass | 236.094963011 g/mol |
| Topological Polar Surface Area | 46.3 Ų |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Complexity | 326 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 14 | |
|---|---|
| Drug Name | Carbamazepine |
| PubMed Health | Carbamazepine (By mouth) |
| Drug Classes | Anticonvulsant, Neuropathic Pain Agent |
| Drug Label | Carbamazepine USP is an anticonvulsant and specific analgesic for trigeminal neuralgia, available for oral administration as chewable tablets of 100 mg and tablets of 200 mg. Its chemical name is 5H-dibenz[b,f]azepine-5-carboxamide, and its structura... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Tablet, extended release; Tablet; Capsule, extended release; Tablet, chewable; Suspension |
| Route | oral; Oral |
| Strength | 300mg; 200mg; 100mg; 100mg/5ml; 400mg |
| Market Status | Tentative Approval; Prescription |
| Company | Wockhardt; Teva Pharms; Apotex; Teva Pharms Usa; Taro Pharm Inds; Taro; Torrent Pharms; Nostrum |
| 2 of 14 | |
|---|---|
| Drug Name | Carbatrol |
| PubMed Health | Carbamazepine (By mouth) |
| Drug Classes | Anticonvulsant, Neuropathic Pain Agent |
| Drug Label | CARBATROL* is an anticonvulsant and specific analgesic for trigeminal neuralgia, available for oral administration as 100 mg, 200 mg and 300 mg extended-release capsules of Carbamazepine, USP. Carbamazepine is a white to off-white powder, practically... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Capsule, extended release |
| Route | Oral |
| Strength | 300mg; 200mg; 100mg |
| Market Status | Prescription |
| Company | Shire |
| 3 of 14 | |
|---|---|
| Drug Name | Epitol |
| PubMed Health | Carbamazepine (By mouth) |
| Drug Classes | Anticonvulsant, Neuropathic Pain Agent |
| Drug Label | Epitol, carbamazepine, USP, is an anticonvulsant and specific analgesic for trigeminal neuralgia, available for oral administration as tablets of 200 mg. Its chemical name is 5H-dibenz[b,f]azepine-5-carboxamide, and its structural formula is: C15H12N... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Tablet; Tablet, chewable |
| Route | Oral |
| Strength | 200mg; 100mg |
| Market Status | Prescription |
| Company | Teva |
| 4 of 14 | |
|---|---|
| Drug Name | Equetro |
| PubMed Health | Carbamazepine (By mouth) |
| Drug Classes | Anticonvulsant, Neuropathic Pain Agent |
| Drug Label | EQUETRO (carbamazepine) is a mood stabilizer available for oral administration as 100 mg, 200 mg, and 300 mg extended-release capsules of carbamazepine, USP. Carbamazepine is a white to off-white powder, practically insoluble in water and soluble in... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Capsule, extended release |
| Route | Oral |
| Strength | 300mg; 200mg; 100mg |
| Market Status | Prescription |
| Company | Validus Pharms |
| 5 of 14 | |
|---|---|
| Drug Name | Tegretol |
| Drug Label | Tegretol, carbamazepine USP, is an anticonvulsant and specific analgesic for trigeminal neuralgia, available for oral administration as chewable tablets of 100mg, tablets of 200mg, XR tablets of 100, 200, and 400mg, and as a suspension of 100... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Tablet; Suspension; Tablet, chewable |
| Route | Oral |
| Strength | 200mg; 100mg/5ml; 100mg |
| Market Status | Prescription |
| Company | Novartis |
| 6 of 14 | |
|---|---|
| Drug Name | Tegretol-xr |
| Active Ingredient | Carbamazepine |
| Dosage Form | Tablet, extended release |
| Route | Oral |
| Strength | 200mg; 400mg; 100mg |
| Market Status | Prescription |
| Company | Novartis |
| 7 of 14 | |
|---|---|
| Drug Name | Teril |
| Active Ingredient | Carbamazepine |
| Dosage Form | Suspension |
| Route | Oral |
| Strength | 100mg/5ml |
| Market Status | Prescription |
| Company | Taro |
| 8 of 14 | |
|---|---|
| Drug Name | Carbamazepine |
| PubMed Health | Carbamazepine (By mouth) |
| Drug Classes | Anticonvulsant, Neuropathic Pain Agent |
| Drug Label | Carbamazepine USP is an anticonvulsant and specific analgesic for trigeminal neuralgia, available for oral administration as chewable tablets of 100 mg and tablets of 200 mg. Its chemical name is 5H-dibenz[b,f]azepine-5-carboxamide, and its structura... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Tablet, extended release; Tablet; Capsule, extended release; Tablet, chewable; Suspension |
| Route | oral; Oral |
| Strength | 300mg; 200mg; 100mg; 100mg/5ml; 400mg |
| Market Status | Tentative Approval; Prescription |
| Company | Wockhardt; Teva Pharms; Apotex; Teva Pharms Usa; Taro Pharm Inds; Taro; Torrent Pharms; Nostrum |
| 9 of 14 | |
|---|---|
| Drug Name | Carbatrol |
| PubMed Health | Carbamazepine (By mouth) |
| Drug Classes | Anticonvulsant, Neuropathic Pain Agent |
| Drug Label | CARBATROL* is an anticonvulsant and specific analgesic for trigeminal neuralgia, available for oral administration as 100 mg, 200 mg and 300 mg extended-release capsules of Carbamazepine, USP. Carbamazepine is a white to off-white powder, practically... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Capsule, extended release |
| Route | Oral |
| Strength | 300mg; 200mg; 100mg |
| Market Status | Prescription |
| Company | Shire |
| 10 of 14 | |
|---|---|
| Drug Name | Epitol |
| PubMed Health | Carbamazepine (By mouth) |
| Drug Classes | Anticonvulsant, Neuropathic Pain Agent |
| Drug Label | Epitol, carbamazepine, USP, is an anticonvulsant and specific analgesic for trigeminal neuralgia, available for oral administration as tablets of 200 mg. Its chemical name is 5H-dibenz[b,f]azepine-5-carboxamide, and its structural formula is: C15H12N... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Tablet; Tablet, chewable |
| Route | Oral |
| Strength | 200mg; 100mg |
| Market Status | Prescription |
| Company | Teva |
| 11 of 14 | |
|---|---|
| Drug Name | Equetro |
| PubMed Health | Carbamazepine (By mouth) |
| Drug Classes | Anticonvulsant, Neuropathic Pain Agent |
| Drug Label | EQUETRO (carbamazepine) is a mood stabilizer available for oral administration as 100 mg, 200 mg, and 300 mg extended-release capsules of carbamazepine, USP. Carbamazepine is a white to off-white powder, practically insoluble in water and soluble in... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Capsule, extended release |
| Route | Oral |
| Strength | 300mg; 200mg; 100mg |
| Market Status | Prescription |
| Company | Validus Pharms |
| 12 of 14 | |
|---|---|
| Drug Name | Tegretol |
| Drug Label | Tegretol, carbamazepine USP, is an anticonvulsant and specific analgesic for trigeminal neuralgia, available for oral administration as chewable tablets of 100mg, tablets of 200mg, XR tablets of 100, 200, and 400mg, and as a suspension of 100... |
| Active Ingredient | Carbamazepine |
| Dosage Form | Tablet; Suspension; Tablet, chewable |
| Route | Oral |
| Strength | 200mg; 100mg/5ml; 100mg |
| Market Status | Prescription |
| Company | Novartis |
| 13 of 14 | |
|---|---|
| Drug Name | Tegretol-xr |
| Active Ingredient | Carbamazepine |
| Dosage Form | Tablet, extended release |
| Route | Oral |
| Strength | 200mg; 400mg; 100mg |
| Market Status | Prescription |
| Company | Novartis |
| 14 of 14 | |
|---|---|
| Drug Name | Teril |
| Active Ingredient | Carbamazepine |
| Dosage Form | Suspension |
| Route | Oral |
| Strength | 100mg/5ml |
| Market Status | Prescription |
| Company | Taro |
Analgesics, Non-Narcotic; Anticonvulsants
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
Carbamazepine has been shown to be effective in certain psychiatric disorders including schizoaffective illness, resistant schizophrenia, and dyscontrol syndrome, associated with limbic system dysfunction. /NOT included in US or Canadian product labeling/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Carbamazepine is used for the detoxification of alcoholics. It has been found to be effective in rapidly relieving anxiety and distress of acute alcohol withdrawal and for such symptoms as seizures, hyperexcitability, and sleep disturbances. /NOT included in US product labeling/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Carbamazepine is used alone or with other agents such as clofibrate or chlorpropamide in the treatment of partial central diabetes insipidus. /NOT included in US or Canadian product labeling/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
For more Therapeutic Uses (Complete) data for CARBAMAZEPINE (10 total), please visit the HSDB record page.
There have been a few cases of seizures and/or respiratory depression in neonates born to women receiving carbamazepine concomitantly with other anticonvulsant agents. A few cases of vomiting, diarrhea, and/or decreased feeding also have been reported in neonates born to women receiving carbamazepine; these symptoms may represent a neonatal withdrawal syndrome
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2223
Carbamazepine should not be used prophylactically during long periods of remission in trigeminal neuralgia.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Although carbamazepine has ... been reported to relieve dystonic attacks in children, reduce migraine attacks, and relieve intractable hiccups in some patients, its therapeutic efficacy in such cases has not been established.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Carbamazepine is not indicated for atypical or generalized absence seizures (petit mal) or myoclonic or atonic seizures.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
For more Drug Warnings (Complete) data for CARBAMAZEPINE (30 total), please visit the HSDB record page.
Carbamazepine is indicated for the treatment of epilepsy and pain associated with true trigeminal neuralgia. In particular, carbamazepine has shown efficacy in treating mixed seizures, partial seizures with complex symptoms, and generalized tonic-clonic seizures. Carbamazepine is also indicated for the treatment of manic episodes and mixed manic-depressive episodes caused by bipolar I disorder. Some off-label, unapproved uses of carbamazepine include the treatment of alcohol withdrawal syndrome and restless leg syndrome.
FDA Label
**General effects** Carbamazepine treats seizures and the symptoms of trigeminal neuralgia by inhibiting sodium channels. In bipolar 1 disorder, carbamazepine has been found to decrease mania symptoms in a clinically significant manner according to the Young Mania Rating Scale (YMRS). Carbamazepine has a narrow therapeutic index. **A note on genetic variation and carbamazepine use** In studies of Han Chinese ancestry patients, a pronounced association between the HLA-B*1502 genotype and Steven Johnson syndrome and/or toxic epidermal necrolysis (SJS/TEN) resulting from carbamazepine use was observed.
Antimanic Agents
Agents that are used to treat bipolar disorders or mania associated with other affective disorders. (See all compounds classified as Antimanic Agents.)
Anticonvulsants
Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)
Cytochrome P-450 CYP3A Inducers
Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inducers.)
Analgesics, Non-Narcotic
A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)
Sodium Channel Blockers
A class of drugs that act by inhibition of sodium influx through cell membranes. Blockade of sodium channels slows the rate and amplitude of initial rapid depolarization, reduces cell excitability, and reduces conduction velocity. (See all compounds classified as Sodium Channel Blockers.)
N03AF01
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
N03AF01
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
N03AF01
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
N03AF01
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
N - Nervous system
N03 - Antiepileptics
N03A - Antiepileptics
N03AF - Carboxamide derivatives
N03AF01 - Carbamazepine
Absorption
The bioavailability of carbamazepine is in the range of 75-85% of an ingested dose. After one 200 mg oral extended-release dose of carbamazepine in a pharmacokinetic study, the Cmax carbamazepine was measured to be 1.9 0.3 mcg/mL. The Tmax was 19 7 hours. After several doses of 800 mg every 12 hours, the peak concentrations of carbamazepine were measured to be 11.0 2.5 mcg/mL. The Tmax was reduced to 5.9 1.8 hours. Extended-release carbamazepine demonstrated linear pharmacokinetics over a range of 200800 mg. **Effect of food on absorption** A meal containing high-fat content increased the rate of absorption of one 400 mg dose but not the AUC of carbamazepine. The elimination half-life remained unchanged between fed and fasting state. The pharmacokinetics of an extended-release carbamazepine dose was demonstrated to be similar when administered in the fasted state or with food. Based on these findings, food intake is unlikely to exert significant effects on carbamazepine absorption.
Route of Elimination
After an oral dose of radiolabeled carbamazepine, 72% of the administered radioactive dose was detected in the urine and the remainder of the ingested dose was found in the feces. Carbamazepine is mainly excreted as hydroxylated and conjugated metabolites, and minimal amounts of unchanged drug.
Volume of Distribution
The volume of distribution of carbamazepine was found to be 1.0 L/kg in one pharmacokinetic study. Another study indicates that the volume of distribution of carbamazepine ranges between 0.7 to 1.4 L/kg.. Carbamazepine crosses the placenta, and higher concentrations of this drug are found in the liver and kidney as opposed to lung and brain tissue. Carbamazepine crosses variably through the blood-brain barrier.
Clearance
In a pharmacokinetic study, the apparent oral clearance of carbamazepine was 25 5 mL/min after one dose of carbamazepine and 80 30 mL/min after several doses.
Absorption: Slow and variable, but almost completely absorbed from gastrointestinal tract.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Patients in whom carbamazepine monotherapy is discontinued for preoperative EEG/video monitoring often display toxicity if their previous maintenance dosage is resumed, even after a few days without carbamazepine. To determine whether this is due to rapid reversibility of autoinduction of carbamazepine metabolism, single-dose studies of carbamazepine pharmacokinetics were performed before and after discontinuation for monitoring in 6 adults receiving carbamazepine monotherapy. The carbamazepine-free period was 5.7 + or - 1.1 days (mean + or - SD). The pharmacokinetic parameters of carbamazepine before and after discontinuation were volume of distribution 1.28 + or - 0.29 versus 1.22 + or - 0.331/kg, elimination half-life (tl/2) 13.7 + or - 1.67 versus 22.2 + or - 2.36 hr (p < 0.001), and clearance 1.54 + or - 0.39 versus 0.92 + or - 0.32 L/kg/day (p = 0.012). Assuming that deinduction is a first-order process, a deinduction tl/2 of 3.84 days was obtained by log linear regression analysis. We showed that after carbamazepine discontinuation half of the enzymatic autoinduction is already lost after 3.84 days, indicating very rapid deinduction. Our results also provide the necessary information to predict clearance and appropriate dosage reduction for carbamazepine at time of reintroduction.
PMID:8112245 Schaffler L et al; Epilepsia 35 (1): 195-8 (1994)
This study was designed to evaluate the usefulness of carbamazepine as a probe in screening for host factor influences on human drug metabolism. Nine healthy nonsmoking volunteers ingested a single oral dose of carbamazepine in doses ranging from 400 to 500 milligrams. Fluorescence polarization immunoassay measurements of carbamazepine concentrations in plasma and plasma ultrafiltrates from 0 to 48 hours after dosing were used to calculate clearance, volume of distribution, and clearance of plasma unbound drug. Blood samples collected 48 hours after dosing gave single sample estimates of carbamazepine clearance which were closest to multiple sample values for clearance. This was also the case for plasma total carbamazepine and plasma unbound carbamazepine. In calculating all single sample estimates of clearance, a value of 1.1 L/kg was used for V and a value of 4.3 L/kg was used to calculate the single sample estimates of clearance of plasma unbound drug. The mean prediction error was less than 5 percent errant for clearance and less than 1 percent errant for clearance of plasma unbound drug when the parameters were calculated from 48 hour concentrations of plasma total carbamazepine or plasma unbound carbamazepine, respectively. ...
PMID:2773507 Bachmann KA et al; Xenobiotica 19 (7): 711-719 (1989)
A fatal overdose of carbamazepine with both timely antemortem and postmortem carbamazepine concentrations /was reported/. Carbamazepine concentrations were 47.7 ug/mL 2 hr antemortem and 53 ug/mL at 9 hr postmortem. The slight rise in drug concentration may reflect continued absorption of the drug in the last 2 hr before death. Postmortem carbamazepine concentrations drawn from a peripheral vessel in this patient appeared to reflect drug concentrations at the time of death.
PMID:11714170 Spiller HA, Carlisle RD; J Forensic Sci 46 (6): 1510-2 (2001)
For more Absorption, Distribution and Excretion (Complete) data for CARBAMAZEPINE (15 total), please visit the HSDB record page.
Carbamazepine is largely metabolized in the liver. CYP3A4 hepatic enzyme is the major enzyme that metabolizes carbamazepine to its active metabolite, carbamazepine-10,11-epoxide, which is further metabolized to its trans-diol form by the enzyme epoxide hydrolase. Other hepatic cytochrome enzymes that contribute to the metabolism of carbamazepine are CYP2C8, CYP3A5, and CYP2B6. Carbamazepine also undergoes hepatic glucuronidation by UGT2B7 enzyme and several other metabolic reactions occur, resulting in the formation of minor hydroxy metabolites and quinone metabolites. Interestingly, carbamazepine induces its own metabolism. This leads to enhanced clearance, reduced half-life, and a reduction in serum levels of carbamazepine.
The pharmacokinetics of a single oral dose of carbamazepine-10,11-epoxide, (100 mg) were compared in 10 patients on chronic monotherapy with lamotrigine, (200-300 mg/day) and in 10 drug-free healthy control subjects. Carbamazepine-10,11-epoxide pharmacokinetic parameters in lamotridge-treated patients were found to be similar to those observed in controls (half-life: 7.2 + or - 1.6 vs 6.1 + or - 0.9 hr; apparent oral clearance: 110.8 + or - 53.1 vs 120.5 + or - 29.9 ml/h/kg; apparent volume of distribution: 1.08 + or 0.37 vs 1.04 + or - 0.25 l/kg respectively; means + or - s.d.). These data indicate that, contrary to previous suggestions, lamotridge has no effect on the metabolic disposition of carbamazepine-10,11-epoxide.
PMID:7698101 Pisani F et al; Epilepsy Res 19 (3): 245-8 (1994)
Placental transfer and metabolism of carbamazepine was studied in a dual recirculating placental cotyledon perfusion system and was also evaluated in 16 pairs of maternal venous and cord blood samples. ... Carbamazepine added into the maternal circulation crosses the placenta in the beginning quicker than antipyrine which is in agreement with the different lipid solubilities of these compounds. Because the transfer rates of antipyrine and carbamazepine were about the same, the mechanism of transfer of carbamazepine is probably similar to that of antipyrine (passive diffusion). No metabolites of carbamazepine could be detected in the perfusate by high-performance liquid chromatography or gas chromatography/mass spectrometry. With the improved HPLC methodology for carbamazepine metabolites, six metabolites were detected in clinical samples, including 10-hydroxy-10,11-dihydro-carbamazepine (10-OH-CBZ), which has been described earlier in only 1 uremic patient. Relative levels of metabolites showed significant individual differences. Carbamazepine crosses perfused placenta rapidly, but this does not contribute to carbamazepine metabolites detected in maternal and fetal circulation.
PMID:7614907 Pienimaki P et al; Epilepsia 36 (3): 241-8 (1995)
The aim of this work was to study the transport across the blood-brain barrier, blood and liver distribution kinetics, metabolic interaction and local liver metabolism of carbamazepine in the rat, using microdialysis with the internal standard technique as in vivo calibration method. Carbamazepine and its major metabolite, carbamazepine-10,11-epoxide, are homogeneously distributed to hippocampus and cerebellum. The ratios of the areas under the concentration-time curve for both brain regions to blood areas under the concentration-time curve were not different from unity for carbamazepine; they were 0.46 + or - 0.08 (hippocampus) and 0.45 + or - 0.05 (cerebellum) for carbamazepine-10,11-epoxide. In addition, the disposition of carbamazepine and carbamazepine-10,11-epoxide in blood and liver, after a single dose of carbamazepine, was studied in control animals and in rats after pretreatment with clomipramine. A 2-fold increase in the blood areas under concentration curve of carbamazepine and a decrease to 33% of the blood areas under concentration curve of carbamazepine-10,11-epoxide in the pretreated group demonstrate the metabolic inhibition of carbamazepine-10,11-epoxide formation by clomipramine. The ratios of the areas under concentration curve carbamazepine-10,11-epoxide to the areas under the concentration curve carbamazepine, as a measure of carbamazepine-10,11-epoxide formation, were not different for blood and liver within the control and the clomipramine-pretreated groups, but the ratios were significantly lower for liver and blood in the clomipramine group compared with the control animals. In addition, carbamazepine was administered locally in the extracellular fluid of the liver via the microdialysis probe. The liver metabolic ratio, expressed as the ratio of the formed carbamazepine-10,11-epoxide concentration to the carbamazepine concentration administered, ranged from 18.2 + or - 1.2% to 19.6 + or - 1.6%.
PMID:7891336 Van Belle K et al; J Pharmacol Exp Ther 272 (3): 1217-22 (1995)
Carbamazepine has known human metabolites that include 2-Hydroxycarbamazepine, 3-Hydroxycarbamazepine, 9-Hydroxycarbamazepine, and Carbamazepine 10,11-epoxide.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
The mean elimination half-life of carbamazepine was 35 to 40 hours after one dose of carbamazepine extended-release formulations. The half-life ranged from 12-17 hours after several doses of carbamazepine. One pharmacokinetic study determined the elimination half-life of carbamazepine to range between 27 to 36.8 hours in healthy volunteers.
Initial single dose: May range from 25 to 65 hours. Chronic dosing: May decrease to 8 to 29 hours (average 12 to 17 hours) because of autoinduciton of metabolism.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Carbamazepine-10,11-epoxide: 5 to 8 hours. /Carbamazepine-10,11-epoxide/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Carbamazepine's mechanism of action is not fully elucidated and is widely debated. One major hypothesis is that carbamazepine inhibits sodium channel firing, treating seizure activity. Animal research studies have demonstrated that carbamazepine exerts its effects by lowering polysynaptic nerve response and inhibiting post-tetanic potentiation. In both cats and rats, carbamazepine was shown to decrease pain caused by infraorbital nerve stimulation. A decrease in the action potential in the nucleus ventralis of the thalamus in the brain and inhibition of the lingual mandibular reflex were observed in other studies after carbamazepine use. Carbamazepine causes the above effects by binding to voltage-dependent sodium channels and preventing action potentials, which normally lead to stimulatory effects on nerves. In bipolar disorder, carbamazepine is thought to increase dopamine turnover and increase GABA transmission, treating manic and depressive symptoms. A common issue that has arisen is resistance to this drug in up to 30% of epileptic patients, which may occur to altered metabolism in patients with variant genotypes. A potential therapeutic target to combat carbamazepine resistance has recently been identified as the EPHX1 gene promoter, potentially conferring resistance to carbamazepine through methylation.
Anticonvulsant: Exact mechanism unknown; may act postsynaptically by limiting the ability of neurons to sustain high frequency repetitive firing of action potentials through enhancement of sodium channel inactivation; in addition to altering neuronal excitability, may act presynaptically to block the release of neurotransmitter by blocking presynaptic sodium channels and the firing of action potentials, which in turn decreases synaptic transmission.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Antineuralgic: Exact mechanism unknown; may involve gamma-aminobutyric acid (GABAB) receptors, which may be linked to calcium channels.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Antimanic; antipsychotic: Exact mechanism is unknown; may be related to either the anticonvulsant or the antineuralgic effects of carbamazepine, or to tis effects on neurotransmitter modulator systems.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
Antidiuretic: Exact mechanism unknown; may exert a hypothalamic effect on the osmoreceptors mediated via secretion of antidiuretic hormone (ADH), or may have a direct effect on the renal tubule.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 703
For more Mechanism of Action (Complete) data for CARBAMAZEPINE (8 total), please visit the HSDB record page.
LOOKING FOR A SUPPLIER?
