Oxcarbazepine vs Carbamazepine: what is the difference?

How they differ

Oxcarbazepine was designed as a gentler carbamazepine: the two share a tricyclic dibenzazepine skeleton, and oxcarbazepine adds one oxygen as a ketone, C15H12N2O2 at 252.3 against C15H12N2O at 236.3. That one atom changes the route through the body. The liver turns carbamazepine into an epoxide, and carbamazepine speeds up the liver enzymes that clear it and many other medicines, while oxcarbazepine is reduced to a different active form and does far less of that. Both block sodium channels in nerve cells and are used for epilepsy and nerve pain, and both are prescription medicines, sold as Tegretol and Trileptal.

Side by side

Structural similarity 0.46 of 1, computed as a Morgan fingerprint Tanimoto coefficient. It measures shape, not effect.

Common questions

What is the difference between Oxcarbazepine and Carbamazepine?

Oxcarbazepine was designed as a gentler carbamazepine: the two share a tricyclic dibenzazepine skeleton, and oxcarbazepine adds one oxygen as a ketone, C15H12N2O2 at 252.3 against C15H12N2O at 236.3. That one atom changes the route through the body. The liver turns carbamazepine into an epoxide, and carbamazepine speeds up the liver enzymes that clear it and many other medicines, while oxcarbazepine is reduced to a different active form and does far less of that.

Is Oxcarbazepine bigger than Carbamazepine?

Oxcarbazepine is the heavier molecule, 252.27 g/mol against 236.27 g/mol for Carbamazepine. Oxcarbazepine is C15H12N2O2 and Carbamazepine is C15H12N2O.