10,11-Dihydroxycarbamazepine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 10,11-Dihydroxycarbamazepine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 10,11-Dihydroxycarbamazepine?

The molecule 10,11-Dihydroxycarbamazepine presents a molecular formula of C15H14N2O3 and its IUPAC name is (5S,6S)-5,6-dihydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide.

Carbamazepine is a molecule with the molecular formula C15H12N2O2. It is a white, crystalline solid with a melting point of 156 °C (313 °F). Carbamazepine is used as an anticonvulsant and mood-stabilizing drug. It is also used to treat trigeminal neuralgia, a type of nerve pain. Carbamazepine is structurally similar to tricyclic antidepressants such as amitriptyline..

Carbamazepine was first synthesized in 1953 by Swiss chemist Walter Schindler. It was first marketed as Tegretol in 1963 by Ciba-Geigy (now Novartis). The drug is also marketed under the brand names Carbatrol, Equetro, and Epitol..

The mechanism of action of carbamazepine is not completely understood. It is thought to work by inhibiting voltage-gated sodium channels, which prevents the spread of electrical impulses in the brain. Carbamazepine is also a potent inhibitor of the enzyme CYP3A4..

Carbamazepine is well-absorbed from the gastrointestinal tract and is widely distributed in the body. It is metabolized in the liver by the enzymes CYP3A4 and CYP2C19. The major metabolites are 10,11-dihydroxycarbamazepine and 5-hydroxycarbamazepine. These metabolites are also pharmacologically active..

The half-life of carbamazepine is 12-24 hours. The drug is eliminated in the urine..

Carbamazepine is a pregnancy category D drug. This means that it is known to be harmful to fetuses. Women who are pregnant or planning to become pregnant should not take carbamazepine..

Carbamazepine can cause serious side effects including rash, Stevens-Johnson syndrome, and aplastic anemia. Less serious side effects include dizziness, drowsiness, and nausea..

Carbamazepine is a potentially dangerous drug and should be used with caution..

3D structure

Cartesian coordinates

Geometry of 10,11-Dihydroxycarbamazepine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

10,11-Dihydroxycarbamazepine PRGQOPPDPVELEG-KBPBESRZSA-N chemical compound 2D structure molecule svg
10,11-Dihydroxycarbamazepine

 

Molecule descriptors

 
IUPAC name(5S,6S)-5,6-dihydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide
InChI codeInChI=1S/C15H14N2O3/c16-15(20)17-11-7-3-1-5-9(11)13(18)14(19)10-6-2-4-8-12(10)17/h1-8,13-14,18-19H,(H2,16,20)/t13-,14-/m0/s1
InChI KeyPRGQOPPDPVELEG-KBPBESRZSA-N
SMILESNC(=O)N1c2ccccc2[C@H](O)[C@@H](O)c2ccccc21

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (10S,11S)-dihydroxy-10,11-dihydrocarbamazepine
  • (5S,6S)-5,6-dihydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide
  • 10,11-DIHYDROXY-10,11-DIHYDROCARBAZEPINE, TRANS-
  • 10,11-Dihydroxycarbamazepine
  • 10,11-trans-Dihydroxy-10,11-dihydrocarbamazepine
  • 58955-93-4
  • 5H-Dibenz(b,f)azepine-5-carboxamide, 10,11-dihydro-10,11-dihydroxy-, (10R,11R)-rel-
  • 5H-Dibenz(b,f)azepine-5-carboxamide, 10,11-dihydro-10,11-dihydroxy-, trans-
  • 9WR2Y6JJ6A
  • CARBAMAZEPINE, 10,11-DIHYDRO-10,11-DIHYDROXY-
  • CGP 10000
  • CGP-10000
  • Carbamazepine diol
  • Dihydrocarbamazepine-10,11-trans-diol
  • Q27157255
  • TRANS-10,11-DIHYDROXY-10,11-DIHYDROCARBAMAZEPINE
  • trans-10,11-Dihydro-10,11-dihydroxy-5H-dibenz(b,f)azepine-5-carboxamide
  • trans-10,11-Dihydroxy-10,11-dihydrocarbazepine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC896945
  • UNII-9WR2Y6JJ6A
  • DTXSID10891461
  • CHEBI:83815

Physico-Chemical properties

IUPAC name(5S,6S)-5,6-dihydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide
Molecular formulaC15H14N2O3
Molecular weight270.283
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity77.26
LogP2.7
Topological polar surface area86.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.