Fludiazepam

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

What is the Fludiazepam?

The molecule Fludiazepam presents a molecular formula of C16H12ClFN2O and its IUPAC name is 7-chloro-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one.

Fludiazepam is a molecule of the benzodiazepine class. Benzodiazepines are a class of psychoactive drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. This class of drugs also includes well-known medications such as diazepam (Valium), alprazolam (Xanax), and clonazepam (Klonopin). Benzodiazepines work by binding to the GABA receptors in the brain and enhancing the effects of the neurotransmitter GABA..

Fludiazepam was first synthesized in 1960 by Leo Sternbach and his team at Hoffmann-La Roche. It is a relatively potent benzodiazepine, with an LD50 of 200 mg/kg in mice. The therapeutic dose range in humans is 2-20 mg. Fludiazepam has a half-life of 36-72 hours, which is much longer than other benzodiazepines. This makes it useful for treating anxiety and seizure disorders, as well as for alcohol withdrawal. However, the long half-life also means that fludiazepam can accumulate in the body and cause side effects such as drowsiness, impaired coordination, and memory problems..

Fludiazepam is not currently available in the United States, but it is marketed in some European and Asian countries..

3D structure

Cartesian coordinates

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

2D drawing

 

Fludiazepam ROYOYTLGDLIGBX-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Fludiazepam

 

Molecule descriptors

 
IUPAC name7-chloro-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
InChI codeInChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3
InChI KeyROYOYTLGDLIGBX-UHFFFAOYSA-N
SMILESCN1C(=O)CN=C(c2ccccc2F)c2cc(Cl)ccc21

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.

  • 2H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-chloro-5-(o-fluorophenyl)-1-methyl-
  • 2H-1,4-Benzodiazepin-2-one, 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-1-methyl-
  • 2H-1,4-Benzodiazepin-2-one, 7-chloro-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-
  • 3900-31-0
  • 7-Chloro-5-(2-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one
  • 7-Chloro-5-(2-fluorophenyl)-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
  • 7-Chloro-5-(2-fluorophenyl)-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one #
  • 7-Chloro-5-(2-fluorophenyl)-1-methyl-1H-1,4-benzodiazepin-2(3H)-one
  • 7-Chloro-5-(o-Fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one
  • 7-chloro-5-(2-fluorophenyl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
  • 7-chloro-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
  • 7F64A2K16Z
  • 900F310
  • BRN 0686115
  • D01354
  • DB01567
  • DEA No. 2759
  • Erispan
  • Fludiazepam
  • Fludiazepam (JP17/INN)
  • Fludiazepamum
  • ID 540
  • ID-540
  • Q3486981
  • Ro-5-3438
  • fludiazepam

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • UNII-7F64A2K16Z
  • DTXSID00192277
  • CHEMBL13291
  • CHEBI:31618
  • SCHEMBL156039

Physico-Chemical properties

IUPAC name7-chloro-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
Molecular formulaC16H12ClFN2O
Molecular weight302.731
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity87.91
LogP2.8
Topological polar surface area32.7

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.