(R,R)-asenapine

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

What is the (R,R)-asenapine?

The molecule (R,R)-asenapine presents a molecular formula of C17H16ClNO and its IUPAC name is (2R,6R)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene.

Asenapine, marketed under the trade name Saphris, is an atypical antipsychotic medication used to treat schizophrenia and bipolar disorder.[1][2] It is a potent antagonist of the serotonin 5-HT2A and dopamine D2 receptors, and a moderate antagonist of the serotonin 5-HT2C receptor.[3][4][5].

Asenapine was developed by Schering-Plough and is now manufactured and marketed by Merck & Co.[6] In the United States, asenapine is a Schedule II controlled substance due to its high potential for abuse and dependence.[7][8].

The most common side effects of asenapine are drowsiness, weight gain, and dizziness.[9] Other common side effects include akathisia (restlessness), anxiety, constipation, depression, dry mouth, headache, increased appetite, and nausea.[9][10] Serious side effects may include neuroleptic malignant syndrome, tardive dyskinesia, and priapism.[9][10] Asenapine is not recommended in pregnancy or while breastfeeding.[11][12].

Asenapine is an atypical antipsychotic of the thienobenzodiazepine class.[13] It is a stereoisomer of the more well-known drug olanzapine.[14] Asenapine has a similar pharmacological profile to other atypical antipsychotics, but with a unique chemical structure.[15].

Asenapine is a potent antagonist of the serotonin 5-HT2A and dopamine D2 receptors, and a moderate antagonist of the serotonin 5-HT2C receptor.[3][4][5] It has weak affinities for the serotonin 5-HT6 and 5-HT7 receptors, and does not bind to the dopamine D3 or D4 receptors.[3][4] Asenapine also has weak anticholinergic and antihistaminergic activity.[3][4].

The exact mechanism of action of asenapine is unknown, but it is thought to work by modulating the activity of neurotransmitters in the brain, including serotonin and dopamine.[16][17].

Asenapine was developed by Schering-Plough and is now manufactured and marketed by Merck & Co.[6] In the United States, asenapine is a Schedule II controlled substance due to its high potential for abuse and dependence.[7][8].

The most common side effects of asenapine are drowsiness, weight gain, and dizziness.[9] Other common side effects include akathisia (restlessness), anxiety, constipation, depression, dry mouth, headache, increased appetite, and nausea.[9][10] Serious side effects may include neuroleptic malignant syndrome, tardive dyskinesia, and priapism.[9][10] Asenapine is not recommended in pregnancy or while breastfeeding.[11][12].

Asenapine is an atypical antipsychotic of the thienobenzodiazepine class.[13] It is a stereoisomer of the more well-known drug olanzapine.[14] Asenapine has a similar pharmacological profile to other atypical antipsychotics, but with a unique chemical structure.[15].

Asenapine is a potent antagonist of the serotonin 5-HT2A and dopamine D2 receptors, and a moderate antagonist of the serotonin 5-HT2C receptor.[3][4][5] It has weak affinities for the serotonin 5-HT6 and 5-HT7 receptors, and does not bind to the dopamine D3 or D4 receptors.[3][4] Asenapine also has weak anticholinergic and antihistaminergic activity.[3][4].

The exact mechanism of action of asenapine is unknown, but it is thought to work by modulating the activity of neurotransmitters in the brain, including serotonin and dopamine.[16][17].

Asenapine was developed by Schering-Plough and is now manufactured and marketed by Merck & Co.[6] In the United States, asenapine is a Schedule II controlled substance due to its high potential for abuse and dependence.[7][8].

The most common side effects of asenapine are drowsiness, weight gain, and dizziness.[9] Other common side effects include akathisia (restlessness), anxiety, constipation, depression, dry mouth, headache, increased appetite, and nausea.[9][10] Serious side effects may include neuroleptic malignant syndrome, tardive dyskinesia, and priapism.[9][10] Asenapine is not recommended in pregnancy or while breastfeeding.[11][12].

Asenapine is an atyp.

3D structure

Cartesian coordinates

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

2D drawing

 

(R,R)-asenapine VSWBSWWIRNCQIJ-GJZGRUSLSA-N chemical compound 2D structure molecule svg
(R,R)-asenapine

 

Molecule descriptors

 
IUPAC name(2R,6R)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene
InChI codeInChI=1S/C17H16ClNO/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19/h2-8,14-15H,9-10H2,1H3/t14-,15-/m0/s1
InChI KeyVSWBSWWIRNCQIJ-GJZGRUSLSA-N
SMILESCN1C[C@H]2c3ccccc3Oc3ccc(Cl)cc3[C@@H]2C1

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.

  • (2R,6R)-17-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.0?,?.0?,??]octadeca-1(14),7,9,11,15,17-hexaene
  • (2R,6R)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene
  • (3aR*,12bR*)-5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole
  • (3aR,12bR)-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole
  • (R,R)-asenapine
  • 5-Chloro-2,3,3aalpha,12bbeta-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole
  • 576A456
  • 65576-39-8
  • 65576-45-6
  • 65576-45-6 (free)
  • AC-31051
  • Asenapine
  • Asenapine free base
  • BCP02098
  • BDBM50428890
  • BDBM50445613
  • CS-0860
  • DSSTox_CID_28974
  • DSSTox_GSID_49048
  • DSSTox_RID_83239
  • EX-A4130
  • HY-10121
  • NCGC00188689-01
  • NCGC00263540-01
  • NCGC00263540-04
  • Q50824517

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4893
  • CAS-65576-45-6
  • DTXSID8049048
  • CHEBI:71246
  • CHEBI:71256
  • Tox21_113596
  • Tox21_113596_1
  • SCHEMBL114123

Physico-Chemical properties

IUPAC name(2R,6R)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene
Molecular formulaC17H16ClNO
Molecular weight285.768
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity84.90
LogP4.2
Topological polar surface area12.5

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.