Agomelatine

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

What is the Agomelatine?

The molecule Agomelatine presents a molecular formula of C15H17NO2 and its IUPAC name is N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide.

Agomelatine (BAN, USAN, INN; trade names Valdoxan, Melitor, Thymanax) is an atypical antidepressant which functions as a selective melatonin receptor agonist and serotonin 5-HT2C receptor antagonist. It was discovered and developed by the pharmaceutical company Servier. In a number of countries it is licensed for the treatment of major depressive disorder..

Agomelatine is a melatonin receptor agonist with both high affinity for MT1 and MT2 receptors and antagonistic activity at the 5-HT2C receptor. It also inhibits the reuptake of monoamines, but to a lesser extent than most other antidepressants..

The antidepressant effect of agomelatine has been demonstrated in animal models of depression, including the forced swim test and the olfactory bulbectomy model. These effects are mediated by the activation of melatonin receptors and the 5-HT2C receptor..

The exact mechanism of action of agomelatine in humans is unknown. However, it is thought to work by modulating the circadian rhythm, which is often disturbed in people with depression..

Agomelatine has a good safety profile and is well tolerated. The most common side effects are nausea, headache, and dizziness..

Agomelatine is a promising new antidepressant with a unique mechanism of action. Further research is needed to determine its place in the treatment of depression..

3D structure

Cartesian coordinates

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

2D drawing

 

Agomelatine YJYPHIXNFHFHND-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Agomelatine

 

Molecule descriptors

 
IUPAC nameN-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
InChI codeInChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17)
InChI KeyYJYPHIXNFHFHND-UHFFFAOYSA-N
SMILESCOc1ccc2cccc(CCNC(C)=O)c2c1

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.

  • (4-Chlorophenyl)-[(9H-fluoren-9-ylmethoxycarbonylamino)]-aceticacid
  • 112A762
  • 137R1N49AD
  • 138112-76-2
  • A19445
  • AB01274769-01
  • AB01274769_02
  • AC-3395
  • AGO 178
  • AGO-178
  • AGO178
  • AGO178C
  • AM20090763
  • AWY
  • Acetamide, N-(2-(7-methoxy-1-naphthalenyl)ethyl)-
  • Acetamide, N-[2-(7-methoxy-1-naphthalenyl)ethyl]-
  • Agomelatine
  • Agomelatine (INN)
  • Agomelatine- Bio-X
  • Agomelatine-[d4]
  • B2262
  • BA167079
  • BBL029084
  • BCP02084
  • BCP9000250
  • BCPP000421
  • BDBM50035179
  • CCG-221950
  • CS-0740
  • D02578
  • DB06594
  • DSSTox_CID_31431
  • DSSTox_GSID_57642
  • DSSTox_RID_97317
  • F0001-2383
  • FT-0657383
  • GTPL198
  • HMS3604N09
  • HMS3648G18
  • HMS3654B07
  • HMS3884A07
  • HY-17038
  • KS-1247
  • L000528
  • MFCD00916659
  • MLS006011913
  • Melitor
  • N-(2-(7-Methoxy-1-naphthalenyl)ethyl)acetamide
  • N-(2-(7-Methoxynaphth-1-yl)ethyl)acetamide
  • N-(2-(7-Methoxynaphthalen-1-yl)ethyl)acetamide
  • N-(2-(7-methoxy-1-naphthyl)ethyl)acetamide
  • N-[2-(7-Methoxy-1-naphthalenyl)ethyl]acetamide
  • N-[2-(7-Methoxy-naphthalen-1-yl)-ethyl]-acetamide
  • N-[2-(7-Methoxy-naphthalen-1-yl)-ethyl]-acetamide(Agomelatine)
  • N-[2-(7-Methoxynaphth-1-Yl)Ethyl]Acetamide
  • N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide
  • N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
  • NCGC00253646-01
  • NCGC00253646-10
  • PDSP1_001305
  • PDSP1_001784
  • PDSP2_001289
  • PDSP2_001767
  • Q-102507
  • Q395229
  • S 20098
  • S-20098
  • S20098
  • SB19508
  • SMR002530056
  • SR-01000944938
  • SR-01000944938-1
  • SR-01000944938-3
  • STL237728
  • SW219177-1
  • Thymanax
  • Valdoxan
  • s1243

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC5608
  • CAS-138112-76-2
  • UNII-137R1N49AD
  • AKOS005145681
  • DTXSID3057642
  • CHEMBL10878
  • CHEBI:134990
  • Tox21_113772
  • SCHEMBL114476

Physico-Chemical properties

IUPAC nameN-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
Molecular formulaC15H17NO2
Molecular weight243.301
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity72.83
LogP2.9
Topological polar surface area38.3

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.