Gaboxadol

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

What is the Gaboxadol?

The molecule Gaboxadol presents a molecular formula of C6H8N2O2 and its IUPAC name is 4,5,6,7-tetrahydro-[1,2]oxazolo[5,4-c]pyridin-3-one.

Gaboxadol is a molecule that was first synthesized in the early 1970s by scientists working for the pharmaceutical company Merck. It is a member of the class of drugs known as hypnotics, which are used to induce sleep. Gaboxadol is thought to work by binding to a specific site in the brain known as the GABA receptor. This action results in the inhibition of the neurotransmitter GABA, which is responsible for promoting wakefulness..

Gaboxadol was originally developed as a treatment for insomnia, but it was found to be ineffective and was never approved for use in humans. However, recent studies have suggested that gaboxadol may be useful in the treatment of other conditions, such as Alzheimer's disease, Huntington's disease, and schizophrenia..

Alzheimer's disease is a condition characterized by the loss of cognitive function and the accumulation of beta-amyloid plaques in the brain. Huntington's disease is a neurological disorder that results in the degeneration of nerve cells in the brain. Schizophrenia is a mental disorder that is characterized by delusions and hallucinations..

The exact mechanism of action of gaboxadol is not fully understood, but it is thought to work by modulating the activity of the neurotransmitter GABA. GABA is responsible for promoting wakefulness, so by inhibiting its activity, gaboxadol may help to induce sleep. In addition, gaboxadol may also help to reduce the symptoms of Alzheimer's disease, Huntington's disease, and schizophrenia..

Gaboxadol is currently being studied in clinical trials as a potential treatment for Alzheimer's disease, Huntington's disease, and schizophrenia. If these trials are successful, gaboxadol may become the first FDA-approved treatment for these conditions..

3D structure

Cartesian coordinates

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

2D drawing

 

Gaboxadol ZXRVKCBLGJOCEE-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Gaboxadol

 

Molecule descriptors

 
IUPAC name4,5,6,7-tetrahydro-[1,2]oxazolo[5,4-c]pyridin-3-one
InChI codeInChI=1S/C6H8N2O2/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9)
InChI KeyZXRVKCBLGJOCEE-UHFFFAOYSA-N
SMILESOc1noc2c1CCNC2

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,3H,4H,5H,6H,7H-[1,2]oxazolo[5,4-c]pyridin-3-one
  • 4,5,6,7-TETRAHYDROISOXAZOLO(5,4-C)PYRIDIN-3(2H)-ONE
  • 4,5,6,7-Tetrahydro-isoxazolo[5,4-c]pyridin-3-ol
  • 4,5,6,7-Tetrahydroisoxazole(5,4-c)pyridin-3-ol
  • 4,5,6,7-Tetrahydroisoxazolo(5,4-c)pyridin-3-ol
  • 4,5,6,7-Tetrahydroisoxazolo[5,4-c]pyridin-3(2H)-one
  • 4,5,6,7-tetrahydro-[1,2]oxazolo[5,4-c]pyridin-3-one
  • 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol
  • 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-one
  • 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-3-ol
  • 4H,5H,6H,7H-[1,2]oxazolo[5,4-c]pyridin-3-ol
  • 64603-91-4
  • AB00053777
  • AB00053777_07
  • BCP07031
  • BDBM50224809
  • BDBM82002
  • BPBio1_000420
  • BPBio1_001105
  • BSPBio_001003
  • BSPBio_002256
  • Biomol-NT_000235
  • CAS_64603-91-4
  • CCG-205307
  • CS-0002507
  • D04282
  • DB06554
  • DSSTox_CID_25206
  • DSSTox_GSID_45206
  • DSSTox_RID_80750
  • DivK1c_000211
  • EI7
  • FT-0774669
  • GTPL4322
  • Gaboxadol
  • Gaboxadol (USAN/INN)
  • Gaboxadolum
  • HY-10232
  • IDI1_000211
  • Isoxazolo(5,4-c)pyridin-3(2H)-one, 4,5,6,7-tetrahydro-
  • Isoxazolo[5,4-c]pyridin-3(2H)-one, 4,5,6,7-tetrahydro-
  • K1M5RVL18S
  • KBio1_000211
  • KBio2_001964
  • KBio2_004532
  • KBio2_007100
  • KBio3_001476
  • KBioGR_000683
  • KBioSS_001964
  • LU-02030
  • Lopac-T-101
  • Lopac0_001233
  • Lu 02-030
  • Lu-02-030
  • MFCD05664626
  • MK-0928
  • NCGC00015982-01
  • NCGC00015982-02
  • NCGC00015982-03
  • NCGC00015982-04
  • NCGC00015982-05
  • NCGC00015982-06
  • NCGC00015982-07
  • NCGC00015982-13
  • NCGC00024801-01
  • NCGC00024801-02
  • NCGC00024801-03
  • NCGC00263653-01
  • NINDS_000211
  • NSC 759585
  • NSC-759585
  • NSC_3448
  • OV-101
  • Prestwick-13B03
  • Prestwick0_000972
  • Prestwick1_000972
  • Prestwick2_000972
  • Prestwick3_000972
  • Q4130924
  • SB18782
  • SBI-0051200.P003
  • SDCCGSBI-0051200.P004
  • SY253214
  • THIP
  • Tocris-0807
  • gaboxadol

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC19795995
  • CAS-64603-91-4
  • UNII-K1M5RVL18S
  • AKOS006282519
  • DTXSID0045206
  • CHEMBL312443
  • CHEBI:34373
  • Tox21_110271
  • Tox21_110271_1
  • EINECS 264-963-0
  • SPBio_001560
  • SPBio_002914
  • Spectrum_001484
  • Spectrum2_001590
  • Spectrum3_000728
  • Spectrum4_000172
  • Spectrum5_001907

Physico-Chemical properties

IUPAC name4,5,6,7-tetrahydro-[1,2]oxazolo[5,4-c]pyridin-3-one
Molecular formulaC6H8N2O2
Molecular weight140.14
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity37.87
LogP0.4
Topological polar surface area58.3

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.