Hopantenic acid

Hopantenic acid (homopantothenic acid), also known as N-pantoyl-GABA, is a central nervous system depressant. Formulated as the calcium salt, it is used as a pharmaceutical drug in the Russian Federation for a variety of neurological, psychological and psychiatric conditions and sold as Pantogam (Russian: Пантогам).[1] It is not approved for use in Europe or the United States.

Hopantenic acid
Names
Preferred IUPAC name
4-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanamido]butanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C10H19NO5/c1-10(2,6-12)8(15)9(16)11-5-3-4-7(13)14/h8,12,15H,3-6H2,1-2H3,(H,11,16)(H,13,14)/t8-/m0/s1 Y
    Key: SBBDHANTMHIRGW-QMMMGPOBSA-N Y
SMILES
  • CC(C)(CO)[C@@H](O)C(=O)NCCCC(O)=O
Properties
Chemical formula
 C10H19NO5
Molar mass 233.264 g·mol−1
Related compounds
Related alkanoic acids
Related compounds
 Panthenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Chemistry

Hopantenic acid is a homologue of pantothenic acid. While pantothenic acid is the amide of D-pantoate and β-alanine, hopantenic acid is the amide of D-pantoate and γ-aminobutyric acid (GABA). This change leads to an additional CH2 in the molecule.[2]

See also

References
  1. Pantogam, drugs.com
  2. Kopelevich VM, Evdokimova GS, Marieva TD, Shmuilovich LM (1971). "Synthesis of D-homopantothenic acid". Pharmaceutical Chemistry Journal. 5 (9): 534–536. doi:10.1007/BF00771659. S2CID 33296093.


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