4744. Hopantenic Acid

Nomenclature

CAS number: 18679-90-8
4-[[(2R)-2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl]amino]butanoic acid; d-(+)-4-(2,4-dihydroxy-3,3-dimethylbutyramido)butyric acid; d-homopantothenic acid.
C10H19NO5; mol wt 233.26.
C 51.49%, H 8.21%, N 6.00%, O 34.30%.

Description and references

Homolog of pantothenic acid, q.v. Prepn: R. Fuerst, L. L. Li, Biochim. Biophys. Acta 86, 26 (1964); C. M. DeSha, R. Fuerst, ibid. 33. Prepn of the calcium salt: Y. Nishizawa et al., JP 66 732 (1966 to Tanabe), C.A. 64, 12555c (1965). Series of articles on analysis, physicochemical properties, electrophysiology, pharmacology, toxicity studies, teratology: Bitamin 33, 603-632 (1966), C.A. 65, 5949a-g (1966). Colorimetric determn, properties: T. Kodama et al., J. Vitaminol. 13, 298 (1967), C.A. 68, 62755n (1968). Peri- and postnatal studies in rats: Y. Asano et al., Oyo Yakuri 19, 1011 (1980), C.A. 94, 58160 (1981). Mechanism of action: V. M. Arakumov, M. A. Kovler, Farmakol. Toksikol. 44, 30 (1981), C.A. 94, 114577 (1981). Determn in plasma: Y. Umeno et al., J. Chromatogr. 226, 333 (1981). Toxicology studies: Y. Nishizawa et al., J. Vitaminol. 15, 26 (1969). Pharmacology and acute toxicity study: Y. Nishizawa, Med. J. Osaka Univ. 35, 41 (1984).

Chemical structure

Properties

Sol in water; stable at pH 5-6. [α]D20 +23.8°. pKa 4.52 at 25°. LD50 in male, female mice, male, female rats (mg/kg): 850, 954, 1575, 1458 i.p.; 2063, 2495, 5940, 7348 s.c.; 6297, 7935, 16810, 13350 orally (Nishizawa).

Derivative

Calcium salt hemihydrate.

Nomenclature

Calcium homopantothenate; hopantenate calcium; pantogam; Hopate (Tanabe).
C20H36CaNO5.H2O; mol wt 419.59.
C 57.25%, H 8.89%, Ca 9.55%, N 3.34%, O 20.97%.

Properties

White powder, mp 155-165°. [α]D20 +24.19° (c = 2 in water). Bitter taste. Sol in water, slightly sol in methanol. Practically insol in organic solvents. Stable at pH 5-6.

Therapeutic Category

Cerebral activator.