7113. Pentagastrin

Nomenclature

CAS number: 5534-95-2
N-[(1,1-Dimethylethoxy)carbonyl]-β-alanyl-l-tryptophyl-l-methionyl-l-α-aspartyl-l-phenylalaninamide; N-carboxy-β-alanyl-l-tryptophyl-l-methionyl-l-aspartylphenyl-l-alaninamide N-tert-butyl ester; N-(α-carbamoylphenethyl)-3-[2-[2-[3-(carboxyamino)propionamido]-3-indol-3-ylpropionamido]-4-(methylthio)butyramido]succinamic acid N-tert-butyl ester; N-[N-[N-[N-(N-tert-butoxycarbonyl-β-alanyl)-l-tryptophanyl]-l-methionyl]-l-aspartyl]-l-phenylalaninamide; Boc-β-Ala-Trp-Met-Asp-Phe(NH2); AY-6608; ICI-50123; Gastrodiagnost (Merck KGaA); Peptavlon (Ayerst).
C37H49N7O9S; mol wt 767.89.
C 57.87%, H 6.43%, N 12.77%, O 18.75%, S 4.18%.

Description and references

Prepn: P. M. Hardy et al., BE 665591; eidem, US 3896103 (1965, 1975 to I.C.I.); Davey et al., J. Chem. Soc. C 1966, 555; Sakakibara et al., Bull. Chem. Soc. Jpn. 41, 438 (1968). Structure-function relationship studies: Morley et al., Nature 207, 1356 (1965). Formulation and pharmacological studies: Wai et al., J. Pharm. Pharmacol. 22, 923 (1970). Reviews: Makhlouf, Fed. Proc. 27, 1322 (1968); Sanders, Schimmel, Am. J. Med. 49, 380 (1970).

Chemical structure

Properties

Fine, colorless needle-shaped crystals from 2-ethoxyethanol + water; mp 229-230° (dec). [α]D22 -28.8 ±0.5° (DMF). uv max (2N NH4OH): 280, 289 nm (ε 5340, 4590). Sol in DMF, DMSO. Almost insol in water, ethanol, ether, benzene.

Therapeutic Category

Diagnostic aid (gastric secretion stimulant).

Keywords

Diagnostic Aid