Biomaterial Database

Prodrugs of etilefrine: synthesis and evaluation of 3'-(O-acyl) derivatives. 1980

J Wagner, and H Grill, and D Henschler

A series of 3'-(O-acyl) derivatives of etilefrine (alpha-[(ethylamino)methyl]-3'-hydroxybenzyl alcohol) was synthesized. Correlations between structure and solubility, pKa value, lipophilicity, and esterase-catalyzed hydrolysis were demonstrated. Of special interest is the 3'-(O-pivaloyl) derivative, which shows, in addition to favorable solubility and improved lipophilicity, marked stability against enzymatic cleavage in blood along with a high rate of hydrolysis in the liver.

UI	MeSH Term	Description	Entries
D007700	Kinetics	The rate dynamics in chemical or physical systems.
D010656	Phenylephrine	An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.	(R)-3-Hydroxy-alpha-((methylamino)methyl)benzenemethanol,Metaoxedrin,Metasympatol,Mezaton,Neo-Synephrine,Neosynephrine,Phenylephrine Hydrochloride,Phenylephrine Tannate,Neo Synephrine,Tannate, Phenylephrine
D002627	Chemistry, Physical	The study of CHEMICAL PHENOMENA and processes in terms of the underlying PHYSICAL PHENOMENA and processes.	Physical Chemistry,Chemistries, Physical,Physical Chemistries
D005039	Etilefrine	A phenylephrine-related beta-1 adrenergic and alpha adrenergic agonist used as a cardiotonic and antihypotensive agent.	Ethylnorphenylephrine,Ethylphenylephrine,Adrenam,Bioflutin,Cardanat,Circupon,Effortil,Efortil,Ethyl Adrianol,Ethyladrianol,Eti-Puren,Etilefrin,Etilefrin AL,Etilefrin-ratiopharm,Etilefrine Hydrochloride,Etilefrine Pivalate Hydrochloride,Fetanol,Phetanol,Thomasin,etil von ct,Adrianol, Ethyl,Eti Puren,Etilefrin ratiopharm,Hydrochloride, Etilefrine,Hydrochloride, Etilefrine Pivalate,Pivalate Hydrochloride, Etilefrine
D005260	Female		Females
D006801	Humans	Members of the species Homo sapiens.	Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D006868	Hydrolysis	The process of cleaving a chemical compound by the addition of a molecule of water.
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D012995	Solubility	The ability of a substance to be dissolved, i.e. to form a solution with another substance. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed)	Solubilities
D051381	Rats	The common name for the genus Rattus.	Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus