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Synthesis of a steroidal A ring aromatic sulfonic acid as an inhibitor of steroid 5 alpha-reductase. 1991

D A Holt, and H J Oh, and M A Levy, and B W Metcalf
Department of Medicinal Chemistry, SmithKline Beecham Pharmaceuticals, King of Prussia, PA 19406-0939.

The synthesis of 17 beta-(N,N-diisopropylcarbamoyl)estra-1,3,5(10)-triene-3-sulfonic acid (3) has been accomplished. Sulfonate 3 was designed as a novel inhibitor of human steroid 5 alpha-reductase based on considerations of enzyme mechanisms, and exhibits an inhibition constant in the low nanomolar range.

UI MeSH Term Description Entries
D008297 Male Males
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D004963 Estrenes Unsaturated derivatives of the ESTRANES with methyl groups at carbon-13, with no carbon at carbon-10, and with no more than one carbon at carbon-17. They must contain one or more double bonds. 19-Norandrostenes,19 Norandrostenes
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
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
D013045 Species Specificity The restriction of a characteristic behavior, anatomical structure or physical system, such as immune response; metabolic response, or gene or gene variant to the members of one species. It refers to that property which differentiates one species from another but it is also used for phylogenetic levels higher or lower than the species. Species Specificities,Specificities, Species,Specificity, Species
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
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
D058891 5-alpha Reductase Inhibitors Drugs that inhibit 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE. They are commonly used to reduce the production of DIHYDROTESTOSTERONE. 3-Oxo-5-alpha-Steroid 4-Dehydrogenase Inhibitor,5-alpha Reductase Inhibitor,Steroid 5-alpha-Reductase Inhibitor,Testosterone 5-alpha-Reductase Inhibitor,3-Oxo-5-alpha-Steroid 4-Dehydrogenase Inhibitors,Steroid 5-alpha-Reductase Inhibitors,Testosterone 5-alpha-Reductase Inhibitors,3 Oxo 5 alpha Steroid 4 Dehydrogenase Inhibitor,3 Oxo 5 alpha Steroid 4 Dehydrogenase Inhibitors,4-Dehydrogenase Inhibitor, 3-Oxo-5-alpha-Steroid,4-Dehydrogenase Inhibitors, 3-Oxo-5-alpha-Steroid,5 alpha Reductase Inhibitor,5 alpha Reductase Inhibitors,5-alpha-Reductase Inhibitor, Steroid,5-alpha-Reductase Inhibitor, Testosterone,5-alpha-Reductase Inhibitors, Steroid,5-alpha-Reductase Inhibitors, Testosterone,Inhibitor, 3-Oxo-5-alpha-Steroid 4-Dehydrogenase,Inhibitor, 5-alpha Reductase,Inhibitor, Steroid 5-alpha-Reductase,Inhibitor, Testosterone 5-alpha-Reductase,Inhibitors, 3-Oxo-5-alpha-Steroid 4-Dehydrogenase,Inhibitors, 5-alpha Reductase,Inhibitors, Steroid 5-alpha-Reductase,Inhibitors, Testosterone 5-alpha-Reductase,Reductase Inhibitor, 5-alpha,Reductase Inhibitors, 5-alpha,Steroid 5 alpha Reductase Inhibitor,Steroid 5 alpha Reductase Inhibitors,Testosterone 5 alpha Reductase Inhibitor,Testosterone 5 alpha Reductase Inhibitors
D066298 In Vitro Techniques Methods to study reactions or processes taking place in an artificial environment outside the living organism. In Vitro Test,In Vitro Testing,In Vitro Tests,In Vitro as Topic,In Vitro,In Vitro Technique,In Vitro Testings,Technique, In Vitro,Techniques, In Vitro,Test, In Vitro,Testing, In Vitro,Testings, In Vitro,Tests, In Vitro,Vitro Testing, In

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