DU-41165 (original) (raw)
DU-41165, also known as 6-fluoro-16-methylene-17α-acetoxy-δ6-retroprogesterone, is a progestin which was developed by Philips-Duphar in the 1970s and was never marketed. It is a combined derivative of 17α-hydroxyprogesterone and retroprogesterone. The drug shows extremely high potency as a progestogen in animals. It has been found to possess 158% of the relative binding affinity of promegestone for the progesterone receptor expressed in rat uterus (relative to 74% for the closely related progestin DU-41164). DU-41165 also showed 28% of the affinity of RU-28362 for the glucocorticoid receptor expressed in rat liver, but no affinity for the mineralocorticoid receptor expressed in rat kidney (<0.003% of that of ). The drug showed no androgenic, anabolic, or estrogenic activity in animals, but
| Property | Value |
|---|---|
| dbo:abstract | DU-41165, also known as 6-fluoro-16-methylene-17α-acetoxy-δ6-retroprogesterone, is a progestin which was developed by Philips-Duphar in the 1970s and was never marketed. It is a combined derivative of 17α-hydroxyprogesterone and retroprogesterone. The drug shows extremely high potency as a progestogen in animals. It has been found to possess 158% of the relative binding affinity of promegestone for the progesterone receptor expressed in rat uterus (relative to 74% for the closely related progestin DU-41164). DU-41165 also showed 28% of the affinity of RU-28362 for the glucocorticoid receptor expressed in rat liver, but no affinity for the mineralocorticoid receptor expressed in rat kidney (<0.003% of that of ). The drug showed no androgenic, anabolic, or estrogenic activity in animals, but did show some antiandrogenic and glucocorticoid activity at high doses. Although highly potent in animals, DU-41165 produced little or no progestogenic effect at dosages of 50 and 200 µg/day in women, suggesting major species differences. DU-41165 has been studied as a potential photoaffinity label for the progesterone receptor. (en) |
| dbo:casNumber | 34184-58-2 |
| dbo:class | dbr:Progestin dbr:Progestogen |
| dbo:fdaUniiCode | 5M4PL394K5 |
| dbo:pubchem | 169573 |
| dbo:thumbnail | wiki-commons:Special:FilePath/DU-41165.svg?width=300 |
| dbo:wikiPageID | 57842733 (xsd:integer) |
| dbo:wikiPageLength | 4593 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1107938654 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Potency_(pharmacology) dbr:Progestin dbr:Promegestone dbr:Progestogen dbr:Androgen dbr:Retroprogesterone dbc:Abandoned_drugs dbc:Acetate_esters dbc:Conjugated_dienes dbc:Diketones dbc:Enones dbc:Fluoroarenes dbc:Glucocorticoids dbc:Pregnanes dbc:Progestogens dbc:Steroidal_antiandrogens dbc:Vinylidene_compounds dbr:Estrogen_(medication) dbr:Oral_administration dbr:Antiandrogen dbr:Liver dbr:Progesterone_receptor dbr:Anabolic dbr:DU-41164 dbr:Glucocorticoid dbr:Glucocorticoid_receptor dbr:Kidney dbr:RU-28362 dbr:Mineralocorticoid_receptor dbr:Photoaffinity_label dbr:17α-hydroxyprogesterone dbr:Chemical_derivative dbr:Relative_binding_affinity dbr:RU-26752 |
| dbp:c | 24 (xsd:integer) |
| dbp:casNumber | 34184 (xsd:integer) |
| dbp:chemspiderid | 148298 (xsd:integer) |
| dbp:class | dbr:Progestin dbr:Progestogen |
| dbp:f | 1 (xsd:integer) |
| dbp:h | 29 (xsd:integer) |
| dbp:iupacName | [-17-Acetyl-6-fluoro-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate (en) |
| dbp:o | 4 (xsd:integer) |
| dbp:pubchem | 169573 (xsd:integer) |
| dbp:routesOfAdministration | dbr:Oral_administration |
| dbp:smiles | CC[C@]1OCC (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | XSSIGSNQDKHHLD-JBARXXBASA-N (en) |
| dbp:synonyms | 6 (xsd:integer) |
| dbp:unii | 5 (xsd:integer) |
| dbp:width | 250 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Androgen_receptor_modulators dbt:Drugbox dbt:Glucocorticoid_receptor_modulators dbt:Progesterone_receptor_modulators dbt:Reflist dbt:Short_description dbt:Cascite dbt:Fdacite |
| dct:subject | dbc:Abandoned_drugs dbc:Acetate_esters dbc:Conjugated_dienes dbc:Diketones dbc:Enones dbc:Fluoroarenes dbc:Glucocorticoids dbc:Pregnanes dbc:Progestogens dbc:Steroidal_antiandrogens dbc:Vinylidene_compounds |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 dbo:Drug |
| rdfs:comment | DU-41165, also known as 6-fluoro-16-methylene-17α-acetoxy-δ6-retroprogesterone, is a progestin which was developed by Philips-Duphar in the 1970s and was never marketed. It is a combined derivative of 17α-hydroxyprogesterone and retroprogesterone. The drug shows extremely high potency as a progestogen in animals. It has been found to possess 158% of the relative binding affinity of promegestone for the progesterone receptor expressed in rat uterus (relative to 74% for the closely related progestin DU-41164). DU-41165 also showed 28% of the affinity of RU-28362 for the glucocorticoid receptor expressed in rat liver, but no affinity for the mineralocorticoid receptor expressed in rat kidney (<0.003% of that of ). The drug showed no androgenic, anabolic, or estrogenic activity in animals, but (en) |
| rdfs:label | DU-41165 (en) |
| owl:sameAs | wikidata:DU-41165 https://global.dbpedia.org/id/85f4e |
| prov:wasDerivedFrom | wikipedia-en:DU-41165?oldid=1107938654&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/DU-41165.svg |
| foaf:isPrimaryTopicOf | wikipedia-en:DU-41165 |
| is dbo:wikiPageRedirects of | dbr:DU-41,165 dbr:DU41165 dbr:DU_41,165 dbr:DU_41165 |
| is dbo:wikiPageWikiLink of | dbr:DU-41164 dbr:C24H29FO4 dbr:DU-41,165 dbr:DU41165 dbr:DU_41,165 dbr:DU_41165 |
| is foaf:primaryTopic of | wikipedia-en:DU-41165 |
