Bolandione (original) (raw)
19-去甲-4-雄烯二酮（英語：19-norandrostenedione，也被称为Bolandione，19-去甲雄甾-4-烯-3,17-二酮，19-norandrost-4-en-3,17-dione 或雌-4-烯-3,17-二酮，estr-4-ene-3,17-dione）是同化類固醇（AAS）19-去甲睾酮（诺龙）的前体物质。世界反運動禁藥機構将其列为兴奋剂，禁止在奥林匹克运动会与其它运动会中使用。Bolandione进入人体后，会很快代谢为19-去甲睾酮，但其对雄激素受体依赖性基因表达的影响比双氢睾酮（DHT）低了10倍。
| Property | Value |
|---|---|
| dbo:abstract | Bolandione, also known as 19-norandrostenedione, as well as 19-norandrost-4-en-3,17-dione or estr-4-ene-3,17-dione, is a precursor of the anabolic-androgenic steroid (AAS) nandrolone (19-nortestosterone). Until 2005, bolandione was available without prescription in United States, where it was marketed as a prohormone, but it is now classified as a Schedule III drug. It is also banned from use in many sports, including the Olympic Games, under the World Anti-Doping Code. Bolandione is readily metabolized to nandrolone after oral administration, but its potency to transactivate the androgen receptor dependent reporter gene expression is 10 times lower as compared to dihydrotestosterone (DHT). Scientific studies have shown that oral administration of bolandione is "a very ineffective strategy for stimulating skeletal muscle mass increases but may be associated with side effects". In vivo experiments in castrated rats demonstrated that subcutaneous treatment with bolandione resulted only in a stimulation of the weight of the levator ani muscle, while the prostate and seminal vesicle weights remained completely unaffected. In contrast to its metabolite nandrolone, bolandione highly selectively stimulates the growth of the skeletal muscles but has only weak androgenic properties. In the early 2000s, contamination of androstenedione products with traces of bolandione caused false positives for doping tests for nandrolone because 19-norandrosterone is a metabolite of both nandrolone and bolandione. In a randomized controlled trial trace contamination of androstenedione with bolandione was sufficient for users of androstenedione to test positive for nandrolone. This detail became less relevant after bolandione and 4-androstenedione were banned by major sporting bodies. (en) 19-去甲-4-雄烯二酮（英語：19-norandrostenedione，也被称为Bolandione，19-去甲雄甾-4-烯-3,17-二酮，19-norandrost-4-en-3,17-dione 或雌-4-烯-3,17-二酮，estr-4-ene-3,17-dione）是同化類固醇（AAS）19-去甲睾酮（诺龙）的前体物质。世界反運動禁藥機構将其列为兴奋剂，禁止在奥林匹克运动会与其它运动会中使用。Bolandione进入人体后，会很快代谢为19-去甲睾酮，但其对雄激素受体依赖性基因表达的影响比双氢睾酮（DHT）低了10倍。 (zh) |
| dbo:casNumber | 734-32-7 |
| dbo:drugbank | DB01434 |
| dbo:fdaUniiCode | U90987PVU5 |
| dbo:pubchem | 92834 |
| dbo:thumbnail | wiki-commons:Special:FilePath/Bolandione.svg?width=300 |
| dbo:wikiPageID | 20871814 (xsd:integer) |
| dbo:wikiPageLength | 5826 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1084541901 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Prostate dbr:19-norandrosterone dbr:Androgen_receptor dbr:List_of_androgens/anabolic_steroids dbr:Levator_ani dbc:Androgens_and_anabolic_steroids dbc:Diketones dbc:Estranes dbc:Estrogens dbc:Prodrugs dbc:Progestogens dbc:World_Anti-Doping_Agency_prohibited_substances dbr:Controlled_Substances_Act dbr:Oral_administration dbr:Androgenic dbr:Androstenedione dbr:Subcutaneous_injection dbr:Precursor_(chemistry) dbr:Randomized_controlled_trial dbr:Prohormone dbr:Dihydrotestosterone dbr:Nandrolone dbr:Olympic_Games dbr:World_Anti-Doping_Code dbr:Skeletal_muscle dbr:Doping_(sport) dbr:Transactivate dbr:Anabolic-androgenic_steroid dbr:Castrated |
| dbp:c | 18 (xsd:integer) |
| dbp:casNumber | 734 (xsd:integer) |
| dbp:chemspiderid | 83803 (xsd:integer) |
| dbp:drugbank | DB01434 (en) |
| dbp:h | 24 (xsd:integer) |
| dbp:iupacName | -13 (xsd:integer) |
| dbp:legalUs | Schedule III (en) |
| dbp:o | 2 (xsd:integer) |
| dbp:pubchem | 92834 (xsd:integer) |
| dbp:routesOfAdministration | dbr:Oral_administration |
| dbp:smiles | O=C4/C=C3/CC[C@@H]2[C@H][C@H]3CC4 (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | JRIZOGLBRPZBLQ-QXUSFIETSA-N (en) |
| dbp:synonyms | 19 (xsd:integer) |
| dbp:unii | U90987PVU5 (en) |
| dbp:verifiedfields | changed (en) |
| dbp:verifiedrevid | 477209395 (xsd:integer) |
| dbp:watchedfields | changed (en) |
| dbp:width | 225 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Androgen_receptor_modulators dbt:Drugbox dbt:Estrogen_receptor_modulators dbt:Genito-urinary-drug-stub dbt:Progesterone_receptor_modulators dbt:Reflist dbt:Short_description dbt:Steroid-stub dbt:Cascite dbt:Chemspidercite dbt:Drugbankcite dbt:Fdacite dbt:Stdinchicite |
| dct:subject | dbc:Androgens_and_anabolic_steroids dbc:Diketones dbc:Estranes dbc:Estrogens dbc:Prodrugs dbc:Progestogens dbc:World_Anti-Doping_Agency_prohibited_substances |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 dbo:Drug umbel-rc:DrugProduct |
| rdfs:comment | 19-去甲-4-雄烯二酮（英語：19-norandrostenedione，也被称为Bolandione，19-去甲雄甾-4-烯-3,17-二酮，19-norandrost-4-en-3,17-dione 或雌-4-烯-3,17-二酮，estr-4-ene-3,17-dione）是同化類固醇（AAS）19-去甲睾酮（诺龙）的前体物质。世界反運動禁藥機構将其列为兴奋剂，禁止在奥林匹克运动会与其它运动会中使用。Bolandione进入人体后，会很快代谢为19-去甲睾酮，但其对雄激素受体依赖性基因表达的影响比双氢睾酮（DHT）低了10倍。 (zh) Bolandione, also known as 19-norandrostenedione, as well as 19-norandrost-4-en-3,17-dione or estr-4-ene-3,17-dione, is a precursor of the anabolic-androgenic steroid (AAS) nandrolone (19-nortestosterone). Until 2005, bolandione was available without prescription in United States, where it was marketed as a prohormone, but it is now classified as a Schedule III drug. It is also banned from use in many sports, including the Olympic Games, under the World Anti-Doping Code. Bolandione is readily metabolized to nandrolone after oral administration, but its potency to transactivate the androgen receptor dependent reporter gene expression is 10 times lower as compared to dihydrotestosterone (DHT). (en) |
| rdfs:label | Bolandione (en) 19-去甲-4-雄烯二酮 (zh) |
| owl:sameAs | yago-res:Bolandione http://www4.wiwiss.fu-berlin.de/drugbank/resource/drugs/DB01434 wikidata:Bolandione dbpedia-sh:Bolandione dbpedia-sr:Bolandione dbpedia-zh:Bolandione https://global.dbpedia.org/id/4Dhrk |
| prov:wasDerivedFrom | wikipedia-en:Bolandione?oldid=1084541901&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/Bolandione.svg |
| foaf:isPrimaryTopicOf | wikipedia-en:Bolandione |
| is dbo:wikiPageRedirects of | dbr:19-N-Andro dbr:19-Nor-4-Androstene-3,17-dione dbr:Estr-4-ene-3,17-dione |
| is dbo:wikiPageWikiLink of | dbr:List_of_androgens/anabolic_steroids_(alternate) dbr:List_of_androgens_and_anabolic_steroids dbr:List_of_drugs_banned_by_the_World_Anti-Doping_Agency dbr:Methoxydienone dbr:19-Norandrostenedione dbr:Bolandiol dbr:Androgen_prohormone dbr:C18H24O2 dbr:19-Norandrosterone dbr:19-Nordehydroepiandrosterone dbr:19-N-Andro dbr:19-Nor-5-androstenedione dbr:19-Noretiocholanolone dbr:Linford_Christie dbr:7α-Methyl-19-norandrostenedione dbr:2009_National_Games_of_China dbr:Anabolic_steroid dbr:Dienedione dbr:Nandrolone dbr:Nandrolone_decanoate dbr:Structure–activity_relationships_of_anabolic_steroids dbr:19-Nor-4-Androstene-3,17-dione dbr:Estr-4-ene-3,17-dione |
| is foaf:primaryTopic of | wikipedia-en:Bolandione |
