7801-30-1

Basic information

• Product Name: 11β,17β-Dihydroxy-5α-androstan-3-one
• Synonyms: 11β,17β-Dihydroxy-5α-androstan-3-one
• CAS NO: 7801-30-1
• Molecular Formula: C19H30O3
• Molecular Weight: 306.4397
• Mol File: 7801-30-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 11β,17β-Dihydroxy-5α-androstan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 11β,17β-Dihydroxy-5α-androstan-3-one(7801-30-1)
• EPA Substance Registry System: 11β,17β-Dihydroxy-5α-androstan-3-one(7801-30-1)

Safety Data

• Hazardous Substances Data: 7801-30-1(Hazardous Substances Data)

Upstream product

• 382-44-5 (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 1816-85-9 11β-hydroxytestosterone 

Downstream Products

• 15375-19-6 (5α)-androst-9(11)-ene-3,17-dione 

Relevant articles and documents

Synthesis of 11β-Fluoro-5α-dihydrotestosterone and 11β-Fluoro-19-nor-5α-dihydrotestosterone: Preparation via Halofluorination-Reduction, Receptor Binding, and Tissue Distribution

We have prepared 11β-fluoro-5α-dihydrotestosterone (11β-F-DHT, 1) and 11β-fluoro-19-nor-5α-dihydrotestosterone (11β-F-19-nor-DHT, 2) in order to investigate the properties of these new androgens labeled with fluorine-18 as potential androgen receptor (AR)-based imaging agents for prostate cancer.These compounds were synthesized in 6 steps from hydrocortisone and in 13 steps from 1,4-androstadiene-3,11,17-trione, respectively.Relative binding affinities (RBA) of 11β-F-DHT and 11β-F-19-nor-DHT to AR are 53.1 and 75.3 (R1881 = 100), respectively, the latter being the highest reported among fluorine-substituted androgens.The fluorination step, which involves addition of halogen fluoride across the 9(11)-double bond, followed by reductive dehalogenation at the 9α-position has been adapted to introduce a fluorine-18-label at the 11β-position of DHT and 19-nor-DHT.The two high-affinity F-18-labeled ligands -1 and -2 were evaluated in vivo, in tissue distribution studies using diethylstilbestrol-pretreated mature male rats. 11β-F-DHT shows high prostate uptake and selective prostate to blood and prostate to muscle uptake ratios, the latter two ratios increasing from 5 and 8 at 1 h to 12 and 19 at 4 h postinjection.Moreover, this compound has low uptake in bone, displaying the lowest in vivo defluorination among all androgens labeled with fluorine-18 tested so far.The in vivo properties of 11β-F-DHT in rats are thus favorable for imaging of prostate cancer.On the other hand, 11β-F-19-nor-DHT shows low prostate uptake with low selectivity and high uptake in liver, kidney, and bladder.Even though this ligand has the highest RBA and undergoes little metabolic defluorination, it appears to suffer from rapid metabolism in vivo.Therefore, it is apparent that the biodistribution properties of androgens are affected by their structure and metabolism as well as by their RBA.