Steroidal[3,2-c]pyrazoles. II.<sup>1</sup> Androstanes, 19-Norandrostanes and their Unsaturated Analogs

Clinton, R. O.; Manson, A. J.; Stonner, F. W.; Neumann, Helmut; Christiansen, Robert G.; Clarke, Robert L.; Ackerman, James H.; Pagé, Daniel; Dean, John W.; Dickinson, William B.; Carabateas, Clarissa D.

doi:10.1021/ja01467a047

Cited by 129 publications

(35 citation statements)

References 2 publications

(2 reference statements)

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“…Stanozolol, (17α-methyl-5α-androstano-[3,2-c]-pyrazol-17β-ol) ( Figure 1) was initially synthesized in 1959 [4] and clinically used in cases of deficiency in protein synthesis and osteoporosis [5]. Stanozolol, commonly sold under the name Winstrol (oral) and Winstrol Depot (intramuscular) and often called Winny was commercially developed by Winthrop Laboratories (Sterling Drug) in 1962, and has been approved for human use.…”

Section: Generic Namementioning

confidence: 99%

Urine Fingerprints of Stanozolol Treated Horses by Liquid Chromatography High Resolution Mass Spectrometry

Stojiljkovic¹,

Bubanj²,

Đorđević³

et al. 2017

J Sports Med Dop Stud

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The current detection methods for stanozolol are all based on targeted approach. The present study aimed to assess the global biological effect of stanozolol-treatment by means of chemometric models, after generating and comparing horse urine LC-HRMS fingerprints collected from control and stanozolol-treated horses. The animal study was conducted according to an ethically approved protocol at two different places in France: Chamberet and Coye la Forêt. The total duration of the animal phase was seven months and only females were selected to partake. The sixteen mares in this study were not actively racing horses, but were in good physical condition. SIMCA-P+ software and R free software environment were used for multivariate data analysis. Principal Component Analysis (PCA) and Orthogonal Projections to Latent Structures-Discriminant Analysis (OPLS-DA) were applied to build some descriptive and predictive models. The analyzed horse urine fingerprints based on the 220 features selected after suppression of confounding factors show changes in metabolic states after chronic stanozolol treatment. This proof of concept study confirms the power of untargeted approach in doping control since the changes are present over seven months after anabolic administration.

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Section: Generic Namementioning

confidence: 99%

Urine Fingerprints of Stanozolol Treated Horses by Liquid Chromatography High Resolution Mass Spectrometry

Stojiljkovic¹,

Bubanj²,

Đorđević³

et al. 2017

J Sports Med Dop Stud

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“…Compound 117 was prepared in 95% yield by formylation of C-3 ketone 104 with ethyl formate in the presence of sodium methoxide in benzene. 8 Nitrile 12 was synthesized in three steps (yield, 30%) from 11 according to the same synthetic route as for 30, which was prepared previously.' Enal 13 was prepared from 11…”

Section: Chemistrymentioning

confidence: 99%

Triterpenoids and Prevention of Prostate Cancer

Sporn¹

1999

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REPORT DOCUMENTATION PAGE e OMB No. ,ublic reporting burden forthis collection of information is estimated to average 1 hour perresponse, including the time for reviewing instructions, searching xisting data sources, gathering and maintaining the data needed, ancompletn "Td reviewing this collection of information. Send comments regarding this borden estimate or any other aspect of this collection of information, inctading suggestions for reducing this burden to Washington Headquarters Services, 3irectorate for Information Operations and Reports, 1215 Jefferson Davis Highway, Saite 1204, Adington, VA 22202-4302, and to the Office of Management and Budget, This entire project is based on the hypothesis that we can design and develop new synthetic triterpenoids that would eventually be useful for chemoprevention of prostate cancer. With the known importance of oxidative stress and the known involvement of the enzymes, inducible cyclooxygenase (COX-2) and inducible nitric oxide synthase (iNOS), in the process of carcinogenesis in several other organs, and our own preliminary findings that new synthetic triterpenoids can block de novo induction and synthesis of both these enzymes, there is now a sound mechanistic basis for this hypothesis. Furthermore, since we have already shown that new synthetic triterpenoids can inhibit cell growth, without evident cytotoxicity, in non-malignant prostate epithelial cells, we believe that it will be possible to design and synthesize even more effective triterpenoids for this purpose. Finally, it is critical that a receptor (or receptors) for triterpenoids be defined, since these are presently unknown. *E6Where copyrighted material is quoted, permission has been obtained to use such material. ý4Where material from documents designated for limited distribution is quoted, permission has been obtained to use the material.-,ýCitations of commercial organizations and trade names in this report do not constitute an official Department of Army endorsement or approval of the products or services of these organizations.X In conducting research using animals, the investigator(s) INTRODUCTIONThere is a major need for new drug discovery in the field of prostate cancer. There is a particular need for developing new agents to prevent this disease, since screening techniques are now identifying large numbers of men with early, pre-malignant lesions in their prostate. Such lesions do not require surgery and are not treatable with conventional chemotherapy. However, men with this type of pre-malignant condition are at definite risk for future development of invasive, metastatic prostate cancer which is life-threatening. This project will attempt to develop a new class of molecules, the triterpenoids, as chemopreventive agents which could eventually be used to prevent prostate cancer in men at high risk. In addition to the pentacyclic triterpenoids described in the above preprint, we have also been attempting to simplify the structural requirements for inhibition of de novo synthesis of iNOS. Ac...

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“…This assumes that the target receptors associated with these two effects are sufficiently different to be sensitive to small changes in the structure of the drug molecule and to react accordingly. One successful approach has been to introduce different A-ring fused heterocycles [see, for example, Clinton et al (1961), Ohta, Takegoshi, Veno & Shimizu (1965) and Kasahara, Ondera, Mogi, Oshima & Shimizu (1965)]. [ 1,2,5]oxadiazol-20-ol (HS1011) (Fig.…”

Section: Prudomestinmentioning

confidence: 99%

Structure of (20R)-5α-pregnano[3,4-c][1,2,5]oxadiazol-20-ol (HS1011)

Maes¹,

Wyns²,

Lisgarten³

et al. 1992

Acta Crystallogr C

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Steroidal[3,2-c]pyrazoles. II.¹ Androstanes, 19-Norandrostanes and their Unsaturated Analogs

Cited by 129 publications

References 2 publications

Urine Fingerprints of Stanozolol Treated Horses by Liquid Chromatography High Resolution Mass Spectrometry

Urine Fingerprints of Stanozolol Treated Horses by Liquid Chromatography High Resolution Mass Spectrometry

Triterpenoids and Prevention of Prostate Cancer

Structure of (20R)-5α-pregnano[3,4-c][1,2,5]oxadiazol-20-ol (HS1011)

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Steroidal[3,2-c]pyrazoles. II.1 Androstanes, 19-Norandrostanes and their Unsaturated Analogs

Cited by 129 publications

References 2 publications

Urine Fingerprints of Stanozolol Treated Horses by Liquid Chromatography High Resolution Mass Spectrometry

Urine Fingerprints of Stanozolol Treated Horses by Liquid Chromatography High Resolution Mass Spectrometry

Triterpenoids and Prevention of Prostate Cancer

Structure of (20R)-5α-pregnano[3,4-c][1,2,5]oxadiazol-20-ol (HS1011)

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Steroidal[3,2-c]pyrazoles. II.¹ Androstanes, 19-Norandrostanes and their Unsaturated Analogs