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Chemical compound
Quadrosilan Trade names Cisobitan Other names Quadrosilane; KABI-1774; 2,6-cisdiphenylhexa- methylcyclotetrasiloxane Drug class Nonsteroidal estrogen
2,2,4,6,6,8-hexamethyl-4,8-diphenyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 18 H 28 O 4 Si 4 Molar mass 420.758 g·mol−1 3D model (JSmol )
InChI=1S/C18H28O4Si4/c1-23(2)19-25(5,17-13-9-7-10-14-17)21-24(3,4)22-26(6,20-23)18-15-11-8-12-16-18/h7-16H,1-6H3
Key:ZTQZMPQJXABFNC-UHFFFAOYSA-N
Quadrosilan (INN Tooltip International Nonproprietary Name , BAN Tooltip British Approved Name ) (brand name Cisobitan ; former developmental code name KABI-1774 ) is a synthetic nonsteroidal estrogen that was developed in the 1970s and that is or has been used as an antigonadotropic agent in the treatment of prostate cancer .[ 1] [ 2] [ 3] [ 4] It is an organosilicon compound, and is also known as 2,6-cisdiphenylhexamethylcyclotetrasiloxane .[ 3] [ 5] Quadrosilan has estrogenic activity equivalent to that of estradiol ,[ 6] and can produce feminization and gynecomastia as side effects in male patients.[ 7] [ 8]
See also
References
^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 629–. ISBN 978-1-4757-2085-3 .
^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Science & Business Media. pp. 243–. ISBN 978-94-011-4439-1 .
^ a b Alfthan O, Andersson L, Esposti PL, Fosså SD, Gammelgaard PA, Gjöres JE, et al. (1983). "Cisobitan in treatment of prostatic cancer. A prospective controlled multicentre study". Scandinavian Journal of Urology and Nephrology . 17 (1): 37–43. doi :10.3109/00365598309179778 . PMID 6346476 .
^ Chisholm GD (1985). "Treatment of advanced cancer of the prostate". Seminars in Surgical Oncology . 1 (1): 38–55. doi :10.1002/ssu.2980010106 . PMID 3887539 .
^ Apeloig Y (1989). The Chemistry of Organic Silicon Compounds . John Wiley & Sons Canada, Limited. p. 1154. ISBN 978-0-471-91993-3 .
^ Mills JS, Showell GA (September 2004). "Exploitation of silicon medicinal chemistry in drug discovery". Expert Opinion on Investigational Drugs . 13 (9): 1149–1157. doi :10.1517/13543784.13.9.1149 . PMID 15330746 . S2CID 26669175 .
^ Strindberg B (1978). "Biochemical Effects of 2, 6-cis-Diphenylhexamethylcyclotetrasiloxane in Man". Biochemistry of Silicon and Related Problems . pp. 515–520. doi :10.1007/978-1-4613-4018-8_23 . ISBN 978-1-4613-4020-1 .
^ Krarup T, Rasmussen F, Gammelgaard PA (1978). "Prostatic carcinoma treated with 2,6-cis-diphenylhexamethylcyclotetrasiloxane (Cisobitan)". Scandinavian Journal of Urology and Nephrology . 12 (1): 11–15. PMID 345431 .
Estrogens
ER Tooltip Estrogen receptor agonists
Steroidal: Alfatradiol
Certain androgens /anabolic steroids (e.g., testosterone , testosterone esters , methyltestosterone , metandienone , nandrolone esters ) (via estrogenic metabolites)
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Estetrol †
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