Quadrosilan

Quadrosilan (INN, BAN) (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]

Quadrosilan
Clinical data
Trade namesCisobitan
Other namesQuadrosilane; KABI-1774; 2,6-cisdiphenylhexa-
methylcyclotetrasiloxane
Drug classNonsteroidal estrogen
Identifiers
IUPAC name
  • 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)
Chemical and physical data
FormulaC18H28O4Si4
Molar mass420.758 g·mol−1
3D model (JSmol)
SMILES
  • C[Si]1(O[Si](O[Si](O[Si](O1)(C)C2=CC=CC=C2)(C)C)(C)C3=CC=CC=C3)C
InChI
  • 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

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 629–. ISBN 978-1-4757-2085-3.
  2. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 243–. ISBN 978-94-011-4439-1.
  3. Alfthan, Olof; Andersson, Lennart; Luigi Esposti, Pier; Dorothea Fosså, Sophie; Arne Gammelgaard, Peter; Erik Gjöres, Jan; Isacson, Sune; Rasmussen, Finn; Ruutu, Mirja; von Schreeb, Tor; Setterberg, Gun; Strandell, Per; Strindberg, Bengt (1983). "Cisobitan® in Treatment of Prostatic Cancer". Scandinavian Journal of Urology and Nephrology. 17 (1): 37–43. doi:10.3109/00365598309179778. ISSN 0036-5599. PMID 6346476.
  4. Chisholm, Geoffrey D. (1985). "Treatment of advanced cancer of the prostate". Seminars in Surgical Oncology. 1 (1): 38–55. doi:10.1002/ssu.2980010106. ISSN 8756-0437. PMID 3887539.
  5. Yitzhak Apeloig (1989). The Chemistry of Organic Silicon Compounds. John Wiley & Sons Canada, Limited. p. 1154. ISBN 978-0-471-91993-3.
  6. Mills, John S; Showell, Graham A (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. ISSN 1354-3784. PMID 15330746. S2CID 26669175.
  7. Strindberg, Bengt (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.
  8. Krarup T, Rasmussen F, Gammelgaard PA (1978). "Prostatic carcinoma treated with 2,6-cis-diphenylhexamethylcyclotetrasiloxane (Cisobitan)". Scand. J. Urol. Nephrol. 12 (1): 11–5. PMID 345431.
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