Quadrosilan

Quadrosilan
Clinical data
Trade names	Cisobitan
Other names	Quadrosilane; KABI-1774; 2,6-cisdiphenylhexa-; methylcyclotetrasiloxane
Drug class	Nonsteroidal 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	4657-20-9;
PubChem CID	20774;
ChemSpider	19557;
Chemical and physical data
Formula	C18H28O4Si4
Molar mass	420.1065 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References

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.
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.
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.
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.
Yitzhak Apeloig (1989). The Chemistry of Organic Silicon Compounds. John Wiley & Sons Canada, Limited. p. 1154. ISBN 978-0-471-91993-3.
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.
Strindberg, Bengt (1978). "Biochemical Effects of 2, 6-cis-Diphenylhexamethylcyclotetrasiloxane in Man": 515–520. doi:10.1007/978-1-4613-4018-8_23. Cite journal requires |journal= (help)
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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[Elks2014-1] 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.

[MortonHall2012-2] 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.

[AlfthanAndersson1983-3] 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.

[Chisholm1985-4] 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.

[Apeloig1989-5] Yitzhak Apeloig (1989). The Chemistry of Organic Silicon Compounds. John Wiley & Sons Canada, Limited. p. 1154. ISBN 978-0-471-91993-3.

[MillsShowell2004-6] 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.

[Strindberg1978-7] Strindberg, Bengt (1978). "Biochemical Effects of 2, 6-cis-Diphenylhexamethylcyclotetrasiloxane in Man": 515–520. doi:10.1007/978-1-4613-4018-8_23. Cite journal requires |journal= (help)

[pmid345431-8] 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.

Quadrosilan

See also

References