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Quadrosilan

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Quadrosilan
Clinical data
Trade names Cisobitan
Other namesQuadrosilane; KABI-1774; 2,6-cisdiphenylhexa-
methylcyclotetrasiloxane
Drug class Nonsteroidal estrogen
Identifiers
  • 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
Formula C18H28O4Si4
Molar mass 420.758 g·mol−1
3D model (JSmol)
  • C[Si]1(O[Si](O[Si](O[Si](O1)(C)C2=CC=CC=C2)(C)C)(C)C3=CC=CC=C3)C
  • 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

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References

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  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ Apeloig Y (1989). The Chemistry of Organic Silicon Compounds. John Wiley & Sons Canada, Limited. p. 1154. ISBN 978-0-471-91993-3.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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
Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonists
(incl. SERMs Tooltip selective estrogen receptor modulators/SERDs Tooltip selective estrogen receptor downregulators)
Aromatase inhibitors
Antigonadotropins
Others
GnRH Tooltip Gonadotropin-releasing hormone and gonadotropins
GnRH modulators
(incl. analogues)
Agonists
Antagonists
Gonadotropins
Preparations
Others
(indirect)
Progonadotropins
Antigonadotropins
ER Tooltip Estrogen receptor
Agonists
Mixed
(SERMs Tooltip Selective estrogen receptor modulators)
Antagonists
GPER Tooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown

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