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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 )
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]
^ 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)
Certain progestins (e.g., norethisterone , noretynodrel , etynodiol diacetate , tibolone )
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
Esterified estrogens
Estetrol †
Estradiol
Estradiol esters (e.g., estradiol acetate , estradiol benzoate , estradiol cypionate , estradiol enanthate , estradiol undecylate , estradiol valerate , polyestradiol phosphate , estradiol ester mixtures (Climacteron ))
Estramustine phosphate
Estriol
Estriol esters (e.g., estriol succinate , polyestriol phosphate )
Estrogenic substances
Estrone
Estrone esters
Ethinylestradiol #
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
Promestriene
Quinestradol
Quinestrol
Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonists (incl. SERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )Aromatase inhibitors Antigonadotropins
Androgens /anabolic steroids (e.g., testosterone , testosterone esters , nandrolone esters , oxandrolone , fluoxymesterone )
D2 receptor antagonists (prolactin releasers) (e.g., domperidone , metoclopramide , risperidone , haloperidol , chlorpromazine , sulpiride )
GnRH agonists (e.g., leuprorelin , goserelin )
GnRH antagonists (e.g., cetrorelix , elagolix )
Progestogens (e.g., chlormadinone acetate , cyproterone acetate , gestonorone caproate , hydroxyprogesterone caproate , medroxyprogesterone acetate , megestrol acetate )
Others
GnRH modulators (incl. analogues )
Gonadotropins
Others (indirect)
Progonadotropins Antigonadotropins
Sex steroid agonists (via negative feedback on the HPG axis ): Androgens /anabolic steroids (e.g., testosterone , nandrolone esters , oxandrolone )
D2 receptor antagonists (prolactin releasers ) (incl., domperidone , metoclopramide , risperidone , haloperidol , chlorpromazine , sulpiride )
Estrogens (incl., bifluranol , estradiol , estradiol esters , ethinylestradiol , diethylstilbestrol , paroxypropione )
Progestogens (incl. progestins , e.g., chlormadinone acetate , cyproterone acetate , hydroxyprogesterone caproate , gestonorone caproate , medroxyprogesterone acetate , megestrol acetate )
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β べーた -ol
3α あるふぁ -Androstanediol
3α あるふぁ ,5α あるふぁ -Dihydrolevonorgestrel
3β べーた ,5α あるふぁ -Dihydrolevonorgestrel
3α あるふぁ -Hydroxytibolone
3β べーた -Hydroxytibolone
3β べーた -Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α あるふぁ -Hydroxy-DHEA
7α あるふぁ -Methylestradiol
7β べーた -Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β べーた -VE2
10β べーた ,17β べーた -Dihydroxyestra-1,4-dien-3-one (DHED)
11β べーた -Chloromethylestradiol
11β べーた -Methoxyestradiol
15α あるふぁ -Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α あるふぁ -Fluoroestradiol
16α あるふぁ -Hydroxy-DHEA
16α あるふぁ -Hydroxyestrone
16α あるふぁ -Iodoestradiol
16α あるふぁ -LE2
16β べーた -Hydroxyestrone
16β べーた ,17α あるふぁ -Epiestriol (16β べーた -hydroxy-17α あるふぁ -estradiol)
17α あるふぁ -Estradiol (alfatradiol )
17α あるふぁ -Dihydroequilenin
17α あるふぁ -Dihydroequilin
17α あるふぁ -Epiestriol (16α あるふぁ -hydroxy-17α あるふぁ -estradiol)
17α あるふぁ -Ethynyl-3α あるふぁ -androstanediol
17α あるふぁ -Ethynyl-3β べーた -androstanediol
17β べーた -Dihydroequilenin
17β べーた -Dihydroequilin
17β べーた -Methyl-17α あるふぁ -dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β べーた -epiestriol, 16β べーた -hydroxy-17β べーた -estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )
Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )
Coumestans (e.g., coumestrol , psoralidin )
Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )
Lavender oil
Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g., cadmium )
Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )
Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )
Phytosterols (e.g., β べーた -sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α あるふぁ -zearalenol , β べーた -zearalenol , zearalenone , zeranol (α あるふぁ -zearalanol) , taleranol (teranol, β べーた -zearalanol) )
Steroid -like (e.g., deoxymiroestrol , miroestrol )
Stilbenoids (e.g., resveratrol , rhaponticin )
Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )
Others (e.g., agnuside , rotundifuran )
Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown