Dienestrol

Dienestrol
Clinical data
Trade names	Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Cycladiene, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol
Other names	Dienoestrol; p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol; 3,4-Di(para-hydroxyphenyl)-2,4-hexadiene
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Drug class	Nonsteroidal estrogen
ATC code	G03CB01 (WHO) G03CC02 (WHO);
Identifiers
	IUPAC name 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol;
CAS Number	13029-44-2 ;
PubChem CID	667476;
IUPHAR/BPS	7160;
DrugBank	DB00890 ;
ChemSpider	580857 ;
UNII	RRW32X4U1F;
KEGG	D00898 ;
ChEBI	CHEBI:4518 ;
ChEMBL	ChEMBL1018 ;
Chemical and physical data
Formula	C18H18O2
Molar mass	266.340 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2;
	InChI InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+ ; Key:NFDFQCUYFHCNBW-SCGPFSFSSA-N ;
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Short description: Chemical compound

Dienestrol (INN, USAN) (brand names Dienoestrol, Denestrolin, Dienol and many others^{[lower-alpha 1]}), also known as dienoestrol (BAN), is a synthetic nonsteroidal estrogen medication of the stilbestrol group which is or was used to treat menopausal symptoms in the United States and Europe.^[1]^[2]^[3]^[4] It has been studied for use by rectal administration in the treatment of prostate cancer in men as well.^[5] The medication was introduced in the U.S. in 1947 by Schering as Synestrol and in France in 1948 as Cycladiene.^[4] Dienestrol is a close analogue of diethylstilbestrol.^[6] It has approximately 223% and 404% of the affinity of estradiol at the ERα and ERβ, respectively.^[7]

Dienestrol diacetate (brand names Faragynol, Gynocyrol, others) also exists and has been used medically.^[2]

Isomers

Dienestrol (unspecified) - CAS 84-17-3
E,E-Dienestrol - CAS 13029-44-2
Z,Z-Dienestrol - CAS 35495-11-5

Notes

↑ Other trade names of the medication include Ortho Dienestrol, Dienoestrol Ortho, Sexadien, Dinovex, Follormon, Oestrodiene, and Synestrol

References

↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 331–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA331.
↑ ^2.0 ^2.1 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 390–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA390.
↑ Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 361–. ISBN 978-3-7692-2114-5. https://books.google.com/books?id=2HBPHmclMWIC&pg=PA361.
↑ ^4.0 ^4.1 William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1286–. ISBN 978-0-8155-1856-3. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1286.
↑ "Somministrazione degli estrogeni per via rettale nel carcinoma prostatico." (in it). Minerva Urol 5 (1): 28–32. 1953. ISSN 0026-4989. PMID 13063334.
↑ VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0. https://archive.org/details/in.ernet.dli.2015.5563.
↑ "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology 138 (3): 863–70. 1997. doi:10.1210/endo.138.3.4979. PMID 9048584.

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Original source: https://en.wikipedia.org/wiki/Dienestrol. Read more

[1] Other trade names of the medication include Ortho Dienestrol, Dienoestrol Ortho, Sexadien, Dinovex, Follormon, Oestrodiene, and Synestrol

[2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 331–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA331.

[Elks2014-3] 2.0 ^2.1 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 390–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA390.

[Muller1998-4] Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 361–. ISBN 978-3-7692-2114-5. https://books.google.com/books?id=2HBPHmclMWIC&pg=PA361.

[Publishing2013-5] 4.0 ^4.1 William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1286–. ISBN 978-0-8155-1856-3. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1286.

[pmid13063334-6] "Somministrazione degli estrogeni per via rettale nel carcinoma prostatico." (in it). Minerva Urol 5 (1): 28–32. 1953. ISSN 0026-4989. PMID 13063334.

[7] VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0. https://archive.org/details/in.ernet.dli.2015.5563.

[pmid9048584-8] "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology 138 (3): 863–70. 1997. doi:10.1210/endo.138.3.4979. PMID 9048584.

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Dienestrol

Topic: Chemistry

Contents

Isomers

See also

Notes

References