ICI-164384 - Misplaced Pages

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ICI-164384
Clinical data

Other names	N-n-Butyl-N-methyl-11-(3,17β-dihydroxyestra-1,3,5(10)-trien-7α-yl)undecanamide
Identifiers
IUPAC name N-butyl-11-phenanthren-7-yl]-N-methylundecanamide
CAS Number	98007-99-9
PubChem CID	104772
ChemSpider	94580
UNII	84LT43726C
KEGG	C14758
ChEBI	CHEBI:40710
ChEMBL	ChEMBL1222035
CompTox Dashboard (EPA)	DTXSID3022376
Chemical and physical data
Formula	C₃₄H₅₅NO₃
Molar mass	525.818 g·mol
3D model (JSmol)	Interactive image
SMILES CCCCN(C)C(=O)CCCCCCCCCC1CC2=C(C=CC(=C2)O)314CC(4(CC3)C)O
InChI InChI=1S/C34H55NO3/c1-4-5-22-35(3)32(38)15-13-11-9-7-6-8-10-12-14-25-23-26-24-27(36)16-17-28(26)29-20-21-34(2)30(33(25)29)18-19-31(34)37/h16-17,24-25,29-31,33,36-37H,4-15,18-23H2,1-3H3/t25-,29-,30+,31+,33-,34+/m1/s1 Key:BVVFOLSZMQVDKV-KXQIQQEYSA-N

ICI-164384, also known as N-n-butyl-N-methyl-11-(3,17β-dihydroxyestra-1,3,5(10)-trien-7α-yl)undecanamide, is a steroidal antiestrogen and a synthetic derivative of estradiol which is closely related to fulvestrant and was never marketed. It is a silent antagonist of the estrogen receptor (ER) with no intrinsic estrogenic activity and hence is a pure antiestrogen, unlike selective estrogen receptor modulators (SERMs) like tamoxifen. The drug was under development by AstraZeneca for the treatment of breast cancer but was discontinued in favor of fulvestrant, which is very similar to ICI-164384 but is more potent in comparison.

References

^ Pavlik EJ (6 December 2012). Estrogens, Progestins, and Their Antagonists: Health Issues. Springer Science & Business Media. pp. 133–. ISBN 978-1-4612-4096-9.
^ Howell A (15 October 1990). The Role of Antihormones. CRC Press. pp. 119–124. ISBN 978-1-85070-295-5.
"ICI 164384". AdisInsight. Springer Nature Switzerland AG.
Miller WR, Ingle JN (8 March 2002). Endocrine Therapy in Breast Cancer. CRC Press. pp. 64–. ISBN 978-0-203-90983-6.

ERTooltip Estrogen receptor

Agonists

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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