ICI-164384

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.[1][2] 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.[1][2] The drug was under development by AstraZeneca for the treatment of breast cancer but was discontinued in favor of fulvestrant,[3] which is very similar to ICI-164384 but is more potent in comparison.[4]

ICI-164384
Clinical data
Other namesN-n-Butyl-N-methyl-11-(3,17β-dihydroxyestra-1,3,5(10)-trien-7α-yl)undecanamide
Identifiers
IUPAC name
  • N-butyl-11-[(7R,8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl]-N-methylundecanamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC34H55NO3
Molar mass525.818 g·mol−1
3D model (JSmol)
SMILES
  • CCCCN(C)C(=O)CCCCCCCCCC[C@@H]1CC2=C(C=CC(=C2)O)[C@@H]3[C@@H]1[C@@H]4CC[C@@H]([C@]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

See also

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