Nafoxidine

Nafoxidine
Clinical data

Routes of administration	Oral
ATC code	None
Identifiers
IUPAC name 1-[2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine
Synonyms	U-11,000A; NSC-70735
CAS Number	1845-11-0
PubChem CID	4416
IUPHAR/BPS	4263
ChemSpider	4263
UNII	4RIY10WM82
KEGG	C14212
ChEBI	CHEBI:34881
ChEMBL	CHEMBL28211
ECHA InfoCard	100.222.756
Chemical and physical data
Formula	C₂₉H₃₁NO₂
Molar mass	425.562 g/mol
3D model (Jmol)	Interactive image
SMILES COC1=CC2=C(C=C1)C(=C(CC2)C3=CC=CC=C3)C4=CC=C(C=C4)OCCN5CCCC5
InChI InChI=1S/C29H31NO2/c1-31-26-14-16-28-24(21-26)11-15-27(22-7-3-2-4-8-22)29(28)23-9-12-25(13-10-23)32-20-19-30-17-5-6-18-30/h2-4,7-10,12-14,16,21H,5-6,11,15,17-20H2,1H3 Key:JEYWNNAZDLFBFF-UHFFFAOYSA-N

Nafoxidine (INN) (developmental code names U-11,000A, NSC-70735), or nafoxidine hydrochloride (USAN), is a non-steroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of advanced breast cancer by Upjohn in the 1970s but was never marketed. It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives. The drug was originally synthesized by the fertility control program at Upjohn as a postcoital contraceptive, but was subsequently repurposed for the treatment of breast cancer. Nafoxidine was assessed in clinical trials in the treatment of breast cancer and was found to be effective. However, it produced side effects including ichthyosis, partial hair loss, and phototoxicity of the skin in almost all patients, and this resulted in the discontinuation of its development.

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