NAFOXIDINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C29H31NO2
Molecular Weight	425.5619
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC1=CC2=C(C=C1)C(C3=CC=C(OCCN4CCCC4)C=C3)=C(CC2)C5=CC=CC=C5

InChI

InChIKey=JEYWNNAZDLFBFF-UHFFFAOYSA-N

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

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Description

Nafoxidine is a nonsteroidal antiestrogen available as an investigational agent from the Investigational Drug Branch of the National Cancer Institute. It has been used effectively in the treatment of breast cancer patients. Nafoxidine competes with endogenous estrogen for binding to specific estrogen receptors. This agent also inhibits angiogenesis in some tissues by blocking the effects of fibroblast growth factor (FGF) and vascular endothelial growth factor (VEGF); paradoxically, it may enhance angiogenesis in uterine tissue. Nafoxidine also induces oxidative stress, protein kinase C and calcium signaling.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor 75	Antagonist 2,778		40.9 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 434	Primary		Phase I 428	Unknown
Renal carcinoma 2	Primary		Phase III 656	Unknown

Doses

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Dose	Population	Adverse events
60 mg 3 times / day multiple, oral Studied dose	unhealthy, ADULT n = 49	Disc. AE: Ichthyosis... Other AEs: Serum transaminase increased, Nausea...
60 mg 3 times / day multiple, oral Studied dose	unhealthy, ADULT n = 23	Disc. AE: Hypercalcemia...

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AEs

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AE	Significance	Dose	Population
Hypercalcaemia	2%	60 mg 3 times / day multiple, oral Studied dose	unhealthy, ADULT n = 49
Serum transaminase increased	2%	60 mg 3 times / day multiple, oral Studied dose	unhealthy, ADULT n = 49
Thrombophlebitis leg	2%	60 mg 3 times / day multiple, oral Studied dose	unhealthy, ADULT n = 49
Ichthyosis	Disc. AE	60 mg 3 times / day multiple, oral Studied dose	unhealthy, ADULT n = 49
Nausea	grade 3, 2%	60 mg 3 times / day multiple, oral Studied dose	unhealthy, ADULT n = 49

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
AChemBlock	10755	http://www.achemblock.com/catalogsearch/result/?q=10755
AK Scientific	3697AL	https://aksci.com/item_detail.php?cat=3697AL
Angene	AGN-PC-0QDKPN	http://www.angenechemical.com/productshow/AGN-PC-0QDKPN.html
AstaTech	42119	http://astatechinc.com/CPSResult.php?CRNO=42119
BOC Sciences	1845-11-0	http://www.bocsci.com/description.asp?cas=1845-11-0

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PubMed

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Title	Date	PubMed
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.	1997 Mar	9048584
Inhibition of volume-regulated anion channels in cultured endothelial cells by the anti-oestrogens clomiphene and nafoxidine.	2001 Jan	11156570
Tracing the origins of COX-2 inhibitors' structures.	2002 Aug	12173976
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
Comparison of the antiproliferative properties of antiestrogenic drugs (nafoxidine and clomiphene) on glioma cells in vitro.	2004 Aug	15289732

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Patents

Sample Use Guides

In Vivo Use Guide

Most breast cancer patients have been treated with a dose of 60 mg three times a day.

Route of Administration: Oral

In Vitro Use Guide

In vitro nafoxidine competitively inhibits binding of [3H]oestradiol in nuclear extracts. The Ki for the inhibition is 43 nM, which indicates an affinity of nafoxidine for the binding protein about 4% of that of oestradiol.

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Name

Type

Language

NAFOXIDINE

Official Name

English

Nafoxidine [WHO-DD]

Common Name

English

nafoxidine [INN]

Common Name