Nafoxidine - CAS 1845-11-0
Catalog number:
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
Estrogen Receptor/ERR
Nafoxidine, a triphenylethylene nonsteroidal agent, is a partial estrogen antagonist.
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Clear, colourless to yellow liquid
1-(2-(p-(3,4-Dihydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy)ethyl)pyrrolidine; 5-20-01-00210 (Beilstein Handbook Reference); BRN 1440873; Nafoxidina; Nafoxidina [INN-Spanish]; Nafoxidine; Nafoxidinum; Nafoxidinum [INN-Latin]; NSC 70735; UNII-4RIY10WM82
Boiling Point:
241.00 to 242.00 ºC at 760.00 mmHg (est)
Canonical SMILES:
1.Tracing the origins of COX-2 inhibitors' structures.
Lednicer D1. Curr Med Chem. 2002 Aug;9(15):1457-61.
This review traces the origins of the chemical structure of the cyclooxygenase inhibitors celecoxib and rofecoxib. Early results from the search for non-steroid estrogens led to the triaryl-ethylenes such as chlortrianisene. A congener that incorporated a water-solubilizing basic ether grouping unexpectedly led to an estrogen antagonist and eventually the drug clomiphene. Elaboration of the structure gave the widely used drug used to treat breast cancer tamoxifen. Cyclized analogues such as nafoxidine showed equivalent activity but were not pursued. Later elaboration of those structures gave the now-marketed drug raloxifene. An indole analogue, indoxole, (2,3-dianisylindole) surprisingly showed anti-inflammatory activity. An analogue program designed to reduce photosensitivity from that compound eventually led to the discovery that the indole ring could be replaced by a simple thiazole, This resulted in the experimental cyclooxygenase inhibitor itazagrel.
2.Multifactorial activities of nonsteroidal antiestrogens against leukemia.
Hayon T1, Atlas L, Levy E, Dvilansky A, Shpilberg O, Nathan I. Cancer Detect Prev. 2003;27(5):389-96.
The antileukemic activity of nonsteroidal antiestrogens was investigated. Tamoxifen, clomiphene and nafoxidine caused a decrease in viability of the estrogen receptor-negative T-lymphoblastic leukemia cell line CCRF/CEM, nafoxidine being the most active. A combination of clomiphene and genistein resulted in a synergistic cytotoxic effect when applied to Molt-3, another T-lymphblastic leukemic cell line. The antiestrogens arrested the cells at G(0)/G(1) phase and induced apoptosis. Using the CCRF/VCR(1000) cell line, which is resistant to vincristine, it was observed that the effect of nafoxidine on modulating drug resistance was manifested at a lower concentration than that causing a direct cytotoxic effect. Nafoxidine inhibited the Pgp pump activity as measured by rhodamine 123 efflux. Combination with verapamil was found to be more effective in abrogating the pump activity. This study points to the multifactorial activities of nonsteroidal antiestrogens against lymphoblastic leukemia and implies their potential use in clinical treatment as antileukemic drugs.
3.Thermotropic liquid crystalline drugs.
Bunjes H1, Rades T. J Pharm Pharmacol. 2005 Jul;57(7):807-16.
Crystalline solids are characterized by long-range positional and orientational order in three dimensions, whereas amorphous liquids lack long-range order in any dimension. Liquid crystals (mesophases) show structural, mechanical and optical properties intermediate to those of crystalline solids and the amorphous, liquid state of matter. There are two principle types of liquid crystals: thermotropic liquid crystals (TLCs) and lyotropic liquid crystals (LLCs). TLCs can be formed by heating a crystalline solid or by cooling an isotropic melt of a TLC-forming molecule (mesogen). In the first part of this review the types of liquid crystals are defined and classified and the structural properties of mesogens are explained. In the second part, ten case studies of thermotropic mesomorphous drugs and pharmaceutically relevant molecules (arsphenamine, nafoxidine hydrochloride, L-660711, palmitoyl propranolol hydrochloride, penbutolol sulfate, itraconazole hydrochloride, fenoprofen sodium, fenoprofen calcium, ciclosporin and cholesteryl esters) are presented and their thermotropic mesomorphism is described.
4.Kinetic analysis of estrogen receptor/ligand interactions.
Rich RL1, Hoth LR, Geoghegan KF, Brown TA, LeMotte PK, Simons SP, Hensley P, Myszka DG. Proc Natl Acad Sci U S A. 2002 Jun 25;99(13):8562-7. Epub 2002 Jun 19.
Surface plasmon resonance biosensor technology was used to directly measure the binding interactions of small molecules to the ligand-binding domain of human estrogen receptor. In a screening mode, specific ligands of the receptor were easily discerned from nonligands. In a high-resolution mode, the association and dissociation phase binding responses were shown to be reproducible and could be fit globally to a simple interaction model to extract reaction rate constants. On average, antagonist ligands (such as tamoxifen and nafoxidine) were observed to bind to the receptor with association rates that were 500-fold slower than agonists (such as estriol and beta-estradiol). This finding is consistent with these antagonists binding to an altered conformation of the receptor. The biosensor assay also could identify subtle differences in how the same ligand interacted with two different isoforms of the receptor (alpha and beta). The biosensor's ability to determine kinetic rate constants for small molecule/protein interactions provides unique opportunities to understand the mechanisms associated with complex formation as well as new information to drive the optimization of drug candidates.
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CAS 1845-11-0 Nafoxidine

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