Nafoxidine HCl - CAS 1847-63-8
Catalog number:
B0084-294307
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C29H32CINO2
Molecular Weight:
462.03
COA:
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Targets:
Estrogen Receptor/ERR
Description:
Nafoxidine HCl is the hydrochloride salt of nafoxidine. Nafoxidine, structurally related to Tamoxifen, is a non-steroidal partial estrogen antagonist.
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B0084-294307 1 g $299 In stock
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Purity:
95%
Appearance:
Solid powder
Synonyms:
1-[2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine;hydrochloride; NAFOXIDINEHYDROCHLORIDE; NafoxidineHCl; 1847-63-8; U11100A
MSDS:
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Quantity:
Data not available, please inquire.
InChIKey:
HJOOGTROABIIIU-UHFFFAOYSA-N
InChI:
1S/C29H31NO2.ClH/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;1H
Canonical SMILES:
COC1=CC2=C(C=C1)C(=C(CC2)C3=CC=CC=C3)C4=CC=C(C=C4)OCCN5CCCC5.Cl
1.The evolution of nonsteroidal antiestrogens to become selective estrogen receptor modulators.
Craig Jordan V1, McDaniel R2, Agboke F2, Maximov PY2. Steroids. 2014 Nov;90:3-12. doi: 10.1016/j.steroids.2014.06.009. Epub 2014 Jun 17.
The discovery of the first nonsteroidal antiestrogen ethamoxytriphetol (MER25) in 1958, opened the door to a wide range of clinical applications. However, the finding that ethamoxytriphetol was a "morning after" pill in laboratory animals, energized the pharmaceutical industry to discover more potent derivatives. In the wake of the enormous impact of the introduction of the oral contraceptive worldwide, contraceptive research was a central focus in the early 1960's. Numerous compounds were discovered e.g., clomiphene, nafoxidine, and tamoxifen, but the fact that clinical studies showed no contraceptive actions, but, in fact, induced ovulation, dampened enthusiasm for clinical development. Only clomiphene moved forward to pioneer an application to induce ovulation in subfertile women. The fact that all the compounds were antiestrogenic made an application in patients to treat estrogen responsive breast cancer, an obvious choice. However, toxicities and poor projected commercial returns severely retarded clinical development for two decades.
2.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.
3.Estrogen receptor ligands affect mitochondrial activity in SH-SY5Y human neuroblastoma cells.
Simpson PB1, Woollacott AJ, Moneer Z, Rand V, Seabrook GR. Neuroreport. 2002 May 24;13(7):957-60.
We have studied the pharmacological regulation of mitochondrial activity in a human neuroblastoma cell line. Cyclosporin A was found to directly alter mitochondrial membrane potential and to decrease mitochondrial permeability as measured using calcein. The estrogen receptor ligands tamoxifen, nafoxidine and clomiphene were identified as agents which affect mitochondrial membrane potential in a cyclosporin A-like manner. Also when mitochondrial permeability was measured using calcein, tamoxifen, nafoxidine and clomiphene were effective in inhibiting dye loss from mitochondria. Nafoxidine and cyclosporin A inhibit effects of mastoparan on SH-SY5Y mitochondria. These studies indicate that estrogen receptor ligands appear to affect mitochondria in a cyclosporin A-like manner in human neuroblastoma cells.
4.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.
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CAS 1847-63-8 Nafoxidine HCl

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