Details
| Stereochemistry | RACEMIC |
| Molecular Formula | 2C14H13N3.2ClH.H2O |
| Molecular Weight | 537.483 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.Cl.N#CC1=CC=C(C=C1)C2CCCC3=CN=CN23.N#CC4=CC=C(C=C4)C5CCCC6=CN=CN56
InChI
InChIKey=RBNOZCGLHXZRLF-UHFFFAOYSA-N
InChI=1S/2C14H13N3.2ClH.H2O/c2*15-8-11-4-6-12(7-5-11)14-3-1-2-13-9-16-10-17(13)14;;;/h2*4-7,9-10,14H,1-3H2;2*1H;1H2
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8595171
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8595171
Fadrozole (CGS 16949A) is a tetrahydroimidazole-pyridine derivative is a non-steroidal inhibitor of aromatase. In the third phase of clinical trials it was shown, that this drug has good therapeutic effect as a second-line treatment in postmenopausal women with metastatic breast cancer.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Are differences in the available aromatase inhibitors and inactivators significant? | 2001 Dec |
|
| A comparative approach to structure-function studies of mammalian aromatases. | 2001 Dec |
|
| A summary of second-line randomized studies of aromatase inhibitors. | 2001 Dec |
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| [An elderly woman with breast cancer and multiple liver metastasis that responded well to combination therapy of fadrozole and tamoxifen]. | 2001 Dec |
|
| Enantioselectivity of some 1-[(benzofuran-2-yl) phenylmethyl] imidazoles as aromatase (P450AROM) inhibitors. | 2001 Nov |
|
| Relationship of serum HER-2/neu and serum CA 15-3 in patients with metastatic breast cancer. | 2002 Aug |
|
| Development of sexual partner preference in the zebra finch: a socially monogamous, pair-bonding animal. | 2002 Feb |
|
| Aromatase inhibitors block natural sex change and induce male function in the protandrous black porgy, Acanthopagrus schlegeli Bleeker: possible mechanism of natural sex change. | 2002 Jun |
|
| Elevated serum Her-2/neu level predicts decreased response to hormone therapy in metastatic breast cancer. | 2002 Mar 15 |
|
| Detection of aromatase inhibitors in vitro using rat ovary microsomes. | 2002 Mar 24 |
|
| Post-hatching hormonal modulation of a sexually dimorphic neuromuscular system controlling song in zebra finches. | 2002 Mar 8 |
|
| Applicability of the intratumor aromatase preclinical model to predict clinical trial results with endocrine therapy. | 2003 Aug |
|
| Lack of efficacy of fadrozole in treating precocious puberty in girls with the McCune-Albright syndrome. | 2003 Dec |
|
| DMRT1 is upregulated in the gonads during female-to-male sex reversal in ZW chicken embryos. | 2003 Feb |
|
| Aromatase inhibition affects testosterone-induced masculinization of song and the neural song system in female canaries. | 2003 Feb 5 |
|
| Double-blind randomised trial comparing the non-steroidal aromatase inhibitors letrozole and fadrozole in postmenopausal women with advanced breast cancer. | 2003 Jan |
|
| Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
|
| Delayed implantation induced by fadrozole hydrochloride in rats. | 2003 Jul |
|
| Estradiol in the male rat amygdala facilitates mounting but not ejaculation. | 2003 Jul |
|
| Endogenous estrogen formation is neuroprotective in model of cerebellar ataxia. | 2003 Jun |
|
| Vitellogenin synthesis via androgens in primary cultures of tilapia hepatocytes. | 2003 Jun 15 |
|
| Estrogen regulates tyrosine hydroxylase expression in the neonate mouse midbrain. | 2003 Mar |
|
| Neuroprotection by the steroids pregnenolone and dehydroepiandrosterone is mediated by the enzyme aromatase. | 2003 Sep 15 |
|
| Characterization of stable human aromatase expressed in E. coli. | 2004 Apr |
|
| Glial aromatization decreases neural injury in the zebra finch (Taeniopygia guttata): influence on apoptosis. | 2004 Aug |
|
| Presynaptic N-methyl-D-aspartate receptor expression is increased by estrogen in an aromatase-rich area of the songbird hippocampus. | 2004 Feb 16 |
|
| A comparison of human H295R and rat R2C cell lines as in vitro screening tools for effects on aromatase. | 2004 Jan 15 |
|
| Differential expression pattern and steroid hormone sensitivity of SNAP-25 and synaptoporin mRNA in the telencephalic song control nucleus HVC of the zebra finch. | 2004 Jul 12 |
|
| Modulation by steroid hormones of a "sexy" acoustic signal in an Oscine species, the Common Canary Serinus canaria. | 2004 Jun |
|
| Effects of follicle stimulating hormone on estradiol-17 beta production and P-450 aromatase (CYP19) activity and mRNA expression in brown trout vitellogenic ovarian follicles in vitro. | 2004 Jun |
|
| Sex inversion of sexually immature honeycomb grouper (Epinephelus merra) by aromatase inhibitor. | 2004 Mar |
|
| Aromatase inhibitor induces complete sex change in the protogynous honeycomb grouper (Epinephelus merra). | 2004 Mar |
|
| Expression of aromatase mRNA and effects of aromatase inhibitor during ovarian development in the medaka, Oryzias latipes. | 2004 Mar 1 |
|
| Aromatase inhibition in the treatment of advanced breast cancer: is there a relationship between potency and clinical efficacy? | 2004 May 4 |
|
| Successful detection of (anti-)androgenic and aromatase inhibitors in pre-spawning adult fathead minnows (Pimephales promelas) using easily measured endpoints of sexual development. | 2004 Oct 18 |
|
| Combined effect of testosterone and apocynin on nitric oxide and superoxide production in PMA-differentiated THP-1 cells. | 2004 Sep 17 |
|
| Aromatase inhibition abolishes courtship behaviours in the ring dove (Streptopelia risoria) and reduces androgen and progesterone receptors in the hypothalamus and anterior pituitary gland. | 2005 Aug |
|
| Estrogen provision by reactive glia decreases apoptosis in the zebra finch (Taeniopygia guttata). | 2005 Aug |
|
| Three-dimensional model of cytochrome P450 human aromatase. | 2005 Dec |
|
| Co-culture of primary human mammary fibroblasts and MCF-7 cells as an in vitro breast cancer model. | 2005 Feb |
|
| Antiandrogenic effects in short-term in vivo studies of the fungicide fenarimol. | 2005 Feb 1 |
|
| Evidence that estrogen regulates the sex change of honeycomb grouper (Epinephelus merra), a protogynous hermaphrodite fish. | 2005 Jun 1 |
|
| Enantiomeric resolution of new aromatase inhibitors by liquid chromatography on cellulose chiral stationary phases. | 2005 Mar |
|
| Synthesis and evaluation of (pyridylmethylene)tetrahydronaphthalenes/-indanes and structurally modified derivatives: potent and selective inhibitors of aldosterone synthase. | 2005 Mar 10 |
|
| Synthesis and evaluation of imidazolylmethylenetetrahydronaphthalenes and imidazolylmethyleneindanes: potent inhibitors of aldosterone synthase. | 2005 Mar 24 |
|
| Zebrafish sex determination and differentiation: involvement of FTZ-F1 genes. | 2005 Nov 10 |
|
| Cyp2a6 is a principal enzyme involved in hydroxylation of 1,7-dimethylxanthine, a main caffeine metabolite, in humans. | 2005 Sep |
|
| Extragonadal synthesis of estradiol is protective against kainic acid excitotoxic damage to the hippocampus. | 2005 Sep 28 |
|
| Inhibition of human CYP19 by azoles used as antifungal agents and aromatase inhibitors, using a new LC-MS/MS method for the analysis of estradiol product formation. | 2006 Feb 15 |
|
| Relationship between brain and ovary aromatase activity and isoform-specific aromatase mRNA expression in the fathead minnow (Pimephales promelas). | 2006 Mar 10 |
Sample Use Guides
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11954367
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100000127581
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O5207G4XQ9
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SUB33655
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176702-70-8
Created by
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
