Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H24O2 |
Molecular Weight | 272.382 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4
InChI
InChIKey=VOXZDWNPVJITMN-SFFUCWETSA-N
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1
Molecular Formula | C18H24O2 |
Molecular Weight | 272.382 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Alfatradiol (17a-estradiol, Ell-Cranell® alpha) is a stereoisomer of the female hormone 17b-estradiol. It inhibits the conversion of testosterone to the metabolite dihydrotestosterone (DHT) by suppressing 5a-reductase activity. In addition, by inhibiting 17b-dehydrogenase, it impedes the conversion process of androstenedione to testosterone, resulting in a reduction in the syntheses of testosterone and DHT. It also accelerates the conversion of testosterone to estradiol by stimulating aromatase, decreasing the level of testosterone and leading to a reduction in DHT. In addition, alfatradiol (17a-estradiol) has been reported to stimulate the generation of hair follicular matrix cells.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9048584 |
0.2 nM [Ki] | ||
Target ID: CHEMBL3021 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9048584 |
1.2 nM [Ki] | ||
Target ID: CHEMBL1978 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Ell-Cranell® alpha Approved UseAndrogenetic alopecia in women. |
PubMed
Title | Date | PubMed |
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The antihyperglycemic effect of estrone sulfate in genetically obese-diabetic (ob/ob) mice is associated with reduced hepatic glucose-6-phosphatase. | 2001 Dec |
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Tamoxifen eliminates estrogen's neuroprotective effect upon MPTP-induced neurotoxicity of the nigrostriatal dopaminergic system. | 2001 Jul |
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Temporal effects of 17beta-estradiol on caveolin-1 mRNA and protein in bovine aortic endothelial cells. | 2001 Sep |
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The effects of beta-estradiol on SHSY5Y neuroblastoma cells during heavy metal induced oxidative stress, neurotoxicity and beta-amyloid secretion. | 2002 |
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Acute relaxant effects of 17-beta-estradiol through non-genomic mechanisms in rabbit carotid artery. | 2002 Apr |
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17alpha-estradiol induces aromatase activity in intact human anagen hair follicles ex vivo. | 2002 Aug |
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Evaluation of the protective effect of oestradiol against toxicity induced by 6-hydroxydopamine and 1-methyl-4-phenylpyridinium ion (Mpp+) towards dopaminergic mesencephalic neurones in primary culture. | 2002 Jan |
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Differential interactions of estrogens and antiestrogens at the 17 beta-hydroxyl or counterpart hydroxyl with histidine 524 of the human estrogen receptor alpha. | 2002 Jun 25 |
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Nongenomic regulation of the kinetics of exocytosis by estrogens. | 2002 May |
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[Comparative evaluation of the antiradical and antioxidant activity of estrogens and their nitro derivatives]. | 2002 May-Jun |
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Some new aspects of 17alpha-estradiol metabolism in man. | 2002 Oct |
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Neuroprotective effect of estradiol and phytoestrogens on MPP+-induced cytotoxicity in neuronal PC12 cells. | 2002 Oct 1 |
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17beta-Estradiol reduces excitatory postsynaptic potential (EPSP) amplitude in rat basolateral amygdala neurons. | 2002 Oct 11 |
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Estradiol prevents amyloid-beta peptide-induced cell death in a cholinergic cell line via modulation of a classical estrogen receptor. | 2003 |
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Estradiol inhibits atp-induced intracellular calcium concentration increase in dorsal root ganglia neurons. | 2003 |
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Estrogen prevents the loss of CA1 hippocampal neurons in gerbils after ischemic injury. | 2003 |
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Repeated estradiol treatment prevents MPTP-induced dopamine depletion in male mice. | 2003 Apr |
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[New and established methods in therapy of hair diseases]. | 2003 Aug |
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Estrogen modulation of G-protein-coupled receptor activation of potassium channels in the central nervous system. | 2003 Dec |
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Characterization of a membrane-associated estrogen receptor in a rat hypothalamic cell line (D12). | 2003 Dec |
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Estrogen modulates xanthine dehydrogenase/xanthine oxidase activity by a receptor-independent mechanism. | 2003 Dec |
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17beta-estradiol and tamoxifen regulate a maxi-chloride channel from human placenta. | 2003 Jan 1 |
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Equine estrogens differentially prevent neuronal cell death induced by glutamate. | 2003 Jul |
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Estradiol regulates the slow Ca2+-activated K+ current in hippocampal pyramidal neurons. | 2003 Jul 16 |
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Stationary phase with specific surface properties for the separation of estradiol diastereoisomers. | 2003 Jul 25 |
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Estrogen in the adult male reproductive tract: a review. | 2003 Jul 9 |
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Estrogens and menopause: pharmacology of conjugated equine estrogens and their potential role in the prevention of neurodegenerative diseases such as Alzheimer's. | 2003 Jun |
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Potential role of the interaction between equine estrogens, low-density lipoprotein (LDL) and high-density lipoprotein (HDL) in the prevention of coronary heart and neurodegenerative diseases in postmenopausal women. | 2003 Jun 20 |
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17beta-estradiol inhibits the production of interferon-induced protein of 10 kDa by human keratinocytes. | 2003 Mar |
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17beta-estradiol inhibits NADPH oxidase activity through the regulation of p47phox mRNA and protein expression in THP-1 cells. | 2003 May 12 |
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Reciprocal effects of C/EBPalpha and PKCdelta on JunB expression and monocytic differentiation depend upon the C/EBPalpha basic region. | 2003 May 15 |
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[Anti-arrhythmia activity of estradiol valerate and estradiol nitrate]. | 2003 May-Jun |
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Estradiol modulates acetylcholine-induced Ca2+ signals in LHRH-releasing GT1-7 cells through a membrane binding site. | 2003 Nov |
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Characterization of an organic anion transport system in a placental cell line. | 2003 Nov |
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Testosterone metabolism in human skin cells in vitro and its interaction with estradiol and dutasteride. | 2003 Nov-Dec |
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Estrogen-induced changes in the microtubular system correlate with a decreased susceptibility of aging neurons to beta amyloid neurotoxicity. | 2003 Oct |
|
Short-term activation by low 17beta-estradiol concentrations of the Na+/H+ exchanger in rat aortic smooth muscle cells: physiopathological implications. | 2003 Oct |
|
17Beta-estradiol as a receptor-mediated cardioprotective agent. | 2003 Oct |
|
Protective effects of estrogens on polyglutamine-expanded androgen receptor aggregation in mice. | 2003 Oct 16 |
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Role of steroid sulfatase in local formation of estrogen in post-menopausal breast cancer patients. | 2003 Sep |
|
Estrogens inhibit l-glutamate uptake activity of astrocytes via membrane estrogen receptor alpha. | 2003 Sep |
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Chemical synthesis of two novel diaryl ether dimers of estradiol-17beta. | 2004 Jan |
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The difluoromethylene group as a replacement for the labile oxygen in steroid sulfates: a new approach to steroid sulfatase inhibitors. | 2004 Jan 5 |
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Estradiol binding to maxi-K channels induces their down-regulation via proteasomal degradation. | 2004 Jan 9 |
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Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. | 2004 Jul |
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The unusual binding properties of the third distinct teleost estrogen receptor subtype ERbetaa are accompanied by highly conserved amino acid changes in the ligand binding domain. | 2004 Jun |
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Involvement of insulin/phosphoinositide 3-kinase/Akt signal pathway in 17 beta-estradiol-mediated neuroprotection. | 2004 Mar 26 |
|
Estrogen suppresses IL-1beta-mediated induction of COX-2 pathway in rat cerebral blood vessels. | 2004 May |
|
Aromatase inhibition in the treatment of advanced breast cancer: is there a relationship between potency and clinical efficacy? | 2004 May 4 |
|
17beta-estradiol inhibits cyclic strain-induced endothelin-1 gene expression within vascular endothelial cells. | 2004 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22879713
Ell-Cranell® alpha was applied once a day at 3 ml/application using a pre-dosed applicator, and the head was massaged for approximately one minute to facilitate the absorption of the drug.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16042770
17a- and 17b-estradiol caused a concentration-dependent inhibition of spontaneous rat uterine contractility, with an IC50 value of 89.39 and 8.42 uM, respectively.
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 15:51:16 GMT 2023
by
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on
Sat Dec 16 15:51:16 GMT 2023
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Record UNII |
3VQ38D63M7
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1740
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CHEMBL286452
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100000092026
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C81622
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1926478
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3VQ38D63M7
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8057
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C519808
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68570
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DTXSID8022377
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SUB12672MIG
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ALFATRADIOL
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57-91-0
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m5029
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200-354-8
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Related Record | Type | Details | ||
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TARGET->STIMULATOR |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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