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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O2
Molecular Weight 272.3826
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFATRADIOL

SMILES

C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])CC[C@@]1([H])O)O

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

HIDE SMILES / InChI

Molecular Formula C18H24O2
Molecular Weight 272.3826
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Tamoxifen eliminates estrogen's neuroprotective effect upon MPTP-induced neurotoxicity of the nigrostriatal dopaminergic system.
2001 Jul
Dehydroepiandrosterone and alpha-estradiol limit the functional alterations of rat brain mitochondria submitted to different experimental stresses.
2002
17alpha-estradiol induces aromatase activity in intact human anagen hair follicles ex vivo.
2002 Aug
17Alpha-estradiol and 17beta-estradiol treatments are effective in lowering cerebral amyloid-beta levels in AbetaPPSWE transgenic mice.
2002 Dec
Nuclear receptor agonists stimulate release of arachidonic acid from rat liver cells.
2002 Dec
[Comparative evaluation of the antiradical and antioxidant activity of estrogens and their nitro derivatives].
2002 May-Jun
Some new aspects of 17alpha-estradiol metabolism in man.
2002 Oct
Neuroprotective effect of estradiol and phytoestrogens on MPP+-induced cytotoxicity in neuronal PC12 cells.
2002 Oct 1
17beta-Estradiol reduces excitatory postsynaptic potential (EPSP) amplitude in rat basolateral amygdala neurons.
2002 Oct 11
Estradiol prevents amyloid-beta peptide-induced cell death in a cholinergic cell line via modulation of a classical estrogen receptor.
2003
Estradiol inhibits atp-induced intracellular calcium concentration increase in dorsal root ganglia neurons.
2003
Repeated estradiol treatment prevents MPTP-induced dopamine depletion in male mice.
2003 Apr
[New and established methods in therapy of hair diseases].
2003 Aug
The use of estrogens and related compounds in the treatment of damage from cerebral ischemia.
2003 Dec
Estrogen modulation of G-protein-coupled receptor activation of potassium channels in the central nervous system.
2003 Dec
Characterization of a membrane-associated estrogen receptor in a rat hypothalamic cell line (D12).
2003 Dec
Estrogen modulates xanthine dehydrogenase/xanthine oxidase activity by a receptor-independent mechanism.
2003 Dec
17beta-estradiol and tamoxifen regulate a maxi-chloride channel from human placenta.
2003 Jan 1
Equine estrogens differentially prevent neuronal cell death induced by glutamate.
2003 Jul
Estradiol regulates the slow Ca2+-activated K+ current in hippocampal pyramidal neurons.
2003 Jul 16
Stationary phase with specific surface properties for the separation of estradiol diastereoisomers.
2003 Jul 25
Estrogen in the adult male reproductive tract: a review.
2003 Jul 9
Estrogens and menopause: pharmacology of conjugated equine estrogens and their potential role in the prevention of neurodegenerative diseases such as Alzheimer's.
2003 Jun
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
17beta-estradiol inhibits the production of interferon-induced protein of 10 kDa by human keratinocytes.
2003 Mar
17beta-estradiol inhibits NADPH oxidase activity through the regulation of p47phox mRNA and protein expression in THP-1 cells.
2003 May 12
Reciprocal effects of C/EBPalpha and PKCdelta on JunB expression and monocytic differentiation depend upon the C/EBPalpha basic region.
2003 May 15
[Anti-arrhythmia activity of estradiol valerate and estradiol nitrate].
2003 May-Jun
Estradiol modulates acetylcholine-induced Ca2+ signals in LHRH-releasing GT1-7 cells through a membrane binding site.
2003 Nov
Characterization of an organic anion transport system in a placental cell line.
2003 Nov
Testosterone metabolism in human skin cells in vitro and its interaction with estradiol and dutasteride.
2003 Nov-Dec
Estrogen-induced changes in the microtubular system correlate with a decreased susceptibility of aging neurons to beta amyloid neurotoxicity.
2003 Oct
17Beta-estradiol as a receptor-mediated cardioprotective agent.
2003 Oct
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
Alpha and beta estradiol protect neuronal but not native PC12 cells from paraquat-induced oxidative stress.
2004
Synthetic polymers adsorbing bisphenol A and its analogues prepared by covalent molecular imprinting using bisphenol A dimethacrylate as a template molecule.
2004 Apr
Free energy simulations and MM-PBSA analyses on the affinity and specificity of steroid binding to antiestradiol antibody.
2004 Apr 1
Chemical synthesis of two novel diaryl ether dimers of estradiol-17beta.
2004 Jan
The difluoromethylene group as a replacement for the labile oxygen in steroid sulfates: a new approach to steroid sulfatase inhibitors.
2004 Jan 5
Estradiol binding to maxi-K channels induces their down-regulation via proteasomal degradation.
2004 Jan 9
17beta-estradiol downregulates angiotensin-II-induced endothelin-1 gene expression in rat aortic smooth muscle cells.
2004 Jan-Feb
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
Estrogen content of dairy and swine wastes.
2004 Jul 1
Direct action of estradiol on gonadotropin-releasing hormone-1 neuronal activity via a transcription-dependent mechanism.
2004 Jul 14
Profiling of sulfoconjugates in urine by using precursor ion and neutral loss scans in tandem mass spectrometry. Application to the investigation of heavy metal toxicity in rats.
2004 Jun
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
Involvement of insulin/phosphoinositide 3-kinase/Akt signal pathway in 17 beta-estradiol-mediated neuroprotection.
2004 Mar 26
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

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
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
by admin
on Sat Jun 26 01:28:36 UTC 2021
Edited
by admin
on Sat Jun 26 01:28:36 UTC 2021
Record UNII
3VQ38D63M7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALFATRADIOL
INN   MART.  
INN  
Official Name English
ESTRA-1,3,5(10)-TRIENE-3,17.ALPHA.-DIOL
Systematic Name English
17A-ESTRADIOL [WHO-DD]
Common Name English
ESTRADIOL, .ALPHA.-
Common Name English
ALFATRADIOL [MART.]
Common Name English
17ALPHA-ESTRADIOL
Common Name English
ESTRADIOL HEMIHYDRATE IMPURITY B [EP]
Common Name English
.ALPHA.-ESTRADIOL [MI]
Common Name English
17.ALPHA.-ESTRADIOL
Common Name English
ETHINYLESTRADIOL IMPURITY L [EP]
Common Name English
ALFATRADIOL [INN]
Common Name English
ESTRADIOL HEMIHYDRATE SPECIFIED IMPURITY B [EP]
Common Name English
ESTRADIOL 17-.ALPHA.
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1740
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL286452
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
NCI_THESAURUS
C81622
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
RXCUI
1926478
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
FDA UNII
3VQ38D63M7
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
INN
8057
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
MESH
C519808
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
PUBCHEM
68570
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
EPA CompTox
57-91-0
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
EVMPD
SUB12672MIG
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
WIKIPEDIA
ALFATRADIOL
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
CAS
57-91-0
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
MERCK INDEX
M5029
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
200-354-8
Created by admin on Sat Jun 26 01:28:37 UTC 2021 , Edited by admin on Sat Jun 26 01:28:37 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY