ALFATRADIOL

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22879713 | https://www.ncbi.nlm.nih.gov/pubmed/17451383

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	Potency
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9048584	Agonist 2678	0.2 nM [Ki]
Estrogen receptor beta 110 Target ID: CHEMBL3021 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9048584	Agonist 2678	1.2 nM [Ki]
3-oxo-5-alpha-steroid 4-dehydrogenase activity 1 Target ID: GO:0003865 Sources: https://gr.fagron.com/sites/default/files/product/document/fadapbprb02_fad_alopecia_pharmacistphysicians_en_web.pdf	Inhibitor 8297
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://gr.fagron.com/sites/default/files/product/document/fadapbprb02_fad_alopecia_pharmacistphysicians_en_web.pdf	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Androgenic alopecia 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17451383	Primary		Approved 8429	Ell-Cranell® alpha Approved Use Androgenetic alopecia in women.

PubMed

Title	Date	PubMed
The antihyperglycemic effect of estrone sulfate in genetically obese-diabetic (ob/ob) mice is associated with reduced hepatic glucose-6-phosphatase.	2001 Dec	11753757
Tamoxifen eliminates estrogen's neuroprotective effect upon MPTP-induced neurotoxicity of the nigrostriatal dopaminergic system.	2001 Jul	15111254
Temporal effects of 17beta-estradiol on caveolin-1 mRNA and protein in bovine aortic endothelial cells.	2001 Sep	11514304
The effects of beta-estradiol on SHSY5Y neuroblastoma cells during heavy metal induced oxidative stress, neurotoxicity and beta-amyloid secretion.	2002	12182891
Acute relaxant effects of 17-beta-estradiol through non-genomic mechanisms in rabbit carotid artery.	2002 Apr	11958789
17alpha-estradiol induces aromatase activity in intact human anagen hair follicles ex vivo.	2002 Aug	12190948
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	11902121
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	12069588
Nongenomic regulation of the kinetics of exocytosis by estrogens.	2002 May	11961067
[Comparative evaluation of the antiradical and antioxidant activity of estrogens and their nitro derivatives].	2002 May-Jun	12227090
Some new aspects of 17alpha-estradiol metabolism in man.	2002 Oct	12234624
Neuroprotective effect of estradiol and phytoestrogens on MPP+-induced cytotoxicity in neuronal PC12 cells.	2002 Oct 1	12237867
17beta-Estradiol reduces excitatory postsynaptic potential (EPSP) amplitude in rat basolateral amygdala neurons.	2002 Oct 11	12361846
Estradiol prevents amyloid-beta peptide-induced cell death in a cholinergic cell line via modulation of a classical estrogen receptor.	2003	14580942
Estradiol inhibits atp-induced intracellular calcium concentration increase in dorsal root ganglia neurons.	2003	12732239
Estrogen prevents the loss of CA1 hippocampal neurons in gerbils after ischemic injury.	2003	12573724
Repeated estradiol treatment prevents MPTP-induced dopamine depletion in male mice.	2003 Apr	12766322
[New and established methods in therapy of hair diseases].	2003 Aug	12942187
Estrogen modulation of G-protein-coupled receptor activation of potassium channels in the central nervous system.	2003 Dec	14993035
Characterization of a membrane-associated estrogen receptor in a rat hypothalamic cell line (D12).	2003 Dec	14709794
Estrogen modulates xanthine dehydrogenase/xanthine oxidase activity by a receptor-independent mechanism.	2003 Dec	14588143
17beta-estradiol and tamoxifen regulate a maxi-chloride channel from human placenta.	2003 Jan 1	12532277
Equine estrogens differentially prevent neuronal cell death induced by glutamate.	2003 Jul	12853093
Estradiol regulates the slow Ca2+-activated K+ current in hippocampal pyramidal neurons.	2003 Jul 16	12867518
Stationary phase with specific surface properties for the separation of estradiol diastereoisomers.	2003 Jul 25	12860035
Estrogen in the adult male reproductive tract: a review.	2003 Jul 9	12904263
Estrogens and menopause: pharmacology of conjugated equine estrogens and their potential role in the prevention of neurodegenerative diseases such as Alzheimer's.	2003 Jun	12943738
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	12848896
17beta-estradiol inhibits the production of interferon-induced protein of 10 kDa by human keratinocytes.	2003 Mar	12603854
17beta-estradiol inhibits NADPH oxidase activity through the regulation of p47phox mRNA and protein expression in THP-1 cells.	2003 May 12	12729920
Reciprocal effects of C/EBPalpha and PKCdelta on JunB expression and monocytic differentiation depend upon the C/EBPalpha basic region.	2003 May 15	12522006
[Anti-arrhythmia activity of estradiol valerate and estradiol nitrate].	2003 May-Jun	12924228
Estradiol modulates acetylcholine-induced Ca2+ signals in LHRH-releasing GT1-7 cells through a membrane binding site.	2003 Nov	14622151
Characterization of an organic anion transport system in a placental cell line.	2003 Nov	12902320
Testosterone metabolism in human skin cells in vitro and its interaction with estradiol and dutasteride.	2003 Nov-Dec	14528059
Estrogen-induced changes in the microtubular system correlate with a decreased susceptibility of aging neurons to beta amyloid neurotoxicity.	2003 Oct	14572470
Short-term activation by low 17beta-estradiol concentrations of the Na+/H+ exchanger in rat aortic smooth muscle cells: physiopathological implications.	2003 Oct	12959986
17Beta-estradiol as a receptor-mediated cardioprotective agent.	2003 Oct	12893838
Protective effects of estrogens on polyglutamine-expanded androgen receptor aggregation in mice.	2003 Oct 16	12962912
Role of steroid sulfatase in local formation of estrogen in post-menopausal breast cancer patients.	2003 Sep	14623544
Estrogens inhibit l-glutamate uptake activity of astrocytes via membrane estrogen receptor alpha.	2003 Sep	12950458
Chemical synthesis of two novel diaryl ether dimers of estradiol-17beta.	2004 Jan	14715378
The difluoromethylene group as a replacement for the labile oxygen in steroid sulfates: a new approach to steroid sulfatase inhibitors.	2004 Jan 5	14684318
Estradiol binding to maxi-K channels induces their down-regulation via proteasomal degradation.	2004 Jan 9	14555652
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	15276617
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	15001543
Involvement of insulin/phosphoinositide 3-kinase/Akt signal pathway in 17 beta-estradiol-mediated neuroprotection.	2004 Mar 26	14711819
Estrogen suppresses IL-1beta-mediated induction of COX-2 pathway in rat cerebral blood vessels.	2004 May	14684367
Aromatase inhibition in the treatment of advanced breast cancer: is there a relationship between potency and clinical efficacy?	2004 May 4	15150604
17beta-estradiol inhibits cyclic strain-induced endothelin-1 gene expression within vascular endothelial cells.	2004 Sep	15130882

Patents

Sample Use Guides

In Vivo Use Guide

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

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 Dec 16 15:51:16 GMT 2023` Edited by `admin` on `Sat Dec 16 15:51:16 GMT 2023`
Record UNII	3VQ38D63M7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALFATRADIOL

Official Name

English

ESTRA-1,3,5(10)-TRIENE-3,17.ALPHA.-DIOL

Systematic Name

English

ESTRADIOL, .ALPHA.-

Common Name

English

ALFATRADIOL [MART.]

Common Name

English

17ALPHA-ESTRADIOL

Common Name

English

ESTRADIOL, ALPHA-

Common Name

English

.ALPHA.-ESTRADIOL [MI]

Common Name

English

ETHINYLESTRADIOL IMPURITY L [EP IMPURITY]

Common Name

English

17.ALPHA.-ESTRADIOL

Common Name

English

17a-estradiol [WHO-DD]

Common Name

English

alfatradiol [INN]

Common Name

English

ESTRADIOL HEMIHYDRATE IMPURITY B [EP IMPURITY]

Common Name

English

ESTRADIOL 17-.ALPHA.

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1740