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
Combined effects of estrogen and progesterone on the anterior cruciate ligament.	2001 Feb	11210964
Gender-related distinctions in protein kinase C activity in rat vascular smooth muscle.	2001 Jan	11121374
Differential neuroprotective effects of equine estrogens against oxidized low density lipoprotein-induced neuronal cell death.	2001 Jul-Aug	11525901
Binding of estrogen and progesterone-BSA conjugates to glyceraldehyde-3-phosphate dehydrogenase (GAPDH) and the effects of the free steroids on GAPDH enzyme activity: physiological implications.	2001 Jun	11182142
Brain region-specific up-regulation of mouse apolipoprotein E by pharmacological estrogen treatments.	2001 Nov	11723172
Modulation by estrogens and xenoestrogens of recombinant human neuronal nicotinic receptors.	2001 Nov 2	11711029
Comparison of the antioxidant effects of equine estrogens, red wine components, vitamin E, and probucol on low-density lipoprotein oxidation in postmenopausal women.	2001 Nov-Dec	11723413
Calcineurin as a potential contributor in estradiol regulation of hippocampal synaptic function.	2002	12123687
Effects of endothelial nitric oxide synthase gene polymorphisms on platelet function, nitric oxide release, and interactions with estradiol.	2002 Jul	12142730
Topical estrogens: their effects on connective tissue synthesis in hairless mouse skin.	2002 Jul	12115026
Estradiol protects dopaminergic neurons in a MPP+Parkinson's disease model.	2002 Jun	12128007
17beta-Estradiol reduces excitatory postsynaptic potential (EPSP) amplitude in rat basolateral amygdala neurons.	2002 Oct 11	12361846
Repeated estradiol treatment prevents MPTP-induced dopamine depletion in male mice.	2003 Apr	12766322
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
[Anti-arrhythmia activity of estradiol valerate and estradiol nitrate].	2003 May-Jun	12924228
Characterization of an organic anion transport system in a placental cell line.	2003 Nov	12902320
17Beta-estradiol as a receptor-mediated cardioprotective agent.	2003 Oct	12893838
Alpha and beta estradiol protect neuronal but not native PC12 cells from paraquat-induced oxidative stress.	2004	15325966
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
Aromatase inhibition in the treatment of advanced breast cancer: is there a relationship between potency and clinical efficacy?	2004 May 4	15150604

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