Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H22O5S.C4H10N2 |
| Molecular Weight | 436.565 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CNCCN1.[H][C@@]23CCC(=O)[C@@]2(C)CC[C@]4([H])C5=C(CC[C@@]34[H])C=C(OS(O)(=O)=O)C=C5
InChI
InChIKey=HZEQBCVBILBTEP-ZFINNJDLSA-N
InChI=1S/C18H22O5S.C4H10N2/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19;1-2-6-4-3-5-1/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);5-6H,1-4H2/t14-,15-,16+,18+;/m1./s1
| Molecular Formula | C4H10N2 |
| Molecular Weight | 86.1356 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C18H22O5S |
| Molecular Weight | 350.429 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugfuture.com/chemdata/estrone.html | http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsat | http://pubs.acs.org/doi/abs/10.1021/ja00536a023https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031Curator's Comment: description was created based on several sources, including
http://www.drugbank.ca/drugs/DB00655
https://www.ncbi.nlm.nih.gov/pubmed/2011412
https://www.ncbi.nlm.nih.gov/pubmed/17943537
Sources: http://www.drugfuture.com/chemdata/estrone.html | http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsat | http://pubs.acs.org/doi/abs/10.1021/ja00536a023https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031
Curator's Comment: description was created based on several sources, including
http://www.drugbank.ca/drugs/DB00655
https://www.ncbi.nlm.nih.gov/pubmed/2011412
https://www.ncbi.nlm.nih.gov/pubmed/17943537
Estrone, one of the major mammalian estrogens, is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone. It is produced in vivo from androstenedione or from testosterone via estradiol. It is produced primarily in the ovaries, placenta, and in peripheral tissues (especially adipose tissue) through conversion of adrostenedione. Estrone may be further metabolized to 16-alpha-hydroxyestrone, which may be reduced to estriol by estradiol dehydrogenase. It’s used as hameopatic in management of premenopausal and postmenopausal symptoms. In 1929, Butenandt isolated estrone from the urine of pregnant women. Estrone is known to be a carcinogen for human females as well as a cause of breast tenderness or pain, nausea, headache, hypertension, and leg cramps in the context of non-endogenous exposure. In men, estrone has been known to cause anorexia, nausea, vomiting, and erectile dysfunction. Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol.
Originator
Sources: http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsathttps://www.ncbi.nlm.nih.gov/pubmed/22469359
Curator's Comment: Estrone is one of the hormones responsible for sexual development and function in females.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL206 |
7.0 nM [EC50] | ||
Target ID: CHEMBL206 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Primary | Estragyn Approved UseEstragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms.
Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma. |
|||
| Primary | Estragyn Approved UseEstragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms.
Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma. |
|||
| Primary | THEELIN Approved UseFor management of Menopausal and postmenopausal disorders |
|||
| Palliative | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
733 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/ |
0.5 mg single, vaginal dose: 0.5 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
ESTRONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
550 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/ |
0.5 mg single, vaginal dose: 0.5 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
ESTRONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/ |
0.5 mg single, vaginal dose: 0.5 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
ESTRONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| major | ||||
| no | ||||
| weak | ||||
| weak | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | weak (co-administration study) Comment: Coadministration with ketoconazole (CYP3A4 inhibitor) resulted in estrone expsoure increase of ~1.4 foold |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. | 2000 Feb 11 |
|
| Biological effects of hormone replacement therapy in relation to serum estradiol levels. | 2001 |
|
| Estrogen sulfamates: a new approach to oral estrogen therapy. | 2001 |
|
| Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women. | 2001 |
|
| Futile cycling of estrone sulfate and estrone in the recirculating perfused rat liver preparation. | 2001 Apr |
|
| Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo. | 2001 Apr |
|
| Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3. | 2001 Apr 15 |
|
| Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines. | 2001 Apr 20 |
|
| Cholesterol sulfate: a new adhesive molecule for platelets. | 2001 Apr 24 |
|
| Prospective randomized study of effects of unopposed estrogen replacement therapy on markers of coagulation and inflammation in postmenopausal women. | 2001 Aug |
|
| Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome. | 2001 Aug 9 |
|
| By the way, Doctor. Whenever I read about the effects of hormone replacement therapy (HRT), the researchers always seem to use 0.625 mg of Premarin. I'm taking 1 mg of Estrace daily. How does this compare to the standard dose of Premarin? | 2001 Dec |
|
| By the way, doctor. I've been taking hormone replacement with Premarin and Provera for 12 years. Now that I'm 68 years old, I'd like to stop taking the hormones, but I don't know how. What is the best way to get off HRT? | 2001 Feb |
|
| Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens. | 2001 Jan |
|
| Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro. | 2001 Jan |
|
| Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins. | 2001 Jan |
|
| Paradoxical effect of estradiol: it can block its own bioformation in human breast cancer cells. | 2001 Jul |
|
| Early postnatal plasma concentrations of testicular steroid hormones, pubertal development, and carcass leanness as potential indicators of boar taint in market weight intact male pigs. | 2001 Jul |
|
| Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone. | 2001 Jun |
|
| Serum lipid profile improved by ultra-low doses of 17 beta-estradiol in elderly women. | 2001 Jun |
|
| Postischemic estrogen reduces hypoperfusion and secondary ischemia after experimental stroke. | 2001 Mar |
|
| Sulfation is rate limiting in the futile cycling between estrone and estrone sulfate in enriched periportal and perivenous rat hepatocytes. | 2001 Mar |
|
| Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer. | 2001 May |
|
| Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
| Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women. | 2001 May-Jun |
|
| Effect of transforming growth factor-beta1, insulin-like growth factor-I and insulin-like growth factor-II on cell growth and oestrogen metabolism in human breast cancer cell lines. | 2001 Nov |
|
| Endocrinology of gynaecomastia. | 2001 Nov |
|
| Regulation of human apolipoprotein A-I gene expression by equine estrogens. | 2001 Nov |
|
| Short-term oral estrogen replacement therapy does not augment endothelium-independent myocardial perfusion in postmenopausal women. | 2001 Oct |
|
| Tibolone: a compound with tissue specific inhibitory effects on sulfatase. | 2001 Oct 25 |
|
| Polymorphisms in OATP-C: identification of multiple allelic variants associated with altered transport activity among European- and African-Americans. | 2001 Sep 21 |
|
| Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe. | 2002 |
|
| Number of years since menopause: spontaneous bone loss is dependent but response to hormone replacement therapy is independent. | 2002 Apr |
|
| Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta. | 2002 Apr |
|
| Bone loss at the femoral neck in premenopausal white women: effects of weight change and sex-hormone levels. | 2002 Apr |
|
| An evolutionarily ancient Oatp: insights into conserved functional domains of these proteins. | 2002 Apr |
|
| Peripheral changes in estrone sulfate concentration during the first trimester of gestation in cattle: comparison with unconjugated estrogens and relationship to fetal number. | 2002 Apr 15 |
|
| Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast. | 2002 Aug |
|
| A randomized isoflavone intervention among premenopausal women. | 2002 Feb |
|
| Influence of letrozole and anastrozole on total body aromatization and plasma estrogen levels in postmenopausal breast cancer patients evaluated in a randomized, cross-over study. | 2002 Feb 1 |
|
| Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer. | 2002 Jan |
|
| Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition. | 2002 Jul 16 |
|
| Alveolar and postcranial bone density in postmenopausal women receiving hormone/estrogen replacement therapy: a randomized, double-blind, placebo-controlled trial. | 2002 Jun 24 |
|
| Characterization of iodothyronine sulfatase activities in human and rat liver and placenta. | 2002 Mar |
|
| Interaction of human organic anion transporters with various cephalosporin antibiotics. | 2002 Mar 8 |
|
| Estrogens affect endothelin-1 mRNA expression in LNCaP human prostate carcinoma cells. | 2002 May |
|
| Effects of lactation length and an exogenous progesterone and estradiol-17beta regimen during embryo attachment on endogenous steroid concentrations and embryo survival in sows. | 2002 May |
|
| The choice of hormone replacement therapy or statin therapy in the treatment of hyperlipidemic postmenopausal women. | 2002 May |
|
| Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory. | 2002 May |
|
| Catalytic asymmetric Torgov cyclization: a concise total synthesis of (+)-estrone. | 2014 Aug 11 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.rxwiki.com/estrone
Curator's Comment: Vaginal route is possible: The recommended dose is 2.0 to 4.0 g intravaginally per day, adjusted to the lowest amount that controls symptoms http://www.rxlist.com/estragyn-drug.htm
Estrone is available in the following doses:
Estrone 2 Mg/ml Intramuscular Solution
Estrone 5 Mg/ml Intramuscular Solution
Estrone Compounding Powder
Forms of Medication
Estrone is available in the following forms:
Injectable Solution
Injectable Suspension
Vaginal Suppository
Route of Administration:
Intramuscular
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:02:08 GMT 2023
by
admin
on
Fri Dec 15 15:02:08 GMT 2023
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| Record UNII |
SVI38UY019
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| Record Status |
Validated (UNII)
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C2181
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m5033
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1255500
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230-696-3
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C47521
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758912
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Estropipate
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SVI38UY019
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CHEMBL494753
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33747
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ACTIVE MOIETY |
