Quinestrol

HCID 9046CAS 152-43-2

Grundinformationen

Standard-SMILES
C#C[C@]1(O)CC[C@H]2[C@@H]3CCc4cc(OC5CCCC5)ccc4[C@H]3CC[C@@]21C
InChIKey
PWZUUYSISTUNDW-VAFBSOEGSA-N
Summenformel
C25H32O2
Durchschnittliche Molmasse
364,5 g/mol
Monoisotopische Masse
364,24023026

Überblick

Quinestrol is a 17-hydroxy steroid and a terminal acetylenic compound. It has a role as a xenoestrogen. It is functionally related to a 17beta-estradiol.

Namen und Bezeichner

Bevorzugter Name
Quinestrol
IUPAC
(8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol

Namen und Synonyme

QUINESTROL152-43-2EstrovisEstrovisterPlestrovisEstonEstradiol-17-beta 3-cyclopentyl etherQuinestrolumEstrovis 4000Quinestrolo17-alpha-Ethinylestradiol 3-cyclopentyl etherQuilea
Weitere Namen anzeigen
W 356617alpha-Ethynylestradiol 3-cyclopentyl etherW-3566DTXSID6046553JR0N7XD5GZ(8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-olNSC-759637CHEBI:8716

Datenbank-Bezeichner

CAS
152-43-2
PubChem CID
9046
DTXSID
DTXSID6046553
ChEMBL
CHEMBL1201165
ChEBI
CHEBI:8716
UNII
JR0N7XD5GZ
EC Number
205-803-1
Nikkaji
J5.865C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,3
Polarare Oberfläche (TPSA)
29,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
3
Schwere Atome
27

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
Solubility1.57e-03 g/L
Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point107.5 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H302 (60.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P263, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 64 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (60.9%)

Toxikologische Informationen

Health EffectsSide effects include liver and kidney dysfunction, high blood pressure, heart disease, degeneration of the testicles, premature baldness, and acne.
Exposure RoutesAbsorbed following oral administration.
Toxicity Summary · 1 Eintrag

Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).

Signs and SymptomsSymptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

Quinestrol is the 3-cyclopentyl ether of ethinyl estradiol (the active metabolite). After gastrointestinal absorption, it is stored in adipose tissue where it is slowly released and metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is a synthetic derivative of the natural estrogen estradiol.

Mechanism of Action · 1 Eintrag

Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).

Metabolism/Metabolites · 2 Einträge

Metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is metabolized in the liver. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.

Metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is metabolized in the liver. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.

MeSH Pharmacological Classification · 1 Eintrag

Compounds that interact with ESTROGEN RECEPTORS in target tissues to bring about the effects similar to those of ESTRADIOL. Estrogens stimulate the female reproductive organs, and the development of secondary female SEX CHARACTERISTICS. Estrogenic chemicals include natural, synthetic, steroidal, or non-steroidal compounds.

Absorption, Distribution and ExcretionAbsorbed following oral administration.
Cellular LocationsCytoplasm

Verwendung und Herstellung

UsesUsed in hormone replacement therapy, treating symptoms of menopause such as hot flashes. Also used to treat breast and prostate cancer.

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