Quinestrol

HCID 9046CAS 152-43-2

基本信息

标准SMILES
C#C[C@]1(O)CC[C@H]2[C@@H]3CCc4cc(OC5CCCC5)ccc4[C@H]3CC[C@@]21C
InChIKey
PWZUUYSISTUNDW-VAFBSOEGSA-N
分子式
C25H32O2
平均分子量
364.5 g/mol
单同位素质量
364.24023026

概述

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.

名称与标识

首选名称
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

名称与别名

QUINESTROL152-43-2EstrovisEstrovisterPlestrovisEstonEstradiol-17-beta 3-cyclopentyl etherQuinestrolumEstrovis 4000Quinestrolo17-alpha-Ethinylestradiol 3-cyclopentyl etherQuilea
展开更多名称
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

数据库标识

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

性质

结构计算性质

XLogP
5.3
极性表面积
29.5 Ų
氢键供体
1
氢键受体
2
可旋转键
3
重原子
27

实验与物化性质

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point107.5 °C

安全与法规

GHS分类

GHS Classification · 4 条

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.

危害信息

Hazard Classes and CategoriesAcute Tox. 4 (60.9%)

毒理信息

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 条

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).

化学与工业

药理信息

Pharmacodynamics · 1 条

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 条

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 条

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 条

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

用途与制造

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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