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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H32O2
Molecular Weight 364.5204
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINESTROL

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(OC5CCCC5)=CC=C34)[C@@H]1CC[C@@]2(O)C#C

InChI

InChIKey=PWZUUYSISTUNDW-VAFBSOEGSA-N
InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1

HIDE SMILES / InChI

Molecular Formula C25H32O2
Molecular Weight 364.5204
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Quinestrol is a synthetic estrogen that is effective in hormone replacement therapy. It is a 3-cyclopentyl ether of ethynyl estradiol. After gastrointestinal absorption, it is stored in adipose tissue, where it is slowly released and metabolized in the liver to its active form, ethinyl estradiol. Quinestrol has found limited use in suppressing lactation in postpartum women and, in combination with synthetic progestogens, as contraceptive therapy, although additional studies are needed for both applications. 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).

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ESTROVIS
Palliative
Unknown
Palliative
Unknown

T1/2

ValueDoseCo-administeredAnalytePopulation
120 h
single, intralymphatic
QUINESTROL plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
1 mg of quinestrol in a one-tablet dose once a month
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
JR0N7XD5GZ
Record Status Validated (UNII)
Record Version