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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

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(OC5CCCC5)C=C4

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
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

Sources: Apotheker-Zeitung (Hanslian Edition) (1908), 22, 769-70,819,840. 

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ESTROVIS

Approved Use

Quinestrol
Palliative
Unknown

Approved Use

Quinestrol
Palliative
Unknown

Approved Use

Quinestrol
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
120 h
single, intralymphatic
QUINESTROL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim
PubMed

PubMed

TitleDatePubMed
The effect of low dose nylestriol-levonorgestrel replacement therapy on bone mineral density in women with postmenopausal osteoporosis.
2003 May
Anti-fertility effect of levonorgestrel and quinestrol in Brandt's voles (Lasiopodomys brandtii).
2007 Dec
Low-dose hormone therapy in postmenopausal women in China.
2010 Dec
Patents

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
Name Type Language
QUINESTROL
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
quinestrol [INN]
Common Name English
19-NORPREGNA-1,3,5(10)-TRIEN-20-YN-17-OL, 3-(CYCLOPENTYLOXY)-, 17.ALPHA.
Common Name English
QUINESTROL [MART.]
Common Name English
ESTROVIS
Common Name English
QUINESTROL [USAN]
Common Name English
NSC-759637
Code English
QUINESTROL [ORANGE BOOK]
Common Name English
Quinestrol [WHO-DD]
Common Name English
QUINESTROL [MI]
Common Name English
W-3566
Code English
3-(Cyclopentyloxy)-19-nor-17α-pregna-1,3,5(10)-trien-20-yn-17-ol
Common Name English
W 3566
Code English
QUINESTROL [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2181
Created by admin on Fri Dec 15 15:01:28 UTC 2023 , Edited by admin on Fri Dec 15 15:01:28 UTC 2023
Code System Code Type Description
WIKIPEDIA
QUINESTROL
Created by admin on Fri Dec 15 15:01:28 UTC 2023 , Edited by admin on Fri Dec 15 15:01:28 UTC 2023
PRIMARY
MERCK INDEX
m9441
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PRIMARY Merck Index
DRUG CENTRAL
2342
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EVMPD
SUB10211MIG
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PUBCHEM
9046
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NSC
759637
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IUPHAR
7097
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CAS
152-43-2
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EPA CompTox
DTXSID6046553
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CHEBI
8716
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NCI_THESAURUS
C66500
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ChEMBL
CHEMBL1201165
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ECHA (EC/EINECS)
205-803-1
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INN
1612
Created by admin on Fri Dec 15 15:01:28 UTC 2023 , Edited by admin on Fri Dec 15 15:01:28 UTC 2023
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MESH
D011800
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DRUG BANK
DB04575
Created by admin on Fri Dec 15 15:01:28 UTC 2023 , Edited by admin on Fri Dec 15 15:01:28 UTC 2023
PRIMARY
RXCUI
9066
Created by admin on Fri Dec 15 15:01:28 UTC 2023 , Edited by admin on Fri Dec 15 15:01:28 UTC 2023
PRIMARY RxNorm
SMS_ID
100000080276
Created by admin on Fri Dec 15 15:01:28 UTC 2023 , Edited by admin on Fri Dec 15 15:01:28 UTC 2023
PRIMARY
FDA UNII
JR0N7XD5GZ
Created by admin on Fri Dec 15 15:01:28 UTC 2023 , Edited by admin on Fri Dec 15 15:01:28 UTC 2023
PRIMARY