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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

Molecular Formula C25H32O2
Molecular Weight 364.5204
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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
[Protective effect of daizein on apoptosis cells of nasal mucosas in ovariectomized rats].
2003 Feb
The effect of low dose nylestriol-levonorgestrel replacement therapy on bone mineral density in women with postmenopausal osteoporosis.
2003 May
[Effect of nylestriol on bone remodeling in ovariectomized rats].
2004 Jun
[Protective effect of estrogens replacement on apoptosis cells of nasal mocosas in ovariectomized rats].
2005 Mar
Anti-fertility effect of levonorgestrel and quinestrol in Brandt's voles (Lasiopodomys brandtii).
2007 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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:01:28 UTC 2023
Edited
by admin
on Fri Dec 15 15:01:28 UTC 2023
Record UNII
JR0N7XD5GZ
Record Status Validated (UNII)
Record Version
  • Download
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
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
DRUG CENTRAL
2342
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
EVMPD
SUB10211MIG
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
PUBCHEM
9046
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
NSC
759637
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
IUPHAR
7097
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
CAS
152-43-2
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
EPA CompTox
DTXSID6046553
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
CHEBI
8716
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
NCI_THESAURUS
C66500
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
ChEMBL
CHEMBL1201165
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
ECHA (EC/EINECS)
205-803-1
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
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
PRIMARY
MESH
D011800
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
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
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY