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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26O2
Molecular Weight 310.4307
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MESTRANOL

SMILES

C#C[C@@]1(CC[C@@]2([H])[C@]3([H])CCc4cc(ccc4[C@@]3([H])CC[C@@]21C)OC)O

InChI

InChIKey=IMSSROKUHAOUJS-MJCUULBUSA-N
InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H26O2
Molecular Weight 310.4307
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Mestranol is a biologically inactive prodrug of estrogen agonist ethinylestradiol. Enovid, a combination of mestranol and noretynodrel, was first oral contraceptive approved by FDA in 1960.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
15 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ENOVID

Approved Use

Combination oral contraceptives inhibit ovulation via a negative feedback mechanism on the hypothalamus, which alters the normal pattern of gonadotropin secretion of a follicle-stimulating hormone (FSH) and luteinizing hormone by the anterior pituitary. The follicular phase FSH and midcycle surge of gonadotropins are inhibited. In addition, combination hormonal contraceptives produce alterations in the genital tract, including changes in the cervical mucus, rendering it unfavorable for sperm penetration even if ovulation occurs. Changes in the endometrium may also occur, producing an unfavorable environment for nidation. Combination hormonal contraceptive drugs may alter the tubal transport of the ova through the fallopian tubes. Progestational agents may also alter sperm fertility.

Launch Date

-278208000000
Primary
ENOVID

Approved Use

Menstrual disorder
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
175 pg/mL
50 μg single, oral
dose: 50 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHINYL ESTRADIOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
963 pg × min/mL
50 μg single, oral
dose: 50 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHINYL ESTRADIOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6 h
50 μg single, oral
dose: 50 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHINYL ESTRADIOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
80 ug 1 times / day multiple, oral
Dose: 80 ug, 1 times / day
Route: oral
Route: multiple
Dose: 80 ug, 1 times / day
Sources:
healthy, 20-26 years
Health Status: healthy
Age Group: 20-26 years
Sex: F
Sources:
50 ug single, intravenous
Dose: 50 ug
Route: intravenous
Route: single
Dose: 50 ug
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes (pharmacogenomic study)
Comment: majority of tested variants exhibited decreased clearance values compared to wild type, except for CYP2C9*40 and *36
PubMed

PubMed

TitleDatePubMed
Depression and oral contraceptives.
1968 Aug 24
Mesenteric venous thrombosis in two women taking oral contraceptives.
1973 May
Cardiovascular birth defects and antenatal exposure to female sex hormones.
1977 Jan 13
Asymptomatic liver cell adenomas. Another case of resolution after discontinuation of oral contraceptive use.
1978 Apr 21
Hormone replacement treatment and benign intracranial hypertension.
1982 Jun 5
Enhancement of hepatocarcinogenesis in female rats by ethinyl estradiol and mestranol but not estradiol.
1984 Sep
Xenobiotic interaction with and alteration of channel catfish estrogen receptor.
1997 Dec
A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells.
2002 Dec
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes.
2003 Mar
Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types.
2004 Jul
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities.
2012 Nov 19
Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein.
2015 Feb
Patents

Sample Use Guides

Dose starts on first day of menstrual cycle taking 1 tablet daily.
Route of Administration: Oral
In Vitro Use Guide
In vitro estrogen receptor binding affinity was determined using uterine cytosol preparation. Reaction mixture contained 0.7 ug of protein from the receptor preparation and 16000 dpm of 17beta[3H]estradiol in 0.25 mL of 0.01 Tris-HCl buffer, pH 8.0, containing 0.001 M EDTA and 0.25 M sucrose. Compound was tested in a dose-response fashion using 8 concentration from 0.1 nM to 100 000 nM in duplicate. After incubation at 4°C for 16-18 h, the compounds bound to the receptor were separated from those free in solution using dextran-coated charcoal. The amount of radioactivity bound to the receptor was quantified in Aquasol using liquid scintillation spectrometer. Mestranol did not bound to estrogen receptor in concetrations up to 100 uM, but its metabolite displaced estradiol with IC50 of 15 nM.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:54:41 UTC 2021
Edited
by admin
on Fri Jun 25 20:54:41 UTC 2021
Record UNII
B2V233XGE7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MESTRANOL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
NSC-84032
Code English
MESTRANOL [EP MONOGRAPH]
Common Name English
EE3-ME
Code English
MESTRANOL [HSDB]
Common Name English
MESTRANOL [VANDF]
Common Name English
OVULEN COMPONENT MESTRANOL
Common Name English
MESTRANOL [JAN]
Common Name English
MESTRANOL COMPONENT OF ENOVID
Common Name English
MESTRANOL [ORANGE BOOK]
Common Name English
EE-3ME
Code English
EE3ME
Code English
MESTRANOL [MI]
Common Name English
33355
Code English
MESTRANOL [USP-RS]
Common Name English
MESTRANOL [USP MONOGRAPH]
Common Name English
MESTRANOL [MART.]
Common Name English
EEI3ME
Code English
MESTRANOL [WHO-DD]
Common Name English
MESTRANOL [INN]
Common Name English
3-METHOXY-19-NOR-17.ALPHA.-PREGNA-1,3,5(10)-TRIEN-20-YN-17-OL.
Common Name English
19-NORPREGNA-1,3,5(10)-TRIEN-20-YN-17-OL, 3-METHOXY-, (17.ALPHA.)-
Common Name English
MESTRANOL COMPONENT OF OVULEN
Common Name English
ENOVID COMPONENT MESTRANOL
Common Name English
MESTRANOL [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000100
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
NCI_THESAURUS C478
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
NDF-RT N0000175825
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
EPA PESTICIDE CODE 115401
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
LIVERTOX 607
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
Code System Code Type Description
CAS
72-33-3
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
WIKIPEDIA
MESTRANOL
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
USP_CATALOG
1394008
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PRIMARY USP-RS
HSDB
3588
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
FDA UNII
B2V233XGE7
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
IUPHAR
7087
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
EPA CompTox
72-33-3
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
RXCUI
6782
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
1714
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PRIMARY
EVMPD
SUB08791MIG
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PRIMARY
INN
1139
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
NCI_THESAURUS
C636
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PRIMARY
PUBCHEM
6291
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
DRUG BANK
DB01357
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
MESH
D008656
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
MERCK INDEX
M7257
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1201151
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-777-8
Created by admin on Fri Jun 25 20:54:41 UTC 2021 , Edited by admin on Fri Jun 25 20:54:41 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG