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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26O2
Molecular Weight 310.4299
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MESTRANOL

SMILES

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

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
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
15.0 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

1961
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
Letter: Oral contraceptives and malignant hepatoma.
1976 Feb 28
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
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
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.
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 Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
NCI_THESAURUS C478
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
NDF-RT N0000175825
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
EPA PESTICIDE CODE 115401
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
LIVERTOX 607
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
Code System Code Type Description
CAS
72-33-3
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
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WIKIPEDIA
MESTRANOL
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
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RS_ITEM_NUM
1394008
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HSDB
3588
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CHEBI
6784
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FDA UNII
B2V233XGE7
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SMS_ID
100000081168
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IUPHAR
7087
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EPA CompTox
DTXSID0020814
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RXCUI
6782
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PRIMARY RxNorm
DRUG CENTRAL
1714
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EVMPD
SUB08791MIG
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INN
1139
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NSC
84032
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
PRIMARY
NCI_THESAURUS
C636
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
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PUBCHEM
6291
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
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DRUG BANK
DB01357
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
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MESH
D008656
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
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MERCK INDEX
m7257
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1201151
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
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ECHA (EC/EINECS)
200-777-8
Created by admin on Fri Dec 15 14:58:16 GMT 2023 , Edited by admin on Fri Dec 15 14:58:16 GMT 2023
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