General
Preferred name
MESTRANOL
Synonyms
Ethynylestradiol 3-methyl ether ()
33355 ()
EE-3ME ()
Mestranol component of ovulen ()
EEI3ME ()
EE3-ME ()
EE3ME ()
NSC-84032 ()
Mestranol component of norinyl ()
EE3 ME ()
Mestranol component of enovid ()
P&D ID
PD003101
CAS
43085-54-7
72-33-3
Tags
available
prodrug
drug
Approved by
FDA
First approval
1961
Drug indication
Contraception
Drug Status
withdrawn
approved
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Mestranol is the inactive prodrug of ethinylestradiol. Marketing authorisation is for a combined norethisterone/mestranol formulation. (GtoPdb)
MOA Mestranol is the 3-methyl ether of ethinylestradiol. Ethinylestradiol, is a synthetic derivative of estradiol. Ethinylestradiol is orally bio-active and the estrogen used in almost all modern formulations of combined oral contraceptive pills. It binds to (and activates) the estrogen receptor. Mestranol is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70%.; ; Estrogens diffuse into their target cells and interact with a protein receptor. 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).
DESCRIPTION Mestranol is an inactive proagent and becomes biologically active on conversion to ethinyl estradiol (EE). Mestranol acts as an estrogen receptor agonist. Mestranol combines with a progestin in vivo and can be used for the research of menopausal hormone or menstrual disorders. Mestranol is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
DESCRIPTION Mestranol is the 3-methyl ether of ethinyl estradiol, which is a potent estrogen receptor agonist. It is used as oral contraceptives. (Enamine Bioactive Compounds)
DESCRIPTION Mestranol is the 3-methyl ether of ethinylestradiol. It was the estrogen used in many of the first oral contraceptives. (BOC Sciences Bioactive Compounds)
Cell lines
1
Organisms
1
Compound Sets
22
AdooQ Bioactive Compound Library
A10572
BOC Sciences Bioactive Compounds
mestranol-cas-72-33-3-item-84-75945
Cayman Chemical Bioactives
23822
ChEMBL Approved Drugs
CHEMBL1201151
ChEMBL Drugs
CHEMBL1201151
Drug Repurposing Hub
DrugBank
DB01357
DrugBank Approved Drugs
DB01357
DrugCentral
1714
DrugCentral Approved Drugs
1714
DrugMAP
DMG3F94
DrugMAP Approved Drugs
DMG3F94
Enamine Bioactive Compounds
EBC-07794
Enamine BioReference Compounds
Guide to Pharmacology
7087
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1201151
MedChem Express Bioactive Compound Library
HY-B0390
NIH Clinical Collections (NCC)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Mestranol
External IDs
43
Properties
(calculated by RDKit )
Molecular Weight
310.19
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
1
Ring Count
4
Aromatic Ring Count
1
cLogP
3.92
TPSA
29.46
Fraction CSP3
0.62
Chiral centers
5.0
Largest ring
6.0
QED
0.8
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Indication
contraceptive
Target
ESR1
Estrogen/progestogen Receptor
Environmental Pollutants
Estrogen Receptor/ERR
MOA
Estrogen receptor agonist
Therapeutic Class
Estrogens
Pathway
Vitamin D Related/Nuclear Receptor
Source data