mestranol   Click here for help

GtoPdb Ligand ID: 7087

Synonyms: EE3-ME
Approved drug
mestranol is an approved drug (FDA (1962))
Comment: Mestranol is the inactive prodrug of ethinylestradiol. Marketing authorisation is for a combined norethisterone/mestranol formulation.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: mestranol

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 29.46
Molecular weight 310.19
XLogP 4.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES C#CC1(O)CCC2C1(C)CCC1C2CCc2c1ccc(c2)OC
Isomeric SMILES C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OC
InChI 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
InChI Key IMSSROKUHAOUJS-MJCUULBUSA-N
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1962))
Is prodrug? Yes
Active form ethinylestradiol
IUPAC Name Click here for help
(8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
International Nonproprietary Names Click here for help
INN number INN
1139 mestranol
Synonyms Click here for help
EE3-ME
Database Links Click here for help
CAS Registry No. 72-33-3
ChEBI CHEBI:6784
ChEMBL Ligand CHEMBL1201151
DrugBank Ligand DB01357
DrugCentral Ligand 1714
GtoPdb PubChem SID 178103665
PubChem CID 6291
Search Google for chemical match using the InChIKey IMSSROKUHAOUJS-MJCUULBUSA-N
Search Google for chemicals with the same backbone IMSSROKUHAOUJS
Search PubMed clinical trials mestranol
Search PubMed titles mestranol
Search PubMed titles/abstracts mestranol
Search UniChem for chemical match using the InChIKey IMSSROKUHAOUJS-MJCUULBUSA-N
Search UniChem for chemicals with the same backbone IMSSROKUHAOUJS
Wikipedia Mestranol