estradiol valerate   

GtoPdb Ligand ID: 7655

Synonyms: Climaval®
estradiol valerate is an approved drug (FDA (1954))
Compound class: Synthetic organic
Comment: Estradiol valerate is a synthetic ester of the endogenous estrogen, 17β-estradiol. This ester is absorbed more slowly and has a longer duration of action than the native hormone. Estradiol valerate is cleaved in vivo by plasma and liver esterases to form 17β-estradiol and valeric acid.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 46.53
Molecular weight 356.24
XLogP 6.36
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCCC(=O)OC1CCC2C1(C)CCC1C2CCc2c1ccc(c2)O
Isomeric SMILES CCCCC(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O
InChI InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1
InChI Key RSEPBGGWRJCQGY-RBRWEJTLSA-N
No information available.
Summary of Clinical Use
Several brands of combined oral contraceptives (Natazia®, Qlaira® and Delestrogen® for example) contain estradiol valerate and dienogest. Such drug combinations are covered by PubChem CID 9874560. In the UK, estradiol valerate is used as hormone replacement therapy (HRT) for oestrogen deficiency symptoms in postmenopausal women who have been hysterectomised.
Mechanism Of Action and Pharmacodynamic Effects
COCs reduce the risk of pregnancy by primarily by supressing ovulation, but also effect changes which render the cervix and endometrium hostile to sperm.
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