clomiphene   

GtoPdb Ligand ID: 4159

Synonyms: Androxal® | Clomid® | clomifene | MER-41 | MRL-41 | Omifin® | RMI-16289
clomiphene is an approved drug (FDA (1967))
Compound class: Synthetic organic
Comment: Clomiphene is an estrogen receptor alpha modulator, it can act an agonist or antagonist depending on the target tissue. The approved drug clomiphene is a racemic mixture of the two geometric isomers, E and Z clomiphene (also known as enclomiphene and zuclomiphene). Zuclomifene is the more active isomer.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 12.47
Molecular weight 405.19
XLogP 7.28
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCN(CCOc1ccc(cc1)C(=C(c1ccccc1)Cl)c1ccccc1)CC
Isomeric SMILES CCN(CCOc1ccc(cc1)C(=C(c1ccccc1)Cl)c1ccccc1)CC
InChI InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3
InChI Key GKIRPKYJQBWNGO-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Clomiphene is used to treat female infertility due to diseases such as polycystic ovary syndrome, where ovulation fails due to deficient hormonal stimulation.
Mechanism Of Action and Pharmacodynamic Effects
Although te precise mechanism is not well defined (direct activation of the hypothalamic-pituitary axis, or altered estrogen-induced feed-back inhibition), the outcome of treatment with clomiphene is drug-induced release of the gonadotropins FSH and LH, resulting in the development and maturation of an ovarian follicle and subsequent ovulation.