clomiphene   Click here for help

GtoPdb Ligand ID: 4159

Synonyms: Androxal® | Clomid® | clomifene | MER-41 | MRL-41 | Omifin® | RMI-16289
Approved drug
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.
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2D Structure
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Physico-chemical Properties
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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
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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
Bioactivity Comments
Clomiphene is one of a number of drugs that are cationic amphiphilic in nature, for which anti-SARS-CoV-2 activity has been identified in drug repurposing screens. Tummino et al. (2021; bioRxiv preprint PMID: 33791693 target="_blank") suggest that this antiviral activity is most likely a result of the drug promoting phospholipidosis via disruption of lipid homeostasis.
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
VRAC Hs Channel blocker - - - -
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Estrogen receptor-α Primary target of this compound Hs Antagonist Antagonist 8.9 pKi - 1
pKi 8.9 (Ki 1.3x10-9 M) [1]