Classification  |
|
| Compound class | Synthetic organic |
| IUPAC Name |
| 2-[4-[(E)-2-chloro-1,2-di(phenyl)ethenyl]phenoxy]-N,N-diethylethanamine |
| International Nonproprietary Names |
|
| INN number | INN |
| 1309 | clomifene |
| 2334 | enclomifene |
| Synonyms |
| Androxal® | enclomiphene citrate |
| Database Links |
|
| CAS Registry No. | 15690-57-0 (source: Scifinder) |
| ChEMBL Ligand | CHEMBL954 |
| GtoPdb PubChem SID | 223365954 |
| PubChem CID | 1548953 |
| RCSB PDB Ligand | 53Q |
| Search Google for chemical match using the InChIKey | GKIRPKYJQBWNGO-OCEACIFDSA-N |
| Search Google for chemicals with the same backbone | GKIRPKYJQBWNGO |
| Search PubMed clinical trials | enclomifene |
| Search PubMed titles | enclomifene |
| Search PubMed titles/abstracts | enclomifene |
| UniChem Compound Search for chemical match using the InChIKey | GKIRPKYJQBWNGO-OCEACIFDSA-N |
| UniChem Connectivity Search for chemical match using the InChIKey | GKIRPKYJQBWNGO-OCEACIFDSA-N |
What is Enclomiphene?
Enclomiphene is a selective estrogen receptor modulator, more appropriately known as a SERM, not to be confused with a SARMS UK This is one of the isomers of clomiphene citrate—the trans-isomer that acts mainly as an anti-estrogen. Enclomiphene works by preventing the receptors in the hypothalamus from accepting estrogen, which in return activates these receptors to stimulate the release of other hormones such as luteinizing hormone (LH) and follicle-stimulating hormone (FSH). This results in increased production of testosterone and may be indicated for conditions such as male hypogonadism.
Applications of Enclomiphene
Male Hypogonadism: Enclomiphene is commonly applied in managing secondary hypogonadism; this presents when there is an inability of the testes to produce adequate levels of testosterone in men. It increases natural levels of testosterone without compromising sperm count, unlike TRT medications.
Fertility Treatment: Although not as commonly used to treat male factor infertility as clomiphene citrate, enclomiphene has some promise in increasing endogenous testosterone levels while maintaining spermatogenesis.
Mechanism of Action
Enclomiphene works in the following manner:
- Estrogen receptor blockade in the hypothalamus.
- Inhibition leads to increased release of GnRH.
- Stimulation of the pituitary gland to release LH and FSH.
These lead to increased testosterone production by the testes.
Figure 1 – Enclomiphene Structure
What can we see in Encomiphene’s structure?
- Enclomiphene is a triphenylethylene derivative, which is the basis for its activity as a selective estrogen receptor modulator (SERM).
- It contains a stilbene backbone (a structure with a double bond between two phenyl rings) that is substituted with a chloro group and a phenoxy side chain.
- The structure includes the following functional groups:
- Aromatic rings (phenyl groups)
- Ether linkage (phenoxy group)
- Tertiary amine group
