Clomifene citrate

Clomifene

Clinical data
Trade names	Clomid, others
AHFS/Drugs.com	Monograph
Pregnancy category	AU: B3 US: X (Contraindicated)
Routes of administration	by mouth
ATC code	G03GB02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	High (>90%)
Metabolism	liver (with enterohepatic circulation)
Biological half-life	5-7 days
Excretion	mainly kidney, some biliary
Identifiers
IUPAC name (E,Z)-2-(4-(2-chloro-1,2-diphenylethenyl) phenoxy)-N,N-diethyl-ethanamine
CAS Number	911-45-5 Y
PubChem CID	2800
IUPHAR/BPS	4159
DrugBank	DB00882 Y
ChemSpider	2698 Y
UNII	1HRS458QU2
KEGG	D07726 Y
ChEBI	CHEBI:3752 Y
ChEMBL	CHEMBL1200667 N
ECHA InfoCard	100.011.826
Chemical and physical data
Formula	C26H28ClNO
Molar mass	406 or 598.10 g/mol (with citrate)
3D model (Jmol)	Interactive image
SMILES Cl/C(c1ccccc1)=C(/c2ccc(OCCN(CC)CC)cc2)c3ccccc3
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 Y Key:GKIRPKYJQBWNGO-UHFFFAOYSA-N Y
NY (what is this?)

Clomifene, also known as clomiphene, is a medication used to treat infertility in women who do not ovulate. This includes those who have polycystic ovary syndrome. Use results in a greater chance of twins. It is taken by mouth once a day.

Common side effects include pelvic pain and hot flushes. Other side effects can include changes in vision, vomiting, trouble sleeping, ovarian cancer, and seizures. It is not recommended in people with liver disease or who are pregnant. Clomifene is in the selective estrogen receptor modulator (SERM) family of medication. It works by causing the release of gonadotrophin by the hypothalamus.

Clomifene was approved for medical use in the United States in 1967. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is about 0.79 to 2.00 USD for a course of treatment. In the United States the wholesale cost of a course of treatment is 4.80 USD. Its introduction began the era of assisted reproductive technology.

Clomifene is useful in those who are infertile due to anovulation or oligoovulation. Evidence is lacking for the use of clomifene in those who are infertile without a known reason. In such cases, studies have observed a clinical pregnancy rate 5.6% per cycle with clomifene treatment vs. 1.3%–4.2% per cycle without treatment.