Clomifene

Clomifene
Clinical data
Trade names	Clomid, Serophene, others
Other names	Clomiphene; Chloramifene; Chloramiphene; MRL-41; MRL/41; NSC-35770
AHFS/Drugs.com	Monograph
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
Drug class	Selective estrogen receptor modulator; Progonadotropin
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 CYP2D6 (with enterohepatic circulation)
Metabolites	4-Hydroxyclomiphene (4-OH-CLO), 4-Hydroxy-N-desethylclomiphene (4-OH-DE-CLO)
Elimination half-life	4 – 7 days ; active metabolites: ; 4-OH-CLO : 13 - 34 hrs ; 4-OH-DE-CLO : 15 - 37 hrs
Excretion	Mainly feces, some in urine
Identifiers
	IUPAC name (E,Z)-2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine;
CAS Number	911-45-5 ;
PubChem CID	2800;
IUPHAR/BPS	4159;
DrugBank	DB00882 ;
ChemSpider	2698 ;
UNII	1HRS458QU2;
KEGG	D07726 ;
ChEBI	CHEBI:3752 ;
ChEMBL	ChEMBL2355051 ;
CompTox Dashboard (EPA)	DTXSID1022843 ;
ECHA InfoCard	100.011.826
Chemical and physical data
Formula	C26H28ClNO
Molar mass	405.97 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC(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 ; Key:GKIRPKYJQBWNGO-UHFFFAOYSA-N ;
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Clomifene, also known as clomiphene, is a medication used to treat infertility in women who do not ovulate, including those with polycystic ovary syndrome. Use results in a greater chance of twins. It is taken by mouth once a day, with a course of treatment that usually lasts for five days.

Common side effects include pelvic pain and hot flashes. 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 abnormal vaginal bleeding of unknown cause or who are pregnant. Clomifene is in the selective estrogen receptor modulator (SERM) family of medication and is a nonsteroidal medication. It works by causing the release of GnRH by the hypothalamus, and subsequently gonadotropin from the anterior pituitary.

Clomifene was approved for medical use in the United States in 1967. It is on the World Health Organization's List of Essential Medicines, under the category "Ovulation inducers" (Complementary List). Its introduction began the era of assisted reproductive technology.

Clomifene (particularly the purified enclomiphene isomer) has also been found to have a powerful ability to boost or restore testosterone levels in hypogonadal men.

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