Clomifene

Clomifene
Clinical data
Trade names	Clomid, Serophene, others
Other names	Clomiphene; Chloramifene; Chloramiphene; MRL-41; MRL/41; NSC-35770
AHFS/Drugs.com	Monograph
MedlinePlus	a682704
License data	US DailyMed: Clomiphene;
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 ;
	(what is this?) (verify)

Clomifene, also known as clomiphene, is a medication used to treat infertility in women who do not ovulate, including those with polycystic ovary syndrome.^[5] It is taken by mouth.^[5]

Common side effects include pelvic pain and hot flashes.^[5] Other side effects can include changes in vision, vomiting, trouble sleeping, ovarian cancer, and seizures.^[5]^[6] It is not recommended in people with liver disease or abnormal vaginal bleeding of unknown cause or who are pregnant.^[6]^[7] Clomifene is in the selective estrogen receptor modulator (SERM) family of medication and is a nonsteroidal medication.^[7]^[8] It works by causing the release of GnRH by the hypothalamus, and subsequently gonadotropin from the anterior pituitary.^[6]

Clomifene was approved for medical use in the United States in 1967.^[5] It is on the World Health Organization's List of Essential Medicines.^[9] Its introduction began the era of assisted reproductive technology.^[10]

Clomifene (particularly the purified enclomiphene isomer) has also been found to have a powerful ability to boost or restore testosterone levels in hypogonadal men.^[11] It can be used to enhance performance in sports and is banned by the World Anti-Doping Agency.

^ Cite error: The named reference Brands was invoked but never defined (see the help page).
^ ^a ^b ^c ^d Cite error: The named reference pmid29516347 was invoked but never defined (see the help page).
^ Yilmaz S, Yilmaz Sezer N, Gönenç İM, İlhan SE, Yilmaz E (April 2018). "Safety of clomiphene citrate: a literature review". Cytotechnology. 70 (2): 489–495. doi:10.1007/s10616-017-0169-1. PMC 5851961. PMID 29159661.
^ Cite error: The named reference singledosekinetics was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e "Clomiphene Citrate". The American Society of Health-System Pharmacists. Archived from the original on 14 September 2017. Retrieved 8 December 2016.
^ ^a ^b ^c World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 385–386. hdl:10665/44053. ISBN 9789241547659.
^ ^a ^b Cite error: The named reference FDAlabel was invoked but never defined (see the help page).
^ Ghumman S (2015). Principles and Practice of Controlled Ovarian Stimulation in ART. Springer. p. 65. ISBN 9788132216865. Archived from the original on 27 December 2016.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
^ Dickey RP, Holtkamp DE (1996). "Development, pharmacology and clinical experience with clomiphene citrate". Human Reproduction Update. 2 (6): 483–506. doi:10.1093/humupd/2.6.483. PMID 9111183.
^ Rodriguez KM, Pastuszak AW, Lipshultz LI (August 2016). "Enclomiphene citrate for the treatment of secondary male hypogonadism". Expert Opinion on Pharmacotherapy. 17 (11): 1561–7. doi:10.1080/14656566.2016.1204294. PMC 5009465. PMID 27337642.

[Brands-1] Cite error: The named reference Brands was invoked but never defined (see the help page).

[pmid29516347-2] Cite error: The named reference pmid29516347 was invoked but never defined (see the help page).

[pmid29159661-3] Yilmaz S, Yilmaz Sezer N, Gönenç İM, İlhan SE, Yilmaz E (April 2018). "Safety of clomiphene citrate: a literature review". Cytotechnology. 70 (2): 489–495. doi:10.1007/s10616-017-0169-1. PMC 5851961. PMID 29159661.

[singledosekinetics-4] Cite error: The named reference singledosekinetics was invoked but never defined (see the help page).

[AHFS2016-5] "Clomiphene Citrate". The American Society of Health-System Pharmacists. Archived from the original on 14 September 2017. Retrieved 8 December 2016.

[WHO2008-6] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 385–386. hdl:10665/44053. ISBN 9789241547659.

[FDAlabel-7] Cite error: The named reference FDAlabel was invoked but never defined (see the help page).

[8] Ghumman S (2015). Principles and Practice of Controlled Ovarian Stimulation in ART. Springer. p. 65. ISBN 9788132216865. Archived from the original on 27 December 2016.

[WHO23rd-9] World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[Hist-10] Dickey RP, Holtkamp DE (1996). "Development, pharmacology and clinical experience with clomiphene citrate". Human Reproduction Update. 2 (6): 483–506. doi:10.1093/humupd/2.6.483. PMID 9111183.

[Enclomiphene_citrate_for_the_treatm-11] Rodriguez KM, Pastuszak AW, Lipshultz LI (August 2016). "Enclomiphene citrate for the treatment of secondary male hypogonadism". Expert Opinion on Pharmacotherapy. 17 (11): 1561–7. doi:10.1080/14656566.2016.1204294. PMC 5009465. PMID 27337642.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]