Clomifene

Not to be confused with Clonidine.

Clomifene
Clinical data
Trade namesClomid, Serophene, others[1]
Other namesClomiphene; Chloramifene; Chloramiphene; MRL-41; MRL/41; NSC-35770
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
Drug classSelective estrogen receptor modulator; Progonadotropin
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
BioavailabilityHigh (>90%)
MetabolismLiver CYP2D6 (with enterohepatic circulation)[2]
Metabolites4-Hydroxyclomiphene (4-OH-CLO), 4-Hydroxy-N-desethylclomiphene (4-OH-DE-CLO)
Elimination half-life4 – 7 days [2][3][4]

active metabolites:
4-OH-CLO : 13 - 34 hrs[2]

4-OH-DE-CLO : 15 - 37 hrs[2]
ExcretionMainly feces, some in urine
Identifiers
  • (E,Z)-2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.011.826 Edit this at Wikidata
Chemical and physical data
FormulaC26H28ClNO
Molar mass405.97 g·mol−1
3D model (JSmol)
  • ClC(c1ccccc1)=C(c2ccc(OCCN(CC)CC)cc2)c3ccccc3
  • 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 checkY
  • Key:GKIRPKYJQBWNGO-UHFFFAOYSA-N checkY
 ☒NcheckY (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, under the category "Ovulation inducers" (Complementary List).[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.

  1. ^ Cite error: The named reference Brands was invoked but never defined (see the help page).
  2. ^ a b c d Cite error: The named reference pmid29516347 was invoked but never defined (see the help page).
  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.
  4. ^ Cite error: The named reference singledosekinetics was invoked but never defined (see the help page).
  5. ^ 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.
  6. ^ 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.
  7. ^ a b 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.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  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.
  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.