Back كلوميفين Arabic کلومیفن سیترات AZB Clomifen German Clomifeno Spanish کلومیفن سیترات Persian Klomifeeni Finnish Clomifène French Clomifen Hausa Clomifeno Interlingua Clomifene Italian
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| Clinical data | |
|---|---|
| Trade names | Clomid, Serophene, others[1] |
| Other names | Clomiphene; Chloramifene; Chloramiphene; MRL-41; MRL/41; NSC-35770 |
| AHFS/Drugs.com | Monograph |
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| Routes of administration | By mouth |
| Drug class | Selective estrogen receptor modulator; Progonadotropin |
| ATC code | |
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| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | High (>90%) |
| Metabolism | Liver CYP2D6 (with enterohepatic circulation)[2] |
| Metabolites | 4-Hydroxyclomiphene (4-OH-CLO), 4-Hydroxy-N-desethylclomiphene (4-OH-DE-CLO) |
| Elimination half-life | 4 – 7 days [2][3][4] active metabolites: |
| Excretion | Mainly feces, some in urine |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.011.826 |
| Chemical and physical data | |
| Formula | C26H28ClNO |
| Molar mass | 405.97 g·mol−1 |
| 3D model (JSmol) | |
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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.[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]
- ^ Cite error: The named reference
Brandswas invoked but never defined (see the help page). - ^ a b c d Cite error: The named reference
pmid29516347was 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
singledosekineticswas 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
FDAlabelwas 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 (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.
- ^ 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.