Clomifeneのソースを表示

{{Short description|Infertility treatment for women}}
{{Distinguish|Clonidine}}
{{Use dmy dates|date=May 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460044105
| image = Clomiphene.svg
| image_class = skin-invert-image
| width = 250
| alt =
| image2 = Clomifene-based-on-xtal-3D-bs-17.png
| image_class2 = bg-transparent
| width2 = 250
| alt2 =

<!-- Clinical data -->
| pronounce         =
| tradename = Clomid, Serophene, others<ref name=Brands/>
| Drugs.com = {{drugs.com|monograph|clomiphene-citrate}}
| MedlinePlus       = a682704
| DailyMedID        = Clomiphene
| pregnancy_AU = B3
| pregnancy_AU_comment =
| pregnancy_category =
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Selective estrogen receptor modulator]]; [[Progonadotropin]]
| ATC_prefix = G03
| ATC_suffix = GB02
| ATC_supplemental  =

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment  =
| legal_BR          = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C5, D1, D2, E, F1, F2, F3, F4 -->
| legal_BR_comment  =
| legal_CA          = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment  =
| legal_DE          = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment  =
| legal_NZ          = <!-- Class A, B, C -->
| legal_NZ_comment  =
| legal_UK = POM
| legal_UK_comment  =
| legal_US = Rx-only
| legal_US_comment  =
| legal_EU          =
| legal_EU_comment  =
| legal_UN          = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment  =
| legal_status      = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = High (>90%)
| protein_bound =
| metabolism = [[Liver]] [[CYP2D6]] (with [[enterohepatic circulation]])<ref name="pmid29516347"/>
| metabolites = 4-Hydroxyclomiphene (4-OH-CLO), 4-Hydroxy-N-desethylclomiphene (4-OH-DE-CLO)
| onset             =
| elimination_half-life = 4–7 days <ref name="pmid29516347"/><ref name="pmid29159661" >{{cite journal | vauthors = Yilmaz S, Yilmaz Sezer N, Gönenç İM, İlhan SE, Yilmaz E | title = Safety of clomiphene citrate: a literature review | journal = Cytotechnology | volume = 70 | issue = 2 | pages = 489–495 | date = April 2018 | pmid = 29159661 | pmc = 5851961 | doi = 10.1007/s10616-017-0169-1 }}</ref><ref name="singledosekinetics"/> <br>
active metabolites: <br>
4-OH-CLO : 13–34 hrs<ref name="pmid29516347"/> <br>
4-OH-DE-CLO : 15–37 hrs<ref name="pmid29516347"/>
| duration_of_action =
| excretion = Mainly [[feces]], some in [[urine]]

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 911-45-5
| PubChem = 2800
| IUPHAR_ligand = 4159
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00882
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2698
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1HRS458QU2
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07726
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3752
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 2355051
| NIAID_ChemDB      =
| PDB_ligand        =
| synonyms = Clomiphene; Chloramifene; Chloramiphene; MRL-41; MRL/41; NSC-35770

<!-- Chemical and physical data -->
| IUPAC_name = (''E'',''Z'')-2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-''N'',''N''-diethylethanamine
| C=26 | H=28 | Cl=1 | N=1 | O=1
| SMILES = ClC(c1ccccc1)=C(c2ccc(OCCN(CC)CC)cc2)c3ccccc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GKIRPKYJQBWNGO-UHFFFAOYSA-N
| density           =
| density_notes     =
| melting_point     =
| melting_high      =
| melting_notes     =
| boiling_point     =
| boiling_notes     =
| solubility        =
| sol_units         =
| specific_rotation =
}}

<!-- Definition and medical uses -->
'''Clomifene''', also known as '''clomiphene''', is a medication used to treat [[infertility]] in women who [[anovulation|do not ovulate]], including those with [[polycystic ovary syndrome]].<ref name=AHFS2016/> It is taken [[by mouth]].<ref name=AHFS2016>{{cite web|title=Clomiphene Citrate|url= https://www.drugs.com/monograph/clomiphene-citrate.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url= https://web.archive.org/web/20170914035548/https://www.drugs.com/monograph/clomiphene-citrate.html|archive-date=14 September 2017}}</ref>

<!-- Side effects and mechanism -->
Common side effects include [[pelvic pain]] and [[hot flashes]].<ref name=AHFS2016/> Other side effects can include changes in vision, vomiting, trouble sleeping, [[ovarian cancer]], and [[seizures]].<ref name=AHFS2016/><ref name=WHO2008/> It is not recommended in people with [[liver disease]] or [[abnormal vaginal bleeding]] of unknown cause or who are [[pregnant]].<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free | pages= 385–386 }}</ref><ref name=FDAlabel/> Clomifene is in the [[selective estrogen receptor modulator]] (SERM) family of medication and is a nonsteroidal medication.<ref name=FDAlabel/><ref>{{cite book| vauthors = Ghumman S |title =Principles and Practice of Controlled Ovarian Stimulation in ART|date=2015|publisher=Springer|isbn=9788132216865|page=65|url=https://books.google.com/books?id=UxecCgAAQBAJ&pg=PA65|url-status=live|archive-url= https://web.archive.org/web/20161227055405/https://books.google.ca/books?id=UxecCgAAQBAJ&pg=PA65|archive-date=27 December 2016}}</ref> It works by causing the release of [[GnRH]] by the [[hypothalamus]], and subsequently [[gonadotropin]] from the [[anterior pituitary]].<ref name=WHO2008/>

<!-- History, society and culture -->
Clomifene was approved for medical use in the United States in 1967.<ref name=AHFS2016/> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> Its introduction began the era of [[assisted reproductive technology]].<ref name=Hist>{{cite journal | vauthors = Dickey RP, Holtkamp DE | title = Development, pharmacology and clinical experience with clomiphene citrate | journal = Human Reproduction Update | volume = 2 | issue = 6 | pages = 483–506 | date = 1996 | pmid = 9111183 | doi = 10.1093/humupd/2.6.483 | doi-access = free | title-link = doi }}</ref>

Clomifene (particularly the purified enclomiphene isomer) has also been found to have a powerful ability to boost or restore testosterone levels in [[hypogonadism|hypogonadal]] men.<ref name="Enclomiphene citrate for the treatm">{{cite journal | vauthors = Rodriguez KM, Pastuszak AW, Lipshultz LI | title = Enclomiphene citrate for the treatment of secondary male hypogonadism | journal = Expert Opinion on Pharmacotherapy | volume = 17 | issue = 11 | pages = 1561–7 | date = August 2016 | pmid = 27337642 | pmc = 5009465 | doi = 10.1080/14656566.2016.1204294 }}</ref> It can be used to enhance performance in sports and is banned by the [[World Anti-Doping Agency]].
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