Cetrorelix

{{Short description|Drug used in IVF procedures}} {{Use dmy dates|date=November 2022}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 460026591 | image = Cetrorelix.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = Cetrorelix ball-and-stick.png | image_class2 = bg-transparent | width2 = 250 | alt2 =

| tradename = Cetrotide, others | Drugs.com = {{drugs.com|monograph|cetrorelix}} | routes_of_administration = Subcutaneous injection | class = GnRH analogue; GnRH antagonist; Antigonadotropin | ATC_prefix = H01 | ATC_suffix = CC02

| legal_AU = S4 | legal_AU_comment = <ref>{{cite web | title=Cetrorelix RBX (Sun Pharma ANZ Pty Ltd) | website=Therapeutic Goods Administration (TGA) | date=13 March 2025 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/cetrorelix-rbx-sun-pharma-anz-pty-ltd | access-date=24 March 2025}}</ref> | legal_US = Rx-only | legal_EU = Rx-only

| bioavailability = 85% | protein_bound = 86% | metabolism = | elimination_half-life = 62.8 hours / 3 mg single dose; 5 hours / 0.25 mg single dose; 20.6 hours / 0.25 mg multiple doses | excretion = feces (5% to 10% as unchanged drug and metabolites); urine (2% to 4% as unchanged drug)

| IUPHAR_ligand = 1190 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 120287-85-6 | PubChem = 16130924 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00050 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10482082 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = OON1HFZ4BA | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D07665 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 59224 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1200490 | synonyms =

| IUPAC_name = Acetyl-D-3-(2{{prime}}-naphtyl)-alanine-D-4-chlorophenylalanine-D-3-(3{{prime}}-pyridyl)- alanine-L-serine-L-tyrosine-D-citrulline-L-leucine-L-arginine-L-proline-D-alanine-amide | C=70 | H=92 | Cl=1 | N=17 | O=14 | smiles = CC(=O)N[C@H](Cc1ccc2ccccc2c1)C(=O)N[C@H](Cc1ccc(Cl)cc1)C(=O)N[C@H](Cc1cccnc1)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H](CCCNC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C70H92ClN17O14/c1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44/h5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = SBNPWPIBESPSIF-MHWMIDJBSA-N }}

'''Cetrorelix''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}), or '''cetrorelix acetate''' ({{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|JAN|Japanese Accepted Name}}), sold under the brand name '''Cetrotide''', is an injectable gonadotropin-releasing hormone (GnRH) antagonist. A synthetic decapeptide, it is used in assisted reproduction to inhibit premature luteinizing hormone surges<ref>{{Cite web |url=http://www.emdserono.com/ms.country.us/en/images/Cetrotide_PI_tcm115_140012.pdf?Version= |title=Cetrotide 0.25 mg|access-date=30 January 2016 |archive-url=https://web.archive.org/web/20160405130625/http://emdserono.com/ms.country.us/en/images/Cetrotide_PI_tcm115_140012.pdf?Version= |archive-date=5 April 2016 |url-status=dead|website=emdserono.com }}</ref> The drug works by blocking the action of GnRH upon the pituitary, thus rapidly suppressing the production and action of luteinizing hormone (LH) and follicle-stimulating hormone (FSH). In addition, cetrorelix can be used to treat hormone-sensitive cancers of the prostate{{cn|date=January 2016}} and breast (in pre-/perimenopausal women){{cn|date=January 2016}} and some benign gynaecological disorders (endometriosis, uterine fibroids and endometrial thinning).{{cn|date=January 2016}} It is administered as either multiple 0.25 mg daily subcutaneous injections or as a single-dose 3 mg subcutaneous injection. The duration of the 3 mg single dose is four days; if human chorionic gonadotropin (hCG) is not administered within four days, a daily 0.25 mg dose is started and continued until hCG is administered.

It is available as a generic medication.<ref>{{cite web | title=2022 First Generic Drug Approvals | website=U.S. Food and Drug Administration (FDA) | date=3 March 2023 | url=https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/2022-first-generic-drug-approvals | archive-url=https://web.archive.org/web/20230630003602/https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/2022-first-generic-drug-approvals | archive-date=30 June 2023 | url-status=dead | access-date=30 June 2023}}</ref><ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. Food and Drug Administration (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=dead }}</ref>

==Medical uses== Cetrorelix is marketed by Merck Serono for use in in-vitro fertilization in all countries except Japan, where it is marketed by Shionogi and Nippon Kayaku.<ref>[https://web.archive.org/web/20110707092526/http://www.aezsinc.com/en/page.php?p=20&prod=43 Aeternia Zentaris product page]</ref> Aeterna Zentaris receives royalties on these sales and retains rights to develop cetrorelix for other indications. In IVF use it is injected daily after follicle stimulation has been initiated and evidence of follicle maturation is approaching; given daily it prevents an endogenous LH surge that would trigger an untimely ovulation prior to the hCG administration by the treating physician. As an alternative to the GnRH antagonist, also a GnRH agonist could be given, but agonist have to be started earlier to overcome the agonistic effect. Cetrorelix can be mixed with follitropin alpha without compromising their reported safety and efficacy.<ref>{{cite journal | vauthors = Lin YH, Wen YR, Chang Y, Seow KM, Hsieh BC, Hwang JL, Tzeng CR | title = Safety and efficacy of mixing cetrorelix with follitropin alfa: a randomized study | journal = Fertility and Sterility | volume = 94 | issue = 1 | pages = 179–83 | date = June 2010 | pmid = 19339001 | doi = 10.1016/j.fertnstert.2009.02.062 | doi-access = free }}</ref>

==Contraindications== The use of cetrorelix is contraindicated in severe renal impairment. It is not intended for women aged 65 years or older. Use in women with severe allergic conditions is not recommended. Use with caution in women with active allergies or history of allergies.{{cn|date=January 2025}}

==Research== Cetrorelix was under development for the treatment of benign prostatic hyperplasia, premenopausal breast cancer, endometriosis, ovarian cancer, prostate cancer, and uterine fibroids, but development for these indications was discontinued.<ref name="AdisInsight">{{cite web | url=http://adisinsight.springer.com/drugs/800001307 | title=Cetrorelix |work=AdisInsight}}</ref>

Cetrorelix was shown to prevent development of reproductive defects induced by injection of anti-Müllerian hormone in a mouse model of polycystic ovary syndrome (PCOS), suggesting its potential as PCOS therapeutic.<ref>{{Cite journal |vauthors=Tata B, Mimouni NE, Barbotin AL, Malone SA, Loyens A, Pigny P, Dewailly D, Catteau-Jonard S, Sundström-Poromaa I, Piltonen TT, Dal Bello F, Medana C, Prevot V, Clasadonte J, Giacobini P |date=June 2018 |title=Elevated prenatal anti-Müllerian hormone reprograms the fetus and induces polycystic ovary syndrome in adulthood |journal=Nature Medicine |volume=24 |issue=6 |pages=834–846 |doi=10.1038/s41591-018-0035-5 |pmc=6098696 |pmid=29760445}}</ref>

In another study, over a period of 3 weeks, daily injections of cetrorelix were administered to 12 men in order to suppress testosterone levels. Testosterone levels were significantly suppressed as compared to a control group. During this time of suppression, increases in high density lipoproteins (HDLs) were seen. HDLs are responsible for removing cholesterol from the blood and higher amounts are correlated with increased cardiovascular health.<ref name=":0">{{cite journal |vauthors=von Eckardstein A |date=1997 |title=Suppression of Endogenous Testosterone in Young Men Increases Serum Levels of High Density Lipoprotein Subclass Lipoprotein A-I and Lipoprotein(a) |journal=Journal of Clinical Endocrinology |volume=82 |issue=10 |pages=3367}}</ref>

== References == {{Reflist}}

== External links == * {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/rn/120287-85-6 | archive-url = https://web.archive.org/web/20190628233647/https://druginfo.nlm.nih.gov/drugportal/rn/120287-85-6 | url-status = dead | archive-date = 28 June 2019 | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Cetrorelix }} * {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/rn/145672-81-7 | archive-url = https://web.archive.org/web/20190628233651/https://druginfo.nlm.nih.gov/drugportal/rn/145672-81-7 | url-status = dead | archive-date = 28 June 2019 | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Cetrorelix acetate }}

Category:Fertility medicine Category:Gonadotropin-releasing hormone antagonists Category:Decapeptides Category:Drugs developed by Merck