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Revision as of 13:32, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 457031218 of page Nafarelin for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').  Latest revision as of 07:40, 1 September 2024 edit Citation bot (talk | contribs)Bots5,424,322 edits Add: publisher, doi. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Feminizing hormone therapy | #UCB_Category 2/5 
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{{Short description|Pharmaceutical drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = verified
| Watchedfields = changed | Watchedfields = verified
| verifiedrevid = 400321082 | verifiedrevid = 462258124
| IUPAC_name = (2''R'')-''N''-pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-formamido}propanamido]-3-(1''H''-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-3-(naphthalen-2-yl)propanamido]-4-methylpentanamide | IUPAC_name = (2''R'')-''N''-pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-formamido}propanamido]-3-(1''H''-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-3-(naphthalen-2-yl)propanamido]-4-methylpentanamide
| image = Nafarelin.svg | image = Nafarelin.svg
| width = 250px


<!--Clinical data--> <!--Clinical data-->
| tradename = Synarel | tradename = Synarel, Nasanyl, others
| Drugs.com = {{drugs.com|monograph|synarel}} | Drugs.com = {{drugs.com|monograph|synarel}}
| MedlinePlus = a601082 | MedlinePlus = a601082
| pregnancy_category = X | pregnancy_category = X
| legal_status = ℞-only | legal_status = Rx-only
| routes_of_administration = ] | routes_of_administration = ]<ref name="pmid2140979" /><ref name="SynarelLabel" />
| class = ]; ]; ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = {{abbrlink|IN|Intranasal administration}}: 2.8% (1.2–5.6%)<ref name="SynarelLabel" />
| elimination_half-life = 2.6 to 4 hours
| protein_bound = 80%<ref name="SynarelLabel" />
| excretion = renal
| metabolism = ]s (not {{abbrlink|CYP450|cytochrome P450}})<ref name="SynarelLabel" />
| elimination_half-life = {{abbr|IN|Intranasal administration}}: 2.5–3.0 hours<ref name="SynarelLabel" /><br />{{Font|size=98%|{{abbrlink|SC|Subcutaneous injection}}: 86 hours (]s)<ref name="SynarelLabel" />}}
| excretion = ]: 44–55%<ref name="SynarelLabel" /><br />]: 19–44%<ref name="SynarelLabel" />


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 76932-56-4 | CAS_number = 76932-56-4
| CAS_supplemental = <br />76932-60-0 (])
| ATC_prefix = H01 | ATC_prefix = H01
| ATC_suffix = CA02 | ATC_suffix = CA02
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00666 | DrugBank = DB00666
| IUPHAR_ligand = 3902
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10482014 | ChemSpiderID = 10482014
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1X0094V6JV | UNII = 1X0094V6JV
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 7445
| ChEMBL = <!-- blanked - oldvalue: 1201309 -->
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | C=66 | H=83 | N=17 | O=13
| ChEMBL = 1201309
| molecular_weight = 1321.6344 g/mol
| KEGG = D08241
| InChI = 1/C66H83N17O13/c1-36(2)25-48(58(89)76-47(13-7-23-71-66(68)69)65(96)83-24-8-14-54(83)64(95)73-33-55(67)86)77-60(91)50(28-38-15-18-39-9-3-4-10-40(39)26-38)78-59(90)49(27-37-16-19-43(85)20-17-37)79-63(94)53(34-84)82-61(92)51(29-41-31-72-45-12-6-5-11-44(41)45)80-62(93)52(30-42-32-70-35-74-42)81-57(88)46-21-22-56(87)75-46/h3-6,9-12,15-20,26,31-32,35-36,46-54,72,84-85H,7-8,13-14,21-25,27-30,33-34H2,1-2H3,(H2,67,86)(H,70,74)(H,73,95)(H,75,87)(H,76,89)(H,77,91)(H,78,90)(H,79,94)(H,80,93)(H,81,88)(H,82,92)(H4,68,69,71)/t46-,47-,48-,49-,50+,51-,52-,53-,54-/m0/s1
| synonyms = Nafareline; Nafarelin acetate; RS-94991; RS-94991-298; -GnRH
| InChIKey = RWHUEXWOYVBUCI-ITQXDASVBR

<!--Chemical data-->
⚫ | C=66 | H=83 | N=17 | O=13
| SMILES = CC(C)C(NC(=O)(Cc1ccc2ccccc2c1)NC(=O)(Cc1ccc(O)cc1)NC(=O)(CO)NC(=O)(Cc1cc2ccccc12)NC(=O)(Cc1ccn1)NC(=O)1CCC(=O)N1)C(=O)N(CCCNC(=N)N)C(=O)N1CCC1C(=O)NCC(N)=O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C66H83N17O13/c1-36(2)25-48(58(89)76-47(13-7-23-71-66(68)69)65(96)83-24-8-14-54(83)64(95)73-33-55(67)86)77-60(91)50(28-38-15-18-39-9-3-4-10-40(39)26-38)78-59(90)49(27-37-16-19-43(85)20-17-37)79-63(94)53(34-84)82-61(92)51(29-41-31-72-45-12-6-5-11-44(41)45)80-62(93)52(30-42-32-70-35-74-42)81-57(88)46-21-22-56(87)75-46/h3-6,9-12,15-20,26,31-32,35-36,46-54,72,84-85H,7-8,13-14,21-25,27-30,33-34H2,1-2H3,(H2,67,86)(H,70,74)(H,73,95)(H,75,87)(H,76,89)(H,77,91)(H,78,90)(H,79,94)(H,80,93)(H,81,88)(H,82,92)(H4,68,69,71)/t46-,47-,48-,49-,50+,51-,52-,53-,54-/m0/s1 | StdInChI = 1S/C66H83N17O13/c1-36(2)25-48(58(89)76-47(13-7-23-71-66(68)69)65(96)83-24-8-14-54(83)64(95)73-33-55(67)86)77-60(91)50(28-38-15-18-39-9-3-4-10-40(39)26-38)78-59(90)49(27-37-16-19-43(85)20-17-37)79-63(94)53(34-84)82-61(92)51(29-41-31-72-45-12-6-5-11-44(41)45)80-62(93)52(30-42-32-70-35-74-42)81-57(88)46-21-22-56(87)75-46/h3-6,9-12,15-20,26,31-32,35-36,46-54,72,84-85H,7-8,13-14,21-25,27-30,33-34H2,1-2H3,(H2,67,86)(H,70,74)(H,73,95)(H,75,87)(H,76,89)(H,77,91)(H,78,90)(H,79,94)(H,80,93)(H,81,88)(H,82,92)(H4,68,69,71)/t46-,47-,48-,49-,50+,51-,52-,53-,54-/m0/s1
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| StdInChIKey = RWHUEXWOYVBUCI-ITQXDASVSA-N | StdInChIKey = RWHUEXWOYVBUCI-ITQXDASVSA-N
}} }}
<!-- Definition and medical uses -->
'''Nafarelin''', sold under the brand name '''Synarel''' among others, is a ] (GnRH agonist) medication which is used in the treatment of ] and ].<ref name="pmid2140979">{{cite journal | vauthors = Chrisp P, Goa KL | title = Nafarelin. A review of its pharmacodynamic and pharmacokinetic properties, and clinical potential in sex hormone-related conditions | journal = Drugs | volume = 39 | issue = 4 | pages = 523–551 | date = April 1990 | pmid = 2140979 | doi = 10.2165/00003495-199039040-00005 }}</ref><ref name="SynarelLabel">{{cite web |title=Synarel® (nafarelin acetate) nasal solution |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019886s033s035lbl.pdf |access-date=10 July 2024 |archive-date=3 January 2020 |archive-url=https://web.archive.org/web/20200103181633/https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019886s033s035lbl.pdf |url-status=live }}</ref> It is also used to treat ]s, to ] in ] (IVF), and as part of ].<ref name="pmid10900582">{{cite journal | vauthors = Minaguchi H, Wong JM, Snabes MC | title = Clinical use of nafarelin in the treatment of leiomyomas. A review of the literature | journal = The Journal of Reproductive Medicine | volume = 45 | issue = 6 | pages = 481–489 | date = June 2000 | pmid = 10900582 }}</ref><ref name="Mutschler2001" /><ref name="pmid27241976" /><ref name="pmid23385274" /> The medication is used as a ] two to three times per day.<ref name="pmid2140979" /><ref name="SynarelLabel" /><ref name="pmid22028996">{{cite journal | vauthors = Magon N | title = Gonadotropin releasing hormone agonists: Expanding vistas | journal = Indian Journal of Endocrinology and Metabolism | volume = 15 | issue = 4 | pages = 261–267 | date = October 2011 | pmid = 22028996 | pmc = 3193774 | doi = 10.4103/2230-8210.85575 | doi-access = free }}</ref>

<!-- Side effects and mechanism -->
]s of nafarelin are related to ] ] and include ]s of ] and ] such as ]es, ], ], and ].<ref name="SynarelLabel" /> Nafarelin is a ] (GnRH agonist) and works by preventing the ] of ]s by the ]s.<ref name="pmid2140979" /><ref name="SynarelLabel" /> It can lower sex hormone levels by 95% in both sexes.<ref name="pmid2140979" /><ref name="SynarelLabel" /> Nafarelin is a ] and an ] of {{abbrlink|GnRH|gonadotropin-releasing hormone}}.<ref name="Srivastava2017">{{cite book| vauthors = Srivastava V |title=Peptide-based Drug Discovery: Challenges and New Therapeutics|url=https://books.google.com/books?id=sbcpDwAAQBAJ&pg=PA182|date=26 June 2017|publisher=Royal Society of Chemistry|isbn=978-1-78262-732-6|pages=182–}}</ref>

<!-- History, society, and culture -->
Nafarelin was introduced for medical use in 1990.<ref name="Drugs@FDA" /><ref name="pmid2140979" /><ref name="pmid1984190" /> It is available widely throughout the world, including in ], ], and elsewhere throughout the world.<ref name="Drugs.com" /><ref name="IndexNominum2000" /> The medication is one of only two medically used GnRH analogues that are available as nasal sprays, the other being ].<ref name="Önerci2013">{{cite book|vauthors=Önerci TM|title=Nasal Physiology and Pathophysiology of Nasal Disorders|url=https://books.google.com/books?id=qfu8BAAAQBAJ&pg=PA208|date=17 August 2013|publisher=Springer Science & Business Media|isbn=978-3-642-37250-6|pages=208–|access-date=10 July 2024|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113020305/https://books.google.com/books?id=qfu8BAAAQBAJ&pg=PA208|url-status=live}}</ref>

==Medical uses==
Nafarelin is approved and used in the treatment of ] and ].<ref name="SynarelLabel" /><ref name="pmid2140979" /> It is also used in the treatment of ]s.<ref name="pmid10900582" /><ref name="pmid2533618">{{cite journal | vauthors = Monroe SE, Andreyko J | title = Treatment of uterine leiomyomas and hirsutism with nafarelin | journal = The Journal of Reproductive Medicine | volume = 34 | issue = 12 Suppl | pages = 1029–1033 | date = December 1989 | pmid = 2533618 }}</ref> The medication is used to ] in ] (IVF).<ref name="Mutschler2001">{{Cite book| vauthors = Mutschler E, Schäfer-Korting M |title=Arzneimittelwirkungen|language=de|location=Stuttgart|publisher=Wissenschaftliche Verlagsgesellschaft|year=2001|edition=8|pages=372–3|isbn=3-8047-1763-2}}</ref><ref>{{cite journal | vauthors = Wuttke W, Jarry H, Feleder C, Moguilevsky J, Leonhardt S, Seong JY, Kim K | title = The neurochemistry of the GnRH pulse generator | journal = Acta Neurobiologiae Experimentalis | volume = 56 | issue = 3 | pages = 707–713 | year = 1996 | doi = 10.55782/ane-1996-1176 | pmid = 8917899 | url = http://www.ane.pl/linkout.php?vol=56&no=3&fpp=707 | access-date = 2015-11-27 | archive-date = 2015-12-08 | archive-url = https://web.archive.org/web/20151208053059/http://www.ane.pl/linkout.php?vol=56&no=3&fpp=707 | url-status = dead }}</ref> Nafarelin is used as a ] in ] and to suppress ] levels in ].<ref name="LeePerl2018">{{cite book| vauthors = Lee JY, Perl L, Rosenthal SM |title=Pediatric Endocrinology |chapter=Care of Gender Nonconforming/Transgender Youth |year=2018|pages=813–823|publisher=Springer |doi=10.1007/978-3-319-73782-9_36|isbn=978-3-319-73781-2}}</ref><ref name="pmid27241976">{{cite journal | vauthors = Olshan J, Eimicke T, Belfort E | title = Gender Incongruity in Children With and Without Disorders of Sexual Differentiation | journal = Endocrinology and Metabolism Clinics of North America | volume = 45 | issue = 2 | pages = 463–482 | date = June 2016 | pmid = 27241976 | doi = 10.1016/j.ecl.2016.02.001 }}</ref><ref name="pmid24972421">{{cite journal | vauthors = Olson J, Garofalo R | title = The peripubertal gender-dysphoric child: puberty suppression and treatment paradigms | journal = Pediatric Annals | volume = 43 | issue = 6 | pages = e132–e137 | date = June 2014 | pmid = 24972421 | doi = 10.3928/00904481-20140522-08 }}</ref><ref name="pmid23385274">{{cite journal | vauthors = Spack NP | title = Management of transgenderism | journal = JAMA | volume = 309 | issue = 5 | pages = 478–484 | date = February 2013 | pmid = 23385274 | doi = 10.1001/jama.2012.165234 }}</ref><ref name="Nakatsuka2014">{{cite journal | vauthors = Nakatsuka M | title = Endocrine treatment of transsexuals: assessment of cardiovascular risk factors | journal = Expert Review of Endocrinology & Metabolism | volume = 5 | issue = 3 | pages = 319–322 | date = May 2010 | pmid = 30861686 | doi = 10.1586/eem.10.18 | s2cid = 73253356 | doi-access = free }}</ref> Nafarelin can also be used to treat ] and ] by lowering ] and ] levels.<ref name="pmid2140979" /><ref name="pmid2533618" /><ref name="pmid2969835">{{cite journal | vauthors = Shaw RW | title = GnRH agonists-antagonists--clinical applications | journal = European Journal of Obstetrics, Gynecology, and Reproductive Biology | volume = 28 | issue = 2 | pages = 109–116 | date = June 1988 | pmid = 2969835 | doi = 10.1016/0028-2243(88)90086-X | doi-access = free }}</ref> It is effective in the treatment of ].<ref name="pmid2140979" />

===Dosages===
Nafarelin is used to treat precocious puberty at a dosage of 1,600 to 1,800&nbsp;μg per day.<ref name="SynarelLabel" /> The 1,600&nbsp;μg/day dosage is achieved by two sprays (400&nbsp;μg total) into each nostril in the morning (four sprays, 800&nbsp;μg total) and two sprays (400&nbsp;μg total) into each nostril in the evening (four sprays, 800&nbsp;μg total).<ref name="SynarelLabel" /> If 1,600&nbsp;μg/day is insufficient for adequate pubertal suppression, the 1,800&nbsp;μg/day dosage can be used instead. This is achieved by three sprays (600&nbsp;μg total) into alternating nostrils three times per day (nine sprays per day total).<ref name="SynarelLabel" /> When administering the sprays, the head should be tilted back slightly and 30&nbsp;seconds should elapse between each spray.<ref name="SynarelLabel" /> A bottle of nafarelin nasal spray (brand name Synarel) lasts for about 7&nbsp;days at a dosage of 1,600&nbsp;μg/day.<ref name="SynarelLabel" />

Nafarelin is used to treat endometriosis at lower dosages of 400 to 800&nbsp;μg per day.<ref name="SynarelLabel" /> This is achieved by one or two sprays (200 or 400&nbsp;μg total) into alternating nostrils once in the morning and once in the evening (two to four sprays per day total).<ref name="SynarelLabel" /> A bottle of nafarelin nasal spray (brand name Synarel) lasts for about 30&nbsp;days at a dosage of 400&nbsp;μg/day.<ref name="SynarelLabel" />

===Available forms===
Nafarelin is available in the form of a 0.2% ] for use one, two, or three times per day.<ref name="LemkeWilliams2012">{{cite book|vauthors=Lemke TL, Williams DA|title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA230|date=24 January 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-345-0|pages=230–|access-date=10 July 2024|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113020305/https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA230|url-status=live}}</ref><ref name="SynarelLabel" /><ref name="pmid2140979" /> Each bottle of nafarelin nasal spray (brand name Synarel) contains about 60&nbsp;sprays delivering approximately 200&nbsp;μg nafarelin in 100&nbsp;μL solution per actuation.<ref name="SynarelLabel" /> Nafarelin is not available for use by any other ]s than ].<ref name="FalconeHurd2017" />

==Side effects==
]s of nafarelin are related to ] and include ]es, ], ]s, ], and ]. Nafarelin causes ] in more than half of men with ] treated with it.<ref name="MunarrizTraish2009">{{cite book| vauthors = Munarriz R, Traish A |title=Sexual Function in the Prostate Cancer Patient|chapter=Impact of Androgen Deprivation on Male Sexual Function|year=2009|pages=163–175|publisher=Humana Press |doi=10.1007/978-1-60327-555-2_11|isbn=978-1-60327-554-5}}</ref> Some people may experience ], ], ], and ]. These side effects are reversible and should resolve after stopping the medication.<ref>DailyMed: {{Webarchive|url=https://web.archive.org/web/20140330153247/http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=d0aa57cb-d2f4-46d7-af43-7c8b06aa81a6 |date=2014-03-30 }}</ref> There is a ] of severe ] during nafarelin therapy in a woman with uterine fibroids.<ref name="pmid8569395">{{cite journal | vauthors = Hata T, Hata K, Kawamura T | title = Severe hyperkalaemia with nafarelin | journal = Lancet | volume = 347 | issue = 8997 | pages = 333 | date = February 1996 | pmid = 8569395 | doi = 10.1016/S0140-6736(96)90514-0 | s2cid = 39987508 | doi-access = free }}</ref> The mechanism is unknown.<ref name="pmid8569395" />

==Pharmacology==

===Pharmacodynamics===
Nafarelin is a ], or an ] of the ], the ] of ].<ref name="pmid2140979" /><ref name="SynarelLabel" /> It works by continuously activating the GnRH receptor, which results in profound ] of the receptor such that it becomes non-functional.<ref name="pmid2140979" /><ref name="SynarelLabel" /> As a result, nafarelin suppresses the GnRH-induced ] of the ]s, ] and ], from the ].<ref name="pmid2140979" /><ref name="SynarelLabel" /> This, in turn, results in profound suppression of ]al ] ], as well as reversible suppression of ].<ref name="pmid2140979" /><ref name="SynarelLabel" />

===Pharmacokinetics===
The ] of nafarelin with ] is 2.8% on average, with a range of 1.2 to 5.6%.<ref name="SynarelLabel" /> The ] of nafarelin is 80%.<ref name="SynarelLabel" /> It is ] primarily by ]s and not by ] ]s.<ref name="SynarelLabel" /> The ] of nafarelin is 2.5 to 3.0&nbsp;hours by intranasal administration, whereas the half-life of nafarelin and its ]s by ] is 85.5&nbsp;hours.<ref name="SynarelLabel" /> Nafarelin is ] 44 to 55% in ] and 18.5 to 44.2% in ].<ref name="SynarelLabel" />

==Chemistry==
Nafarelin is a ], or a ] ] of GnRH.<ref name="pmid2140979" /><ref name="SynarelLabel" /><ref name="FalconeHurd2017" /> It is a ] and is also known as -GnRH.<ref name="FalconeHurd2017">{{cite book|vauthors=Falcone T, Hurd WW|title=Clinical Reproductive Medicine and Surgery: A Practical Guide|url=https://books.google.com/books?id=pzgoDwAAQBAJ&pg=PA9|date=14 June 2017|publisher=Springer|isbn=978-3-319-52210-4|pages=9–|access-date=10 July 2024|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113020331/https://books.google.com/books?id=pzgoDwAAQBAJ&pg=PA9|url-status=live}}</ref><ref name="pmid8477775">{{cite journal | vauthors = Kreuser ED, Klingmüller D, Thiel E | title = The role of LHRH-analogues in protecting gonadal functions during chemotherapy and irradiation | journal = European Urology | volume = 23 | issue = 1 | pages = 157–63; discussion 163–4 | date = 1993 | pmid = 8477775 | doi = 10.1159/000474586 }}</ref> Nafarelin is marketed for medical use in both its ] (nafarelin) and ] ] (nafarelin acetate) forms.<ref name="IndexNominum2000" />

==History==
Nafarelin was introduced for medical use in 1990.<ref name="Drugs@FDA">{{Cite web|url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=019886|title=Drugs@FDA: FDA-Approved Drugs|access-date=2024-07-10|archive-date=2021-03-23|archive-url=https://web.archive.org/web/20210323051150/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=019886|url-status=live}}</ref><ref name="pmid2140979" /><ref name="pmid1984190">{{cite journal | vauthors = Conn PM, Crowley WF | title = Gonadotropin-releasing hormone and its analogues | journal = The New England Journal of Medicine | volume = 324 | issue = 2 | pages = 93–103 | date = January 1991 | pmid = 1984190 | doi = 10.1056/NEJM199101103240205 }}</ref>

==Society and culture==

===Generic names===
''Nafarelin'' is the ] of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}}, while ''nafaréline'' is its {{abbrlink|DCF|Dénomination Commune Française}} and ''nafarelin acetate'' is its {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BANM|British Approved Name}}, and {{abbrlink|JAN|Japanese Accepted Name}}.<ref name="Elks2014">{{cite book|vauthors=Elks J|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA846|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=846–|access-date=10 July 2024|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113020305/https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA846|url-status=live}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA712|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=712–|access-date=2024-07-10|archive-date=2023-01-13|archive-url=https://web.archive.org/web/20230113020304/https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA712|url-status=live}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA189|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=189–}}</ref><ref name="Drugs.com">{{Cite web|url=https://www.drugs.com/international/nafarelin.html|title=Nafarelin nasal Uses, Side Effects & Warnings|access-date=2024-07-10|archive-date=2018-08-28|archive-url=https://web.archive.org/web/20180828001729/https://www.drugs.com/international/nafarelin.html|url-status=live}}</ref> It is also known by its former developmental code name ''RS-94991'' or ''RS-94991-298''.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

===Brand names===
The major brand names of nafarelin are Synarel and Synarela.<ref name="IndexNominum2000" /><ref name="Drugs.com" /> It has also been marketed under a number of other brand names including Synrelin, Synrelina, Nafarelil 0.2%, and Nasanyl 0.2%.<ref name="IndexNominum2000" /><ref name="Drugs.com" />

===Availability===
Nafarelin is available widely throughout the world, including in the ], ], the ], ], other ]an countries, ], ], ], ], ], and ].<ref name="IndexNominum2000" /><ref name="Drugs.com" />

==See also==
* ]

==References==
{{Reflist}}

==Further reading==
{{refbegin}}
* {{cite journal | vauthors = Barbieri RL | title = Comparison of the pharmacology of nafarelin and danazol | journal = American Journal of Obstetrics and Gynecology | volume = 162 | issue = 2 | pages = 581–585 | date = February 1990 | pmid = 2137975 | doi = 10.1016/0002-9378(90)90436-B }}
* {{cite journal | vauthors = Chrisp P, Goa KL | title = Nafarelin. A review of its pharmacodynamic and pharmacokinetic properties, and clinical potential in sex hormone-related conditions | journal = Drugs | volume = 39 | issue = 4 | pages = 523–551 | date = April 1990 | pmid = 2140979 | doi = 10.2165/00003495-199039040-00005 }}
* {{cite journal | vauthors = Burry KA | title = Nafarelin in the management of endometriosis: quality of life assessment | journal = American Journal of Obstetrics and Gynecology | volume = 166 | issue = 2 | pages = 735–739 | date = February 1992 | pmid = 1531576 | doi = 10.1016/0002-9378(92)91705-F }}
* {{cite journal | vauthors = Minaguchi H, Wong JM, Snabes MC | title = Clinical use of nafarelin in the treatment of leiomyomas. A review of the literature | journal = The Journal of Reproductive Medicine | volume = 45 | issue = 6 | pages = 481–489 | date = June 2000 | pmid = 10900582 }}
{{refend}}

{{GnRH and gonadotropins}}
{{GnRH and gonadotropin receptor modulators}}

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]