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Nafarelin information


Nafarelin
Clinical data
Trade namesSynarel, Nasanyl, others
Other namesNafareline; Nafarelin acetate; RS-94991; RS-94991-298; [6-D-(2-naphthyl)alanine]-GnRH
AHFS/Drugs.comMonograph
MedlinePlusa601082
Pregnancy
category
  • X
Routes of
administration
Nasal spray[1][2]
Drug classGnRH analogue; GnRH agonist; Antigonadotropin
ATC code
  • H01CA02 (WHO)
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityINTooltip Intranasal administration: 2.8% (1.2–5.6%)[2]
Protein binding80%[2]
MetabolismPeptidases (not CYP450Tooltip cytochrome P450)[2]
Elimination half-lifeIN: 2.5–3.0 hours[2]
SCTooltip Subcutaneous injection: 86 hours (metabolites)[2]
ExcretionUrine: 44–55%[2]
Feces: 19–44%[2]
Identifiers
IUPAC name
  • (2R)-N-[(2R)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-2-[(2R)-2-[(2R)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2R)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-3-(naphthalen-2-yl)propanamido]-4-methylpentanamide
CAS Number
  • 76932-56-4 checkY
    76932-60-0 (acetate)
PubChem CID
  • 25077649
IUPHAR/BPS
  • 3902
DrugBank
  • DB00666 checkY
ChemSpider
  • 10482014 checkY
UNII
  • 1X0094V6JV
KEGG
  • D08241
ChEBI
  • CHEBI:7445 checkY
ChEMBL
  • ChEMBL1201309 checkY
ECHA InfoCard100.212.186 Edit this at Wikidata
Chemical and physical data
FormulaC66H83N17O13
Molar mass1322.496 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CC(C)C[C@H](NC(=O)[C@@H](Cc1ccc2ccccc2c1)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)NCC(N)=O
InChI
  • InChI=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 checkY
  • Key:RWHUEXWOYVBUCI-ITQXDASVSA-N checkY
  (verify)

Nafarelin, sold under the brand name Synarel among others, is a gonadotropin-releasing hormone agonist (GnRH agonist) medication which is used in the treatment of endometriosis and early puberty.[1][2] It is also used to treat uterine fibroids, to control ovarian stimulation in in vitro fertilization (IVF), and as part of transgender hormone therapy.[3][4][5][6] The medication is used as a nasal spray two to three times per day.[1][2][7]

Side effects of nafarelin are related to sex hormone deprivation and include symptoms of low testosterone levels and low estrogen levels such as hot flashes, sexual dysfunction, vaginal atrophy, and osteoporosis.[2] Nafarelin is a gonadotropin-releasing hormone agonist (GnRH agonist) and works by preventing the production of sex hormones by the gonads.[1][2] It can lower sex hormone levels by 95% in both sexes.[1][2] Nafarelin is a peptide and an analogue of GnRHTooltip gonadotropin-releasing hormone.[8]

Nafarelin was introduced for medical use in 1990.[9][1][10] It is available widely throughout the world, including in North America, Europe, and elsewhere throughout the world.[11][12] The medication is one of only two medically used GnRH analogues that are available as nasal sprays, the other being buserelin.[13]

  1. ^ a b c d e f Chrisp P, Goa KL (April 1990). "Nafarelin. A review of its pharmacodynamic and pharmacokinetic properties, and clinical potential in sex hormone-related conditions". Drugs. 39 (4): 523–551. doi:10.2165/00003495-199039040-00005. PMID 2140979.
  2. ^ a b c d e f g h i j k l m https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019886s033s035lbl.pdf [bare URL PDF]
  3. ^ Minaguchi H, Wong JM, Snabes MC (June 2000). "Clinical use of nafarelin in the treatment of leiomyomas. A review of the literature". The Journal of Reproductive Medicine. 45 (6): 481–489. PMID 10900582.
  4. ^ Cite error: The named reference Mutschler2001 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference pmid27241976 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference pmid23385274 was invoked but never defined (see the help page).
  7. ^ Magon N (October 2011). "Gonadotropin releasing hormone agonists: Expanding vistas". Indian Journal of Endocrinology and Metabolism. 15 (4): 261–267. doi:10.4103/2230-8210.85575. PMC 3193774. PMID 22028996.
  8. ^ Srivastava V (26 June 2017). Peptide-based Drug Discovery: Challenges and New Therapeutics. Royal Society of Chemistry. pp. 182–. ISBN 978-1-78262-732-6.
  9. ^ Cite error: The named reference Drugs@FDA was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference pmid1984190 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  13. ^ Önerci TM (17 August 2013). Nasal Physiology and Pathophysiology of Nasal Disorders. Springer Science & Business Media. pp. 208–. ISBN 978-3-642-37250-6.

and 21 Related for: Nafarelin information

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Nafarelin

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Nafarelin, sold under the brand name Synarel among others, is a gonadotropin-releasing hormone agonist (GnRH agonist) medication which is used in the...

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Buserelin

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used GnRH analogues that are available as nasal sprays, the other being nafarelin. Buserelin is available as a generic medication. Buserelin is approved...

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Luteinizing hormone

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Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 3474

Menotropin

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

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ATC code H01

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Gonadorelin H01CA02 Nafarelin QH01CA90 Buserelin QH01CA91 Fertirelin QH01CA92 Lecirelin QH01CA93 Deslorelin QH01CA94 Azagly-nafarelin QH01CA95 Peforelin...

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Human chorionic gonadotropin

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 5369

Gonadotropin preparations

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 1654

Leuprorelin

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 3632

Triptorelin

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 981

Gonadotropin

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 1114

Puberty blocker

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used. These include the GnRH agonists buserelin, histrelin, leuprorelin, nafarelin, and triptorelin. GnRH agonists are available and used as daily subcutaneous...

Word Count : 8119

Ganirelix

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 974

Antigonadotropin

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 794

Deslorelin

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 654

Cryptorchidism

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hormonal intervention used in Europe is the use of GnRH analogs such as nafarelin or buserelin; the success rates and putative mechanism of action are similar...

Word Count : 4490

Nasal administration

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as Rockbone, Fortical and Miacalcin Nasal Spray. GnRH analogues like nafarelin and busurelin are used for the treatment of anovulatory infertility, hypogonadotropic...

Word Count : 1991

Relugolix

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Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 1920

Goserelin

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 934

Progonadotropin

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Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

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Schedule H

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MOXIFLOXACIN 340. MYCOPHENOLATE MOFETIL 341. NADIFLOXACIN 342. NADOLOL 343. NAFARELIN ACETATE 344. NALIDIXIC ACID 345. NAPROXEN 346. Narcotic Drugs and Psychotropic...

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Gonadorelin

Last Update:

Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin...

Word Count : 814

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