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User:Mr. Ibrahem/Nafarelin

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Mr. Ibrahem/Nafarelin
Clinical data
Trade namesSynarel, 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
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
  • (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
Chemical and physical data
FormulaC66H83N17O13
Molar mass1322.496 g·mol−1
3D model (JSmol)
  • CC(C)C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)[C@@H](CC2=CC3=CC=CC=C3C=C2)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC5=CNC6=CC=CC=C65)NC(=O)[C@H](CC7=CNC=N7)NC(=O)[C@@H]8CCC(=O)N8
  • 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 medication used to treat endometriosis and early puberty.[3][2] It is also used for uterine fibroids, as part of in vitro fertilization (IVF), and as part of transgender hormone therapy.[4][5][6] It is used as a nasal spray two to three times per day.[3]

Common side effects in women include hot flushes, vaginal dryness, muscle pain, and sexual dysfunction.[3] Common side effects in children include acne, mood changes, increased pubic hair, and vaginal bleeding.[3] Other side effects may include allergic reactions, osteoporosis, and pituitary apoplexy.[3] Use in pregnancy may harm the baby.[3] It is a gonadotropin-releasing hormone agonist (GnRH agonist) and works by briefly increasing than decreasing the production of sex hormones by the gonads.[2]

Nafarelin was approved for medical use in the United States in 1990.[3] In the United Kingdom 60 doses of 200 mcg cost the NHS about £50 as of 2021.[7] In the United States this amount costs about 2,800 USD.[8] It is available in many countries globally.[9] It is one of two GnRH analogues available as a nasal spray, the other being buserelin.[10]

References[edit]

  1. ^ 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): 523–51. doi:10.2165/00003495-199039040-00005. PMID 2140979.
  2. ^ a b c d e f g h i j k "DailyMed - SYNAREL- nafarelin acetate spray, metered". dailymed.nlm.nih.gov. Archived from the original on 30 March 2021. Retrieved 11 November 2021.
  3. ^ a b c d e f g h i j "Nafarelin Monograph for Professionals". Drugs.com. Archived from the original on 4 March 2021. Retrieved 11 November 2021.
  4. ^ Minaguchi H, Wong JM, Snabes MC (June 2000). "Clinical use of nafarelin in the treatment of leiomyomas. A review of the literature". J Reprod Med. 45 (6): 481–9. PMID 10900582.
  5. ^ Elder, Kay; Dale, Brian (2 December 2010). In-Vitro Fertilization. Cambridge University Press. p. 24. ISBN 978-1-139-49285-0. Archived from the original on 13 November 2021. Retrieved 11 November 2021.
  6. ^ Olshan J, Eimicke T, Belfort E (June 2016). "Gender Incongruity in Children With and Without Disorders of Sexual Differentiation". Endocrinol. Metab. Clin. North Am. 45 (2): 463–82. doi:10.1016/j.ecl.2016.02.001. PMID 27241976.
  7. ^ BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 782. ISBN 978-0857114105.
  8. ^ "Nafarelin Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 11 November 2021.
  9. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 712–. ISBN 978-3-88763-075-1. Archived from the original on 2021-10-28. Retrieved 2021-08-23.
  10. ^ T. Metin Önerci (17 August 2013). Nasal Physiology and Pathophysiology of Nasal Disorders. Springer Science & Business Media. pp. 208–. ISBN 978-3-642-37250-6. Archived from the original on 28 October 2021. Retrieved 23 August 2021.
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