Nafarelin

Nafarelin
Systematic (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
Clinical data
Trade names	Synarel
AHFS/Drugs.com
MedlinePlus
Pregnancy cat.	X
Legal status	℞-only
Routes	Nasal spray
Pharmacokinetic data
Half-life	2.6 to 4 hours
Excretion	renal
Identifiers
CAS number	^Y
ATC code	H01
PubChem
DrugBank
ChemSpider	^Y
UNII	^Y
ChEMBL	^N
Chemical data
Formula	C₆₆H₈₃N₁₇O₁₃
Mol. mass	1321.6344 g/mol
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^Y Key:RWHUEXWOYVBUCI-ITQXDASVSA-N^Y
N

Nafarelin is a gonadotropin-releasing hormone agonist (GnRH agonist). By causing constant stimulation of the pituitary gland, it decreases pituitary secretion of the gonadotropins luteinizing hormone (LH) and follicle stimulating hormone (FSH). Nafarelin may be used in the treatment of estrogen-dependent conditions (such as endometriosis or uterine fibroids), to treat central precocious puberty, or to control ovarian stimulation in IVF.

Nafarelin acetate is marketed by Searle (now part of Pfizer) under the brand name Synarel. It is delivered via a nasal spray.

Side effects

Side effects of nafarelin are related to the low estrogen state. Side effects include hot flashes, vaginal dryness, headaches, mood changes, and decreased interest in sex. Some patients may experience acne, muscle pain, reduced breast size, and irritation of the tissue inside the nose. These side effects are reversible and should resolve after stopping the medication.^[1]

References

^ http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=d0aa57cb-d2f4-46d7-af43-7c8b06aa81a6

Gonadotropins and GnRH (G03G)

Gonadotropin
preparations

Gonadotropins	Follicle-stimulating hormone Human chorionic gonadotropin Luteinizing hormone Menotropin Urofollitropin

Antigonadotropins	Sex steroids (via negative feedback): Androgens Estrogens Progestogens Steroid synthesis inhibitors: Danazol Gestrinone

GnRH analogues

Agonists	Avorelin Buserelin Deslorelin Gonadorelin Goserelin Histrelin Leuprorelin Lutrelin Nafarelin Peforelin Triptorelin

Antagonists	Abarelix Cetrorelix Degarelix Detirelix Ganirelix Iturelix Ozarelix Prazarelix Ramorelix Teverelix

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Hypothalamic-pituitary hormones and analogues (H01)

Hypothalamic

GNRH	Agonists: Gonadorelin Nafarelin Histrelin Antagonists: Cetrorelix Ganirelix

Somatostatin	Agonists: Lanreotide Octreotide Pasireotide Vapreotide

Anterior pituitary

ACTH	Agonists: Corticotropin Cosyntropin Tetracosactide

GH	Agonists: IGF-1 (Mecasermin/Mecasermin rinfabate) Sermorelin Somatrem Tesamorelin Antagonists: Pegvisomant

TSH	Agonists: Thyrotropin

Posterior pituitary

Oxytocin	Agonists: Argiprestocin Aspartocin Carbetocin Cargutocin Demoxytocin Nacartocin Antagonists: Atosiban Barusiban

Vasopressin	Agonists: Argipressin Desmopressin Felypressin Lypressin Ornipressin Terlipressin Antagonists: Conivaptan Demeclocycline Lixivaptan Mozavaptan Nelivaptan Relcovaptan Satavaptan Tolvaptan

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Categories

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Nafarelin

Nafarelin

Side effects

References

Categories

Carbon

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Nitrogen

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Oxygen

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Gonadotropin-releasing hormone

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Gonadotropin-releasing hormone agonist

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ATC code H01

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Antigonadotropin

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