Nafarelin

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Nafarelin
Nafarelin.svg
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 Monograph
MedlinePlus a601082
Pregnancy
category
  • X
Routes of
administration
Nasal spray
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Biological half-life 2.6 to 4 hours
Excretion renal
Identifiers
CAS Number 76932-56-4 YesY
ATC code H01CA02 (WHO)
PubChem CID 25077649
IUPHAR/BPS 3902
DrugBank DB00666 YesY
ChemSpider 10482014 YesY
UNII 1X0094V6JV YesY
ChEMBL CHEMBL1201309 N
Chemical data
Formula C66H83N17O13
Molar mass 1321.6344 g/mol
 NYesY (what is this?)  (verify)

Nafarelin is a gonadotropin-releasing hormone agonist (GnRH agonist). Its proposed mechanism of action is the desensitization of pituitary GnRH receptors leading to a decrease in gonadotropin release, and ovarian hormone serum concentrations similar to those achieved in postmenopausal women. 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 in vitro fertilisation (IVF).[1][2]

Nafarelin acetate is marketed by Searle (now part of Pfizer) under the brand name Synarel. It is delivered via a nasal spray.[3]

Side effects[edit]

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.[4]

References[edit]

  1. ^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 372–3. ISBN 3-8047-1763-2. 
  2. ^ Wuttke, W; Jarry, H; Feleder, C; Moguilevsky, J; Leonhardt, S; Seong, J. Y.; Kim, K (1996). "The neurochemistry of the GnRH pulse generator". Acta neurobiologiae experimentalis 56 (3): 707–13. PMID 8917899. 
  3. ^ Drugs.com: Synarel Monograph
  4. ^ DailyMed: Synarel – nafarelin acetate spray