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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00666
rdf:type
n3:Drug
n3:description
A potent synthetic agonist of gonadotropin-releasing hormone with 3-(2-naphthyl)-D-alanine substitution at residue 6. Nafarelin has been used in the treatments of central precocious puberty and endometriosis. [PubChem]
n3:dosage
n12:271B3EBE-363D-11E5-9242-09173F13E4C5 n12:271B3EBF-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Hugues JN, Cedrin Durnerin IC: Revisiting gonadotrophin-releasing hormone agonist protocols and management of poor ovarian responses to gonadotrophins. Hum Reprod Update. 1998 Jan-Feb;4(1):83-101. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9622415 # Garner C: Uses of GnRH agonists. J Obstet Gynecol Neonatal Nurs. 1994 Sep;23(7):563-70. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/7996307 # Henzl MR: Gonadotropin-releasing hormone analogs: update on new findings. Am J Obstet Gynecol. 1992 Feb;166(2):757-61. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1531579 # Burry KA: Nafarelin in the management of endometriosis: quality of life assessment. Am J Obstet Gynecol. 1992 Feb;166(2):735-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1531576 # Saltiel E, Garabedian-Ruffalo SM: Pharmacologic management of endometriosis. Clin Pharm. 1991 Jul;10(7):518-31. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1830521 # Chrisp P, Goa KL: Nafarelin. A review of its pharmacodynamic and pharmacokinetic properties, and clinical potential in sex hormone-related conditions. Drugs. 1990 Apr;39(4):523-51. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/2140979 # Letassy NA, Thompson DF, Britton ML, Suda RR Sr: Nafarelin acetate: a gonadotropin-releasing hormone agonist for the treatment of endometriosis. DICP. 1990 Dec;24(12):1204-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/2151003
n3:group
approved
n3:halfLife
3 hours
n3:indication
For treatment of central precocious puberty (true precocious puberty, GnRH-dependent precocious precocity, complete isosexual precocity) in children of both sexes and for the treatment of endometriosis.
n3:manufacturer
n23:271B3EBA-363D-11E5-9242-09173F13E4C5
owl:sameAs
n10:DB00666 n28:DB00666
dcterms:title
Nafarelin
adms:identifier
n7:10605761 n8:DB00666 n11:25077649 n15:46506496 n16:0025-0166-08 n19:PA164754805 n20:Nafarelin n21:C07613
n3:mechanismOfAction
Like GnRH, initial or intermittent administration of nafarelin stimulates release of the gonadotropins luteinizing hormone (LH) and follicle-stimulating hormone (FSH) from the pituitary gland, which in turn transiently increases production of estradiol in females and testosterone in both sexes. However, with continuous daily administration, nafarelin continuously occupies the GnRH receptor, leading to a reversible down-regulation of the GnRH receptors in the pituitary gland and desensitization of the pituitary gonadotropes. This causes a significant and sustained decline in the production of LH and FSH. A decline in gonadotropin production and release causes a dramatic reversible decrease in synthesis of estradiol, progesterone, and testosterone by the ovaries or testes. Like normal endometrium, endometriotic implants contain estrogen receptors. Estrogen stimulates the growth of endometrium. Use of nafarelin induces anovulation and amenorrhea and decreases serum concentrations of estradiol to the postmenopausal range, which induces atrophy of endometriotic implants. However, nafarelin does not abolish the underlying pathophysiology of endometriosis. In children with central precocious puberty receiving nafarelin, serum LH, testosterone, and estradiol concentrations return to prepubertal levels. This results in the supression of secondary sexual characteristics and decrased rate of linear growth and skeletal maturation. Following disconinuation of nafarelin, the effects of the drug is reversed, meaning FSH and LH concentrations usually return to pretreatment levels.
n3:packager
n23:271B3EB8-363D-11E5-9242-09173F13E4C5 n23:271B3EB9-363D-11E5-9242-09173F13E4C5 n23:271B3EB7-363D-11E5-9242-09173F13E4C5
n3:patent
n29:1336401
n3:synonym
Nafarelinum Nafarelin Nafaréline Nafarelina
n3:toxicity
In experimental animals, a single subcutaneous administration of up to 60 times the recommended human dose (on a µg/kg basis, not adjusted for bioavailability) had no adverse effects. At present, there is no clinical evidence of adverse effects following overdosage of GnRH analogs.
n13:hasAHFSCode
n14:68-18-00
n3:proteinBinding
Approximately 80%.
n3:salt
n25:hasConcept
n26:M0026219
foaf:page
n18:nafarelin.htm n24:nafarelin.html
n3:IUPAC-Name
n4:271B3EC4-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B3ECA-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B3EC9-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B3EC6-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B3EC7-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B3EC8-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B3EC2-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B3EC0-363D-11E5-9242-09173F13E4C5 n4:271B3EC3-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B3EC1-363D-11E5-9242-09173F13E4C5
n13:hasATCCode
n22:H01CA02
n3:H-Bond-Acceptor-Count
n4:271B3ED0-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B3ED1-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B3ECB-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B3ECC-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B3ECE-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B3ECD-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B3ECF-363D-11E5-9242-09173F13E4C5
n3:absorption
Rapidly absorbed into the systemic circulation after intranasal administration. Bioavailability from a 400 µg dose averaged 2.8% (range 1.2 to 5.6%). Not absorbed after oral administration.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
76932-56-4
n3:category
n3:containedIn
n5:271B3EBD-363D-11E5-9242-09173F13E4C5 n5:271B3EBB-363D-11E5-9242-09173F13E4C5 n5:271B3EBC-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B3ED6-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B3ED8-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B3ED9-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B3ED5-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B3ED4-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B3ED7-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B3EC5-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B3ED2-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B3ED3-363D-11E5-9242-09173F13E4C5