ナファレリン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/06/16 11:22:11」(JST)
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Nafarelin
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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
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Legal status
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Routes of
administration
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Nasal spray |
Pharmacokinetic data |
Half-life |
2.6 to 4 hours |
Excretion |
renal |
Identifiers |
CAS Registry Number
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76932-56-4 Y |
ATC code
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H01CA02 |
PubChem |
CID: 25077649 |
DrugBank |
DB00666 Y |
ChemSpider |
10482014 Y |
UNII |
1X0094V6JV Y |
ChEMBL |
CHEMBL1201309 N |
Chemical data |
Formula |
C66H83N17O13 |
Molecular mass
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1321.6344 g/mol |
InChI
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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
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N (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 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)
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Gonadotropin
preparations |
Gonadotropins |
- Follicle-stimulating hormone
- Human chorionic gonadotropin
- Luteinizing hormone
- Menotropin
- Urofollitropin
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Antigonadotropins |
- Sex steroids (via negative feedback inhibition): Androgens
- Estrogens
- Progestogens (incl., chlormadinone acetate, cyproterone acetate, delmadinone acetate, medroxyprogesterone acetate, megestrol acetate, nomegestrol acetate, norethisterone acetate)
- Steroid synthesis inhibitors: Danazol
- Gestrinone
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GnRH analogues |
Agonists |
- Buserelin
- Deslorelin
- GnRH (gonadorelin)
- Goserelin
- Histrelin
- Leuprorelin
- Nafarelin
- Triptorelin
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Antagonists |
- Abarelix
- Cetrorelix
- Degarelix
- Ganirelix
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of reproductive medicine
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Description |
- Anatomy
- Physiology
- Development
- sex determination and differentiation
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Disease |
- Infections
- Congenital
- Neoplasms and cancer
- male
- female
- gonadal
- germ cell
- Other
- Symptoms and signs
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Treatment |
- Procedures
- Drugs
- benign prostatic hypertrophy
- erectile dysfunction and premature ejaculation
- sexual dysfunction
- infection
- hormones
- androgens
- estrogens
- progestogens
- GnRH
- prolactin
- Assisted reproduction
- Birth control
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UpToDate Contents
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English Journal
- Spontaneous reports of seizure in association with leuprolide (lupron depot), goserelin (zoladex implant), and naferelin (synarel nasal spray).
- Gatti J, Brinker A, Avigan M.
- Obstetrics and gynecology.Obstet Gynecol.2013 May;121(5):1107. doi: 10.1097/AOG.0b013e31828c9cb3.
- PMID 23635751
- A mathematical model of the human menstrual cycle for the administration of GnRH analogues.
- Röblitz S, Stötzel C, Deuflhard P, Jones HM, Azulay DO, van der Graaf PH, Martin SW.SourceComputational Systems Biology Group, Zuse Institute Berlin (ZIB), Berlin, Germany. susanna.roeblitz@zib.de
- Journal of theoretical biology.J Theor Biol.2013 Mar 21;321:8-27. doi: 10.1016/j.jtbi.2012.11.020. Epub 2012 Dec 1.
- The paper presents a differential equation model for the feedback mechanisms between gonadotropin-releasing hormone (GnRH), follicle-stimulating hormone (FSH), luteinizing hormone (LH), development of follicles and corpus luteum, and the production of estradiol (E2), progesterone (P4), inhibin A (Ih
- PMID 23206386
- Restart of steroidogenesis in dogs during recrudescence of testicular function following downregulation with a GnRH-agonist implant.
- Gentil M, Hoffmann B, Spang A, Failing K, Goericke-Pesch S.SourceClinic for Obstetrics, Gynecology and Andrology of Large and Small Animals, Justus-Liebig-University Giessen, Germany. schulzmichaela@gmx.de
- Cell and tissue research.Cell Tissue Res.2012 Dec;350(3):513-23. doi: 10.1007/s00441-012-1506-5. Epub 2012 Oct 9.
- To date, no details are available concerning the restart of steroidogenesis following the downregulation of testicular endocrine and germinative function by gonadotrophin-releasing hormone (GnRH)-agonist implants. This restart was assessed by determining the expression of steroidogenic acute regulat
- PMID 23053053
Related Links
- Accurate, FDA approved Synarel information for healthcare professionals and patients - brought to you by Drugs.com. ... Synarel Nasal Solution contains nafarelin acetate (2 mg/mL, content expressed as nafarelin base) in a solution ...
- Easy to read patient leaflet for Synarel. Includes indications, proper use, special instructions, precautions, and possible side effects. ... Treating endometriosis, including relieving pain and reducing lesions. It is also used to treat early ...
- Synarel - Nafarelin nasal is a man-made form of a protein that is like a hormone in the body that helps regulate the menstrual cycle, fertility, and sexual development during puberty. - Nafarelin nasal can harm an unborn baby or cause ...
Related Pictures
★リンクテーブル★
[★]
- 英
- nafarelin
- 化
- 酢酸ナファレリン nafarelin acetate
- 商
- ナサニール、ナファレリール、Synarel
- 関
- GnRHアゴニスト
- ゴナドトロピン放出ホルモン誘導体;子宮内膜症治療薬