Nafarelin

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 monograph

MedlinePlus a601082

Pregnancy cat. X

Legal status ℞-only

Routes Nasal spray

Pharmacokinetic data

Half-life 2.6 to 4 hours

Excretion renal

Identifiers

CAS number 76932-56-4^Y

ATC code H01CA02

PubChem CID 25077649

DrugBank APRD01129

ChemSpider 10482014^Y

UNII 1X0094V6JV^N

ChEMBL CHEMBL1201309^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(what is this?) (verify)

Nafarelin is a gonadotropin-releasing hormone agonist (GnRH agonist). By causing constant stimulation of the pituitary, it decreases pituitary secretion of 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, and to control ovarian stimulation in IVF.

It is normally delivered via a nasal spray.

Nafarelin acetate is marketed by Searle (now part of Pfizer) under the brand name Synarel.

Side effects

Side effects of nafarelin are mostly 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 should disappear after stopping the medication.

v · d · eGonadotropins and GnRH (G03G)

Gonadotropin
preparations

Agonist

Menotropin • Urofollitropin

Antigonadotropin

Danazol • Gestrinone

GnRH

Agonist

Buserelin • Goserelin • Histrelin • Leuprorelin • Nafarelin • Triptorelin • Deslorelin

Antagonist

Abarelix • Cetrorelix • Degarelix • Ganirelix

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 ^‡Withdrawn from market.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

v · d · eHypothalamic-pituitary hormones and analogues (H01)

Hypothalamic

GNRH

Agonists: Gonadorelin • Nafarelin • Histrelin
Antagonists: Cetrorelix • Ganirelix

Somatostatin

Agonists: Lanreotide • Octreotide

Anterior pituitary

ACTH

Agonists: Corticotropin • Cosyntropin • Tetracosactide

GH

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

TSH

Agonists: Thyrotropin

Posterior pituitary

Oxytocin

Agonists: Carbetocin • Demoxytocin
Antagonists: Atosiban

Vasopressin

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

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

Categories:
GnRH agonists

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	monograph
MedlinePlus	a601082
Pregnancy cat.	X
Legal status	℞-only
Routes	Nasal spray
Pharmacokinetic data
Half-life	2.6 to 4 hours
Excretion	renal
Identifiers
CAS number	76932-56-4^Y
ATC code	H01CA02
PubChem	CID 25077649
DrugBank	APRD01129
ChemSpider	10482014^Y
UNII	1X0094V6JV^N
ChEMBL	CHEMBL1201309^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
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Look at other dictionaries:

nafarelin acetate — naf·a·rel·in ace·tate (nafґə rel″in) a synthetic preparation of gonadotropin releasing hormone, used in the treatment of central precocious puberty and of endometriosis; administered by nasal spray … Medical dictionary
Cetrorelix — Systematic (IUPAC) name Acetyl D 3 (2´ naphtyl) alanine D 4 chlorophenylalanine D 3 (3´ pyridyl) alanine L serine L tyrosine D citruline L leucine L arginine L proline D alanine amide Clinical da … Wikipedia
Эндометриоз — МКБ 10 N … Википедия
Oxytocin — Systematic (IUPAC) name 1 ({(4R,7S,10S … Wikipedia
Cryptorchidism — Classification and external resources ICD 10 Q53 … Wikipedia
Desmopressin — Systematic (IUPAC) name (2S) N [(2R) 1 [(2 amino 2 oxoethyl)amino] 5 (diaminomethylideneamino) 1 oxopentan 2 yl] 1 [(4R,7S,10S,13S,16S) 7 (2 amino 2 oxoethyl) 10 (3 amino 3 oxopropyl) 16 [(4 hydroxyphenyl) … Wikipedia
ATC code H01 — A section of the Anatomical Therapeutic Chemical Classification System.H Systemic hormonal preparations, excluding sex hormones and insulinsH01A Anterior pituitary lobe hormones and analoguesH01AA Adrenocorticotropic hormone:H01AA01 Corticotropin … Wikipedia
Conivaptan — Systematic (IUPAC) name N (4 (4,5 dihydro 2 methylimidazo[4,5 d][1]benzazepin 6(1H) yl)carbonyl)phenyl) (1,1 biphenyl) 2 carboxamide Clinical data … Wikipedia
Octreotide — Systematic (IUPAC) name (4R,7S,10S,13R,16S … Wikipedia
Felypressin — IUPAC name 1 [19 Amino 13,16 dibenzyl 10 (2 carbamoyl ethyl) 7 carbamoylmethyl 6,9,12,15,18 pentaoxo 1,2 dithia 5,8,11,14,17 pentaaz … Wikipedia

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Nafarelin

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