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L2761

Sigma-Aldrich

[des-Gly10, D-His(Bzl)6]-LH-RH ethylamide

≥97% (HPLC), powder

Synonyme(s) :

Histrelin

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About This Item

Formule empirique (notation de Hill):
C66H86N18O12
Numéro CAS:
76712-82-8
Poids moléculaire :
1323.50
Numéro MDL:
MFCD00133494
Code UNSPSC :
12352209
ID de substance PubChem :
24896325
Nomenclature NACRES :
NA.32

Niveau de qualité

200

Essai

≥97% (HPLC)

Forme

powder

Composition

Peptide content, ~70%

Numéro d'accès UniProt

P55248
P01148
P07490
P13562
P30968
P30969
Q01776

Température de stockage

−20°C

Chaîne SMILES 

CCNC(=O)C1CCCN1C(=O)C(CCCNC(N)=N)NC(=O)C(CC(C)C)NC(=O)C(Cc2cn(Cc3ccccc3)cn2)NC(=O)C(Cc4ccc(O)cc4)NC(=O)C(CO)NC(=O)C(Cc5c[nH]c6ccccc56)NC(=O)C(Cc7cnc[nH]7)NC(=O)C8CCC(=O)N8

InChI

1S/C66H86N18O12/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71)

Clé InChI

HHXHVIJIIXKSOE-UHFFFAOYSA-N

Informations sur le gène

human ... GNRH1(2796) , GNRHR(2798)
mouse ... GNRH1(14714) , GNRHR(14715)
rat ... GNRH1(25194) , GNRHR(81668)

Amino Acid Sequence

Glp-His-Trp-Ser-Tyr-His(Bzl)-Leu-Arg-Pro-NHEt

Application

[des-Gly10, D-His(Bzl)6]-LH-RH ethylamide has been used:
  • for inducing Batrachoseps gravid females to oviposit
  • for comparing the effect of LHRH (luteinizing hormone-releasing hormone) agonists and dopamine antagonists in Lithobates pipiens
  • for inducing oviposition in females of Taricha granulosa and Ensatina eschscoltzii
  • to induce spawning in Spea hammondii adults

Actions biochimiques/physiologiques

Glp-His-Trp-Ser-Tyr-His(Bzl)-Leu-Arg-Pro-NHEt ([des-Gly10, D-His(Bzl)6]-LH-RH) is a GnRH (gonadotropin-releasing hormone) agonist, histerelin. GnRH (Glp-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2), which is also referred as LHRH (luteinizing hormone-releasing hormone) or gonadorelin, is crucial for mammalian reproduction and is released from hypothalamic neurons. It is responsible for the secretion of gonadotropins, luteinizing hormone (LH) and follicle-stimulating hormone (FSH), from the pituitary glands. Mutations in GnRH are associated with normosmic congenital hypogonadotropic hypogonadism. Histerelin is used for the treatment of central precocious puberty in children. It inhibits actions of sex steroids on the male and female reproductive organs.

Caractéristiques et avantages

Has greater lipophilicity than other LH-RH agonists, but retains high water solubility

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Danger

Mentions de danger

H360

Conseils de prudence

P201 - P308 + P313

Classification des risques

Repr. 1B

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
0000388422
SLCQ5265
SLBZ7465
SLBS8365
SLBL5285V

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Consulter la Bibliothèque de documents

Harry J Hirsch et al.
The Journal of clinical endocrinology and metabolism, 95(6), 2841-2844 (2010-03-27)
Gonadotropin free alpha-subunit (FAS) levels paradoxically increase during GnRH agonist (GnRHa) treatment of central precocious puberty (CPP). The histrelin implant suppresses gonadotropins and estradiol (E(2)) levels for 1 yr, but effects on FAS have not been described. We aimed to
The antiandrogenic action of gonadotropin-releasing hormone and its agonists on the mouse kidney.
P Lecomte et al.
Endocrinology, 110(1), 1-6 (1982-01-01)
Peter N Schlegel
The Journal of urology, 175(4), 1353-1358 (2006-03-07)
This open label, multicenter study was done to evaluate the efficacy and safety of the gonadotropin hormone-releasing hormone agonist histrelin acetate administered as a 50 mg subdermal implant in men with advanced prostatic cancer. The 3 cm x 3.5 mm
Techniques for obtaining and raising plethodontid salamander eggs.
E L Jockusch
The International journal of developmental biology, 40(4), 911-912 (1996-08-01)
Graham C Boorse et al.
Integrative and comparative biology, 43(5), 646-657 (2003-11-01)
Amphibian larvae respond to heterogeneous environments by varying their rates of growth and development. Several amphibian species are known to accelerate metamorphosis in response to pond drying or resource restriction. Some of the most extensive studies to date on developmental
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