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Merck

L2761

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

≥97% (HPLC), powder

Sinónimos:

Histrelin

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Fórmula empírica (notación de Hill):
C66H86N18O12
Número CAS:
76712-82-8
Peso molecular:
1323.50
NACRES:
NA.32
PubChem Substance ID:
24896325
UNSPSC Code:
12352209
MDL number:
MFCD00133494

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Nombre del producto

[des-Gly10, D-His(Bzl)6]-LH-RH ethylamide, ≥97% (HPLC), powder

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)

SMILES string

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 key

HHXHVIJIIXKSOE-UHFFFAOYSA-N

assay

≥97% (HPLC)

form

powder

composition

Peptide content, ~70%

UniProt accession no.

P55248
P01148
P07490
P13562
P30968
P30969
Q01776

storage temp.

−20°C

Quality Level

200

Gene Information

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

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

Biochem/physiol Actions

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.

Features and Benefits

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

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Clase de almacenamiento

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
0000454884
0000454884
0000388422
SLCQ5265
SLBZ7465

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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
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
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
Techniques for obtaining and raising plethodontid salamander eggs.
E L Jockusch
The International journal of developmental biology, 40(4), 911-912 (1996-08-01)
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