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Merck
CN

L2761

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

≥97% (HPLC), powder

别名:

Histrelin

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关于此项目

经验公式（希尔记法）:
C66H86N18O12
化学文摘社编号:
76712-82-8
分子量:
1323.50
NACRES:
NA.32
PubChem Substance ID:
24896325
UNSPSC Code:
12352209
MDL number:
MFCD00133494

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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

存储类别

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

法规信息

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分析证书(COA)

Lot/Batch Number
0000454884
0000454884
0000388422
SLCQ5265
SLBZ7465

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Harry J Hirsch et al.
Pediatrics, 116(6), e798-e802 (2005-12-03)
Standard treatment of central precocious puberty (CPP) consists of intramuscular or subcutaneous administration of a gonadotropin-releasing hormone (GnRH) agonist (GnRHa) at 3- to 4-week intervals. Although generally effective in suppressing clinical and laboratory parameters of puberty, GnRHa injections are painful
Techniques for obtaining and raising plethodontid salamander eggs.
E L Jockusch
The International journal of developmental biology, 40(4), 911-912 (1996-08-01)
Erica A Eugster et al.
The Journal of clinical endocrinology and metabolism, 92(5), 1697-1704 (2007-03-01)
GnRH analog (GnRHa) therapy for central precocious puberty (CPP) typically involves im injections. The histrelin implant is a new treatment that provides a continuous slow release of the GnRHa histrelin. The objective of the study was to investigate the safety
Vance L Trudeau et al.
Reproductive biology and endocrinology : RB&E, 8, 36-36 (2010-04-20)
It is well known that many anurans do not reproduce easily in captivity. Some methods are based on administration of mammalian hormones such as human chorionic gonadotropin, which are not effective in many frogs. There is a need for simple
K O Klein et al.
The Journal of clinical endocrinology and metabolism, 86(10), 4711-4716 (2001-10-16)
We report 98 children who have reached final adult height in a long-term trial of LHRH agonist treatment. These children were 5.3 +/- 2.1 yr old at the start of treatment and were treated with either deslorelin (4 microg/kg.d sc)
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