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L2761

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

Name: [des-Gly<SUP>10</SUP>, <SC>D</SC>-His(Bzl)<SUP>6</SUP>]-LH-RH ethylamide
Brand: SIGMA

≥97% (HPLC), powder

Synonym(s):

Histrelin

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About This Item

Empirical Formula (Hill Notation):

C₆₆H₈₆N₁₈O₁₂

CAS Number:

76712-82-8

Molecular Weight:

1323.50

NACRES:

NA.32

PubChem Substance ID:

24896325

UNSPSC Code:

12352209

MDL number:

MFCD00133494

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Properties

Quality Segment

200

assay

≥97% (HPLC)

form

powder

composition

Peptide content, ~70%

UniProt accession no.

P55248, P01148, P07490, P13562, P30968, P30969, Q01776

storage temp.

−20°C

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

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)

InChI key

HHXHVIJIIXKSOE-UHFFFAOYSA-N

Gene Information

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

Description

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

GHS08

signalword

Danger

hcodes

H360

pcodes

P201 - P308 + P313

Hazard Classifications

Repr. 1B

Storage Class

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