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L2761

Sigma-Aldrich

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

≥97% (HPLC), powder

Sinónimos:

Histrelin

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About This Item

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

Quality Level

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)

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

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Martina Weise et al.
The Journal of clinical endocrinology and metabolism, 89(1), 103-107 (2004-01-13)
In children with precocious puberty (PP), treatment with GnRH analogs (GnRHa) often decreases height velocity below normal. Based on previous animal studies, we hypothesized that this impaired growth is due to excessive advancement in growth plate senescence induced by the
Andres Collazo et al.
EvoDevo, 1(1), 6-6 (2010-09-21)
Comparative analyses between amphibians, concentrating on the cellular mechanisms of morphogenesis, reveal a large variability in the early developmental processes that were thought to be conserved during evolution. Increased egg size is one factor that could have a strong effect
Geoffrey D Smith et al.
Journal of thermal biology, 51, 89-95 (2015-05-13)
We investigated the effects of temperature on the growth and development of embryonic and early larval stages of a western North American amphibian, the rough-skinned newt (Taricha granulosa). We assigned newt eggs to different temperatures (7, 14, or 21°C); after
Talia Eldar-Geva et al.
European journal of endocrinology, 162(1), 177-181 (2009-10-13)
Medical castration with long-acting GnRH-agonist (GnRHa) is a well-established treatment for metastatic prostate cancer. Our aim was to explore the relationships between FSH, inhibin B, anti-Mullerian hormone (AMH), and testosterone during treatment with an implant releasing GnRHa. Analysis of hormone
Katherine A Lewis et al.
The Journal of pediatrics, 162(3), 562-565 (2012-10-09)
To investigate the use of random ultrasensitive (US) luteinizing hormone (LH) levels to monitor children being treated with a histrelin implant for central precocious puberty (CPP). This was a prospective, uncontrolled, observational study at a pediatric endocrinology tertiary center. Thirty-three
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