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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
SLBZ7465
SLBS8365
SLBL5285V
SLBC7335V
071M8721V

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Consulter la Bibliothèque de documents

Inhibition of the action of sex steroids by gonadotropin-releasing hormone (GnRH) agonists: a new biological effect.
K Sundaram et al.
Life sciences, 28(1), 83-88 (1981-01-05)
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)
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
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
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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