L2761

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

≥97% (HPLC), powder

• Synonym(s): Histrelin
• Empirical Formula (Hill Notation): C₆₆H₈₆N₁₈O₁₂
• CAS Number: 76712-82-8
• Molecular Weight: 1323.50
• MDL number: MFCD00133494
• UNSPSC Code: 12352209
• PubChem Substance ID: 24896325
• NACRES: NA.32

Properties

• 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)

Description

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

Safety Information

• 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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges