L2761

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

≥97% (HPLC), powder

• Sinónimos: Histrelin
• 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

Propiedades

• 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)

Descripción

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[1]
• for comparing the effect of LHRH (luteinizing hormone-releasing hormone) agonists and dopamine antagonists in Lithobates pipiens[2]
• for inducing oviposition in females of Taricha granulosa[3] and Ensatina eschscoltzii[4]
• to induce spawning in Spea hammondii adults[5]

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.[6] 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.[7][8][6] Mutations in GnRH are associated with normosmic congenital hypogonadotropic hypogonadism.[8] Histerelin is used for the treatment of central precocious puberty in children.[9] 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

Información de seguridad

• 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