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L2761

Sigma-Aldrich

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

≥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
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

Signal Word

Danger

Hazard Statements

H360

Precautionary Statements

P201 - P308 + P313

Hazard Classifications

Repr. 1B

Storage Class Code

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)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Harry J Hirsch et al.
The Journal of clinical endocrinology and metabolism, 95(6), 2841-2844 (2010-03-27)
Gonadotropin free alpha-subunit (FAS) levels paradoxically increase during GnRH agonist (GnRHa) treatment of central precocious puberty (CPP). The histrelin implant suppresses gonadotropins and estradiol (E(2)) levels for 1 yr, but effects on FAS have not been described. We aimed to
Peter N Schlegel
The Journal of urology, 175(4), 1353-1358 (2006-03-07)
This open label, multicenter study was done to evaluate the efficacy and safety of the gonadotropin hormone-releasing hormone agonist histrelin acetate administered as a 50 mg subdermal implant in men with advanced prostatic cancer. The 3 cm x 3.5 mm
Techniques for obtaining and raising plethodontid salamander eggs.
E L Jockusch
The International journal of developmental biology, 40(4), 911-912 (1996-08-01)
Graham C Boorse et al.
Integrative and comparative biology, 43(5), 646-657 (2003-11-01)
Amphibian larvae respond to heterogeneous environments by varying their rates of growth and development. Several amphibian species are known to accelerate metamorphosis in response to pond drying or resource restriction. Some of the most extensive studies to date on developmental
The antiandrogenic action of gonadotropin-releasing hormone and its agonists on the mouse kidney.
P Lecomte et al.
Endocrinology, 110(1), 1-6 (1982-01-01)
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