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L2761

Sigma-Aldrich

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

≥97% (HPLC), powder

Sinonimo/i:

Histrelin

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About This Item

Formula empirica (notazione di Hill):
C66H86N18O12
Numero CAS:
76712-82-8
Peso molecolare:
1323.50
Numero MDL:
MFCD00133494
Codice UNSPSC:
12352209
ID PubChem:
24896325
NACRES:
NA.32

Livello qualitativo

200

Saggio

≥97% (HPLC)

Forma fisica

powder

Composizione

Peptide content, ~70%

N° accesso UniProt

P55248
P01148
P07490
P13562
P30968
P30969
Q01776

Temperatura di conservazione

−20°C

Stringa SMILE

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)
HHXHVIJIIXKSOE-UHFFFAOYSA-N

Informazioni sul gene

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

Applicazioni

[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

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

Has greater lipophilicity than other LH-RH agonists, but retains high water solubility

Pittogrammi

Health hazard
GHS08

Avvertenze

Danger

Indicazioni di pericolo

H360

Consigli di prudenza

P201 - P308 + P313

Classi di pericolo

Repr. 1B

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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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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