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Merck

L0399

Leuprolide acetate salt

≥98% (HPLC), GnRH agonist

Sinónimos:

des-Gly10-[D-Leu6]-LH-RH ethylamide, Leuprorelin

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Fórmula empírica (notación de Hill):
C59H84N16O12 · xC2H4O2
Número CAS:
74381-53-6
Peso molecular:
1209.40 (free base basis)
UNSPSC Code:
12352200
PubChem Substance ID:
24896252
NACRES:
NA.32
MDL number:
MFCD00167544
Assay:
≥98% (HPLC)
Quality level:
200

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Nombre del producto

Leuprolide acetate salt, ≥98% (HPLC)

SMILES string

CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H](CO)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)[C@H](Cc5c[nH]cn5)NC(=O)[C@@H]6CCC(=O)N6

InChI

1S/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43+,44-,45-,46-,47-,48-/m0/s1

InChI key

GFIJNRVAKGFPGQ-LIJARHBVSA-N

assay

≥98% (HPLC)

storage temp.

−20°C

Quality Level

200

Gene Information

human ... GNRHR(2798)
rat ... Gnrhr(81668)

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Application

In mice, leuprolide acetate salt has been used to check the need of estrogen receptor α in spermatogenic cells, for development or function in fertilization.

Biochem/physiol Actions

Glp-His-Trp-Ser-Tyr-Leu-Leu-Arg-Pro-NHEt (des-Gly10-[D-Leu6]-LH-RH) is a GnRH (gonadotropin-releasing hormone) agonist, leuprolide. 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. Low concentration of leuprolide can be used for the treatment of endometriosis, uterine fibroids, central precocious puberty and advanced prostate cancer.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
SLCM2049
SLCF5105
SLCC7252
SLCC1785
SLCB2154

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Visite la Librería de documentos

Syed Nuruddin et al.
PloS one, 9(8), e103607-e103607 (2014-08-05)
Research on Alzheimer's disease (AD) has indicated an association between hormones of the hypothalamic-pituitary-gonadal (HPG) axis and cognitive senescence, indicating that post meno-/andropausal changes in HPG axis hormones are implicated in the neuropathology of AD. Studies of transgenic mice with
Daniela Jakubowicz et al.
Clinical science (London, England : 1979), 125(9), 423-432 (2013-05-22)
In women with PCOS (polycystic ovary syndrome), hyperinsulinaemia stimulates ovarian cytochrome P450c17α activity that, in turn, stimulates ovarian androgen production. Our objective was to compare whether timed caloric intake differentially influences insulin resistance and hyperandrogenism in lean PCOS women. A
Tim M van der Sluis et al.
Urology, 81(5), 1005-1009 (2013-03-08)
To evaluate the relationship between the body mass index (BMI) and serum testosterone concentrations in men receiving luteinizing hormone-releasing hormone (LHRH) agonist therapy for prostate cancer. A total of 66 white men were included in the present study. All subjects
R Sharifi et al.
The Journal of urology, 143(1), 68-71 (1990-01-01)
In a phase III, open, multicenter study we evaluated the safety and efficacy of the depot formulation of leuprolide (7.5 mg. injected intramuscularly every 4 weeks) in patients with stage D2 prostate cancer who had not previously received systemic treatment.
Gina Lama et al.
PloS one, 8(1), e52530-e52530 (2013-01-18)
High cell-surface GnRH receptor (GnRH-R) levels have been shown to have a major influence on the extent of GnRH agonist-mediated tumor growth inhibition. The ability of the GnRH agonist leuprorelin acetate (LA) to induce a post-transcriptional upregulation of GnRH-R at
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