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L0399

Sigma-Aldrich

Leuprolide acetate salt

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C59H84N16O12 · xC2H4O2
CAS Number:
74381-53-6
Molecular Weight:
1209.40 (free base basis)
MDL number:
MFCD00167544
UNSPSC Code:
12352200
PubChem Substance ID:
24896252
NACRES:
NA.32

assay

≥98% (HPLC)

storage temp.

−20°C

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

Gene Information

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

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Amino Acid Sequence

Glp-His-Trp-Ser-Tyr-Leu-Leu-Arg-Pro-NHEt

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
Michael T Schweizer et al.
Cancer, 119(20), 3610-3618 (2013-08-15)
The current trial evaluated 2 common therapies for patients with advanced prostate cancer, docetaxel and hormonal therapy (HT), in the surgical adjuvant setting. TAX-3501 was a randomized, phase 3, adjuvant study post-radical prostatectomy (RP) in high-risk patients with prostate cancer
D Mahato et al.
Endocrinology, 141(3), 1273-1276 (2000-03-04)
Estrogen receptors alpha (ERalpha) and beta (ERbeta) are ligand-dependent transcription factors and members of the nuclear hormone receptor superfamily encoded by separate genes. Male mice homozygous for a mutation in the gene encoding ERalpha are infertile. To determine whether germ
Paul G Corn et al.
International journal of radiation oncology, biology, physics, 86(3), 540-545 (2013-04-02)
To evaluate the feasibility of administering sunitinib in combination with androgen deprivation therapy and external-beam intensity modulated radiation therapy (XRT) in patients with localized high-risk prostate cancer. Seventeen men with localized adenocarcinoma of the prostate with cT2c-cT4 or Gleason 8-10
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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