Leuprorelin

Leuprorelin Basic information
Description Mechanism of action Uses Pharmacokinetics Adverse reactions
Product Name:Leuprorelin
Synonyms:LH-RH LEUPROLIDE;LEUPROLIDE;LEUPROLIDE (HUMAN);LEUPRORELIN;[DES-GLY10, D-LEU6, PRO-NHET9]-LUTEINIZING HORMONE-RELEASING HORMONE HUMAN;(DES-GLY10,D-LEU6,PRO-NHET9)-LUTEINIZING HORMONE-RELEASING HORMONE;(DES-GLY10,D-LEU6,PRO-NHET9)-LUTEINIZING HORMONE-RELEASING FACTOR;[DES-GLY10, D-LEU6, PRO-NHET9]-LH-RH (HUMAN)
CAS:53714-56-0
MF:C59H84N16O12
MW:1209.4
EINECS:633-395-9
Product Categories:Amino Acid Derivatives;Peptide;API
Mol File:53714-56-0.mol
Leuprorelin Structure
Leuprorelin Chemical Properties
alpha D25 -31.7° (c = 1 in 1% acetic acid)
density 1.44±0.1 g/cm3(Predicted)
storage temp. −20°C
solubility DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form neat
pka9.82±0.15(Predicted)
Water Solubility Soluble in water at 1mg/ml
Stability:Hygroscopic
InChIKeyRGLRXNKKBLIBQS-VAZQWRJQNA-N
CAS DataBase Reference53714-56-0(CAS DataBase Reference)
Safety Information
Safety Statements 22-24/25
WGK Germany 2
RTECS OH6390000
Hazardous Substances Data53714-56-0(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Leuprorelin English
SigmaAldrich English
Leuprorelin Usage And Synthesis
DescriptionLeuprorelin(Leuprolide ) is a synthetic water-soluble nonapeptide with both ends closed, and also a highly active analogue of luteinizing hormone releasing hormone (LHRH or GnRH) produced by the hypothalamus. It can stimulate the pituitary gland to secrete gonadotropins and induce the production of steroids in the reproductive organs. 
Mechanism of actionLeuprorelin is a nonapeptide synthetic analogue of Luteinizing Hormone Releasing Hormone (LHRH), which can promote the release of follicle stimulating hormone from the anterior pituitary, thereby reducing the increased testosterone concentration to castrate levels. When the administration is stopped, gonadotropins and androgens can return to normal concentrations.
UsesLeuprorelin is a nonapeptide synthetic analogue of gonadotropin (GnRH), which can promote the release of luteinizing hormone (LHRH) and follicle stimulating hormone (FSH) from the anterior pituitary, regulate the secretion of gonadal hormones, and increase the serum levels of testosterone and dihydrotestosterone. Concentration, so as to achieve the function of treating reproductive system diseases. It is used to treat prostate cancer, uterine fibroids, ovarian cysts, breast cancer and cryptorchidism in children.
PharmacokineticsLeuprolide acetate(Leuprorelin) is ineffective orally. Good absorption by subcutaneous or intramuscular injection. A single subcutaneous injection of 3.75mg, the blood concentration of 1 to 2 days peaked at 1 to 2ng/ml. For prostate cancer, 3.75mg is injected subcutaneously each time, once every 4 Chemicalbook weeks, for a total of 3 injections, reaching a steady-state blood concentration of 0.1-1ng/ml. This product is hydrolyzed into 4 degradation products in the body and excreted by the kidneys. The urinary excretion rates of the original drug and metabolites were 2.9% and 1.5% after a single subcutaneous injection 28 days.
Adverse reactionsThe main side effects of Leuprorelin are fever, heat sensation and elevated AST, ALT, γ-GTP and AKP. Sometimes there are facial flushing, sweating, loss of libido, impotence, feminized breasts, testicular atrophy, perineal discomfort and other endocrine system phenomena; abnormal electrocardiogram and increased ratio of heart and chest, bone pain, shoulder, lower back, limb pain, Urinary retention, frequent urination, hematuria, nausea, vomiting, loss of appetite, rash, itching and other allergic reactions and pain, induration, and redness at the injection site. Rarely, edema, chest pressure, chills, tiredness, weight gain, abnormal perception, tinnitus, hearing loss, TG, uric acid and BUN are increased.
Chemical PropertiesHygroscopic, white or almost white powder.
OriginatorEligard,Atrix Laboratories, Inc.
UsesHighly active luteinizing hormone releasing hormone (LHRH) agonist
UsesGonadotropin releasing hormone (gonadorelin) analogue; treatment of prostate cancer.
DefinitionChEBI: An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-leucyl, leucyl, arginyl, and N-ethylprolinamide residues joined in sequence. Leuprorelin is a synthetic nonapeptide analogue of gonadotropin-releasi g hormone, and is used as a subcutaneous hydrogel implant (particularly as the acetate salt) for the treatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.
IndicationsLeuprolide is a potent LH-RH agonist for the first several days to a few weeks after initiation of therapy, and therefore, it initially stimulates testicular and ovarian steroidogenesis. Because of this initial stimulation of testosterone production, it is recommended that patients with prostatic cancer be treated concurrently with leuprolide and the antiandrogen flutamide (discussed earlier). Leuprolide is generally well tolerated, with hot flashes being the most common side effect.
Therapeutic FunctionAntineoplastic
SynthesisThe synthesis process of Leuprorelin includes the following steps:
(1) Fmoc-Pro-HMPB-AM resin is obtained from Fmoc-Pro-OH and HMPB-AM resin with a substitution degree of 0.2mmol/g~1.2mmol/g as starting materials;
(2) The Fmoc-Pro-HMPB-AM resin was coupled one by one by Fmoc/tBu solid phase method to connect amino acids with protective groups in sequence, and the side chain fully protected leuprolide precursor peptide-HMPB-AM was synthesized Resin;
(3) Cut the side chain fully protected leuprolide precursor peptide-HMPB-AM resin to obtain the side chain fully protected leuprolide precursor peptide;
(4) Fully protected side chain leuprolide precursor peptide undergoes ethylamination to obtain side chain fully protected leuprolide;
(5) Leuprolide is fully protected on the side chain by removing the side chain protecting group to obtain the crude leuprolide peptide;
(6) The crude leuprorelin peptide is separated and purified by a high-pressure liquid phase column and lyophilized to obtain the leuprolide refined peptide.
Lixisenatide Taspoglutide Oxytocin Octreotide acetate Triptorelin Leuprorelin Acetate Sermorelin Leuprolide=Leuprorelin (D-TLE6)-LEUPRORELIN L-Prolinamide ([125I]-TYR)-(DES-GLY10,D-LEU6,PRO-NHET9)-LHRH (LEU6)-LEUPRORELIN (D-SER4)-LEUPRORELIN LEUPRORELIN - REFERENCE SPECTRUM (DES-PYR1)-LEUPRORELIN (SER(AC)4)-LEUPRORELIN Leuprorelin Leuprorelin-d5

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