Basic information Description Mechanism of action Uses Pharmacokinetics Preparation Adverse reactions Safety Related Supplier
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Leuprorelin

Basic information Description Mechanism of action Uses Pharmacokinetics Preparation Adverse reactions Safety Related Supplier
Leuprorelin Basic information
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
  • form neat
  • pka9.82±0.15(Predicted)
  • Water Solubility Soluble in water at 1mg/ml
  • CAS DataBase Reference53714-56-0(CAS DataBase Reference)
Safety Information
MSDS
Leuprorelin Usage And Synthesis
  • DescriptionLeuprorelin/Leuprolideacetate (LA) is a highly active analogue (LHRH-A, GnRHA) of luteinizing hormone releasing hormone (LHRH, or gonadotropin releasing hormone, GnRH) produced by the hypothalamus. It is a synthetic water-soluble nonapeptide with both ends closed, and its amino acid sequence is 5-oxo-L-prolyl-L-histidyl-L-tryptophan-L-seryl-L-tyrosyl -D-Leucyl-L-Leucyl-L-Arginyl-N-Ethyl-L-Prolinamide Monoacetate (5-oxo-Pro-His-Trp-Ser-Tyr-D- Leu-Leu-Arg-Pro-NH-C2H5), soluble in water, ethanol and propylene glycol, pKa6.9. It can stimulate the pituitary gland to secrete gonadotropins and induce the production of steroids in the reproductive organs. Long-term large-scale use can inhibit the secretion of gonadotropins from the pituitary gland and the production of testicular or ovarian steroids, and can treat or alleviate a variety of sex hormone-dependent diseases such as prostate cancer, endometriosis, uterine fibroids, and precocious puberty.
  • Mechanism of actionLeuprolide 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 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.
  • PreparationPhenol reacts with phosgene to produce phenyl chloroformate, which then reacts with tert-butanol to produce phenyl tert-butoxyformate, then reacts with hydrazine, then nitrosates to produce tert-butyl azide, and then reacts with leucine , Get the leucine side chain. The proline side chain can also be obtained. Serine reacts with benzyl chloride to protect the hydroxyl group, and then reacts with tert-butyl azide to obtain the serine side chain. Similar to serine, you can get the side chains of tyrosine and histidine from Chemicalbook. After the tert-butyl azide formate reacts with tryptophan, it is then reacted with 2,4,6-trimethoxybenzenesulfonyl chloride to form an ester to obtain the tryptophan side chain. The tert-butyl azide formate reacts with arginine, and then reacts with p-toluenesulfonyl chloride to obtain the arginine side chain. After obtaining the above-mentioned side chain, the peptide is then added, and then reacted with ethylamine, and then hydrolyzed or hydrogenolyzed to remove the protective group, and then refined and purified to obtain Lipran.

  • Adverse reactionsThe main side effects 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.
  • 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. It 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.
  • Manufacturing Process5-Oxo-L-prolyl-L-histidyl-L-tryptophanyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-Larginyl-L-prolylethylamideacetate was prepared by using of Boc strategy on a 2%-crosslinking chloromethylated divinylbenzene-styrene copolymer in a the Merrifield automatic sintesizer apparatus. 4.6 g of this resin/aminoacid material is used for the synthesis of the desired nonapeptide. Each N-blocked aminoacid is added in a three-fold access and allowed to couple to them, existing aminoacid-resin ester in the usual coupling cycle. Ordinarily the solvent used for the coupling reaction is dichloromethane or, when the solubility of the blocked aminoacid is low, a mixture of dichloromethane and DMF. Coupling is effected by the addition of a solution of dicyclohexylcarbodiimide in dichloromethane at a 2.9 fold excess. The sequence used for deprotection, neutralization and coupling of the next aminoacid is done in a fully automatic system. In this manner, the peptide is assembled using in turn Boc-Arg(Tos), Boc-Leu, Boc-D-Leu, Boc-Tyr(Cl2Bzl), Boc-Ser(Bzl), Boc-Trp, Boc-His(DNP), and pGlu wherein all aminoacids are in the L-form except in the leucine so designated. A 250 mg sample of the above is placed in a hydrogen fluoride reaction with 250 mg vessel of anisole and about 5 ml of anhydrous hydrogen fluoride is distilled into it. After 1 hour at 0°C, the hydrogen fluoride is removed with a stream of dry nitrogen and the residue is taken up in 1% acetic acid. This solution is extracted with ether, and the aqueous phase applied to a 1 time 30 cm column of a highly basic ion exchange resin (marketed by Bio-Rad as AGl resin) in the acetate form. The product is eluted with 0.1 N acetic acid and localized using thin-layer chromatography (CHCl3/MeOH/32% HOAc: 120/90/40, silica gel G, Cl2/tolidine). The product bearing solution is lyophilized, rechromatographed on a Sephadex G-25 (marketed by Pharmacia of Uppsala, Sweden) column. The product eluted is collected and lyophilized to yield a fluffy white solid. An aminoacid analysis shows the expected ratio of all desired aminoacids assembled in the above fashion.
  • Therapeutic FunctionAntineoplastic
Leuprorelin Preparation Products And Raw materials
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