Description Mechanism of action Uses Pharmacokinetics Adverse reactions
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Leuprorelin

Description Mechanism of action Uses Pharmacokinetics Adverse reactions
Product Name
Leuprorelin
CAS No.
53714-56-0
Chemical Name
Leuprorelin
Synonyms
LEUPROLIDE;Lucrin;Leuplin;a-43818;Carcinil;Enantone;nghormone;LEUPRORELIN;LEUPROPELIN;Leuprorelinum
CBNumber
CB8398455
Molecular Formula
C59H84N16O12
Formula Weight
1209.4
MOL File
53714-56-0.mol
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Leuprorelin Property

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)
pka
9.82±0.15(Predicted)
Water Solubility 
Soluble in water at 1mg/ml
Stability:
Hygroscopic
InChI
InChI=1/C59H84N16O12.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t40-,41-,42-,43+,44-,45-,46-,47-,48-;/s3
InChIKey
RGLRXNKKBLIBQS-VAZQWRJQNA-N
SMILES
C1(C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N2CCC[C@H]2C(=O)NCC)CC2=CC=C(O)C=C2)NC(=O)[C@@H](NC(=O)[C@H]2NC(=O)CC2)CC2NC=NC=2)C2C=CC=CC=2NC=1.C(=O)(O)C |&1:2,6,12,16,24,32,46,63,67,r|
CAS DataBase Reference
53714-56-0(CAS DataBase Reference)
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Safety

Safety Statements 
22-24/25
WGK Germany 
2
RTECS 
OH6390000
Hazardous Substances Data
53714-56-0(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
L0376000
Product name
Leuprorelin
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
l0376000
Price
$220
Updated
2024/03/01
Alfa Aesar
Product number
J62147
Product name
Leuprolide
Packaging
5mg
Price
$182
Updated
2023/06/20
Alfa Aesar
Product number
J62967
Product name
Leuprolide, human, synthetic
Packaging
5mg
Price
$89.1
Updated
2021/12/16
Alfa Aesar
Product number
J62967
Product name
Leuprolide, human, synthetic
Packaging
25mg
Price
$356.4
Updated
2021/12/16
Usbiological
Product number
L2051-01
Product name
Leuprolide
Packaging
1mg
Price
$531
Updated
2021/12/16
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Leuprorelin Chemical Properties,Usage,Production

Description

Leuprorelin(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 action

Leuprorelin 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.

Uses

Leuprorelin 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.

Pharmacokinetics

Leuprolide 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 reactions

The 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 Properties

Hygroscopic, white or almost white powder.

Originator

Eligard,Atrix Laboratories, Inc.

Uses

Highly active luteinizing hormone releasing hormone (LHRH) agonist

Uses

Gonadotropin releasing hormone (gonadorelin) analogue; treatment of prostate cancer.

Definition

ChEBI: 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.

Indications

Leuprolide 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 Function

Antineoplastic

Synthesis

The 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.

Leuprorelin Preparation Products And Raw materials

Raw materials

Benzyl chloride Phenyl chloroformate N-[(tert-Butoxy)carbonyl]-D-tryptophan Boc-D-Tyr-OH Anisole tert-Butanol Tosyl chloride L-Histidine Benzenesulfonyl chloride DL-Serine TERT-BUTYL FORMATE L(+)-Arginine N-CARBOBENZOXY-DL-LEUCINE

Preparation Products

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Leuprorelin Suppliers

China 227 Europe 2 France 2 Germany 3 India 12 Italy 1 Japan 1 South Korea 1 Spain 2 Sweden 1 Switzerland 2 The Netherlands 3 United Kingdom 6 United States 28 Global 291
LGM Pharma
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1-(800)-881-8210
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sales@aladdinsci.com
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United States Biological
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View Lastest Price from Leuprorelin manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Leuprorelin 53714-56-0
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-10-25
Hebei Chuanghai Biotechnology Co,.LTD
Product
Leuprorelin 53714-56-0
Price
US $1.90/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 ton
Release date
2024-08-14
Nantong Guangyuan Chemicl Co,Ltd
Product
Leuprolide TFA 53714-56-0
Price
US $10.00/mg
Min. Order
1mg
Purity
99%
Supply Ability
1000g
Release date
2023-11-14

53714-56-0, LeuprorelinRelated Search:

Taspoglutide Lixisenatide Triptorelin Leuprorelin Acetate Angiotensin acetate Sermorelin Octreotide acetate Oxytocin Teriparatide acetate Pramlintide acetate Teriparatideacetate ARG-LYS-GLU-VAL-TYR ACETATE SALT Desmopressin Secretin Acetate Triptorelin acetate Nafarelin Acetate Ganirelix Eptifibatide Acetate

  • 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
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  • [DES-GLY10, DLEU 6, PRONHET9]
  • [DES-GLY10, DLEU6, PRO9]-LUTEINIZING HORMONE-RELEASING HORMONE, ETHYL AMIDE
  • [DES-GLY10, DLEU6, PRO9]-LH-RH, ETHYL AMIDE
  • GLP-HIS-TRP-SER-TYR-D-LEU-LEU-ARG-PRO-NHET
  • 5-OXOPRO-HIS-TRP-SER-TYR-D-LEU-LEU-ARG-PRO-NHC2H5
  • PGLU-HIS-TRP-SER-TYR-D-LEU-LEU-ARG-PRO-NHET
  • PGLU-HIS-TRP-SER-TYR-P-LEU-LEU-ARG-PRO-NHET
  • PYROGLU-HIS-TRP-SER-TYR-D-LEU-LEU-ARG-PRO NHCH2CH3
  • PYR-HIS-TRP-SER-TYR-D-LEU-LEU-ARG-PRO-NHET
  • N-[1-[[1-[[1-[[1-[[1-[[1-[[5-(diaminomethylideneamino)-1-[2-(ethylcarbamoyl)-1-pyrrolidinyl]-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-(4-h
  • 6-D-Leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamideluteinizing hormone-releasing factor(pig)
  • Carcinil
  • Enantone
  • Leuplin
  • Lucrin
  • (D-Leu6, des-Gly-NH210)-LH-RH ethylamide
  • Des-Gly10-[D-Leu6]-LH-releasing hormone ethylamide
  • N-[1-[[1-[[1-[[1-[[1-[[1-[[5-(Diaminomethylideneamino)-1-[2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxo-pentan-2-yl]carbamoyl]-3-methyl-butyl]carbamoyl]-3-methyl-butyl]carbamoyl]-2-(4-hydroxyphenyl)ethyl]carbamoyl]-2-hydroxy-ethyl]carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl]-2-(3H-imidazol-4-yl)ethyl]-5-oxo-pyrrolidine-2-carboxamide
  • [D-Leu6,des-Gly10]GnRH ethylamide
  • 10-des-Gly-6-D-Leu-LH-RH-ethylamide
  • 5-Oxo-L-Pro-L-His-L-Trp-L-Ser-L-Tyr-D-Leu-L-Leu-L-Arg-L-Pro-N-ethyl-NH2
  • GLP-HIS-TRP-SER-TYR-DLEU-LEU-ARG-PRO-NHET: GLP-HWSY-DL-LRP-NHET
  • 1-9-LUTEINIZING HORMONE-RELEASING FACTOR (SWINE), 6-D-LEUCINE-9-(N-ETHYL-L-PROLINAMIDE)-
  • LEUPROLIDE ACETATE PH. EUR.
  • Pyr-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt acetate salt
  • Leuprorelin Acetate(Leuprolide Acetate)
  • Leuprolide, Leuprorelin, Leuproreline, Leuprorelinum
  • Leuprorelinum
  • LEUPRORELIN (LEUPROLIDE) ACETATE
  • Leuprorelin###Leuprorelin acetate
  • 1-(2-cyclohexyl-1-methylethyl)hydrazine hydrochloride
  • Leuprelin Acetate
  • (d-leu(sup6),des-gly-nh2(sup10),pro-ethylamide(sup9))-gnrh
  • (d-leu(sup6),des-gly-nh2(sup10),pro-ethylamide(sup9))-gonadotropin-releasi
  • (d-leu(sup6),des-gly-nh2(sup10),pro-ethylamide(sup9))-lhrh
  • a-43818
  • de)-10-deglycinamide-
  • luteinizinghormone-releasinghormone(pig),6-d-leucine-9-(n-ethyl-l-prolinami
  • nghormone
  • 5-Oxo-L-prolil-L-histidil-L-tryptophil-L-seril-L-thyrozil-D-leucil-L-arginil-N-ethyl-L-prolinamide
  • LEUPROPELIN
  • Leuprorelin mesylate
  • Leuprorelin Acetate / Leuprorelin
  • Leuprorelin CRS
  • Leuprorelin USP/EP/BP
  • Anti-cancer Leuprorelin acetate 74381-53-6
  • Anti-cancer Leuprorelin acetate