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53714-56-0

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53714-56-0 Usage

Description

Leuprorelin, also known as Leuprolide, is a synthetic water-soluble nonapeptide analogue of gonadotropin-releasing hormone (GnRH). It is produced by the hypothalamus and has both ends closed. Leuprorelin stimulates the pituitary gland to secrete gonadotropins, which in turn induce the production of steroids in the reproductive organs. It is a highly active luteinizing hormone-releasing hormone (LHRH) agonist and is used to regulate the secretion of gonadal hormones, increasing the serum levels of testosterone and dihydrotestosterone. Leuprorelin is hygroscopic, appearing as a white or almost white powder.

Uses

Used in Reproductive System Disease Treatment:
Leuprorelin is used as a therapeutic agent for treating various reproductive system diseases, including prostate cancer, uterine fibroids, ovarian cysts, breast cancer, and cryptorchidism in children. It functions by promoting the release of luteinizing hormone (LHRH) and follicle-stimulating hormone (FSH) from the anterior pituitary, thereby regulating gonadal hormone secretion and increasing serum testosterone and dihydrotestosterone levels.
Used in Prostate Cancer Treatment:
Leuprorelin is used as a highly active LHRH agonist for the treatment of prostate cancer. It helps in suppressing gonadal sex hormone production, which is crucial for the growth and progression of prostate cancer cells.
Used in Central Precocious Puberty Treatment:
Leuprorelin is used as a subcutaneous hydrogel implant, particularly as the acetate salt, for the treatment of central precocious puberty in children. It helps in suppressing the early onset of puberty by regulating the secretion of gonadal hormones.
Used in Pharmaceutical Industry:
Leuprorelin is used as a highly active gonadotropin-releasing hormone (gonadorelin) analogue in the pharmaceutical industry. Its synthetic nature allows for controlled production and consistent quality, making it a valuable asset in the development of medications for various reproductive system diseases and conditions.

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.

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 lookchem 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.

Originator

Eligard,Atrix Laboratories, Inc.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 53714-56-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,7,1 and 4 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 53714-56:
(7*5)+(6*3)+(5*7)+(4*1)+(3*4)+(2*5)+(1*6)=120
120 % 10 = 0
So 53714-56-0 is a valid CAS Registry Number.
InChI:InChI=1/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

53714-56-0 Well-known Company Product Price

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  • (L0376000)  Leuprorelin  European Pharmacopoeia (EP) Reference Standard

  • 53714-56-0

  • L0376000

  • 1,880.19CNY

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53714-56-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name leuprolide

1.2 Other means of identification

Product number -
Other names 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:53714-56-0 SDS

53714-56-0Synthetic route

pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg(Mds)-Pro-NH-Et

pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg(Mds)-Pro-NH-Et

Leuprolide
53714-56-0

Leuprolide

Conditions
ConditionsYield
With methyl-phenyl-thioether; trifluoroacetic acid at 50℃; for 1h; Yield given;
pGlu-His(Trt)-Trp-Ser(tBu)-Tyr(tBu)-D-Leu-Leu-Arg(Pbf)-Pro-NHEt
914200-76-3

pGlu-His(Trt)-Trp-Ser(tBu)-Tyr(tBu)-D-Leu-Leu-Arg(Pbf)-Pro-NHEt

Leuprolide
53714-56-0

Leuprolide

Conditions
ConditionsYield
With chlorotriisopropylsilane; ethane-1,2-dithiol; trifluoroacetic acid at 20℃; for 2h;
C70H95N17O16

C70H95N17O16

Leuprolide
53714-56-0

Leuprolide

Conditions
ConditionsYield
In dimethyl sulfoxide pH=8.5; UV-irradiation;
pGlu-His(Trt)-Trp(Boc)-Ser(tBu)-Tyr(tBu)-D-Leu-Leu-Arg(Pbf)-Pro-NHEt

pGlu-His(Trt)-Trp(Boc)-Ser(tBu)-Tyr(tBu)-D-Leu-Leu-Arg(Pbf)-Pro-NHEt

Leuprolide
53714-56-0

Leuprolide

Conditions
ConditionsYield
With chlorotriisopropylsilane; water; trifluoroacetic acid at 20 - 60℃;
C104H138N16O17S

C104H138N16O17S

Leuprolide
53714-56-0

Leuprolide

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 2h;
Leuprolide
53714-56-0

Leuprolide

6-carboxyfluorescein N-hydroxysuccinimide ester
92557-81-8

6-carboxyfluorescein N-hydroxysuccinimide ester

Pyr-His-Trp-Ser-Tyr-D-Leu-Leu-Arg(6-FAM)-Pro-NHEt

Pyr-His-Trp-Ser-Tyr-D-Leu-Leu-Arg(6-FAM)-Pro-NHEt

Conditions
ConditionsYield
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 5-carboxyfluorescein succinimidyl ester In N,N-dimethyl-formamide at 40℃; for 8h; Inert atmosphere;77%
3-bromo-1,2,4,5-tetrazine

3-bromo-1,2,4,5-tetrazine

Leuprolide
53714-56-0

Leuprolide

C61H84N20O12

C61H84N20O12

Conditions
ConditionsYield
With collidine In water; acetonitrile at 25℃; for 0.416667h;69%
diethyl 4-((3r,5r,7r)-adamantan-1-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

diethyl 4-((3r,5r,7r)-adamantan-1-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Leuprolide
53714-56-0

Leuprolide

C69H98N16O12

C69H98N16O12

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;57%
diethyl 4-(4-(hydroxymethyl)cyclohexyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

diethyl 4-(4-(hydroxymethyl)cyclohexyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Leuprolide
53714-56-0

Leuprolide

C66H96N16O13

C66H96N16O13

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;43%
4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester
1539-59-9

4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

Leuprolide
53714-56-0

Leuprolide

C65H94N16O12

C65H94N16O12

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;41%
4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
1539-32-8

4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

Leuprolide
53714-56-0

Leuprolide

C62H90N16O12

C62H90N16O12

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;40%
diethyl 2,6-dimethyl-4-(4-((tosyloxy)methyl)cyclohexyl)-1,4-dihydropyridine-3,5-dicarboxylate

diethyl 2,6-dimethyl-4-(4-((tosyloxy)methyl)cyclohexyl)-1,4-dihydropyridine-3,5-dicarboxylate

Leuprolide
53714-56-0

Leuprolide

C73H102N16O15S

C73H102N16O15S

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;39%
C18H27NO6

C18H27NO6

Leuprolide
53714-56-0

Leuprolide

C64H92N16O14

C64H92N16O14

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;34%
diethyl 2,6-dimethyl-4-(tetrahydro-2H-pyran-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate

diethyl 2,6-dimethyl-4-(tetrahydro-2H-pyran-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Leuprolide
53714-56-0

Leuprolide

C64H92N16O13

C64H92N16O13

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;33%
diethyl 4-((4-azidomethyl)cyclohexyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

diethyl 4-((4-azidomethyl)cyclohexyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Leuprolide
53714-56-0

Leuprolide

C66H95N19O12

C66H95N19O12

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;30%
(p-hydroxyphenyl)boronic acid
71597-85-8

(p-hydroxyphenyl)boronic acid

Leuprolide
53714-56-0

Leuprolide

C65H88N16O13

C65H88N16O13

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;
Dihydroxy-styryl-boran
4363-35-3, 6783-05-7, 60806-02-2

Dihydroxy-styryl-boran

Leuprolide
53714-56-0

Leuprolide

C67H90N16O12

C67H90N16O12

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;
(E)-(2-cyclohexylvinyl)boronic acid
57002-01-4, 37490-33-8

(E)-(2-cyclohexylvinyl)boronic acid

Leuprolide
53714-56-0

Leuprolide

C67H96N16O12

C67H96N16O12

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;
Leuprolide
53714-56-0

Leuprolide

(E)-tertiobutyl vinyl boronic acid
214907-15-0

(E)-tertiobutyl vinyl boronic acid

C65H94N16O12

C65H94N16O12

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;
3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

Leuprolide
53714-56-0

Leuprolide

C65H87ClN16O12

C65H87ClN16O12

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;
2-carboxyphenylboronic acid
149105-19-1

2-carboxyphenylboronic acid

Leuprolide
53714-56-0

Leuprolide

C66H88N16O14

C66H88N16O14

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;
m-tolylboronic acid
17933-03-8

m-tolylboronic acid

Leuprolide
53714-56-0

Leuprolide

C66H90N16O12

C66H90N16O12

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;
4-nitrophenylboronic acid
24067-17-2

4-nitrophenylboronic acid

Leuprolide
53714-56-0

Leuprolide

C65H87N17O14

C65H87N17O14

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;
Leuprolide
53714-56-0

Leuprolide

4-carbamoylphenylboronic acid
123088-59-5

4-carbamoylphenylboronic acid

C66H89N17O13

C66H89N17O13

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;
(E)-2-(3-(4,5-dimethoxy-2-nitrophenyl)prop-1-en-1-yl)boronic acid pinacol ester

(E)-2-(3-(4,5-dimethoxy-2-nitrophenyl)prop-1-en-1-yl)boronic acid pinacol ester

Leuprolide
53714-56-0

Leuprolide

C70H95N17O16

C70H95N17O16

Conditions
ConditionsYield
With Cu(II) salt In dimethyl sulfoxide at 20℃; pH=8.5;
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Leuprolide
53714-56-0

Leuprolide

ethyl N-propionate-leuprolide

ethyl N-propionate-leuprolide

Conditions
ConditionsYield
With silver(I) acetate; copper (I) acetate; acetic acid; N-acetylglycine In water at 60℃; for 12h;

53714-56-0Downstream Products

53714-56-0Relevant articles and documents

Synthesis, Stability and Direct Antiproliferative Effect of New Cysteine Modified GnRH Analogs

Li, Songtao,Zhao, Hongling,Wang, Ruxing,Wang, Jianping,Mao, Xiaoxia,Hao, Ting,Chang, Xiaomin,Zhao, Enhong,Yin, Zhifeng,Deng, Shuhua,Yang, Yaqi,Wang, Huina

, p. 1361 - 1367 (2019)

It is demonstrated that gonadotropin-releasing hormone (GnRH) analogs can directly inhibit the proliferation of reproductive tissue cancer cells, but the poor pharmacokinetic properties still restrict their application in treating hormone-dependent diseases. Modifications in position 6 and 10 of natural GnRH can improve the metabolic stability. In order to study the effect of incorporation Cys6 substitution with C-terminal Pro9-NHEt modification and dimerization of linear peptides on metabolic stability and antiproliferative activity of GnRH analogs, two new GnRH analogs [l-Cys6, desGly10, Pro9-NHEt]-GnRH (1) and [d-Cys6, desGly10, Pro9-NHEt]-GnRH (2), and their corresponding dimer derivatives ([l-Cys6, desGly10, Pro9-NHEt]-GnRH)2 (3) and ([d-Cys6, desGly10, Pro9-NHEt]-GnRH)2 (4) were synthesized. Incubation of these analogs with human serum was carried out to evaluate their metabolic stability, and direct growth inhibitory effect of the two dimer derivatives 3 and 4 on MCF-7 human breast cancer cell line was examined by MTT assay. The metabolic stability of dimer derivatives 3 and 4 was remarkably improved in comparison with natural GnRH. The d-Cys6 substituted dimer derivative 4 exhibited higher inhibitory effect (29.6–39.7% growth reduction) on cell growth than its corresponding counterpart 3 (21.8–26.2% growth reduction) at concentration range of 50, 100 and 200 μΜ. The cell growth inhibition of leuprolide was 16.4–27.2% at the tested concentrations. The dimer derivative 4 was the most stable and active GnRH analog in this study and has the potential for future preclinical investigations as promising antitumor drug candidate.

A Vinylogous Photocleavage Strategy Allows Direct Photocaging of Backbone Amide Structure

Mangubat-Medina, Alicia E.,Martin, Samuel C.,Hanaya, Kengo,Ball, Zachary T.

supporting information, p. 8401 - 8404 (2018/06/29)

Side-chain modifications that respond to external stimuli provide a convenient approach to control macromolecular structure and function. Responsive modification of backbone amide structure represents a direct and powerful alternative to impact folding and function. Here, we describe a new photocaging method using histidine-directed backbone modification to selectively modify peptides and proteins at the amide N-H bond. A new vinylogous photocleavage method allows photorelease of the backbone modification and, with it, restoration of function.

Solution-phase synthesis of leuprolide

-

, (2008/06/13)

The present application concerns a solution-phase method for the synthesis of leuprolin. Leuprolin is a nonapeptide having strong ovulation-inducing activity, and has the following formula: 5-oxo-L-prolyl- L-histidyl- L-tryptophyl- L-seryl- L-tyrosyl -D-leucyl -L-leucyl- L-arginyl- N-ethyl-L-prolinamide.

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