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53714-56-0

Basic Information
CAS No.: 53714-56-0
Name: Leuprorelin
Article Data: 9
Molecular Structure:
Molecular Structure of 53714-56-0 (Leuprorelin)
Formula: C59H84N16O12
Molecular Weight: 1209.42
Synonyms: Luteinizinghormone-releasing factor (pig),6-D-leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamide-;(D-Leu6,des-Gly-NH210)-LH-RH ethylamide;D-Leu6-des-Gly10-LH-releasing hormone ethylamide;Des-Gly10-[D-Leu6]-LH-releasing hormone ethylamide;Des-Gly10-[D-Leu6]LH-RHethylamide;1-9-Luteinizinghormone-releasing factor (swine), 6-D-leucine-9-(N-ethyl-L-prolinamide)-;Leuprorelin;Lupron SR;NSC 377526;
EINECS: 633-395-9
Density: 1.44 g/cm3
Solubility: Soluble in water at 1mg/ml
Appearance: Fluffy solid.
Safety: 22-24/25
PSA: 466.34000
LogP: 3.44730
Synthetic route

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

53714-56-0

Leuprolide

Conditions
ConditionsYield
With methyl-phenyl-thioether; trifluoroacetic acid at 50℃; for 1h; Yield given;
914200-76-3

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

53714-56-0

Leuprolide

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

C70H95N17O16

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

53714-56-0

Leuprolide

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

C104H138N16O17S

53714-56-0

Leuprolide

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

Leuprolide

92557-81-8

6-carboxyfluorescein N-hydroxysuccinimide ester

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

53714-56-0

Leuprolide

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

53714-56-0

Leuprolide

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

53714-56-0

Leuprolide

C66H96N16O13

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;43%
1539-59-9

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

53714-56-0

Leuprolide

C65H94N16O12

Conditions
ConditionsYield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;41%
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    Product name: Leuprorelin CAS No.:53714-56-0 Molecule Formula:C59H84N16O12 Molecule Weight:1209.40 Purity: 98.0% Package: 25kg/drum Description:White or off-white powder Manufacture Standards:Enterprise Standard TESTING ITEMS

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Specification

1. Introduction of Leuprorelin
Leuprorelin is one kind of white to off-white powder. The IUPAC Name of this chemical is N-[1-[[1-[[1-[[1-[[1-[[1-[[5-(Diaminomethylideneamino)-1-[2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide. Besides, Leuprorelin belongs Amino Acid Derivatives;Peptide. 

Its Classification Code is Antineoplastic Agents; Antineoplastic agents, hormonal; Fertility Agents; Fertility agents, female; Hormone; Human Data; Reproductive Control Agents; Reproductive Effect. Leuprorelin can soluble in water.

2. Properties of Leuprorelin
Physical properties about Leuprorelin are:
(1)Index of Refraction: 1.681; (2)Molar Refractivity: 315.96 cm3; (3)Molar Volume: 834.5 cm3; (4)Surface Tension: 61.7 dyne/cm; (5)Storage Temp.: -20 °C; (6)XLogP3-AA: 0.7; (7)H-Bond Donor: 15; (8)H-Bond Acceptor: 16; (9)Rotatable Bond Count: 32; (10)Tautomer Count: 1000; (11)Exact Mass: 1208.645462; (12)MonoIsotopic Mass: 1208.645462; (13)Topological Polar Surface Area: 432; (14)Heavy Atom Count: 87.

3. Structure Descriptors of Leuprorelin
(1)Canonical SMILES: CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6
(2)InChIKey: GFIJNRVAKGFPGQ-UHFFFAOYSA-N
(3)Smiles: C1[C@@H]([N@@](CC1)[Ar]***[Se]**C([C@@H]1NC(=O)CC1)=O)C(NCC)=O

4. Safety information of Leuprorelin
Safety Statements of Leuprorelin (CAS NO.53714-56-0): 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: OH6390000

5. Uses of Leuprorelin
Leuprorelin (CAS NO.53714-56-0) may be used in treating hormone-responsive cancers such as breast cancer or prostate cancer, estrogen-dependent conditions (such as endometriosis or uterine fibroids), to treat precocious puberty, and to control ovarian stimulation in In Vitro Fertilization (IVF). Leuprorelin is also under investigation for possible use in the treatment of mild to moderate Alzheimer's disease.

6. Production of Leuprorelin
(1)The reaction of phenol and phosgene to generate the phenyl chloroformate, and then tert-butanol, to generate the oxy acid benzyl ester of tert-butoxy. After the hydrazine, then nitrosated generates azido acid tert-butyl ester, and then reacted and leucineobtained leucine side chains.

Production

(2)Serine and benzyl chloride to protect the hydroxyl group, and then the azido carboxylic acid tert-butyl ester reaction serine side chain.

Production

After the reaction of (1) or (2), then pick peptides and ethylamine reaction, hydrolysis or hydrogenolysis to wipe off the protection base and get the Leuprorelin.