Leuprorelin supplier | CasNO.53714-56-0

Name
Leuprorelin
EINECS 633-395-9
CAS No. 53714-56-0
Article Data9
CAS DataBase
Density 1.44 g/cm³
Solubility Soluble in water at 1mg/ml
Melting Point
Formula C₅₉H₈₄N₁₆O₁₂
Boiling Point
Molecular Weight 1209.42
Flash Point
Transport Information
Appearance Fluffy solid.
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
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;
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

Conditions	Yield
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

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

: C70H95N17O16

: 53714-56-0
Leuprolide

Conditions

Conditions	Yield
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

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

: C104H138N16O17S

: 53714-56-0
Leuprolide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;	41%

: 1539-32-8
4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

: 53714-56-0
Leuprolide

: C62H90N16O12

Conditions

Conditions	Yield
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

: 53714-56-0
Leuprolide

: C73H102N16O15S

Conditions

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

: C18H27NO6

: 53714-56-0
Leuprolide

: C64H92N16O14

Conditions

Conditions	Yield
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

: 53714-56-0
Leuprolide

: C64H92N16O13

Conditions

Conditions	Yield
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

: 53714-56-0
Leuprolide

: C66H95N19O12

Conditions

Conditions	Yield
With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 9h; Irradiation; Inert atmosphere; Sealed tube; chemospecific reaction;	30%

: 71597-85-8
(p-hydroxyphenyl)boronic acid

: 53714-56-0
Leuprolide

: C65H88N16O13

Conditions

Conditions	Yield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;

: 4363-35-3, 6783-05-7, 60806-02-2
Dihydroxy-styryl-boran

: 53714-56-0
Leuprolide

: C67H90N16O12

Conditions

Conditions	Yield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;

: 57002-01-4, 37490-33-8
(E)-(2-cyclohexylvinyl)boronic acid

: 53714-56-0
Leuprolide

: C67H96N16O12

Conditions

Conditions	Yield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;

: 53714-56-0
Leuprolide

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

: C65H94N16O12

Conditions

Conditions	Yield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;

: 63503-60-6
3-chlorophenylboronic acid

: 53714-56-0
Leuprolide

: C65H87ClN16O12

Conditions

Conditions	Yield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;

: 149105-19-1
2-carboxyphenylboronic acid

: 53714-56-0
Leuprolide

: C66H88N16O14

Conditions

Conditions	Yield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;

: 17933-03-8
m-tolylboronic acid

: 53714-56-0
Leuprolide

: C66H90N16O12

Conditions

Conditions	Yield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;

: 24067-17-2
4-nitrophenylboronic acid

: 53714-56-0
Leuprolide

: C65H87N17O14

Conditions

Conditions	Yield
With copper diacetate In dimethyl sulfoxide at 20℃; pH=7.4; Chan-Lam Coupling;

: 53714-56-0
Leuprolide

: 123088-59-5
4-carbamoylphenylboronic acid

: C66H89N17O13

Conditions

Conditions	Yield
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

: 53714-56-0
Leuprolide

: C70H95N17O16

Conditions

Conditions	Yield
With Cu(II) salt In dimethyl sulfoxide at 20℃; pH=8.5;

: 292638-85-8
acrylic acid methyl ester

: 53714-56-0
Leuprolide

: ethyl N-propionate-leuprolide

Conditions

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

Leuprorelin 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.

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.

Product Name

Leuprorelin

Synthetic route

Leuprorelin Specification

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