Leuprolide

Leuprolide

Leuprolide is a synthetic nonapeptide analogue of gonadotropin-releasing hormone. Leuprolide binds to and activates gonadotropin-releasing hormone (GnRH) receptors. Continuous, prolonged administration of leuprolide in males results in pituitary GnRH receptor desensitization and inhibition of pituitary secretion of follicle stimulating hormone (FSH) and luteinizing hormone (LH), leading to a significant decline in testosterone production; in females, prolonged administration results in a decrease in estradiol production. This agent reduces testosterone production to castration levels and may inhibit androgen receptor-positive tumor progression.

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CAT No: R1949

CAS No: 53714-56-0

Synonyms/Alias: Leuprorelin;leuprolide;53714-56-0;Leuproreline;Leuprorelinum;Leuporelin;Leuprorelina;(-)-leuprolide;UNII-EFY6W0M8TG;EFY6W0M8TG;TAP-144 FREE BASE;CCRIS 8462;CHEBI:6427;HSDB 6518;CKD-841;Leuprorelin slow release;ABBOTT-43818 FREE BASE;Leuproreline [INN-French];Leuprorelinum [INN-Latin];NSC 377526;NSC-377526;Leuprorelina [INN-Spanish];DTXSID50872411;(D-Leu(sup 6),des-gly-NH2(sup 10),pro-ethylamide(sup 9))-GNRH;(D-Leu(sup 6),des-gly-NH2(sup 10),pro-ethylamide(sup 9))-LHRH;Leuproreline (INN-French);Leuprorelinum (INN-Latin);Leuprorelina (INN-Spanish);LEUPRORELIN (MART.);LEUPRORELIN [MART.];5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide;pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5;Leuprorelin acetate (JAN);Leuprolide acetate (USAN);LEUPRORELIN (EP MONOGRAPH);LEUPRORELIN [EP MONOGRAPH];5-OXO-L-PROLYL-L-HISTIDYL-L-TRYPTOPHYL-L-SERYL-L-TRYOSYL-D-LEUCYL-L-LEUCYL-L-ARGINYL-N-ETHYL-L-PROLINAMIDE;L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-L-proline ethylamide;LEUPRORELIN [INN];MFCD00167544;Leuprolide acetate salt;Leuprorelin [INN:BAN];Leuprorelin?;Leuprolide TFA;LEUPROLIDE [MI];LEUPROLIDE [HSDB];LEUPROLIDE [VANDF];SCHEMBL4585;LEUPRORELIN [WHO-DD];GTPL1175;CHEMBL1201199;DTXCID00820063;L02AE02;GFIJNRVAKGFPGQ-LIJARHBVSA-N;BDBM50369395;AKOS015892744;AKOS030213246;AKOS037515838;CCG-270656;CS-4947;DB00007;HS-2016;NCGC00485984-01;DA-64932;HY-12553;Leuprolide acetate salt, >=98% (HPLC);C75519;pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt;EN300-7481165;Fensolvi (leuprolide acetate injectable suspension);Q907160;BRD-K26323068-001-01-8;Leuprolide acetate, United States Pharmacopeia (USP) Reference Standard;6-D-Leucine-9-(N-ethyl-L-prolinamide)-1-9-luteinizing Hormone-releasing Factor (Pig);(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-4-methylpentanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide;6-D-Leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamide Luteinizing Hormone-Releasing Factor (Pig);

Chemical Name: (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-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

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M.F/Formula	C59H84N16O12
M.W/Mr.	1209.4
Sequence	One Letter Code:XHWSYLLRP Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt
Appearance	Solid powder
Activity	Agonist
Biological Activity	Leuprolide is a peptide-based GnRH receptor superagonist used for the palliative treatment of prostate cancer, uterine leiomyomata, endometriosis, and central precocious puberty.
Target	Gonadotropin-releasing hormone receptor

Long-term Storage Conditions	Soluble in DMSO
InChI	InChI=1S/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
InChI Key	GFIJNRVAKGFPGQ-LIJARHBVSA-N
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)C(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
Isomeric SMILES	CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6

1. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate

2. cRGD-functionalized, DOX-conjugated, and 64Cu-labeled superparamagnetic iron oxide nanoparticles for targeted anticancer drug delivery and PET/MR imaging

4. Effect of Probiotic Lactobacillus plantarum on Streptococcus mutans and Candida albicans Clinical Isolates from Children with Early Childhood Caries

5. Cationic cell-penetrating peptides are potent furin inhibitors

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