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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Leuprolide(CAS 53714-56-0)

CAT No: R1949

CAS No: 53714-56-0

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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Specification Technical Data Publications Customer reviews and Q&A
Synonyms/AliasLeuprorelin;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);
M.F/FormulaC59H84N16O12
M.W/Mr.1209.4
SequenceOne Letter Code:XHWSYLLRP
Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt
AppearanceSolid powder
ActivityAgonist
Biological ActivityLeuprolide is a peptide-based GnRH receptor superagonist used for the palliative treatment of prostate cancer, uterine leiomyomata, endometriosis, and central precocious puberty.
TargetGonadotropin-releasing hormone receptor
Long-term Storage ConditionsSoluble in DMSO
InChIInChI=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 KeyGFIJNRVAKGFPGQ-LIJARHBVSA-N
Canonical SMILESCCNC(=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 SMILESCCNC(=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. C-peptide and its C-terminal fragments improve erythrocyte deformability in type 1 diabetes patients

2. Effect of Short-Term Desiccation, Recovery Time, and CAPA-PVK Neuropeptide on the Immune System of the Burying Beetle Nicrophorus vespilloides

3. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum

4. Odorant binding protein based biomimetic sensors for detection of alcohols associated with Salmonella contamination in packaged beef

5. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function

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