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

    Quick InquiryCustom Peptide Synthesis

    cGMP Peptide

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    IND and NDA support Drug master files (DMF) filing

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

    2. Uncarboxylated osteocalcin decreases insulin-stimulated glucose uptake without affecting insulin signaling and regulators of mitochondrial biogenesis in myotubes

    3. Quantitative Analysis of Ligands Effects on Bioefficacy of Nanoemulsion encapsulating Depigmenting Active

    4. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

    5. Investigating Potential Interactions Between Neurohypophyseal Peptides, their Drug Analogs, and Coagulation Factor VIII

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