Leuprolide

DCTPepD ID  DCTPepD0019

Active Ingredients   Leuprolide

Description  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.

Synonyms  Leuprorelin; 6-D-Leucine-9-(N-ethyl-L-prolinamide)-1-9-luteinizing Hormone-releasing Factor (Pig); 6-D-Leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamide Luteinizing Hormone-Releasing Factor (Pig); Leuprolide

Disease  Advanced Prostate Cancer, Anemia, Central Precocious Puberty (CPP), Endometriosis

Classification

  

Peptide and derivative Hormone and analogue

Structure Information


Molecular Formula  C59H84N16O12

Molecular Weight  1209.4

Active Sequence  XHWSYlLRP

Sequence Length  9

Modification  X=Pyr, N-terminal NHEt

Structure

 

Show IUPAC/InChI/SMILES

IUPAC 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

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

SMILES  O=C([C@H](CC1)NC1=O)N[C@@H](CC2=CN=CN2)C(N[C@@H](CC3=CNC4=C3C=CC=C4)C(N[C@@H](CO)C(N[C@@H](CC5=CC=C(O)C=C5)C(N[C@H](CC(C)C)C(N[C@@H](CC(C)C)C(N[C@@H](CCC/N=C(N)\N)C(N6[C@H](C(NCC)=O)CCC6)=O)=O)=O)=O)=O)=O)=O

External Codes


PubChem CID  657181

DrugBank Accession Number  DB00007

NCI Thesaurus Code  C62042  

UNII  EFY6W0M8TG   GSRS

CAS  53714-56-0



Drug approval


Drug indication
    Leuprolide is indicated for the treatment of advanced prostate cancer and as palliative treatment of advanced prostate cancer.
It is also used for the treatment of pediatric patients with central precocious puberty (CPP).
In combination with oral norethisterone (also known as norethindrone), leuprolide is also indicated for the initial treatment of the symptoms of endometriosis. Finally, in combination with iron supplementation, leuprolide is indicated for the preoperative hematological improvement of anemic patients with uterine leiomyomata (uterine fibroids).

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Camcevi Kit eq 42mg base Emulsion; Subcutaneous Accord Prescription NDA: 211488 2021
Eligard Kit 7.5mg Powder; Subcutaneous Tolmar Therap Prescription NDA: 021343 2002
Eligard Kit 22.5mg Powder; Subcutaneous Tolmar Therap Prescription NDA: 021379 2002
Eligard Kit 30mg Powder; Subcutaneous Tolmar Therap Prescription NDA: 021488 2003
Eligard Kit 45mg Powder; Subcutaneous Tolmar Therap Prescription NDA: 021731 2004
Fensolvi Kit 45mg Powder; Subcutaneous Tolmar Prescription NDA: 213150 2020
Leuprolide Acetate 1mg/0.2ml Injectable; Injection Sandoz Prescription ANDA: 074728 1998
Leuprolide Acetate 1mg/0.2ml Injectable; Injection Teva Pharms Usa Prescription ANDA: 075471 2000
Leuprolide Acetate 1mg/0.2ml Injectable; Injection Genzyme Prescription ANDA: 075721 2001
Leuprolide Acetate 1mg/0.2ml Injectable; Injection Sun Pharm Prescription ANDA: 078885 2009
Leuprolide Acetate 1mg/0.2ml Injectable; Injection Eugia Pharma Prescription ANDA: 212963 2022
Leuprolide Acetate 1mg/0.2ml Injectable; Injection Vgyaan Prescription ANDA: 213829 2021
Lupaneta Pack 3.75mg/vial, n/a; n/a, 5mg Leuprolide Acetate; Norethindrone Acetate Abbvie Endocrine Discontinued NDA: 203696 2012
Lupaneta Pack 11.25mg/vial ,n/a; n/a, 5mg Leuprolide Acetate; Norethindrone Acetate Abbvie Endocrine Discontinued NDA: 203696 2012
Lupron 1mg/0.2ml Injectable; Injection Abbvie Endocrine Inc Discontinued NDA: 019010 1985
Lupron Depot 7.5mg/vial Injectable; Injection Abbvie Endocrine Inc Prescription NDA: 019732 1989
Lupron Depot 3.75mg Injectable; Injection Abbvie Endocrine Inc Prescription NDA: 019943 1995
Lupron Depot 3.75mg/vial Injectable; Injection Abbvie Endocrine Inc Discontinued NDA: 020011 1990
Lupron Depot 3.75mg Injectable; Injection Abbvie Endocrine Inc Prescription NDA: 020011 1990
Lupron Depot 22.5mg/vial Injectable; Injection Abbvie Endocrine Inc Prescription NDA: 020517 1995
Lupron Depot 30mg/vial Injectable; Injection Abbvie Endocrine Inc Prescription NDA: 020517 1995
Lupron Depot 45mg/vial Injectable; Injection Abbvie Endocrine Inc Prescription NDA: 020517 1995
Lupron Depot 11.25mg/vial Injectable; Injection Abbvie Endocrine Inc Prescription NDA: 020708 1997
Lupron Depot-Ped Kit 7.5mg Powder; Intramuscular Abbvie Endocrine Inc Prescription NDA: 020263 1993
Lupron Depot-Ped Kit 3.75mg, 7.5mg Powder; Intramuscular Abbvie Endocrine Inc Discontinued NDA: 020263 1993
Lupron Depot-Ped Kit 7.5mg, 7.5mg Powder; Intramuscular Abbvie Endocrine Inc Discontinued NDA: 020263 1993
Lupron Depot-Ped Kit 11.25mg Powder; Intramuscular Abbvie Endocrine Inc Prescription NDA: 020263 1993
Lupron Depot-Ped Kit 15mg Powder; Intramuscular Abbvie Endocrine Inc Prescription NDA: 020263 1993
Lupron Depot-Ped Kit 11.25mg Powder; Intramuscular Abbvie Endocrine Inc Prescription NDA: 020263 1993
Lupron Depot-Ped Kit 30mg Powder; Intramuscular Abbvie Endocrine Inc Prescription NDA: 020263 1993
Lutrate Depot Kit 22.5mg/vial For Suspension; Intramuscular Gp-Pharm Sa Prescription NDA: 205054 2018
Viadur eq 65mg base Implant; Implantation Ortho Mcneil Janssen Discontinued NDA: 021088 2000
Camcevi unknown Prolonged-Release Suspension; Subcutaneous Accord Healthcare S.L.U. Prescription EMEA/H/C/005034 2022
Camcevi 42 mg / syr Emulsion(Extended-Release); Subcutaneous Accord Healthcare Inc Prescription DIN: 02522446 2021
Eligard 7.5 mg / syr Powder For Suspension(Sustained-Release); Subcutaneous Tolmar International Ltd. Prescription DIN: 02248239 2003
Eligard 22.5 mg / syr Powder For Suspension(Sustained-Release); Subcutaneous Tolmar International Ltd. Prescription DIN: 02248240 2003
Eligard 30 mg / syr Powder For Suspension(Sustained-Release); Subcutaneous Tolmar International Ltd. Prescription DIN: 02248999 2004
Eligard 45 mg / syr Powder For Suspension(Sustained-Release); Subcutaneous Tolmar International Ltd. Prescription DIN: 02268892 2005
Leuprolide Acetate Injection 5 mg / ml Liquid; Subcutaneous Novopharm Limited Cancelled DIN: 02240264 2015
Lupron 5 mg / ml Solution; Subcutaneous Abbvie Corporation Prescription DIN: 00727695 1985
Lupron Depot 7.5 mg / syr Powder For Suspension(Sustained-Release); Intramuscular Abbvie Corporation Prescription DIN: 00836273 1989
Lupron Depot 3.75 mg / syr Powder For Suspension(Sustained-Release); Intramuscular Abbvie Corporation Prescription DIN: 00884502 1992
Lupron Depot 11.25 mg / vial Powder For Suspension(Sustained-Release); Intramuscular Abbvie Corporation Cancelled DIN: 02148722 2016
Lupron Depot 15 mg / vial Powder For Suspension(Sustained-Release); Intramuscular Abbvie Corporation Cancelled DIN: 02148730 2016
Lupron Depot 22.5 mg / syr Powder For Suspension(Sustained-Release); Intramuscular Abbvie Corporation Prescription DIN: 02230248 1997
Lupron Depot 30 mg / syr Powder For Suspension(Sustained-Release); Intramuscular Abbvie Corporation Prescription DIN: 02239833 1999
Lupron Depot 11.25 mg / syr Powder For Suspension(Sustained-Release); Intramuscular Abbvie Corporation Prescription DIN: 02239834 1999
Zeulide Depot 3.75 mg / vial Powder For Suspension(Sustained-Release), Kit; Intramuscular Verity Pharmaceuticals Inc. Prescription DIN: 02429977 2019
Zeulide Depot 22.5 mg / vial Powder For Suspension(Sustained-Release), Kit; Intramuscular Verity Pharmaceuticals Inc. Prescription DIN: 02462699 2019

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT03035032 A Phase IV Interventional Safety Study of ELIGARD® in Prostate Cancer Patients in Asia (ELIGANT) Prostate Cancer Phase 4 Treatment
NCT02319837 A Phase 3, Randomized, Efficacy and Safety Study of Enzalutamide Plus Leuprolide, Enzalutamide Monotherapy, and Placebo Plus Leuprolide in Men With High-Risk Nonmetastatic Prostate Cancer Progressing After Definitive Therapy Hormone Sensitive Prostate Cancer; Prostate Cancer; Cancer of the Prostate Phase 3 Treatment
NCT02508636 Phase II Trial of Definitive Radiotherapy With Leuprolide and Enzalutamide in High Risk Prostate Cancer Prostatic Neoplasms; Pelvic Nodal Phase 2 Treatment
NCT00254397 Study of the Modulatory Activity of an LHRH-Agonist (Leuprolide) on Melanoma Peptide Vaccines as Adjuvant Therapy in Melanoma Patients Melanoma Phase 2 Treatment
NCT00903162 Extended Endocrine Therapy for Premenopausal Women With Breast Cancer Breast Cancer Phase 2 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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