Histrelin

DCTPepD ID  DCTPepD0018

Active Ingredients   Histrelin

Description  A long-acting, synthetic nonapeptide analog of gonadotropin-releasing hormone (GnRH) with potential anti-tumor activity. Upon administration, histrelin binds to and activates GnRH receptors; prolonged administration results in pituitary GnRH receptor desensitization and inhibition of follicle stimulating hormone (FSH) and luteinizing hormone (LH) secretion, leading to a significant decline in testosterone production in males and may inhibit androgen receptor-positive tumor progression; in females, prolonged administration results in decreased estradiol production.

Synonyms  ORF 17070, RWJ 17070; Histrelin

Disease  Central precocious puberty(CPP), Advanced prostate cancer

Classification

  

Peptide and derivative Hormone and analogue

Structure Information


Molecular Formula  C70H94N18O16

Molecular Weight  1323.5

Active Sequence  XHWSYxLRP

Sequence Length  9

Modification  X=Pyr, x=D-His(1-Bn), N-terminal NHEt

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-3-(1-benzylimidazol-4-yl)-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]-1-oxopropan-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/C66H86N18O12/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71)/t47-,48-,49-,50-,51-,52-,53+,54-,55-/m0/s1

InChI_Key HHXHVIJIIXKSOE-QILQGKCVSA-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](CC6=CN(CC7=CC=CC=C7)C=N6)C(N[C@@H](CC(C)C)C(N[C@@H](CCC/N=C(N)\N)C(N8[C@H](C(NCC)=O)CCC8)=O)=O)=O)=O)=O)=O)=O

External Codes


PubChem CID  25077993

DrugBank Accession Number  DB06788

NCI Thesaurus Code  C74270  

UNII  H50H3S3W74   GSRS

CAS  76712-82-8



Drug approval


Drug indication
    As the product Supprelin LA (FDA), histrelin is indicated for the treatment of children with central precocious puberty (CPP). As the product Vantas (FDA), histrelin is indicated for the palliative treatment of advanced prostate cancer.

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Supprelin eq 0.2mg base/ml Injectable; Injection Shire Discontinued NDA: 019836 1991
Supprelin eq 0.5mg base/ml Injectable; Injection Shire Discontinued NDA: 019836 1991
Supprelin eq 1mg base/ml Injectable; Injection Shire Discontinued NDA: 019836 1991
Supprelin La 50mg Implant; Subcutaneous Endo Pharm Prescription NDA: 022058 2007
Vantas 50mg Implant; Subcutaneous Endo Pharm Discontinued NDA: 021732 2004
Vantas 50 mg Implant, Kit; Subcutaneous Paladin Labs Inc. Cancelled DIN: 02278383 2006

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT01394263 Phase III, Open-Label Randomized, Parallel, Active-Control Study to Evaluate Efficacy and Safety of Histrelin Subdermal Implant in Patients With Metastatic Prostate Cancer Prostate Cancer; Adenocarcinoma of the Prostate Phase 3 Treatment
NCT01574846 Prospective, Multicentre, Non-interventional (Observational) Study of VANTAS® for the Treatment of Patients With Advanced Prostate Cancer. Prostate Cancer Treatment
NCT04513717 Parallel Phase III Randomized Trials for High Risk Prostate Cancer Evaluating De-Intensification for Lower Genomic Risk and Intensification of Concurrent Therapy for Higher Genomic Risk With Radiation (PREDICT-RT*) Metastatic Malignant Neoplasm in the Bone; Prostate Adenocarcinoma; Stage III Prostate Cancer AJCC v8; Stage IIIA Prostate Cancer AJCC v8; Stage IIIB Prostate Cancer AJCC v8; Stage IIIC Prostate Cancer AJCC v8; Stage IVA Prostate Cancer AJCC v8 Phase 3 Treatment
NCT05050084 Parallel Phase III Randomized Trials of Genomic-Risk Stratified Unfavorable Intermediate Risk Prostate Cancer: De-Intensification and Intensification Clinical Trial Evaluation (GUIDANCE) Prostate Adenocarcinoma Phase 3 Treatment
NCT00779103 Phase III, Open-Label Study to Evaluate Efficacy and Safety of Histrelin Subdermal Implant in Children With Central Precocious Puberty Central Precocious Puberty Phase 3 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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