Goserelin

DCTPepD ID  DCTPepD0002

Active Ingredients   Goserelin

Description  A synthetic decapeptide analog of luteinizing hormone-releasing hormone (LHRH) with antineoplastic activity. Goserelin binds to and activates pituitary gonadotropin releasing hormone (GnRH) receptors. Prolonged administration of goserelin inhibits the secretion of pituitary gonadotropin, thereby decreasing levels of testosterone (in males) and estradiol (in females). Administration of this agent in a depot formulation may result in the regression of sex hormone-sensitive tumors and a reduction in sex organ size and function.

Synonyms  6-[O-(1,1-Dimethylethyl)-D-serine]-10-deglycinamide Luteinizing Hormone-Releasing Factor (Pig) 2-(aminocarbonyl)hydrazide; Zoladex; Decapeptide I; ICI-118630; Goserelin

Disease  Prostate cancer, Breast cancer

Classification

  

Peptide and derivative Hormone and analogue

Structure Information


Molecular Formula  C59H84N18O14

Molecular Weight  1269.433

Active Sequence  XHWSYxLRP

Sequence Length  9

Modification  X=Pyr, x=D-Ser(tBu), N-terminal NHNHCONH2

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[(carbamoylamino)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-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/C64H82N18O13/c1-34(2)23-46(56(88)75-45(13-7-21-69-64(66)67)63(95)82-22-8-14-52(82)62(94)72-31-53(65)85)76-58(90)48(25-36-28-70-42-11-5-3-9-40(36)42)78-57(89)47(24-35-15-17-39(84)18-16-35)77-61(93)51(32-83)81-59(91)49(26-37-29-71-43-12-6-4-10-41(37)43)79-60(92)50(27-38-30-68-33-73-38)80-55(87)44-19-20-54(86)74-44/h3-6,9-12,15-18,28-30,33-34,44-52,70-71,83-84H,7-8,13-14,19-27,31-32H2,1-2H3,(H2,65,85)(H,68,73)(H,72,94)(H,74,86)(H,75,88)(H,76,90)(H,77,93)(H,78,89)(H,79,92)(H,80,87)(H,81,91)(H4,66,67,69)/t44-,45-,46-,47-,48+,49-,50-,51-,52-/m0/s1

InChI_Key VXKHXGOKWPXYNA-PGBVPBMZSA-N

SMILES  N=C(N)NCCC[C@H](NC([C@@H](NC([C@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H]1CCC(N1)=O)=O)CC2=CNC=N2)=O)CC3=CNC4=C3C=CC=C4)=O)CO)=O)CC5=CC=C(O)C=C5)=O)CC6=CNC7=CC=CC=C67)=O)CC(C)C)=O)C(N8CCC[C@H]8C(NCC(N)=O)=O)=O

External Codes


PubChem CID  5311128

DrugBank Accession Number  DB00014

NCI Thesaurus Code  C1374  

UNII  0F65R8P09N   GSRS

CAS  65807-02-5



Drug approval


Drug indication
    Goserelin is indicated for:
1) Use in combination with flutamide for the management of locally confined carcinoma of the prostate
2) Palliative treatment of advanced carcinoma of the prostate
3) The management of endometriosis
4) Use as an endometrial-thinning agent prior to endometrial ablation for dysfunctional uterine bleeding
5) Use in the palliative treatment of advanced breast cancer in pre- and perimenopausal women

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Zoladex eq 3.6mg base Implant; Implantation Tersera Theraps Llc Prescription NDA: 019726 1989
Zoladex eq 10.8mg base Implant; Implantation Tersera Theraps Llc Prescription NDA: 020578 1996
Zoladex 3.6 mg Implant; Subcutaneous Tersera Therapeutics Llc Prescription DIN: 02049325 1994
Zoladex 10.8 mg Implant; Subcutaneous Tersera Therapeutics Llc Prescription DIN: 02225905 1996

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT03936218 A Two Arm, Multi Centric, Randomised, Open Label, Parallel Study to Compare Pharmacodynamics of Subcutaneous Goserelin 10.8mg Injection (Sponsor) With ZOLADEX® 10.8mg Injection (AstraZeneca) in Patients With Advanced Prostate Cancer Advanced Prostate Cancer Phase 3 Treatment
NCT00186121 A Phase II Trial of Arimidex Plus Zoladex in the Treatment of Hormone Receptor Positive, Metastatic Carcinoma of the Breast in Premenopausal Women Breast Cancer Phase 2 Treatment
NCT01073865 An Open Label, Randomised, Parallel Group, Multicentre Study to Compare ZOLADEX™ 10.8 mg Given Every 12 Weeks With ZOLADEX 3.6 mg Given Every 4 Weeks in Pre-menopausal Women With Oestrogen Receptor Positive Advanced Breast Cancer. Breast Cancer Phase 3 Treatment
NCT02586675 The TEEL Study: A Phase I Trial of Tamoxifen With Ribociclib (LEE011) in Adult Patients With Advanced ER+ (HER2 Negative) Breast Cancer Breast Cancer; Breast Cancer - Female; Breast Cancer - Male Phase 1 Treatment
NCT02430480 Neoadjuvant Androgen Deprivation and Enzalutamide: Using Multiparametric MRI to Evaluate Intraprostatic Tumor Responses and Androgen Resistance Patterns in Newly Diagnosed Prostate Cancer Prostate Cancer Phase 2 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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