Buserelin

DCTPepD ID  DCTPepD0009

Active Ingredients   Buserelin

Description  A synthetic analog of gonadotropin-releasing hormone (GnRH). Buserelin binds to and activates pituitary gonadotropin releasing hormone (GnRH) receptors. Prolonged administration of buserelin results in sustained inhibition of gonadotropin production, suppression of testicular and ovarian steroidogenesis, and reduced levels of circulating gonadotropin and gonadal steroids. Buserelin is more potent that GnRH.

Synonyms  BSRL; Etilamide; HOE 766; ICI 123215; S74-6766; 6-[O-(1,1-Dimethylethyl)-D-serine]-9-(N-ethyl-L-prolinamide)-10-deglycinamide Luteinizing Hormone-Releasing Factor (Pig); Buserelin

Disease  Breast cancer, Contraception, female, Endometriosis, Infertility, in vitro fertilization, Polycystic ovary syndrome, Prostate cancer, Uterine leiomyoma

Classification

  

Peptide and derivative Hormone and analogue

Structure Information


Molecular Formula  C60H86N16O13

Molecular Weight  1239.447

Active Sequence  XHWSYxLRP

Sequence Length  9

Modification  X=Pyr, x=Ser(tBu), 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]-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/C60H86N16O13/c1-7-64-57(87)48-15-11-23-76(48)58(88)41(14-10-22-65-59(61)62)69-51(81)42(24-33(2)3)70-56(86)47(31-89-60(4,5)6)75-52(82)43(25-34-16-18-37(78)19-17-34)71-55(85)46(30-77)74-53(83)44(26-35-28-66-39-13-9-8-12-38(35)39)72-54(84)45(27-36-29-63-32-67-36)73-50(80)40-20-21-49(79)68-40/h8-9,12-13,16-19,28-29,32-33,40-48,66,77-78H,7,10-11,14-15,20-27,30-31H2,1-6H3,(H,63,67)(H,64,87)(H,68,79)(H,69,81)(H,70,86)(H,71,85)(H,72,84)(H,73,80)(H,74,83)(H,75,82)(H4,61,62,65)/t40-,41-,42-,43-,44-,45-,46-,47+,48-/m0/s1

InChI_Key CUWODFFVMXJOKD-UVLQAERKSA-N

SMILES  O=C(N1)CC[C@H]1C(N[C@H](C(N[C@H](C(N[C@@H](CO)C(N[C@H](C(N[C@H](COC(C)(C)C)C(N[C@H](C(N[C@@H](CCCNC(N)=N)C(N2[C@@H](CCC2)C(NCC)=O)=O)=O)CC(C)C)=O)=O)CC3=CC=C(O)C=C3)=O)=O)CC4=CNC5=C4C=CC=C5)=O)CC6=CNC=N6)=O

External Codes


PubChem CID  50225

DrugBank Accession Number  DB06719

NCI Thesaurus Code  C320  

UNII  PXW8U3YXDV   GSRS

CAS  57982-77-1



Drug approval


Drug indication
    Buserelin may be used in the treatment of hormone-responsive cancers such as prostate cancer or breast cancer, estrogen-dependent conditions (such as endometriosis or uterine fibroids), and in assisted reproduction.

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Suprefact 1 mg/ml Solution; Nasal Sanofi-Aventis Canada Inc Prescription DIN: 02225158 1998
Suprefact 1 mg/ml Solution; Subcutaneous Sanofi-Aventis Canada Inc Prescription DIN: 02225166 1996
Suprefact Depot 2 Months 6.3 mg/imp Implant; Subcutaneous Sanofi-Aventis Canada Inc Prescription DIN: 02228955 1997
Suprefact Depot 3 Months 9.45 mg/imp Implant; Subcutaneous Sanofi-Aventis Canada Inc Prescription DIN: 02240749 2000
Suprefact Inj 1Mg/Ml 1 mg/ml Solution; Subcutaneous Sanofi-Aventis Canada Inc Discontinued DIN: 00680028 1988
Suprefact Intranasal Solution 1Mg/Ml 1 mg/ml Spray, Metered; Nasal Hoechst Canada Inc. Discontinued DIN: 00680036 1988
Suprefact Liq 1Mg/Ml 1 mg/ml Spray, Metered; Nasal Hoechst Roussel Canada Inc. Discontinued DIN: 01989669 1993

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT00054106 A Phase I Study Of Combination Neoadjuvant Hormone Therapy And Weekly OGX-011 (Clusterin Antisense Oligonucleotide) Prior To Radical Prostatectomy In Patients With Localized Prostate Cancer Prostate Cancer Phase 1 Treatment
NCT00002633 Phase III Randomized Trial Comparing Total Androgen Blockade Versus Total Androgen Blockade Plus Pelvic Irradiation in Clinical Stage T3-4, N0, M0 Adenocarcinoma of the Prostate Prostate Cancer Phase 3 Treatment
NCT01546987 Phase III Trial of Dose Escalated Radiation Therapy and Standard Androgen Deprivation Therapy (ADT) With a GNRH Agonist vs. Dose Escalated Radiation Therapy and Enhanced ADT With a GNRH Agonist and TAK-700 For Men With High Risk Prostate Cancer Prostate Cancer 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
NCT00627406 A Prospective Randomised Study to Evaluate the Effect of Triggering Ovulation With GnRHa (Buserelin) and Low Dose hCG (Pregnyl) as Compared to the Use of Conventional Doses of hCG (Pregnyl) OHSS (Ovarian Hyperstimulation) Phase 4 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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