Goserelin
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Goserelin

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Goserelin is a gonadotropin releasing hormone agonist with antineoplastic activity. It inhibits estrogen and androgen production and is used predominantly to treat prostate cancer.

Category
Peptide APIs
Catalog number
BAT-010846
CAS number
65807-02-5
Molecular Formula
C59H84N18O14
Molecular Weight
1269.433
Goserelin
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
Synonyms
Zoladex; ZDX; ICI-118630; ICI 118630; ICI118630; Decapeptide I; H-Pyr-His-Trp-Ser-Tyr-D-Ser(tBu)-Leu-Arg-Pro-NHNHCONH2
Appearance
Solid powder
Purity
>98%
Sequence
XHWSYXLRP
Solubility
Soluble
Application
Antineoplastic Agents, Hormonal
InChI
InChI=1S/C59H84N18O14/c1-31(2)22-40(49(82)68-39(12-8-20-64-57(60)61)56(89)77-21-9-13-46(77)55(88)75-76-58(62)90)69-54(87)45(29-91-59(3,4)5)74-50(83)41(23-32-14-16-35(79)17-15-32)70-53(86)44(28-78)73-51(84)42(24-33-26-65-37-11-7-6-10-36(33)37)71-52(85)43(25-34-27-63-30-66-34)72-48(81)38-18-19-47(80)67-38/h6-7,10-11,14-17,26-27,30-31,38-46,65,78-79H,8-9,12-13,18-25,28-29H2,1-5H3,(H,63,66)(H,67,80)(H,68,82)(H,69,87)(H,70,86)(H,71,85)(H,72,81)(H,73,84)(H,74,83)(H,75,88)(H4,60,61,64)(H3,62,76,90)/t38-,39-,40-,41-,42-,43-,44-,45+,46-/m0/s1
InChI Key
BLCLNMBMMGCOAS-URPVMXJPSA-N
Canonical SMILES
CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NNC(=O)N)NC(=O)C(COC(C)(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
1.What is the role of androgen deprivation therapy in the treatment of locally advanced prostate cancer?
Kollmeier MA;Zelefsky MJ Nat Clin Pract Urol. 2008 Nov;5(11):584-5. doi: 10.1038/ncpuro1217. Epub 2008 Sep 23.
This Practice Point commentary discusses the paper by Horwitz and colleagues, which reported the long-term results of the RTOG 92-02 trial in which patients with locally advanced, node-negative prostate cancer who were treated with neoadjuvant-concurrent hormone ablation therapy and external beam radiation therapy (70 Gy) were subsequently randomized to receive either no further androgen deprivation or long-term (2-year) goserelin therapy. The results at 10 years confirm biochemical and clinical outcome benefits with the use of long-term androgen deprivation therapy for patients treated with conventional-dose radiotherapy. How these results should best be incorporated into dose-escalated radiotherapeutic approaches remains unclear, however, and this issue requires further investigation.
2.Goserelin versus danazol in the treatment of endometriosis.
Giorgino FL;Cetera C;de Laurentiis G Clin Exp Obstet Gynecol. 1991;18(2):127-31.
Fourteen patients affected by endometriosis were treated by Danazol and by Goserelin. The two treatments were compared. From the study it emerged that both treatments were equally effective; however, the analogs gave a more favourable therapeutic profile.
3.Adjuvant endocrine therapy plus zoledronic acid in premenopausal women with early-stage breast cancer: 5-year follow-up of the ABCSG-12 bone-mineral density substudy.
Gnant M;Mlineritsch B;Luschin-Ebengreuth G;Kainberger F;Kässmann H;Piswanger-Sölkner JC;Seifert M;Ploner F;Menzel C;Dubsky P;Fitzal F;Bjelic-Radisic V;Steger G;Greil R;Marth C;Kubista E;Samonigg H;Wohlmuth P;Mittlböck M;Jakesz R;Austrian Breast and Colorectal Cancer Study Group (ABCSG) Lancet Oncol. 2008 Sep;9(9):840-9. doi: 10.1016/S1470-2045(08)70204-3. Epub 2008 Aug 19.
BACKGROUND: ;The Austrian Breast and Colorectal Cancer Study Group trial-12 (ABCSG-12) bone substudy assesses zoledronic acid for preventing bone loss associated with adjuvant endocrine therapy and reports on long-term findings of bone-mineral density (BMD) during 3 years of treatment and 2 years after completing adjuvant treatment with or without zoledronic acid. The aim of this substudy is to gain insight into bone health in this setting.;METHODS: ;ABCSG-12 is a randomised, open-label, phase III, 4-arm trial comparing tamoxifen (20 mg/day orally) and goserelin (3.6 mg subcutaneously every 28 days) versus anastrozole (1 mg/day orally) and goserelin (3.6 mg subcutaneously every 28 days), both with or without zoledronic acid (4 mg intravenously every 6 months) for 3 years in premenopausal women with endocrine-responsive breast cancer. This prospective bone subprotocol measured BMD at 0, 6, 12, 36, and 60 months. The primary endpoint of the bone substudy (secondary endpoint in the main trial) was change in BMD at 12 months, assessed by dual-energy X-ray absorptiometry in assessable patients. Analyses were intention to treat. Statistical significance was assessed by t tests. The ABCSG-12 trial is registered on the ClinicalTrials.
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