Goserelin Acetate
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MedKoo CAT#: 100420

CAS#: 145781-92-6 (acetate)

Description: Goserelin is 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.


Chemical Structure

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Goserelin Acetate
CAS# 145781-92-6 (acetate)

Theoretical Analysis

MedKoo Cat#: 100420
Name: Goserelin Acetate
CAS#: 145781-92-6 (acetate)
Chemical Formula: C61H88N18O16
Exact Mass: 0.00
Molecular Weight: 1,329.485
Elemental Analysis: C, 55.11; H, 6.67; N, 18.96; O, 19.25

Price and Availability

Size Price Availability Quantity
25mg USD 225 Ready to ship
50mg USD 350 Ready to ship
100mg USD 585 Ready to ship
200mg USD 1025 Ready to ship
500mg USD 2150 Ready to ship
1g USD 3550 2 weeks
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Related CAS #: 65807-02-5 (free base)   145781-92-6 (acetate)  

Synonym: ICI118630; ICI-118630; ICI 118630; Goserelin Acetate; brand name: Zoladex.

IUPAC/Chemical Name: (S)-N-((6S,9S,12R,15S,18S,21S,24S)-21-((1H-indol-3-yl)methyl)-1-amino-12-(tert-butoxymethyl)-6-((S)-2-(2-carbamoylhydrazine-1-carbonyl)pyrrolidine-1-carbonyl)-15-(4-hydroxybenzyl)-18-(hydroxymethyl)-25-(1H-imidazol-4-yl)-1-imino-9-isobutyl-8,11,14,17,20,23-hexaoxo-2,7,10,13,16,19,22-heptaazapentacosan-24-yl)-5-oxopyrrolidine-2-carboxamide acetate

InChi Key: IKDXDQDKCZPQSZ-JHYYTBFNSA-N

InChi Code: InChI=1S/C59H84N18O14.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t38-,39-,40-,41-,42-,43-,44-,45+,46-;/m0./s1

SMILES Code: OC(C)=O.NC(NCCC[C@H](NC([C@@H](NC([C@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CC1=CNC=N1)NC([C@@H]2CCC(N2)=O)=O)=O)CC3=CNC4=C3C=CC=C4)=O)CO)=O)CC5=CC=C(C=C5)O)=O)COC(C)(C)C)=O)CC(C)C)=O)C(N6CCC[C@H]6C(NNC(N)=O)=O)=O)=N

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO and in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:  Goserelin (free base) Chemical Formula: C59H84N18O14 Exact Mass: 1268.6414 Molecular Weight: 1269.4330 Elemental Analysis: C, 55.82; H, 6.67; N, 19.86; O, 17.64

Biological target: Goserelin acetate (ICI-118630 acetate) functions as a GnRH agonist.
In vitro activity: As shown in Fig. 6A, FOXO1 expression was significantly increased (P<0.05) and the goserelin-mediated promotion of apoptosis was abrogated by FOXO1-siRNA (P<0.05; Fig. 6C). As FOXO1 is a downstream target of the PI3K/AKT signaling pathway, the expression of AKT/p-AKT was analyzed. As shown in Fig. 6B, goserelin downregulated p-AKT (Ser473) expression. Meanwhile, the expression of FOXO1 was increased by AKT-siRNA (P<0.05; Fig. 6D). Taken together, these data suggest that goserelin may promote EOC cell apoptosis by upregulating FOXO1 through the PI3K/AKT signaling pathway. Reference: Oncol Rep. 2018 Mar;39(3):1034-1042. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5802025/
In vivo activity: In vivo images of subcutaneous xenograft tumors in nude mice revealed that the subcutaneous xenograft tumor model was constructed successfully (Fig. 7A). TUNEL staining showed that goserelin significantly increased the proportion of apoptotic cells in the subcutaneous xenograft tumors (P<0.05; Fig. 7B and C). In the goserelin group, p-AKT expression was significantly lower, while the expression of FOXO1 and GnRHR were significantly increased compared with the NS group (P<0.05; Fig. 7B and D). Reference: Oncol Rep. 2018 Mar;39(3):1034-1042. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5802025/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 29.0 21.81

Preparing Stock Solutions

The following data is based on the product molecular weight 1,329.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Zhang N, Qiu J, Zheng T, Zhang X, Hua K, Zhang Y. Goserelin promotes the apoptosis of epithelial ovarian cancer cells by upregulating forkhead box O1 through the PI3K/AKT signaling pathway. Oncol Rep. 2018 Mar;39(3):1034-1042. doi: 10.3892/or.2017.6159. Epub 2017 Dec 15. PMID: 29286125; PMCID: PMC5802025.
In vitro protocol: 1. Zhang N, Qiu J, Zheng T, Zhang X, Hua K, Zhang Y. Goserelin promotes the apoptosis of epithelial ovarian cancer cells by upregulating forkhead box O1 through the PI3K/AKT signaling pathway. Oncol Rep. 2018 Mar;39(3):1034-1042. doi: 10.3892/or.2017.6159. Epub 2017 Dec 15. PMID: 29286125; PMCID: PMC5802025.
In vivo protocol: 1. Zhang N, Qiu J, Zheng T, Zhang X, Hua K, Zhang Y. Goserelin promotes the apoptosis of epithelial ovarian cancer cells by upregulating forkhead box O1 through the PI3K/AKT signaling pathway. Oncol Rep. 2018 Mar;39(3):1034-1042. doi: 10.3892/or.2017.6159. Epub 2017 Dec 15. PMID: 29286125; PMCID: PMC5802025.

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1: Roach M 3rd, Izaguirre A. Goserelin acetate in combination with radiotherapy for prostate cancer. Expert Opin Pharmacother. 2007 Feb;8(2):257-64. Review. PubMed PMID: 17257094.

2: Tsukagoshi S. [A new LH-RH agonist for treatment of prostate cancer, 3-month controlled-release formulation of goserelin acetate (Zoladex LA 10.8 mg depot)--outline of pre-clinical and clinical studies]. Gan To Kagaku Ryoho. 2002 Sep;29(9):1675-87. Review. Japanese. PubMed PMID: 12355959.

3: Koga H, Naito S. [Goserelin acetate depot, LH-RH agonist; its properties and therapeutic effects in prostate cancer]. Nihon Rinsho. 2000 Jul;58 Suppl:186-90. Review. Japanese. PubMed PMID: 11022711.

4: Goldspiel BR, Kohler DR. Goserelin acetate implant: a depot luteinizing hormone-releasing hormone analog for advanced prostate cancer. DICP. 1991 Jul-Aug;25(7-8):796-804. Review. PubMed PMID: 1835221.