Goserelin Acetate
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Goserelin Acetate

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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.

Category
Peptide APIs
Catalog number
BAT-015268
CAS number
145781-92-6
Molecular Formula
C61H88N18O16
Molecular Weight
1329.49
Goserelin Acetate
Size Price Stock Quantity
100 mg $519 In stock
IUPAC Name
acetic acid;(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
(D-Ser(tBu)6,Azagly10)-LHRH Acetate; Zoladex; 6-[O-(1,1-Dimethylethyl)-D-serine]-1-9-luteinizing Hormone-releasing Factor (swine) 2-(Aminocarbonyl)hydrazide Acetate; Fertilan; Pyr-His-Trp-Ser-Tyr-D-Ser(tBu)-Leu-Arg-Pro-Azagly-NH2.CH3CO2H; L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-O-tert-butyl-D-seryl-L-leucyl-L-arginyl-N'-carbamoyl-L-prolinehydrazide acetic acid
Related CAS
65807-02-5 (free base)
Appearance
White to Off-white Solid
Purity
98%
Melting Point
>170°C (dec.)
Sequence
Pyr-HWSY-S(tBu)-LRP-Azagly-NH2.CH3CO2H
Storage
Store at -20°C
Solubility
Soluble in DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
Application
Antineoplastic Agents, Hormonal
InChI
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
InChI Key
IKDXDQDKCZPQSZ-JHYYTBFNSA-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.CC(=O)O
1.Hydronephrosis associated with ureteral metastasis of prostate cancer: A rare case report.
Zhang D1, Li H1, Gan W1. Mol Clin Oncol. 2016 Apr;4(4):597-598. Epub 2016 Feb 10.
Prostate cancer is one of the most common male malignancies, although it rarely metastasizes to the ureter. The present case study reported a 63-year-old man who presented with asymptomatic right hydronephrosis, detected by ultrasound. Computed tomography urography demonstrated right hydronephrosis, secondary to thickening of the distal ureter. The patient's serum concentration of prostate specific antigen was 111.400 ng/ml, and a prostate needle biopsy revealed prostate adenocarcinoma, with a Gleason score of 4+5=9. Renal scintigraphy revealed poor excretion of the right kidney. A nephroureterectomy was subsequently performed, and a histological examination revealed a metastatic prostate adenocarcinoma of the ureter. Combined androgen blockage therapy with bicalutamide (50 mg, once daily) and goserelin (3.6 mg, once a month) was administered to the patient. At 3 months of follow-up, the patient's PSA levels had decreased to 0.322 ng/ml; at 6 months of follow-up, the PSA levels had further decreased to 0.
2.Is Estradiol Monitoring Necessary in Women Receiving Ovarian Suppression for Breast Cancer?
Papakonstantinou A1, Foukakis T1, Rodriguez-Wallberg KA1, Bergh J2. J Clin Oncol. 2016 Mar 7. pii: JCO653493. [Epub ahead of print]
The Oncology Grand Rounds series is designed to place original reports published in the Journal into clinical context. A case presentation is followed by a description of diagnostic and management challenges, a review of the relevant literature, and a summary of the authors' suggested management approaches. The goal of this series is to help readers better understand how to apply the results of key studies, including those published in Journal of Clinical Oncology, to patients seen in their own clinical practice.A 36-year-old premenopausal woman had been diagnosed with stage III breast cancer. After an initial biopsy confirmed breast cancer, she underwent mastectomy and axillary node dissection for a left-sided breast cancer, measuring 7 cm. The tumor had lobular histology and was considered grade 2 of 3. Metastatic carcinoma was identified in 10 of 13 axillary nodes. Immunohistochemical studies showed that the tumor was strongly positive for estrogen and progesterone receptor expression and had a Ki-67 score of 15% (> 20% is considered high according to a Swedish quality control study and the St Gallen Expert Consensus).
3.Effect of goserelin and leuprolide added to the semen on reproductive performance in rabbits - Short communication.
Gogol P1. Acta Vet Hung. 2016 Mar;64(1):116-9. doi: 10.1556/004.2016.012.
The aim of this study was to evaluate the ability of two synthetic GnRH analogues, goserelin and leuprolide, to induce ovulation in rabbit does using intravaginal administration. A total of 252 primiparous lactating does were randomly divided into five groups that, at the time of insemination, received the following treatments for ovulation induction: 1 µg of buserelin administered intramuscularly (control group), 5 µg of goserelin added to the semen dose (Group G5), 10 µg of goserelin added to the semen dose (Group G10), 5 µg of leuprolide added to the semen dose (Group L5), and 10 µg of leuprolide added to the semen dose (Group L10). The kindling rate was 80.5% in Group G10 and 75.0% in Group L10; these values are comparable to the kindling rate obtained in the control group (85.9%). The kindling rates in Groups G5 and L5 were significantly lower than in the control group (60.0%, 54.2% and 85.9%, respectively). The number of live-born rabbits was not significantly affected by the ovulation induction treatment.
4.Association of Remitting Seronegative Symmetrical Synovitis with Pitting Edema, Polymyalgia Rheumatica, and Adenocarcinoma of the Prostate.
Emamifar A1, Hess S2, Gildberg-Mortensen R1, Jensen Hansen IM3. Am J Case Rep. 2016 Feb 3;17:60-4.
BACKGROUND Remitting seronegative symmetrical synovitis with pitting edema (RS3PE) is a rare condition that occurs in elderly individuals. It can present alone or in association with various rheumatic or malignant diseases. CASE REPORT An 83-year-old man presented with anemia, hyper-sedimentation, and pitting edema of the back of the hands. The patient complained of pain and stiffness of the shoulder and hip girdles, especially in the morning. He was previously diagnosed with adenocarcinoma of the prostate. After 3 years of watchful waiting, treatment with goserelin, a gonadotropin releasing hormone agonist, was started, when PSA had increased to 67.9 µg/l. About 1 year before the cancer treatment, the patient also presented with sore and swollen hands, compatible with RS3PE, which remitted after a few months of prostatic cancer treatment. Thorough laboratory evaluation was performed upon admission to the Rheumatology Department and he was referred for FDG PET/CT on suspicion of metastases of the previously diagnosed prostatic cancer.
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