Zoptarelin doxorubicin | CAS#139570-93-7 | LHRH agonist

MedKoo Cat#: 592890 | Name: Zoptarelin doxorubicin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Zoptarelin doxorubicin, also known as AEZS-108, is an LHRH agonist. Zoptarelin doxorubicin is a peptide agonist of the gonadotropin releasing hormone-1 receptor (GnRH-1R) that is conjugated to the anthracycline antibiotic doxorubicin with potential antineoplastic activity. Zoptarelin doxorubicin binds to GnRH-1Rs, which may be highly expressed on endometrial and ovarian tumor cell membrane surfaces, and is internalized. Once inside the cell, the doxorubicin moiety of this agent intercalates into DNA and inhibits the topoisomerase II activity, which may result in the inhibition of tumor cell DNA replication and tumor cell proliferation

Chemical Structure

Zoptarelin doxorubicin

CAS#139570-93-7

Theoretical Analysis

MedKoo Cat#: 592890

Name: Zoptarelin doxorubicin

CAS#: 139570-93-7

Chemical Formula:

Exact Mass:

Molecular Weight:

Elemental Analysis:

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Zoptarelin doxorubicin; AEZS-108; AEZS 108; AEZS108;

IUPAC/Chemical Name

Luteinizing hormone-releasing factor (pig), 6-(N6-(5-(2-(4-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl)-2-oxoethoxy)-1,5-dioxopentyl)-D-lysine)-, (2S-cis)-

InChi Key

OOUACICUAVTCEC-LZHWUUGESA-N

InChi Code

1S/C91H117N19O26/c1-44(2)31-58(83(125)104-57(17-11-29-98-90(94)95)89(131)110-30-12-18-63(110)88(130)100-40-67(93)114)105-81(123)55(16-7-8-28-97-68(115)20-10-21-70(117)134-42-66(113)91(132)36-52-73(65(37-91)136-71-35-53(92)76(118)45(3)135-71)80(122)75-74(78(52)120)77(119)51-14-9-19-64(133-4)72(51)79(75)121)103-84(126)59(32-46-22-24-49(112)25-23-46)106-87(129)62(41-111)109-85(127)60(33-47-38-99-54-15-6-5-13-50(47)54)107-86(128)61(34-48-39-96-43-101-48)108-82(124)56-26-27-69(116)102-56/h5-6,9,13-15,19,22-25,38-39,43-45,53,55-63,65,71,76,99,111-112,118,120,122,132H,7-8,10-12,16-18,20-21,26-37,40-42,92H2,1-4H3,(H2,93,114)(H,96,101)(H,97,115)(H,100,130)(H,102,116)(H,103,126)(H,104,125)(H,105,123)(H,106,129)(H,107,128)(H,108,124)(H,109,127)(H4,94,95,98)/t45-,53-,55+,56-,57-,58-,59-,60-,61-,62-,63-,65-,71-,76+,91-/m0/s1

SMILES Code

COc1c2c(C(c3c(C2=O)c(O)c4c(C[C@](C[C@@H]4O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)N)(C(COC(CCCC(NCCCC[C@H](C(N[C@H](C(N[C@H](C(N6CCC[C@H]6C(NCC(N)=O)=O)=O)CCCNC(N)=N)=O)CC(C)C)=O)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H]7CCC(N7)=O)=O)Cc8[nH]cnc8)=O)Cc(c[nH]9)c%10c9cccc%10)=O)CO)=O)Cc%11ccc(O)cc%11)=O)=O)=O)=O)O)c3O)=O)ccc1

Appearance

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

Shelf Life

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 0.00 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.

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

1: Emons G, Gorchev G, Sehouli J, Wimberger P, Stähle A, Hanker L, Hilpert F, Sindermann H, Gründker C, Harter P. Efficacy and safety of AEZS-108 (INN: zoptarelin doxorubicin acetate) an LHRH agonist linked to doxorubicin in women with platinum refractory or resistant ovarian cancer expressing LHRH receptors: a multicenter phase II trial of the ago-study group (AGO GYN 5). Gynecol Oncol. 2014 Jun;133(3):427-32. doi: 10.1016/j.ygyno.2014.03.576. Epub 2014 Apr 5. PubMed PMID: 24713545. 2: Emons G, Gorchev G, Harter P, Wimberger P, Stähle A, Hanker L, Hilpert F, Beckmann MW, Dall P, Gründker C, Sindermann H, Sehouli J. Efficacy and safety of AEZS-108 (LHRH agonist linked to doxorubicin) in women with advanced or recurrent endometrial cancer expressing LHRH receptors: a multicenter phase 2 trial (AGO-GYN5). Int J Gynecol Cancer. 2014 Feb;24(2):260-5. doi: 10.1097/IGC.0000000000000044. PubMed PMID: 24418927; PubMed Central PMCID: PMC3921259. 3: Engel JB, Tinneberg HR, Rick FG, Berkes E, Schally AV. Targeting of Peptide Cytotoxins to LHRH Receptors For Treatment of Cancer. Curr Drug Targets. 2016;17(5):488-94. Review. PubMed PMID: 26951061. 4: Schally AV, Block NL, Rick FG. New therapies for relapsed castration-resistant prostate cancer based on peptide analogs of hypothalamic hormones. Asian J Androl. 2015 Nov-Dec;17(6):925-8. doi: 10.4103/1008-682X.152819. PubMed PMID: 26112478; PubMed Central PMCID: PMC4814950. 5: Emons G, Kaufmann M, Gorchev G, Tsekova V, Gründker C, Günthert AR, Hanker LC, Velikova M, Sindermann H, Engel J, Schally AV. Dose escalation and pharmacokinetic study of AEZS-108 (AN-152), an LHRH agonist linked to doxorubicin, in women with LHRH receptor-positive tumors. Gynecol Oncol. 2010 Dec;119(3):457-61. doi: 10.1016/j.ygyno.2010.08.003. Epub 2010 Sep 9. PubMed PMID: 20828803. 6: Bajo AM, Schally AV, Halmos G, Nagy A. Targeted doxorubicin-containing luteinizing hormone-releasing hormone analogue AN-152 inhibits the growth of doxorubicin-resistant MX-1 human breast cancers. Clin Cancer Res. 2003 Sep 1;9(10 Pt 1):3742-8. PubMed PMID: 14506166. 7: Hanke N, Teifel M, Moj D, Wojtyniak JG, Britz H, Aicher B, Sindermann H, Ammer N, Lehr T. A physiologically based pharmacokinetic (PBPK) parent-metabolite model of the chemotherapeutic zoptarelin doxorubicin-integration of in vitro results, Phase I and Phase II data and model application for drug-drug interaction potential analysis. Cancer Chemother Pharmacol. 2018 Feb;81(2):291-304. doi: 10.1007/s00280-017-3495-2. Epub 2017 Dec 4. PubMed PMID: 29204687. 8: Krebs LJ, Wang X, Nagy A, Schally AV, Prasad PN, Liebow C. A conjugate of doxorubicin and an analog of Luteinizing Hormone-Releasing Hormone shows increased efficacy against oral and laryngeal cancers. Oral Oncol. 2002 Oct;38(7):657-663. PubMed PMID: 12353491. 9: Seitz S, Buchholz S, Schally AV, Weber F, Klinkhammer-Schalke M, Inwald EC, Perez R, Rick FG, Szalontay L, Hohla F, Segerer S, Kwok CW, Ortmann O, Engel JB. Triple negative breast cancers express receptors for LHRH and are potential therapeutic targets for cytotoxic LHRH-analogs, AEZS 108 and AEZS 125. BMC Cancer. 2014 Nov 19;14:847. doi: 10.1186/1471-2407-14-847. PubMed PMID: 25410881; PubMed Central PMCID: PMC4289186. 10: Liu SV, Tsao-Wei DD, Xiong S, Groshen S, Dorff TB, Quinn DI, Tai YC, Engel J, Hawes D, Schally AV, Pinski JK. Phase I, dose-escalation study of the targeted cytotoxic LHRH analog AEZS-108 in patients with castration- and taxane-resistant prostate cancer. Clin Cancer Res. 2014 Dec 15;20(24):6277-83. doi: 10.1158/1078-0432.CCR-14-0489. Epub 2014 Oct 2. PubMed PMID: 25278449. 11: Popovics P, Schally AV, Szalontay L, Block NL, Rick FG. Targeted cytotoxic analog of luteinizing hormone-releasing hormone (LHRH), AEZS-108 (AN-152), inhibits the growth of DU-145 human castration-resistant prostate cancer in vivo and in vitro through elevating p21 and ROS levels. Oncotarget. 2014 Jun 30;5(12):4567-78. PubMed PMID: 24994120; PubMed Central PMCID: PMC4147346. 12: Szepeshazi K, Schally AV, Block NL, Halmos G, Nadji M, Szalontay L, Vidaurre I, Abi-Chaker A, Rick FG. Powerful inhibition of experimental human pancreatic cancers by receptor targeted cytotoxic LH-RH analog AEZS-108. Oncotarget. 2013 May;4(5):751-60. PubMed PMID: 23744510; PubMed Central PMCID: PMC3742835. 13: Szepeshazi K, Schally AV, Keller G, Block NL, Benten D, Halmos G, Szalontay L, Vidaurre I, Jaszberenyi M, Rick FG. Receptor-targeted therapy of human experimental urinary bladder cancers with cytotoxic LH-RH analog AN-152 [AEZS- 108]. Oncotarget. 2012 Jul;3(7):686-99. PubMed PMID: 22824624; PubMed Central PMCID: PMC3443252. 14: Günthert AR, Gründker C, Bongertz T, Schlott T, Nagy A, Schally AV, Emons G. Internalization of cytotoxic analog AN-152 of luteinizing hormone-releasing hormone induces apoptosis in human endometrial and ovarian cancer cell lines independent of multidrug resistance-1 (MDR-1) system. Am J Obstet Gynecol. 2004 Oct;191(4):1164-72. PubMed PMID: 15507937. 15: Arencibia JM, Schally AV, Krupa M, Bajo AM, Nagy A, Szepeshazi K, Plonowski A. Targeting of doxorubicin to ES-2 human ovarian cancers in nude mice by linking to an analog of luteinizing hormone-releasing hormone improves its effectiveness. Int J Oncol. 2001 Sep;19(3):571-7. PubMed PMID: 11494038. 16: Jaszberenyi M, Schally AV, Block NL, Nadji M, Vidaurre I, Szalontay L, Rick FG. Inhibition of U-87 MG glioblastoma by AN-152 (AEZS-108), a targeted cytotoxic analog of luteinizing hormone-releasing hormone. Oncotarget. 2013 Mar;4(3):422-32. PubMed PMID: 23518876; PubMed Central PMCID: PMC3717305. 17: Günthert AR, Gründker C, Bongertz T, Nagy A, Schally AV, Emons G. Induction of apoptosis by AN-152, a cytotoxic analog of luteinizing hormone-releasing hormone (LHRH), in LHRH-R positive human breast cancer cells is independent of multidrug resistance-1 (MDR-1) system. Breast Cancer Res Treat. 2004 Oct;87(3):255-64. PubMed PMID: 15528968. 18: Gründker C, Völker P, Griesinger F, Ramaswamy A, Nagy A, Schally AV, Emons G. Antitumor effects of the cytotoxic luteinizing hormone-releasing hormone analog AN-152 on human endometrial and ovarian cancers xenografted into nude mice. Am J Obstet Gynecol. 2002 Sep;187(3):528-37. PubMed PMID: 12237622. 19: Westphalen S, Kotulla G, Kaiser F, Krauss W, Werning G, Elsasser HP, Nagy A, Schulz KD, Grundker C, Schally AV, Emons G. Receptor mediated antiproliferative effects of the cytotoxic LHRH agonist AN-152 in human ovarian and endometrial cancer cell lines. Int J Oncol. 2000 Nov;17(5):1063-9. PubMed PMID: 11029513. 20: Engel J, Emons G, Pinski J, Schally AV. AEZS-108 : a targeted cytotoxic analog of LHRH for the treatment of cancers positive for LHRH receptors. Expert Opin Investig Drugs. 2012 Jun;21(6):891-9. doi: 10.1517/13543784.2012.685128. Review. PubMed PMID: 22577891.