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MedKoo Cat#: 598696 | Name: Leurubicin

Description:

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

Leurubicin is a prodrug of doxorubicin.

Chemical Structure

Leurubicin
CAS#70774-25-3

Theoretical Analysis

MedKoo Cat#: 598696

Name: Leurubicin

CAS#: 70774-25-3

Chemical Formula: C33H40N2O12

Exact Mass: 656.2581

Molecular Weight: 656.68

Elemental Analysis: C, 60.36; H, 6.14; N, 4.27; O, 29.24

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
Leurubicin; N-Leucyldoxorubicin; Leurubicina;
IUPAC/Chemical Name
(S)-2-amino-N-((2S,3S,4S,6R)-3-hydroxy-2-methyl-6-(((1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl)oxy)tetrahydro-2H-pyran-4-yl)-4-methylpentanamide
InChi Key
HROXIDVVXKDCBD-ZUWKMVCBSA-N
InChi Code
InChI=1S/C33H40N2O12/c1-13(2)8-17(34)32(43)35-18-9-22(46-14(3)27(18)38)47-20-11-33(44,21(37)12-36)10-16-24(20)31(42)26-25(29(16)40)28(39)15-6-5-7-19(45-4)23(15)30(26)41/h5-7,13-14,17-18,20,22,27,36,38,40,42,44H,8-12,34H2,1-4H3,(H,35,43)/t14-,17-,18-,20-,22-,27+,33-/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)NC([C@H](CC(C)C)N)=O)(C(CO)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 656.68 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
1: Guiu B, Schmitt A, Reinhardt S, Fohlen A, Pohl T, Wendremaire M, Denys A, Blümmel J, Boulin M. Idarubicin-loaded ONCOZENE drug-eluting embolic agents for chemoembolization of hepatocellular carcinoma: in vitro loading and release and in vivo pharmacokinetics. J Vasc Interv Radiol. 2015 Feb;26(2):262-70. doi: 10.1016/j.jvir.2014.08.021. Epub 2014 Oct 11. PubMed PMID: 25311967. 2: Creutzig U, Zimmermann M, Bourquin JP, Dworzak MN, Fleischhack G, Graf N, Klingebiel T, Kremens B, Lehrnbecher T, von Neuhoff C, Ritter J, Sander A, Schrauder A, von Stackelberg A, Starý J, Reinhardt D. Randomized trial comparing liposomal daunorubicin with idarubicin as induction for pediatric acute myeloid leukemia: results from Study AML-BFM 2004. Blood. 2013 Jul 4;122(1):37-43. doi: 10.1182/blood-2013-02-484097. Epub 2013 May 23. PubMed PMID: 23704089. 3: Ozluer C, Kara HE. In vitro DNA binding studies of anticancer drug idarubicin using spectroscopic techniques. J Photochem Photobiol B. 2014 Sep 5;138:36-42. doi: 10.1016/j.jphotobiol.2014.05.015. Epub 2014 May 29. PubMed PMID: 24911270. 4: Boulin M, Hillon P, Cercueil JP, Bonnetain F, Dabakuyo S, Minello A, Jouve JL, Lepage C, Bardou M, Wendremaire M, Guerard P, Denys A, Grandvuillemin A, Chauffert B, Bedenne L, Guiu B. Idarubicin-loaded beads for chemoembolisation of hepatocellular carcinoma: results of the IDASPHERE phase I trial. Aliment Pharmacol Ther. 2014 Jun;39(11):1301-13. doi: 10.1111/apt.12746. Epub 2014 Apr 16. PubMed PMID: 24738629. 5: Gunduz U, Keskin T, Tansık G, Mutlu P, Yalcin S, Unsoy G, Yakar A, Khodadust R, Gunduz G. Idarubicin-loaded folic acid conjugated magnetic nanoparticles as a targetable drug delivery system for breast cancer. Biomed Pharmacother. 2014 Jul;68(6):729-36. doi: 10.1016/j.biopha.2014.08.013. Epub 2014 Aug 22. PubMed PMID: 25194441. 6: Olivier G, Clavert A, Lacotte-Thierry L, Gardembas M, Escoffre-Barbe M, Brion A, Cumin I, Legouffe E, Solal-Celigny P, Chabin M, Ingrand P, Colombat P, Delwail V. A phase 1 dose escalation study of idarubicin combined with methotrexate, vindesine, and prednisolone for untreated elderly patients with primary central nervous system lymphoma. The GOELAMS LCP 99 trial. Am J Hematol. 2014 Nov;89(11):1024-9. doi: 10.1002/ajh.23812. Epub 2014 Aug 27. PubMed PMID: 25052698. 7: Lu T, Lokerse WJM, Seynhaeve ALB, Koning GA, Ten Hagen TLM. Formulation and optimization of idarubicin thermosensitive liposomes provides ultrafast triggered release at mild hyperthermia and improves tumor response. J Control Release. 2015 Dec 28;220(Pt A):425-437. doi: 10.1016/j.jconrel.2015.10.056. Epub 2015 Nov 3. PubMed PMID: 26541464. 8: Li K, Hu C, Mei C, Ren Z, Vera JC, Zhuang Z, Jin J, Tong H. Sequential combination of decitabine and idarubicin synergistically enhances anti-leukemia effect followed by demethylating Wnt pathway inhibitor promoters and downregulating Wnt pathway nuclear target. J Transl Med. 2014 Jun 12;12:167. doi: 10.1186/1479-5876-12-167. PubMed PMID: 24923330; PubMed Central PMCID: PMC4082426. 9: Horton TM, Perentesis JP, Gamis AS, Alonzo TA, Gerbing RB, Ballard J, Adlard K, Howard DS, Smith FO, Jenkins G, Kelder A, Schuurhuis GJ, Moscow JA. A Phase 2 study of bortezomib combined with either idarubicin/cytarabine or cytarabine/etoposide in children with relapsed, refractory or secondary acute myeloid leukemia: a report from the Children's Oncology Group. Pediatr Blood Cancer. 2014 Oct;61(10):1754-60. doi: 10.1002/pbc.25117. Epub 2014 Jun 29. PubMed PMID: 24976003; PubMed Central PMCID: PMC4247259. 10: Advani AS, McDonough S, Copelan E, Willman C, Mulford DA, List AF, Sekeres MA, Othus M, Appelbaum FR. SWOG0919: a Phase 2 study of idarubicin and cytarabine in combination with pravastatin for relapsed acute myeloid leukaemia. Br J Haematol. 2014 Oct;167(2):233-7. doi: 10.1111/bjh.13035. Epub 2014 Jul 18. PubMed PMID: 25039477; PubMed Central PMCID: PMC4188732. 11: Boulin M, Schmitt A, Delhom E, Cercueil JP, Wendremaire M, Imbs DC, Fohlen A, Panaro F, Herrero A, Denys A, Guiu B. Improved stability of lipiodol-drug emulsion for transarterial chemoembolisation of hepatocellular carcinoma results in improved pharmacokinetic profile: Proof of concept using idarubicin. Eur Radiol. 2016 Feb;26(2):601-9. doi: 10.1007/s00330-015-3855-4. Epub 2015 Jun 11. PubMed PMID: 26060065. 12: Trifilio S, Zhou Z, Mehta J, Czerniak C, Pi J, Greenberg D, Koslosky M, Pantiru M, Altman J. Idarubicin appears equivalent to dose-intense daunorubicin for remission induction in patients with acute myeloid leukemia. Leuk Res. 2013 Aug;37(8):868-71. doi: 10.1016/j.leukres.2013.04.009. Epub 2013 May 31. PubMed PMID: 23726414. 13: Eda Satana Kara H. Redox mechanism of anticancer drug idarubicin and in-situ evaluation of interaction with DNA using an electrochemical biosensor. Bioelectrochemistry. 2014 Oct;99:17-23. doi: 10.1016/j.bioelechem.2014.06.002. Epub 2014 Jun 13. PubMed PMID: 24967755. 14: Willemze R, Suciu S, Muus P, Halkes CJ, Meloni G, Meert L, Karrasch M, Rapion J, Vignetti M, Amadori S, de Witte T, Marie JP. Clofarabine in combination with a standard remission induction regimen (cytosine arabinoside and idarubicin) in patients with previously untreated intermediate and bad-risk acute myelogenous leukemia (AML) or high-risk myelodysplastic syndrome (HR-MDS): phase I results of an ongoing phase I/II study of the leukemia groups of EORTC and GIMEMA (EORTC GIMEMA 06061/AML-14A trial). Ann Hematol. 2014 Jun;93(6):965-75. doi: 10.1007/s00277-014-2056-6. Epub 2014 Mar 29. PubMed PMID: 24682421. 15: Iland HJ, Bradstock K, Supple SG, Catalano A, Collins M, Hertzberg M, Browett P, Grigg A, Firkin F, Hugman A, Reynolds J, Di Iulio J, Tiley C, Taylor K, Filshie R, Seldon M, Taper J, Szer J, Moore J, Bashford J, Seymour JF; Australasian Leukaemia and Lymphoma Group. All-trans-retinoic acid, idarubicin, and IV arsenic trioxide as initial therapy in acute promyelocytic leukemia (APML4). Blood. 2012 Aug 23;120(8):1570-80; quiz 1752. Epub 2012 Jun 19. PubMed PMID: 22715121. 16: Hong M, Miao KR, Zhang R, Lu H, Liu P, Xu W, Chen LJ, Zhang SJ, Wu HX, Qiu HX, Li JY, Qian SX. High-dose idarubicin plus busulfan as conditioning regimen to autologous stem cell transplantation: promising post-remission therapy for acute myeloid leukemia in first complete remission? Med Oncol. 2014 Jun;31(6):980. doi: 10.1007/s12032-014-0980-x. Epub 2014 May 7. PubMed PMID: 24802329. 17: Sekine L, Morais VD, Lima KM, Onsten TG, Ziegelmann PK, Ribeiro RA. Conventional and high-dose daunorubicin and idarubicin in acute myeloid leukaemia remission induction treatment: a mixed treatment comparison meta-analysis of 7258 patients. Hematol Oncol. 2015 Dec;33(4):212-9. doi: 10.1002/hon.2173. Epub 2014 Nov 3. PubMed PMID: 25363800. 18: Shi P, Zha J, Guo X, Chen F, Fan Z, Huang F, Meng F, Liu X, Feng R, Xu B. Idarubicin is superior to daunorubicin in remission induction of de novo acute myeloid leukemia patients with high MDR1 expression. Pharmacogenomics. 2013 Jan;14(1):17-23. doi: 10.2217/pgs.12.182. PubMed PMID: 23252945. 19: Nafee N, Hirosue M, Loretz B, Wenz G, Lehr CM. Cyclodextrin-based star polymers as a versatile platform for nanochemotherapeutics: Enhanced entrapment and uptake of idarubicin. Colloids Surf B Biointerfaces. 2015 May 1;129:30-8. doi: 10.1016/j.colsurfb.2015.03.014. Epub 2015 Mar 10. PubMed PMID: 25819363. 20: Ertas N, Satana Kara HE. L-Cysteine capped Mn-doped ZnS quantum dots as a room temperature phosphorescence sensor for in-vitro binding assay of idarubicin and DNA. Biosens Bioelectron. 2015 Aug 15;70:345-50. doi: 10.1016/j.bios.2015.03.055. Epub 2015 Mar 24. PubMed PMID: 25840021.

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