MedKoo Cat#: 461539 | Name: Ruboxyl

Description:

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

Ruboxyl is a nitroxylated analog of daunorubicin that acts as a anthracycline antibiotic.

Chemical Structure

Ruboxyl
Ruboxyl
CAS#80214-88-6

Theoretical Analysis

MedKoo Cat#: 461539

Name: Ruboxyl

CAS#: 80214-88-6

Chemical Formula: C36H47ClN4O10

Exact Mass: 730.2981

Molecular Weight: 731.24

Elemental Analysis: C, 59.13; H, 6.48; Cl, 4.85; N, 7.66; O, 21.88

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 #
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Synonym
Ruboxyl; Ruboxyl hydrochloride;
IUPAC/Chemical Name
(8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-((Z)-1-((1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ylidene)hydrazono)ethyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride
InChi Key
GYPCWHHQAVLMKO-BFPFSNHBSA-N
InChi Code
InChI=1S/C36H46N4O10.ClH/c1-16-29(41)21(37)11-24(49-16)50-23-15-36(46,17(2)38-39-18-12-34(3,4)40(47)35(5,6)13-18)14-20-26(23)33(45)28-27(31(20)43)30(42)19-9-8-10-22(48-7)25(19)32(28)44;/h8-10,16,21,23-24,29,41,43,45-47H,11-15,37H2,1-7H3;1H/b38-17-;/t16-,21-,23-,24-,29+,36-;/m0./s1
SMILES Code
O=C1C2=C(O)C(C[C@](/C(C)=N\N=C3CC(C)(C)N(O)C(C)(C)C/3)(O)C[C@@H]4O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)=C4C(O)=C2C(C6=C1C=CC=C6OC)=O.[H]Cl
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 731.24 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: Kotelnikov AI, Rybkin AY, Khakina EA, Kornev AB, Barinov AV, Goryachev NS, Ivanchikhina AV, Peregudov AS, Martynenko VM, Troshin PA. Hybrid photoactive fullerene derivative-ruboxyl nanostructures for photodynamic therapy. Org Biomol Chem. 2013 Jul 14;11(26):4397-404. doi: 10.1039/c3ob40136g. Epub 2013 May 28. PubMed PMID: 23712714. 2: Seminara P, Franchi F, Konovalova N, Pioli C, Rossetti R, Tubani L, Doria G, Rossi Fanelli F. Activity of a nitroxylated analog of daunorubicin, ruboxyl, in B-lymphoproliferative disorders. Acta Haematol. 2001;105(2):77-82. PubMed PMID: 11408708. 3: Konovalova NP, Volkova LM, Codacci-Pisanelli D, Seminara P, Franchi F. [Effect of Ruboxyl (nitroxyl derivative of daunorubicin) on hepatic metastases of colorectal carcinoma]. Vopr Onkol. 2000;46(4):438-41. Russian. PubMed PMID: 11147420. 4: Rapoport NY, Herron JN, Pitt WG, Pitina L. Micellar delivery of doxorubicin and its paramagnetic analog, ruboxyl, to HL-60 cells: effect of micelle structure and ultrasound on the intracellular drug uptake. J Control Release. 1999 Mar 29;58(2):153-62. PubMed PMID: 10053188. 5: Steed PR, Stein RA, Mishra S, Goodman MC, McHaourab HS. Na⁺-substrate coupling in the multidrug antiporter norm probed with a spin-labeled substrate. Biochemistry. 2013 Aug 27;52(34):5790-9. doi: 10.1021/bi4008935. Epub 2013 Aug 15. PubMed PMID: 23902581; PubMed Central PMCID: PMC3842230. 6: Sirovich I, Konovalova N, Codacci-Pisanelli G, Volkova LM, Giuliani A, Cicconetti F, Seminara P, Mazzocconi G, Franchi F. Activity of ruboxyl, a nitroxyl derivative of daunorubicin, on experimental models of colorectal cancer metastases. Tumour Biol. 1999 Sep-Oct;20(5):270-6. PubMed PMID: 10436420. 7: Gurevish SM, Vartanian LS, Nagler LG. [Disorders in metabolism of superoxide radicals in tumor-bearing mice during development of Ehrlich ascites carcinoma and their normalization under the effect of ruboxyl]. Vopr Med Khim. 1993 Nov-Dec;39(6):16-20. Russian. PubMed PMID: 8303863. 8: Vasilets LA, Ganieva LKh. [Effect of the anthracycline antibiotics rubomycin and ruboxyl on the morphology and electric activity of the rat myocardium]. Biull Eksp Biol Med. 1987 Aug;104(8):233-5. Russian. PubMed PMID: 3620691. 9: Volk SE, Rogova OM. [Comparative study of the effect of daunorubicin and its nitroxyl derivative on in vitro function of rat liver mitochondria]. Antibiot Khimioter. 1991 Mar;36(3):39-42. Russian. PubMed PMID: 1877877. 10: Leonetti C, Aronne T, Konovalova N, Diatchkovskaya R, Shapiro A, Franchi F. Ruboxyl, a new nitroxyl derivative of daunorubicin - acute toxicity and antitumor effect in animals. Int J Oncol. 1993 Oct;3(4):615-8. PubMed PMID: 21573408. 11: Konovalova NP, Diatchkovskaya RF, Kukushkina GV, Volkova LM, Varfolomeev VN, Dombrovsky LS, Shapiro AB. Pharmacokinetics of a spin-labeled rubomycin analog. Neoplasma. 1988;35(2):185-90. PubMed PMID: 2836742. 12: Franchi F, Seminara P, Giannarelli D, Konovalova N. Fractional incorporation of radionucleotides, a marker of in vitro tumor cell chemosensitivity in colorectal cancer. Oncology. 1991;48(6):510-6. PubMed PMID: 1749592. 13: Goncharova SA, Demidova NS, Shiriaeva OA, Shevtsova VN, Konovalova NP. [Characteristics of anthracycline-resistant strains of P388 leukemia]. Eksp Onkol. 1987;9(4):42-7. Russian. PubMed PMID: 3678124. 14: Dederer LIu, Gorbacheva LB. [Effect of rubomycin and its paramagnetic analog on DNA synthesis]. Antibiotiki. 1984 Jun;29(6):442-5. Russian. PubMed PMID: 6476807. 15: Demidova NS, Chernova OB, Siyanova EY, Goncharova AS, Kopnin BP. Newly formed chromosome-like structures in independent mouse P388 sublines with developed in vivo mdr1 gene amplification. Somat Cell Mol Genet. 1991 Nov;17(6):581-90. PubMed PMID: 1685030. 16: Rogova OM, Volk SE. [Effect of rubomycin (daunorubicin) and its nitroxyl analog on the functioning of rat heart mitochondria]. Antibiot Khimioter. 1991 May;36(5):18-20. Russian. PubMed PMID: 1953165. 17: Marin A, Muniruzzaman M, Rapoport N. Mechanism of the ultrasonic activation of micellar drug delivery. J Control Release. 2001 Jul 10;75(1-2):69-81. PubMed PMID: 11451498. 18: Rapoport N, Marin AP, Timoshin AA. Effect of a polymeric surfactant on electron transport in HL-60 cells. Arch Biochem Biophys. 2000 Dec 1;384(1):100-8. PubMed PMID: 11147820. 19: Demidova NS, Goncharova SA, Chernova OB, Kopnin BP, Gudkov AV. [Gene amplification in murine leukemia cells with multiple drug resistance acquired in vivo]. Genetika. 1987 Oct;23(10):1797-806. Russian. PubMed PMID: 3692152. 20: Bukeĭ TI, Filippov AK, Vasilets LA, Porotikov VI. [Effects on anthracycline antibiotics on ionic currents and contraction of frog atrial fibrils associated with Na+/Ca2+ exchange]. Biull Eksp Biol Med. 1988 Oct;106(10):456-8. Russian. PubMed PMID: 3191237.