MedKoo Cat#: 205993 | Name: Ledoxantrone

Description:

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

Ledoxantrone, also known as sedoxantrone or CI-958, is an anthrapyrazole antineoplastic antibiotic molecule with potential antineoplastic activity. Sedoxantrone intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)

Chemical Structure

Ledoxantrone
Ledoxantrone
CAS#113457-05-9 (free base)

Theoretical Analysis

MedKoo Cat#: 205993

Name: Ledoxantrone

CAS#: 113457-05-9 (free base)

Chemical Formula: C21H27N5OS

Exact Mass: 397.1936

Molecular Weight: 397.54

Elemental Analysis: C, 63.45; H, 6.85; N, 17.62; O, 4.02; S, 8.07

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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Synonym
Ledoxantrone; sedoxantrone; CI958; CI-958; CI 958
IUPAC/Chemical Name
5-((2-aminoethyl)amino)-2-(2-(diethylamino)ethyl)-2H-thiochromeno[4,3,2-cd]indazol-8-ol
InChi Key
HPCHDLLMIWHKBW-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H27N5OS/c1-3-25(4-2)11-12-26-17-8-7-16(23-10-9-22)21-19(17)20(24-26)15-6-5-14(27)13-18(15)28-21/h5-8,13,23,27H,3-4,9-12,22H2,1-2H3
SMILES Code
OC1=CC(S2)=C(C3=NN(CCN(CC)CC)C4=C3C2=C(NCCN)C=C4)C=C1
Appearance
Solid powder
Purity
>98%
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, not in water
Shelf Life
>5 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
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Preparing Stock Solutions

The following data is based on the product molecular weight 397.54 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: Brauer CA, Coca-Perraillon M, Cutler DM, Rosen AB. Incidence and mortality of hip fractures in the United States. JAMA. 2009 Oct 14;302(14):1573-9. doi: 10.1001/jama.2009.1462. PubMed PMID: 19826027. 2: Philip Kuebler J, Moore T, Pritchard J, Kraut E. Phase II study of CI-958 in patients with hormone refractory prostate carcinoma. Invest New Drugs. 2004 Apr;22(2):181-4. PubMed PMID: 14739667. 3: Hoffman MA, Blessing JA, Nuñez ER. A phase II trial of CI-958 in recurrent platinum-sensitive ovarian carcinoma: a Gynecologic Oncology Group study. Gynecol Oncol. 2001 Jun;81(3):433-5. PubMed PMID: 11371134. 4: Arndt CA, Krailo MD, Liu-Mares W, Anderson PM, Reaman GH. Phase I study of CI-958 in children and adolescents with recurrent solid tumors. Cancer. 2001 Mar 15;91(6):1166-9. PubMed PMID: 11267962. 5: Hoff PM, Ellerton JA, Dakhil SR, Winn RJ, Abbruzzese JL, Pazdur R. Phase II study of intravenous CI-958 in metastatic colorectal adenocarcinoma. Am J Clin Oncol. 2000 Dec;23(6):602-4. PubMed PMID: 11202806. 6: Hoffman MA, Blessing JA, Morgan M. Phase II trial of CI-958 in recurrent platinum-refractory ovarian carcinoma. A Gynecologic Oncology Group Study. Gynecol Oncol. 2000 Dec;79(3):463-5. PubMed PMID: 11104620. 7: Dees EC, Whitfield LR, Grove WR, Rummel S, Grochow LB, Donehower RC. A phase I and pharmacologic evaluation of the DNA intercalator CI-958 in patients with advanced solid tumors. Clin Cancer Res. 2000 Oct;6(10):3885-94. PubMed PMID: 11051234. 8: Woolley PV, Freiha FS, Smith DC, Carlson L, Hofacker J, Quinn N, Grove W, Trump DL. A phase II trial of CI-958 in patients with hormone-refractory prostate cancer. Cancer Chemother Pharmacol. 1999;44(6):511-7. PubMed PMID: 10550573. 9: Shields AF, Philip PA, LoRusso PM, Ferris AM, Zalupski MM. Phase II study of CI-958 in colorectal cancer. Cancer Chemother Pharmacol. 1999;43(2):162-4. PubMed PMID: 9923823. 10: Lun L, Sun PM, Trubey CM, Bachur NR. Antihelicase action of CI-958, a new drug for prostate cancer. Cancer Chemother Pharmacol. 1998;42(6):447-53. PubMed PMID: 9788570. 11: Kaye SB, Workman P, Graham MA, Cassidy J, Jodrell D. Pharmacokinetics and early clinical studies of selected new drugs. Cancer Surv. 1993;17:371-96. Review. PubMed PMID: 8137348. 12: Fry DW, Besserer JA. Biochemical pharmacology and DNA-drug interactions by Cl-958, a new antitumor intercalator derived from a series of substituted 2H-[1]benzothiopyrano[4,3,2-cd]indazoles. Mol Pharmacol. 1988 Jan;33(1):84-92. PubMed PMID: 2447481.