Ledoxantrone

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

MedKoo CAT#: 205993

CAS#: 113457-05-9

Description: 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

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Ledoxantrone
CAS# 113457-05-9

Theoretical Analysis

MedKoo Cat#: 205993
Name: Ledoxantrone
CAS#: 113457-05-9
Chemical Formula: C21H27N5OS
Exact Mass: 397.19363
Molecular Weight: 397.53698
Elemental Analysis: C, 63.45; H, 6.85; N, 17.62; O, 4.02; S, 8.07

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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

Preparing Stock Solutions

The following data is based on the product molecular weight 397.53698 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

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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.

Ledoxantrone

10.0mg / Not available


Additional Information