Hycanthone

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

MedKoo CAT#: 205735

CAS#: 3105-97-3

Description: hycanthone is a thioxanthene derivative of lucanthone with anti-schistosomal activity and potential antineoplastic activity. Hycanthone interferes with parasite nerve function, resulting in parasite paralysis and death. This agent also intercalates into DNA and inhibits RNA synthesis in vitro. H ycanthone was entered into Phase II clinical trials in 1980s, and was failed to give expected results and thus discontinued for further human clinical trials since then. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Chemical Structure

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Hycanthone
CAS# 3105-97-3

Theoretical Analysis

MedKoo Cat#: 205735
Name: Hycanthone
CAS#: 3105-97-3
Chemical Formula: C20H24N2O2S
Exact Mass: 356.15585
Molecular Weight: 356.48176
Elemental Analysis: C, 67.38; H, 6.79; N, 7.86; O, 8.98; S, 8.99

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Synonym: Hycanthone; US brand name: Etrenol.

IUPAC/Chemical Name: 1-((2-(diethylamino)ethyl)amino)-4-(hydroxymethyl)-9H-thioxanthen-9-one

InChi Key: MFZWMTSUNYWVBU-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H24N2O2S/c1-3-22(4-2)12-11-21-16-10-9-14(13-23)20-18(16)19(24)15-7-5-6-8-17(15)25-20/h5-10,21,23H,3-4,11-13H2,1-2H3

SMILES Code: O=C1C2=C(SC3=C1C=CC=C3)C(CO)=CC=C2NCCN(CC)CC

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, not in water

Shelf Life: >2 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 356.48176 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: Naidu MD, Agarwal R, Pena LA, Cunha L, Mezei M, Shen M, Wilson DM 3rd, Liu Y, Sanchez Z, Chaudhary P, Wilson SH, Waring MJ. Lucanthone and its derivative hycanthone inhibit apurinic endonuclease-1 (APE1) by direct protein binding. PLoS One. 2011;6(9):e23679. Epub 2011 Sep 15. PubMed PMID: 21935361; PubMed Central PMCID: PMC3174134.

2: el-Tarras A, Dubins JS, Warner J, Hoffman C, Cobb RR. Molecular analysis of the TK locus in L5178Y large and small colony mouse lymphoma cell mutants induced by hycanthone methanesulfonate. Mutat Res. 1995 Nov;332(1-2):89-95. PubMed PMID: 7500995.

3: Earle JD, Foley JF, Wieand HS, Kvols LK, McKenna PJ, Krook JE, Tschetter LK, Schutt AJ, Twito DI. Evaluation of external-beam radiation therapy plus 5-fluorouracil (5-FU) versus external-beam radiation therapy plus hycanthone (HYC) in confined, unresectable pancreatic cancer. Int J Radiat Oncol Biol Phys. 1994 Jan 1;28(1):207-11. PubMed PMID: 8270443.

4: Pica-Mattoccia L, Dias LC, Moroni R, Cioli D. Schistosoma mansoni: genetic complementation analysis shows that two independent hycanthone/oxamniquine-resistant strains are mutated in the same gene. Exp Parasitol. 1993 Dec;77(4):445-9. PubMed PMID: 8253157.

5: Bailly C, Waring MJ. Preferential intercalation at AT sequences in DNA by lucanthone, hycanthone, and indazole analogs. A footprinting study. Biochemistry. 1993 Jun 15;32(23):5985-93. PubMed PMID: 8389585.

6: Cioli D, Pica-Mattoccia L, Moroni R. Schistosoma mansoni: hycanthone/oxamniquine resistance is controlled by a single autosomal recessive gene. Exp Parasitol. 1992 Dec;75(4):425-32. PubMed PMID: 1493874.

7: Kliesch U, Adler ID. Sex differences in micronucleus induction with hycanthone methanesulfonate in bone marrow cells of mice. Mutat Res. 1992 Dec;283(4):249-53. PubMed PMID: 1383797.

8: Pica-Mattoccia L, Archer S, Cioli D. Hycanthone resistance in schistosomes correlates with the lack of an enzymatic activity which produces the covalent binding of hycanthone to parasite macromolecules. Mol Biochem Parasitol. 1992 Oct;55(1-2):167-75. PubMed PMID: 1435868.

9: Pica-Mattoccia L, Dias LC, Cioli D. Genetic complementation analysis of two independently isolated hycanthone-resistant strains of Schistosoma mansoni. Mem Inst Oswaldo Cruz. 1992;87 Suppl 4:211-4. PubMed PMID: 1343897.

10: Efferth T, Klett T, Mattern J, Osswald H, Pommerenke EW, Stöhr M, Volm M. Reversing multidrug resistance in L1210 tumor cells by hycanthone or chlorophenoxamine in vitro and in vivo. Anticancer Res. 1991 May-Jun;11(3):1275-9. PubMed PMID: 1888160.

11: Sudman PD, Generoso WM. Female-specific mutagenic response of mice to hycanthone. Mutat Res. 1991 Jan;246(1):31-43. PubMed PMID: 1986266.

12: Archer S, el-Hamouly W, Seyed-Mozaffari A, Butler RH, Pica-Mattoccia L, Cioli D. Mode of action of the schistosomicide hycanthone: site of DNA alkylation. Mol Biochem Parasitol. 1990 Nov;43(1):89-95. PubMed PMID: 2290447.

13: Wong LJ, Tsao GC, Bruce JI, Wong SS. Inhibition of in vitro RNA synthesis by hycanthone, oxamniquine and praziquantel. Experientia. 1990 May 15;46(5):461-4. PubMed PMID: 1693342.

14: Botros SS. Effect of praziquantel versus hycanthone on deoxyribonucleic acid content of hepatocytes in murine schistosomiasis mansoni. Pharmacol Res. 1990 Mar-Apr;22(2):219-29. PubMed PMID: 2109860.

15: Cioli D, Pica-Mattoccia L, Archer S. Resistance of schistosomes to hycanthone and oxamniquine. Mem Inst Oswaldo Cruz. 1989 Oct;84 Suppl 1:38-45. PubMed PMID: 2638729.

16: Brindley PJ, Lewis FA, McCutchan TF, Bueding E, Sher A. A genomic change associated with the development of resistance to hycanthone in Schistosoma mansoni. Mol Biochem Parasitol. 1989 Oct;36(3):243-52. PubMed PMID: 2571929.

17: Hartman PE. Early years of the Salmonella mutagen tester strains: lessons from hycanthone. Environ Mol Mutagen. 1989;14 Suppl 16:39-45. PubMed PMID: 2659330.

18: Pica-Mattoccia L, Cioli D, Archer S. Binding of tritiated hycanthone and hycanthone N-methylcarbamate to macromolecules of drug-sensitive and drug-resistant schistosomes. Mol Biochem Parasitol. 1988 Oct;31(1):87-96. PubMed PMID: 3185615.

19: Sora S, Melchioretto P, Primignani P, Agostoni Carbone ML. Caffeine interactions with methyl methanesulphonate, hycanthone, benlate, and cadmium chloride in chromosomal meiotic segregation of Saccharomyces cerevisiae. Mutat Res. 1988 Sep;201(1):9-16. PubMed PMID: 2458529.

20: Archer S, Pica-Mattoccia L, Cioli D, Seyed-Mozaffari A, Zayed AH. Preparation and antischistosomal and antitumor activity of hycanthone and some of its congeners. Evidence for the mode of action of hycanthone. J Med Chem. 1988 Jan;31(1):254-60. PubMed PMID: 3336024.

21: Hassoni AA, Kerkut GA, Walker RJ. Evidence that levamisole, pyrantel, morantel, amidantel, deacylated amidantel and hycanthone may act on acetylcholine receptors of central neurones of Helix aspersa. Comp Biochem Physiol C. 1988;91(2):525-33. PubMed PMID: 2905966.

22: Brindley PJ, Sher A. Anti-schistosomal drugs: observations on the mechanism of drug resistance to hycanthone, and on the involvement of host antibodies in the mode of action of praziquantel. Mem Inst Oswaldo Cruz. 1987;82 Suppl 4:157-61. PubMed PMID: 3151089.

23: Doong YC, Wong LJ, Bruce JI, Wong SS. Enzymatic differences between hycanthone-resistant and sensitive strains of Schistosoma mansoni. Comp Biochem Physiol B. 1987;87(3):459-64. PubMed PMID: 2957147.

24: Pica-Mattoccia L, Cioli D. Lack of correlation between schistosomicidal and anticholinergic properties of hycanthone and related drugs. J Parasitol. 1986 Aug;72(4):531-9. PubMed PMID: 3783347.

25: de Serres FJ. Hycanthone: an unresolved case study in risk assessment. Mutat Res. 1986 Aug;164(4):199-201. PubMed PMID: 3748057.

26: Gordon RK, Chiang PK. Antimuscarinic activities of hycanthone analogs: possible relationship with animal toxicity. J Pharmacol Exp Ther. 1986 Jan;236(1):85-9. PubMed PMID: 3484525.

27: Simoni IC, Mello ML. Investigation of hycanthone binding to DNA in chromatin with different supra-organization, composition, and function. Acta Histochem. 1986;79(1):97-105. PubMed PMID: 3090842.

28: Enomoto K, Edwards C. Effects of hycanthone on the neuromuscular transmission. Eur J Pharmacol. 1985 Oct 8;116(1-2):81-8. PubMed PMID: 2996913.

29: Cioli D, Pica-Mattoccia L, Rosenberg S, Archer S. Evidence for the mode of antischistosomal action of hycanthone. Life Sci. 1985 Jul 15;37(2):161-7. PubMed PMID: 4010473.

30: Cioli D, Pica Mattoccia L. Genetic analysis of hycanthone resistance in Schistosoma mansoni. Am J Trop Med Hyg. 1984 Jan;33(1):80-8. PubMed PMID: 6696189.

31: Archer S, Zayed AH, Rej R, Rugino TA. Analogues of hycanthone and lucanthone as antitumor agents. J Med Chem. 1983 Sep;26(9):1240-6. PubMed PMID: 6887199.

32: Schutt AJ, Dalton RJ, Kovach JS, Moertel CG, O'Connell MJ. Phase II study of hycanthone in patients with advanced colorectal carcinoma. Cancer Treat Rep. 1983 Jun;67(6):593-4. PubMed PMID: 6861166.

33: Pica Mattoccia L, Cioli D. Effect of hycanthone administered in vivo upon the incorporation of radioactive precursors into macromolecules of Schistosoma mansoni. Mol Biochem Parasitol. 1983 Jun;8(2):99-107. PubMed PMID: 6192338.

34: Kramers PG, Schalet AP, Paradi E, Huiser-Hoogteyling L. High proportion of multi-locus deletions among hycanthone-induced X-linked recessive lethals in Drosophila melanogaster. Mutat Res. 1983 Feb;107(2):187-201. PubMed PMID: 6408464.

35: Mengistu M. Fatal liver toxicity due to hycanthone (Etrenol) in a patient with pre-existing liver disease: a case report. Ethiop Med J. 1982 Jul;20(3):145-7. PubMed PMID: 7106100.

36: de Souza Dias LC, de Jesus Pedro R, Deberaldini ER. Use of praziquantel in patients with schistosomiasis mansoni previously treated with oxamniquine and/or hycanthone: resistance of Schistosoma mansoni to schistosomicidal agents. Trans R Soc Trop Med Hyg. 1982;76(5):652-9. PubMed PMID: 7179419.

37: Kramers PG. Mutagenicity of hycanthone in Drosophila: additional results and a comparison with some analogs. Mutat Res. 1981 Jun;82(1):111-23. PubMed PMID: 6790976.

38: Mattoccia LP, Lelli A, Cioli D. Effect of hycanthone on Schistosoma mansoni macromolecular synthesis in vitro. Mol Biochem Parasitol. 1981 Apr;2(5-6):295-307. PubMed PMID: 6165888.

39: Kim RA, Lukacs J, Tanaka RD, MacInnis AJ. Effects of hycanthone and praziquantel on monoamine oxidase and cholinesterases in Schistosoma mansoni. J Parasitol. 1981 Feb;67(1):20-3. PubMed PMID: 7229816.

40: Ong T, de Serres FJ. Genetic analysis of adenine-3 mutants induced by hycanthone, lucanthone and their indazole analogs in Neurospora crassa. J Environ Pathol Toxicol. 1980 Nov;4(5-6):1-8. PubMed PMID: 6452485.

41: Moore ED, Powis G. Plasma and tissue concentrations of hycanthone in the mouse determined by reversed-phase high-performance liquid chromatography. J Chromatogr. 1980 Sep 12;183(3):372-7. PubMed PMID: 7419657.

42: Haq MM, Legha SS, Wiseman CW, Bodey GP. Hepatotoxicity of hycanthone in patients with metastatic breast cancer. Cancer Treat Rep. 1980 Aug-Sep;64(8-9):929-32. PubMed PMID: 7448830.

43: Lucchini G, Sora S, Panzeri L. Hycanthone as a specific frameshift mutagen in Saccharomyces cerevisiae. Mutat Res. 1980 Aug;72(3):397-404. PubMed PMID: 7005665.

44: Hahon N, Ong T. Action of antischistosomal drugs, hycanthone and its analog 1A-4 N-oxide, on viral interferon induction. J Toxicol Environ Health. 1980 Jul;6(4):705-12. PubMed PMID: 6158576.

45: Lukacs J, Tanaka RD, Kim RA, Macinnis AJ. Development of a cell-free protein-synthesizing system from Schistosoma mansoni and a comparison of the effects of hycanthone and praziquantel on this system. J Parasitol. 1980 Jun;66(3):424-7. PubMed PMID: 7391886.

46: Cioli D, Knopf PM. A study of the mode of action of hycanthone against Schistosoma mansoni in vivo and in vitro. Am J Trop Med Hyg. 1980 Mar;29(2):220-6. PubMed PMID: 7369442.

47: Saéz-Alquézar A, Ohtsuki N, Sette Júnior H, Magnanelli AC, Raia S, da Silva LC. Serum enzymatic changes in patients with schistosomiasis treated with oxamniquine or hycanthone. Comparative study. Rev Inst Med Trop Sao Paulo. 1980 Jan-Feb;22(1 Suppl 4):105-10, 225-31. English, Portuguese. PubMed PMID: 7455503.

48: Kovach JS, Moertel CG, Schutt AJ, Eagan RT. Phase I study of hycanthone. Cancer Treat Rep. 1979 Nov-Dec;63(11-12):1965-9. PubMed PMID: 526930.

49: Tsuda H, Sarma DS, Rajalakshmi S, Zubroff J, Farber E, Batzinger RP, Cha YN, Bueding E. Induction of hepatic neoplastic lesions in mice with a single dose of hycanthone methanesulfonate after partial hepatectomy. Cancer Res. 1979 Nov;39(11):4491-6. PubMed PMID: 498081.

50: Davies BM, Watling DC. Radiosensitization of pulmonary metastases-I. In vivo testing of hycanthone, insulin and razoxane. Int J Radiat Oncol Biol Phys. 1979 Jun;5(6):803-9. PubMed PMID: 500411.



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