9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-4-(hydroxymethyl)-, methanesulfonate (1:1)

452.6 g/mol

452.14396435 g/mol

245-527-9

DTXSID4025408

Yellow-orange powder

145 Ų

143 °C (approx)

greater than or equal to 100 mg/mL at 70° F (NTP, 1992)|Freely soluble in 95% ethanol; slightly soluble in chloroform; very slightly soluble in acetone; practically insoluble or insoluble in benzene and ether.|Very soluble in water.

You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures.

Crystals; MP 100.6-102.8 °C; MW 356.49 g/mol. Absorption max (ethanol): 233, 258, 329, 438 nm (E 19400, 37000, 9700, 6600). Extremely sensitive to acid. /Hycanthone/|Slightly soluble in water. /Hycanthone/

Water soluble.

Salts, Basic

Sensitive to light. A 10% solution in water is stable for at least 24 hours after preparation. Decomposes rapidly in aqueous acid solutions. (NTP, 1992).

This chemical is sensitive to light. A 10% solution in water is stable for at least 24 hours after preparation. It decomposes rapidly in aqueous acid solutions.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Extremely sensitive to acid. /Hycanthone/

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Flash point data for this chemical are not available; however, it is probably combustible.

Fires involving this material can be controlled with a carbon dioxide, dry chemical or Halon extinguisher.

If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Interactions of caffeine with chemicals known for their effects on chromosomal segregation during meiosis of Saccharomyces cerevisiae were studied. It appears that caffeine does interfere with the action of other compounds during the different phases of meiosis. Treatments with methyl methanesulphonate (MMS) and cadmium chloride (CdCl2) resulted in a synergistic effect consisting of an increase in the frequency of recombination. The greatest effects were found on the induction of diploid spores: MMS, hycanthone, and distamycin demonstrated strong, benlate little synergistic action. ...Concerning disomic induction: caffeine reduced (or left unchanged) the effect on non-disjunction when MMS and hycanthone were used. /Salt not specified/

LD50 Rat oral 980 mg/kg /Hycanthone/|LD50 Rat sc 286 mg/kg /Hycanthone/|LD50 Rat iv 75 mg/kg /Hycanthone/|LD50 Mouse oral 1120 mg/kg /Hycanthone/|For more Non-Human Toxicity Values (Complete) data for HYCANTHONE MESYLATE (12 total), please visit the HSDB record page.

This chemical is a thioxanthone. It is a lucanthone metabolite. Clinical use of this compound has been sharply reduced because of reports that it is mutagenic and carcinogenic. It is not available in the United States. /Hycanthone/|Used in treatment of schistosomiasis.

In male Sprague-Dawley rats and in rhesus monkeys of both sexes receiving single im injections of randomly tritiated hycanthone mesylate at doses in the range of those therapeutically recommended for man (3 mg/kg bw), peak blood and tissue levels were found about 30-60 minutes after administration. Highest concentrations were observed in the liver, spleen, kidneys and adrenals but decreased to <20% of the administered dose in 48-72 hr. Unchanged drug was found in blood and tissues, except in the liver where rapid conversion to hycanthone sulphoxide occured in rats and to the N-de-ethylated metabolite in monkeys.|The rate of excretion of labelled hycanthone has been determined in bile and urine from three strains of rats (Sprague-Dawley, hooded and Gunn), and from dogs, cats, rabbits and monkeys. Bile was the major route of excretion in all species; the half-life for excretion of total radioactivity ranged from 1.6 to 3.0 hours. Relatively little of the radioactivity was found in the urine, except in the monkey and notably in the cat. Most of the radioactivity in the bile and urine was found in conjugated form, or as polar metabolites; cat urine, however contained a high percentage of hycanthone and less polar metabolites. Some fifteen metabolites have been seen in bile, and/or urine, and nine from in vitro incubations with microsomal preparations. Five of these, including hycanthone, have been chemically characterized, and two others tentatively identified.

In male Sprague-Dawley rats and in rhesus monkeys of both sexes receiving single im injections of randomly tritiated hycanthone mesylate at doses in the range of those therapeutically recommended for man (3 mg/kg bw), peak blood and tissue levels were found about 30-60 minutes after administration. ... Unchanged drug was found in blood and tissues, except in the liver where rapid conversion to hycanthone sulphoxide occured in rats and to the N-de-ethylated metabolite in monkeys.|The rate of excretion of labelled hycanthone has been determined in bile and urine from three strains of rats (Sprague-Dawley, hooded and Gunn), and from dogs, cats, rabbits and monkeys. ... Most of the radioactivity in the bile and urine was found in conjugated form, or as polar metabolites; cat urine, however contained a high percentage of hycanthone and less polar metabolites. Some fifteen metabolites have been seen in bile, and/or urine, and nine from in vitro incubations with microsomal preparations. Five of these, including hycanthone, have been chemically characterized, and two others tentatively identified.

The rate of excretion of labelled hycanthone has been determined in bile and urine from three strains of rats (Sprague-Dawley, hooded and Gunn), and from dogs, cats, rabbits and monkeys. Bile was the major route of excretion in all species; the half-life for excretion of total radioactivity ranged from 1.6 to 3.0 hours. ...

...A preferential binding of hycanthone to heterochromatin could be demonstrated for the nuclei of the Malpighian tubules of Triatoma infestans. In other cellular systems like cattle kidney cells in culture, plant cells, and mouse lymphocytes, the drug could be demonstrated to bind heterochromatin and euchromatin, irrespective of the packing state of the latter. When penetrating the various heterochromatin types (with the exception of T. infestans), the drug induced a chromatin loosening that could favor incidence of chromatin breaks. The variation of hycanthone binding to DNA in different cell types is possibly related to differences in composition, stereo-arrangement and stability of the DNA-protein complexes involved.|...Inhibition of RNA synthesis can be a possible explanation for the mechanism of the schistosomicidal action of hycanthone. /Salt not specified/|...Hycanthone was shown to be a very potent inhibitor of monoamine oxidases from worms and mouse liver. Hycanthone also inhibited the specific and nonspecific cholinesterases of S. mansoni, but cholinesterase from mouse brain was not affected significantly by this drug. ... /Salt not specified/|...Analysis of the ACh induced noise revealed that 1 microM hycanthone slightly increased the channel lifetime whereas the single channel conductance was not affected. It was concluded that the primary site of action of hycanthone is the 'transient state' or ACh bound but closed conformation of the ACh receptor ion channel, but this drug also has other sites of action (presynaptic nerve terminal and open conformation of ACh receptor-ion channel complex). /Salt not specified/|For more Mechanism of Action (Complete) data for HYCANTHONE MESYLATE (8 total), please visit the HSDB record page.

SYMPTOMS: Symptoms of exposure to this chemical include nausea, vomiting, abdominal discomfort, headache, dizziness, myalgia, liver damage including necrosis, death, anorexia, vertigo, fall in blood pressure, giddiness, psychotic disturbance, toxic hepatitis, acute pancreatitis, icterus and cirrhosis. It may also cause hallucinations and muscle weakness. ACUTE/CHRONIC HAZARDS: When heated to decomposition this chemical emits very toxic fumes of sulfur oxides. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

SKIN CONTACT: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.|INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Respirator Recommendation.|EYE CONTACT: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital.|INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, ... IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital.

/HUMAN EXPOSURE STUDIES/ Two of 8 patients treated with a single im injection of 3 mg/kg bw hycanthone for Schistosoma haematobium infestation developed severe hepatocellular injury, with the histological pattern of acute toxic hepatitis.|/SIGNS AND SYMPTOMS/ Symptoms of exposure to this compound include nausea, vomiting, abdominal discomfort, headache, dizziness, myalgia, anorexia and, rarely, transient and minimal ECG changes, acute hepatic necrosis and death. Other symptoms include weakness, diarrhea and weight loss. Hepatotoxicity occurs. Exposure can cause acute toxic hepatitis, vertigo, fall in blood pressure, giddiness and liver damage (sometimes severe). There have been cases of psychotic disturbance, acute pancreatitis, icterus and cirrhosis. It may also cause hallucinations and muscle weakness.|/SPECIAL STUDIES/ No chromosome abnormalities were observed in lymphocytes from patients treated with a single injection of 2.5 mg/kg bw hycanthone.