Hycanthone
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Hycanthone
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CAS No:
3105-97-3
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Formula:
C20H24N2O2S
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Chemical Name:
Hycanthone
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Synonyms:
9H-Thioxanthen-9-one,1-[[2-(diethylamino)ethyl]amino]-4-(hydroxymethyl)-;Thioxanthen-9-one,1-[[2-(diethylamino)ethyl]amino]-4-(hydroxymethyl)-;1-[[2-(Diethylamino)ethyl]amino]-4-(hydroxymethyl)-9H-thioxanthen-9-one;Win 24933;1-[[2-(Diethylamino)ethyl]amino]-4-(hydroxymethyl)thioxanthen-9-one;Hycanthone;Hycanthon;NSC 142982;NSC 134434;NCI 142982
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CAS No:
Description
Hycanthone is an effective antischistosomai drug.
Hycanthone is an odorless canary yellow to yellow-orange crystalline powder. Bitter taste. (NTP, 1992)
Hycanthone is an odorless canary yellow to yellow-orange crystalline powder. Bitter taste. (NTP, 1992)|Hycanthone is a thioxanthen-9-one compound having a hydroxymethyl substituent at the 1-position and a 2-[(diethylamino)ethyl]amino substituent at the 4-position. It was formerly used (particularly as the monomethanesulfonic acid salt) as a schistosomicide for individual or mass treatement of infection with Schistosoma haematobium and S. mansoni, but due to its toxicity and concern about possible carcinogenicity, it has been replaced by other drugs such as praziquantel. It has a role as a schistosomicide drug and a mutagen. It derives from a lucanthone. It is a conjugate base of a hycanthone(1+).|Potentially toxic, but effective antischistosomal agent, it is a metabolite of LUCANTHONE. Hycanthone was approved by the FDA in 1975 but is no longer used.|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. (NCI04)|Potentially toxic, but effective antischistosomal agent, it is a metabolite of LUCANTHONE.
Hycanthone Basic Attributes
356.48
356.48
221-463-7
2BXX5EVN2A
758434|134434
DTXSID9023128
C550
2932999099
Characteristics
77.9
2.7
Hycanthone is an odorless canary yellow to yellow-orange crystalline powder. Bitter taste. (NTP, 1992)
1.25g/cm3
101.9 °C
570.5°C at 760 mmHg
298.9ºC
1.658
>53.5 [ug/mL]
You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures.
180.4 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
This chemical may be sensitive to prolonged exposure to air and light. Highly soluble in water.
Alcohols and Polyols
HYCANTHONE is very sensitive to acid. (NTP, 1992).
Safety Information
3
45-46-20/21/22
53-36/37/39-45
T: Toxic;
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.
P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, P501
H302
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (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 chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (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)
Drug Information
Agents that act systemically to kill adult schistosomes. (See all compounds classified as Schistosomicides.)
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. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits very toxic fumes of nitrogen oxides and 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)
Hycanthone
Computed Properties
Molecular Weight:356.5
XLogP3:2.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:356.15584919
Monoisotopic Mass:356.15584919
Topological Polar Surface Area:77.9
Heavy Atom Count:25
Complexity:443
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes