N-Ethyl-N′-(5-nitro-2-thiazolyl)urea
-
N-Ethyl-N′-(5-nitro-2-thiazolyl)urea
structure -
-
CAS No:
139-94-6
-
Formula:
C6H8N4O3S
-
Chemical Name:
N-Ethyl-N′-(5-nitro-2-thiazolyl)urea
-
Synonyms:
Urea,N-ethyl-N′-(5-nitro-2-thiazolyl)-;Urea,1-ethyl-3-(5-nitro-2-thiazolyl)-;N-Ethyl-N′-(5-nitro-2-thiazolyl)urea;1-Ethyl-3-(5-nitro-2-thiazolyl)urea;Hepzide;Nithiazide;Hepzide 30;Nithiazid;Ba 32476;8018-00-6;8027-84-7
-
CAS No:
Description
Crystals or brown powder.
Crystals or brown powder. (NTP, 1992)
Crystals or brown powder. (NTP, 1992)|Nithiazide is a C-nitro compound and a member of 1,3-thiazoles.
N-Ethyl-N′-(5-nitro-2-thiazolyl)urea Basic Attributes
216.21772
216.22
205-387-1
G9PO1G721T
DTXSID1020936
Crystals|Solid
2934100090
Characteristics
128
2.17980
solid
1.478 (estimate)
228 °C (decomp)
1.6200 (estimate)
In water, 30 mg/l @ 25 deg C
pKa = 7.3
Insoluble in water.
Amides and Imides
Safety Information
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing 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 store this material under ambient temperatures. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)
Toxicity
LD50 Mouse oral 2150 mg/kg
The bioassay of nithiazide for possible carcinogenicity was conducted using Fischer 344 rats and B6C3F1 mice. Nithiazide was administered in the diet, at either of two concentrations, to groups of 50 male and 50 female animals of each species. The high and low concentrations of nithiazide utilized were, respectively, 1,250 and 625 ppm for rats and 5,000 and 2,500 ppm for mice. /Due to shortage, nithiazide was not administered for 9 of the 104 weeks./ ...Twenty animals of each sex and species were placed on test as controls. ...There was no significant positive association between dosage and mortality for either rats or mice. Compound-related mean body weight /gain/ depression occurred in both sexes of each species. Statistically significant incidences of hepatocellular adenomas and carcinomas were found in high dose male mice but not in female mice. ...Statistically significant increased incidences of a combination of mammary and skin fibroadenomas and cystadenomas NOS were found in the high dose female rats. ...Under the conditions of this bioassay, nithiazide was carcinogenic in male and probably female B6C3F1 mice, causing a combination of hepatocellular carcinomas and hepatocellular adenomas. Nithiazide was also carcinogenic in female Fischer 344 rats, causing an increase in the incidence of mammary neoplasms. The compound was not carcinogenic in male Fischer 344 rats.
Nithiazide's production and use as a veterinary medicine(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 670(SRC), determined from a water solubility of 30 mg/l(2) and a regression-derived equation(3), indicates that nithiazide is expected to have low mobility in soil(SRC). The pKa of nithiazide is 7.3(2), indicating that this compound will partially exist in cation form in the environment; cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(4). Volatilization of nithiazide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-15 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Nithiazide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-7 mm Hg(SRC), determined from a fragment constant method(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 670(SRC), determined from a water solubility of 30 mg/l(2) and a regression-derived equation(3), indicates that nithiazide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.6X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The pKa of nithiazide is 7.3(2), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5). According to a classification scheme(6), an estimated BCF of 90(SRC), from its water solubility(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nithiazide, which has an estimated vapor pressure of 1.3X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase nithiazide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.1 days(SRC), calculated from its estimated rate constant of 5.2X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).
The rate constant for the vapor-phase reaction of nithiazide with photochemically-produced hydroxyl radicals has been estimated as 5.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.1 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Nithiazide is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).
An estimated BCF of 90 was calculated for nithiazide(SRC), using a water solubility of 30 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).
The Koc of nithiazide is estimated as 670(SRC), using water solubility of 30 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that nithiazide is expected to have low mobility in soil(SRC). The pKa of nithiazide is 7.3(1), indicating that this compound will partially exist in cation form in the environment; cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(4).
The Henry's Law constant for nithiazide is estimated as 1.6X10-15 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that nithiazide is expected to be essentially nonvolatile(SRC). Nithiazide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-7 mm Hg(SRC), determined from a fragment constant method(2).
Occupational exposure to nithiazide may occur through dermal contact with this compound at workplaces where nithiazide is produced or used. (SRC)
Drug Information
/FORMER USE:/ Nithiazide was used in veterinary medicine as an antiprotozoal agent. It was most commonly used against Histomonas meleagridis, the organism which causes blackhead in fowl.
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (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. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. 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. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)
/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
1-ethyl-3-(5-nitro-2-thiazole)urea
N-Ethyl-N′-(5-nitro-2-thiazolyl)urea Use and Manufacturing
Prepd by the condensation of ethyl isocyanate with 2-amino-5-nitrothiazole in toluene.|O'Neill et al., US 2755285 (1956 to Merck & Co.)
N-Ethyl-N'-(5-nitro-2-thiazolyl)urea maintains therapeutic activity towards treatment of Salmonella typhimurium and B. fragilis infections due to the nitrothiazole moiety within the substructure.
Computed Properties
Molecular Weight:216.22
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:216.03171130
Monoisotopic Mass:216.03171130
Topological Polar Surface Area:128
Heavy Atom Count:14
Complexity:232
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
N-Ethyl-N′-(5-nitro-2-thiazolyl)urea
SDSRequest for Quotation