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Azaserine

Azaserine structure

Azaserine 

structure
  • CAS No:

    115-02-6

  • Formula:

    C5H7N3O4

  • Chemical Name:

    Azaserine

  • Synonyms:

    L-Serine,O-(2-diazoacetyl)-;Serine,diazoacetate (ester),L-;L-Serine,diazoacetate (ester);O-(2-Diazoacetyl)-L-serine;Azaserine;O-Diazoacetyl-L-serine;L-Azaserine;Azaserin;CN 15757;CI 337;P 165;NSC 742;(S)-2-Amino-3-(2-diazoacetoxy)propanoic acid;(2S)-2-Amino-3-[(2-diazoacetyl)oxy]propanoic acid;438493-22-2

Description

Light-yellow needles from EtOH.ChEBI: A carboxylic ester resulting from the formal condensation of the carboxy group of diazoacetic acid with the alcoholic hydroxy group of L-serine. An antibiotic produced by a Streptomyces species.Pale yellow to green crystals. Used as an antifungal agent.


Azaserine appears as pale yellow to green crystals. Used as an antifungal agent.


Azaserine appears as pale yellow to green crystals. Used as an antifungal agent.|Azaserine is a carboxylic ester resulting from the formal condensation of the carboxy group of diazoacetic acid with the alcoholic hydroxy group of L-serine. An antibiotic produced by a Streptomyces species. It has a role as an antimicrobial agent, an antineoplastic agent, an antifungal agent, an antimetabolite, an immunosuppressive agent, a metabolite and a glutamine antagonist. It is a diazo compound, a carboxylic ester, a L-serine derivative and a non-proteinogenic L-alpha-amino acid.|Azaserine is a naturally occurring serine derivative diazo compound with antineoplastic properties, Azaserine functions as a purine antagonist and glutamine analogue (glutamine amidotransferase inhibitor) that competitively inhibits pathways in which glutamine is metabolized. An antibiotic and antitumor agent, Azaserine is used in clinical studies as a potential antineoplastic agent. (NCI04)|Antibiotic substance produced by various Streptomyces species. It is an inhibitor of enzymatic activities that involve glutamine and is used as an antineoplastic and immunosuppressive agent.

Azaserine Basic Attributes

173.13

173.043655

204-061-6

87299V3Q9W

3462|3077

DTXSID9020118

C289

ORTHORHOMBIC, PALE YELLOW TO GREEN CRYSTALS FROM 90% ETHANOL.

2927000090

Characteristics

127.01000

-1.37

lyophilized powder

1.5830 (rough estimate)

154 °C

303.75°C (rough estimate)

1.6190 (estimate)

H2O: 50 mg/mL, clear, yellow

2-8°C

1.53X10-10 mmHg at 25 °C.

Oral-rat LD50: 170 mg/kg; Oral-Mouse LD50: 150 mg/kg

Flammable; burning produces toxic nitrogen oxide fumes

D27.5 -0.5° (c = 8.46% in H2O at pH 5.18)

Henry's Law constant: 2.56X10-16 atm-cu m/mole at 25 °C (est, SRC)

PKA 8.55

Very soluble in water.

Acids, Carboxylic

AZASERINE is incompatible with acids.

Safety Information

III

6.1(b)

UN 3462 6.1/PG 3

3

25-40

53-36/37/39-45

VT9625000

T

Ventilated, low temperature and dry; stored separately from food materials in warehouse

AQ SOLN ARE MOST STABLE @ PH 8

P281-P301 + P310

H301-H351

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U015, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A poor candidate for incineration.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for AZASERINE (7 total), please visit the HSDB record page.

INCOMPATIBLE WITH ACIDS.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P310, P308+P313, P321, P330, 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.|H301: Toxic if swallowed [Danger Acute toxicity, oral]

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for AZASERINE (9 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

The major hazards encountered in the use and handling of azaserine stem from its toxicologic properties. Exposure to this pale yellow-to-green, crystalline substance may occur from its use as a research chemical, or from veterinary applications as an antineoplastic, antibiotic, or abortifacient. Effects from exposure may include hepatic necrosis and fatty liver. Also, the Intern ational Agency for Research on Cancer (IARC) has designated azaserine as a Group 2B carcinogen, ie, "The agent is possibly carcinogenic to humans." Mechanical exhaust ventilation with a high-efficiency particulate arrestor (HEPA) should be used to minimize airborne levels of this substance. In activities and situations where over-exposure may occur, wear protective clothing and a carefully fitted respirator. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. For shipping and storage, this substance should be enclosed in a securely sealed container which is enclosed in a second unbreakable, leakproof container.

U015; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U015; As stipulated in 40 CFR 261.33, when azaserine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Toxicity

highly toxic

Chemoprevention by a synthetic retinoid, selenium, and these agents in combination during the postinitiation stages of carcinogenesis induced in rats by azaserine was evaluated. Male Lewis rats were given three weekly injections of 30 mg/kg azaserine while being fed a purified diet. One week after completion of carcinogen treatment, groups of rats were switched to the purified diet supplemented with either a retinoid, N-(2-hydroxethyl)retinamide, at a level of 0.5 or 1 mmol/kg diet, or with 5 ppm sodium selenite, or with a combination of retinoid and selenium. One year after the diet change, the incidence of pancreatic and other neoplasms was determined by autopsy and histologic study. The incidence of pancreatic carcinoma (including carcinoma-in-situ, CIS) among nonretinoid-treated controls was 68%. Since the dietary supplements were fed after completion of exposure to the carcinogen, the effects on both pancreatic and liver carcinogenesis were exerted during postinitiation phase of carcinogenesis. As in previous studies, the retinoid inhibited the progression of pancreatic carcinogenesis in a dose-related fashion. Selenium alone had no effect. However, the combination of retinoid plus selenium was more effective than retinoid alone, although the increase in inhibition was not large. The retinoid was also found to inhibit liver carcinogenesis induced by azaserine. Selenium, either alone or in combination with retinoid, was ineffective.|Effect of dietary intake of fish (menhaden) oil and fish (cod) protein on the development of pancreatic preneoplastic lesions was examined in male Wistar rats. Fourteen day old animals were given a single ip injection of 30 mg L-azaserine/kg body weight; diazoacetate serine (ester). At 21 days of age they were weaned and maintained on dietary treatment for 4 months. Fish protein did not appear to produce a significantly different preneoplastic response when compared to casein as a protein source. However, a 20% menhaden oil diet, rich in omega 3 fatty acids, produced a significant decrease in the development of both the size and number of preneoplastic lesions when compared to a 20% corn oil diet rich in omega 6 fatty acids. This study provides evidence that fish oils, rich in omega 3 fatty acids, may have potential as inhibitory agents in cancer development.|Diets containing raw soybean products fed ad libitum caused a reduction in food consumption and growth, pancreatic enlargement, hypersecretion of digestive enzymes, and enlargement of intestinal segments and their contents in rats, chicks and geese. These effects were found to be related to the concentration of trypsin inhibitor in the diet. ... In long-term studies the incidence of pancreatic nodules was correlated to the level of trypsin inhibitor in the diet. Feeding raw soybean products potentiated the carcinogenic effect of azaserine and meal feeding enhanced the incidence and size of the pancreatic nodules in rats fed raw soybean products.|Effects of coffee and dietary fat (alone and in combination) on the development of preneoplastic lesions in exocrine pancreas were investigated in rats and hamsters, treated with azaserine or N-nitrosobis(2-oxopropyl)amine, respectively. Animals were given the respective diets (5% or 25% corn oil) and coffee (instead of drinking water) within one week after the treatment with carcinogen. At four months postinitiation, the pancreata were quantitatively examined for the number and size of preneoplstic foci. In rats, coffee alone inhibited growth of acidophilic foci and, moreover, slightly inhibited the positive modulating effect of fat on growth of these foci, pointing to a negative rather than a positive interaction between these two life-style factors. In hamsters, coffee alone enhanced growth of cystic foci, whereas fat alone enhanced growth of ductular foci. An interaction between fat and coffee on pancreatic carcinogenesis in hamsters could not be demonstrated.|For more Interactions (Complete) data for AZASERINE (8 total), please visit the HSDB record page.

Azaserine is a compound produced by Streptomyces fragilis(1).

As of 1975, azaserine was not commercially manufactured in the US(1). Current production and import/export data were not located in the available literature. It was however, produced in small quantities for research purposes(1). Azaserine has been used in veterinary medicine as an antibiotic, antineoplastic and abortifacient(1). It may be released to the environment via effluents at sites where it is produced or used(SRC).

TERRESTRIAL FATE: Information pertaining to the biodegradation of azaserine in soil was not located in the available literature. Azaserine should hydrolyze rapidly in moist acidic soils. Azaserine is an amino-acid with a pKa of 8.55(1) that will dissociate in soil in varying proportions that are pH dependent. Ions are not expected to volatilize, nor do they generally adsorb to particulate matter as strongly as do their neutral counterparts(2). Both estimates of the Henry's Law constant of 2.56X10-16 atm-cu m/mole(3) and the vapor pressure of 1.53X10-10 at 25 °C indicate that the volatilization of azaserine from either moist or dry soil surfaces should not be important fate processes(3). An estimated Koc of 7(2) indicates azaserine should be highly mobile in soil(4); and it may leach to ground water if released to soil(SRC).|AQUATIC FATE: Information pertaining to the biodegradation of azaserine in water was not located in the available literature. Azaserine should hydrolyze rapidly in acidic waters. Rate constants for the acid, neutral and base hydrolysis of azaserine in aqueous solution at pHs of 3, 7 and 11 and 25 °C were KA = 328 M-1 hr-1, 2.6X10-4 hr-1 and 6.8X10-3 M-1 hr-1(5), which correspond to half-lives of 2.1 hours, 111 days and 425 days, respectively(SRC). Azaserine is an amino-acid with a pKa of 8.55(1) that will dissociate in natural waters in varying proportions that are pH dependent. Ions are not expected to volatilize, nor do they generally adsorb to sediments as strongly as do their neutral counterparts(2). An estimated Henry's Law constant of 2.56X10-16 atm-cu m/mole at 25 °C(3) indicates that the volatilization of azaserine from natural bodies of water should not be an important fate process(3). An estimated Koc of 7(2) indicates azaserine should not partition from the water column to organic matter(4) contained in sediments and suspended solids; and an estimated bioconcentration factor (log BCF) of -0.10(2) indicates that azaserine should not bioconcentrate among aquatic organisms(SRC).|ATMOSPHERIC FATE: Based upon a vapor pressure of 1.53X10-0 mm Hg at 25 °C, which has been calculated from the water solubility and Henry's Law constant, azaserine is expected to exist almost entirely in the particulate phase in ambient air(2). However, if released to the atmosphere as a gas, the vapor phase reaction of azaserine with photochemically produced hydroxyl radicals is likely to be an important fate process. The rate constant for the vapor-phase reaction of azaserine with photochemically produced hydroxyl radicals has been estimated to be 4.0X10-11 cu cm/molecule-sec at 25 °C; which corresponds to an atmospheric half-life of about 10 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). Also, both wet and dry deposition can occur.

Azaserine is incompatible with acids(1). Rate constants for the acid, neutral and base hydrolysis of azaserine in aqueous solution at pHs of 3, 7 and 11 and 25 °C were KA = 328 M-1 hr-1, 2.6X10-4 hr-1 and 6.8X10-3 M-1 hr-1(2), which correspond to half-lives of 2.1 hours, 111 days and 425 days, respectively(SRC). The rate constant for the vapor-phase reaction of azaserine with photochemically produced hydroxyl radicals in air has been estimated to be 4.0X10-11 cu cm/molecule-sec at 25 °C, which corresponds to an atmospheric half-life of about 10 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(3).

Based upon an estimated water solubility of 1.36X10+5 mg/L at 25 °C(1), a bioconcentration factor (log BCF) of -0.10 for azaserine has been calculated using a recommended regression-derived equation(2,SRC). This BCF value indicates that azaserine should not bioconcentrate among aquatic organisms(SRC).

Based upon an estimated water solubility of 1.36X10+5 mg/L at 25 °C(1), a Koc for azaserine of 7 has been calculated using regression-derived equations(2,SRC). This Koc value indicates that azaserine should be highly mobile in soil(3), and it should not partition from the water column to organic matter contained in sediments and suspended solids(SRC). In addition, azaserine is an amino-acid with a pKa of 8.55(4) that will dissociate in environmental media in varying proportions that are pH dependent. Generally ions do not adsorb to particulate matter as strongly as their neutral counterparts(2).

Azaserine is an amino-acid with a pKa of 8.55(1) that will dissociate in environmental media in varying proportions that are pH dependent. Ions are not expected to volatilize from water. The Henry's Law constant of 2.56X10-16 atm- cu m/mole at 25 °C for azaserine has been estimated using a bond contribution method(2). Based upon this Henry's Law constant, volatilization of azaserine from natural bodies of water and moist soil should not be an important fate process(3). Based upon a vapor pressure of about 1.53X10-10 mm Hg at 25 °C, which has been calculated from the water solubility and Henry's Law constant, azaserine is not expected to evaporate from dry surfaces(SRC).

The most probable route of human exposure to azaserine is dermal contact and the inhalation of dust containing it. (SRC)|The most probable human exposure to azaserine would be occupational exposure, which may occur through dermal contact or inhalation of dust at places where it is produced or used as a research chemical with veterinary applications. (SRC)

Drug Information

Antibiotics, Antifungal; Antibiotics, Antineoplastic; Antimetabolites; Antimetabolites, Antineoplastic; Carcinogens; Immunosuppressive Agents|THE GLUTAMINE ANTAGONISTS AZASERINE ... /HAS/ ONLY WEAK CYTOSTATIC ACTIVITY WHEN USED ALONE ... /BUT/ CAN PRODUCE SIGNIFICANT POTENTIATION WHEN ADMIN WITH PURINE ANALOGS SUCH AS MERCAPTOPURINE OR THIOGUANINE.|AZASERINE HAS BEEN TESTED AS AN INHIBITOR OF PURINE SYNTHESIS, & IN CONJUNCTION WITH MERCAPTOPURINE, IN TREATMENT OF ACUTE CHILDHOOD LEUKEMIA.|MEDICATION (VET): IN LIMITED NUMBER OF EXPTL CASES AS ANTIMETABOLITE IN TUMOR THERAPY SINCE MORE EFFECTIVE DRUGS HAVE REPLACED IT.|For more Therapeutic Uses (Complete) data for AZASERINE (6 total), please visit the HSDB record page.

VET: FETAL TOXICITY ASSOC WITH ITS USE ... NARROW MARGIN BETWEEN EFFECTIVE & TOXIC DOSES.

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)|Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

VET: ORAL ABSORPTION IS POOR.|... AFTER TREATMENT OF RATS WITH (3)H-AZASERINE THE PANCREAS HAS BEEN SHOWN TO ATTAIN HIGH LEVELS OF RADIOACTIVITY.

AMINO ACID ANTAGONISTS INHIBIT PROTEIN & NUCLEIC ACID SYNTHESIS BY INTERFERING WITH INCORPORATION OF SPECIFIC AMINO ACIDS REQUIRED FOR PROTEIN OR NUCLEIC ACID SYNTHESIS. THESE CMPD INCL ... AZASERINE ... .|THE GLUTAMINE ... /ANTAGONIST/ AZASERINE ... POTENT ... /INHIBITOR/ OF DE-NOVO PATHWAY OF PURINE NUCLEOTIDE BIOSYNTHESIS. ... INHIBIT/S/ PURINE BIOSYNTHESIS THROUGH FORMATION OF COVALENT BONDS WITH CYSTEINE RESIDUE IN ACTIVE SITE OF KEY ENZYME IN PATHWAY, FORMYLGLYCINAMIDE RIBOTIDE AMIDOTRANSFERASE.|VET: INHIBITS GLUTAMINE USE IN ASPARAGINE BIOSYNTHESIS & IV OR IP USE ENHANCES EFFECT OF L-ASPARAGINASE AGAINST EXPTL SOLID TUMORS. ... ANTIDIURETIC ACTION NOTED IN MICE.|4 ESTABLISHED CELL LINES CONTAINING GAMMA-GLUTAMYL TRANSPEPTIDASE. /A/ POSITIVE CORRELATION WAS OBSERVED BETWEEN CELLULAR GAMMA-GLUTAMYL TRANSPEPTIDASE LEVELS AND SENSITIVITY TO AZASERINE TOXICITY. STRAINS EXPRESSING LOWEST GAMMA-GLUTAMYL TRANSPEPTIDASE ACTIVITIES SHOWED GREATEST RESISTANCE TO AZASERINE TOXICITY.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)|Carcinogens

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

AZASERINE PRODUCES HEPATIC NECROSIS & FATTY LIVER. /FROM TABLE/

Azaserine

Azaserine Use and Manufacturing

Methods of Manufacturing

PRODUCED BY A STREPTOMYCES SPECIES OR BY SYNTHESIS.

Uses

Reagent used to induce pancreatic cancer in experimental animal models.

Production

(1977) NOT PRODUCED COMMERCIALLY IN USA|(1979) NOT PRODUCED COMMERCIALLY IN USA

Health Hazards -> Carcinogens

Computed Properties

Molecular Weight:173.13
XLogP3:-3.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:173.04365571
Monoisotopic Mass:173.04365571
Topological Polar Surface Area:91.6
Heavy Atom Count:12
Complexity:233
Defined Atom Stereocenter Count:1
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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