6-Mercaptopurine monohydrate
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6-Mercaptopurine monohydrate
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CAS No:
6112-76-1
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Formula:
C5H4N4S.H2O
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Chemical Name:
6-Mercaptopurine monohydrate
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Synonyms:
6H-Purine-6-thione,1,2,3,9-tetrahydro-,hydrate (1:1);Purine-6-thiol,monohydrate;6H-Purine-6-thione,1,7-dihydro-,monohydrate;6-Mercaptopurine monohydrate;9H-Purine-6-thiol hydrate;Xaluprine
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CAS No:
Description
6-Mercaptopurine hydrate is a purine analogue which acts as an antagonist of the endogenous purines and has been widely used as antileukemic agent and immunosuppressive drug.
6-mercaptopurine monohydrate is an odorless light yellow to yellow crystalline powder. Becomes anhydrous at 284°F. (NTP, 1992)
6-mercaptopurine monohydrate is an odorless light yellow to yellow crystalline powder. Becomes anhydrous at 284°F. (NTP, 1992)|Mercaptopurine hydrate is a hydrate. It contains a mercaptopurine.|Azathioprine is a purine analogue and prodrug of mercaptopurine that is used as an immunosuppressive agent in organ transplantation to prevent rejection and in autoimmune diseases as a corticosteroid sparing agent. Azathioprine is associated with minor, usually transient and asymptomatic elevations in serum aminotransferase levels during therapy and with rare instances of acute, cholestatic liver injury and, with long term use, noncirrhotic portal hypertension as a result of nodular regenerative hyperplasia or sinusoidal obstruction syndrome.|Mercaptopurine (also referred to as 6-mercaptopurine or 6-MP) is a purine analogue that is effective both as an anticancer and an immunosuppressive agent, and is used to treat leukemia and autoimmune diseases as a corticosteroid-sparing agent. Mercaptopurine therapy is associated with a high rate of serum aminotransferase elevations which can be accompanied by jaundice. In addition, mercaptopurine has been linked to instances of clinically apparent acute liver injury and long term therapy to nodular regenerative hyperplasia.|Mercaptopurine is a thiopurine-derivative antimetabolite with antineoplastic and immunosuppressive activities. Produced through the metabolism of mercaptopurine by hypoxanthine-guanine phosphoribosyltransferase (HGPRT), mercaptopurine metabolites 6-thioguanosine-5'-phosphate (6-thioGMP) and 6-thioinosine monophosphate (T-IMP) inhibit nucleotide interconversions and de novo purine synthesis, thereby blocking the formation of purine nucleotides and inhibiting DNA synthesis. This agent is also incorporated into DNA in the form of deoxythioguanosine, which results in the disruption of DNA replication. In addition, mercaptopurine is converted to 6-methylmercaptopurine ribonucleoside (MMPR) by 6-thiopurine methyltransferase; MMPRs are also potent inhibitors of de novo purine synthesis. (NCI04)|An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.
6-Mercaptopurine monohydrate Basic Attributes
170.19
170.026230
4012091
212-968-3
E7WED276I5
2811
DTXSID9025538
C195
L01BB02
29335995
Characteristics
86.2
0.95120
Yellow Fine Powder
313-315 °C (decomp)
490.6°C at 760 mmHg
250.5ºC
INSOLUBLE
Storeat0-5
This compound is sensitive to light and oxidation. Insoluble in water.
Amines, Phosphines, and Pyridines
6-MERCAPTOPURINE MONOHYDRATE reacts with strong oxidizing agents, strong bases and strong acids. (NTP, 1992)
Safety Information
NONH for all modes of transport
3
22-36/37/38-63-20/21/22
22-36/37/39-45-36/37
UP0400000
Xn,Xi
Stable. Incompatible with strong oxidizing agents, acids, strong bases. Light sensitive.
P261-P305 + P351 + P338
H302-H315-H319-H335
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-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)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. You should then dampen the solid spill material with 60-70% methanol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with methanol to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with 60-70% methanol 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 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)
Toxicity
Azathioprine has been associated with several forms of hepatotoxicity, including mild, transient and asymptomatic rises in serum aminotransferase levels, an acute cholestatic injury developing during the first year of starting therapy, and a chronic hepatic injury marked by peliosis hepatis, veno-occlusive disease or nodular regenerative hyperplasia that typically arises 1 to 5 years after starting azathioprine.|Mercaptopurine has been associated with several forms of hepatotoxicity. Patients receiving mercaptopurine for leukemia often have transient and asymptomatic rises in serum aminotransferase or alkaline phosphatase levels and a proportion of these patients develop jaundice, particularly when it is given in high doses. In case series of patients with autoimmune diseases (such as inflammatory bowel disease) treated with mercaptopurine, up to 30% developed serum aminotransferase elevations and these can be persistent as long as therapy is continued, resolving either with dose reduction or discontinuation. Liver biopsy usually demonstrates steatosis and centrolobular injury with scant inflammation.
Drug Information
Xaluprine is indicated for the treatment of acute lymphoblastic leukaemia (ALL) in adults, adolescents and children.|Treatment of acute lymphoblastic leukaemia
Azathioprine is a purine analogue and prodrug of mercaptopurine that is used as an immunosuppressive agent in organ transplantation to prevent rejection and in autoimmune diseases as a corticosteroid sparing agent. Azathioprine is associated with minor, usually transient and asymptomatic elevations in serum aminotransferase levels during therapy and with rare instances of acute, cholestatic liver injury and, with long term use, noncirrhotic portal hypertension as a result of nodular regenerative hyperplasia or sinusoidal obstruction syndrome.|Mercaptopurine (also referred to as 6-mercaptopurine or 6-MP) is a purine analogue that is effective both as an anticancer and an immunosuppressive agent, and is used to treat leukemia and autoimmune diseases as a corticosteroid-sparing agent. Mercaptopurine therapy is associated with a high rate of serum aminotransferase elevations which can be accompanied by jaundice. In addition, mercaptopurine has been linked to instances of clinically apparent acute liver injury and long term therapy to nodular regenerative hyperplasia.
Antineoplastic Agents
Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)|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.)|Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)
SYMPTOMS: Symptoms following ingestion of this compound include white cell depression, jaundice, nausea, mucosal ulceration, skin rash, and fever. It may cause intestinal ulceration, anorexia, vomiting, diarrhea, sprue-like symptoms, and hyperuricemia. Exposure may also result in bone marrow depression. Chronic exposure may cause congenital malformation in the fetus. ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation, ingestion or skin absorption. It may cause skin irritation. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, 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. 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. 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)
1,7-Dihydro-6H-purine-6-thione
6-Mercaptopurine monohydrate Use and Manufacturing
It can be prepared from 7-aminothiazolo[5, 4-d]pyrimidine, or from 6-hydroxypurine with phosphorus sulfide through substitution.
antihypertensive, ACE inhibitor
Human drugs -> Orphan -> Xaluprine (previously Mercaptopurine Nova Laboratories) -> EMA Drug Category|Antineoplastic agents -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans
Computed Properties
Molecular Weight:170.20
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Exact Mass:170.02623200
Monoisotopic Mass:170.02623200
Topological Polar Surface Area:86.2
Heavy Atom Count:11
Complexity:190
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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