Tìm theo
Mercaptopurine
Các tên gọi khác (8 ) :
  • 1,7-Dihydro-6H-purine-6-thione
  • 3H-Purine-6-thiol
  • 6 MP
  • 6-Mercaptopurine
  • 6-MP
  • 6-Thiohypoxanthine
  • 6-Thioxopurine
  • Mercapurin
Thuốc chống ung thư và tác động vào hệ thống miễn dịch
Thuốc Gốc
Small Molecule
CAS: 50-44-2
ATC: L01BB02
ĐG : Amerisource Health Services Corp. , http://www.amerisourcebergen.com
CTHH: C5H4N4S
PTK: 152.177
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. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C5H4N4S
Phân tử khối
152.177
Monoisotopic mass
152.015666838
InChI
InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChI Key
InChIKey=GLVAUDGFNGKCSF-UHFFFAOYSA-N
IUPAC Name
6,7-dihydro-3H-purine-6-thione
Traditional IUPAC Name
mercaptopurine
SMILES
S=C1N=CNC2=C1NC=N2
Độ tan chảy
313 dec °C
Độ hòa tan
6.85E+004 mg/L
logP
0.01
logS
-2.3
pKa (strongest acidic)
9.5
pKa (Strongest Basic)
2.99
PSA
53.07 Å2
Refractivity
43.6 m3·mol-1
Polarizability
14.04 Å3
Rotatable Bond Count
0
H Bond Acceptor Count
3
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
Dược Lực Học : Mercaptopurine is one of a large series of purine analogues which interfere with nucleic acid biosynthesis and has been found active against human leukemias. It is an analogue of the purine bases adenine and hypoxanthine. It is not known exactly which of any one or more of the biochemical effects of mercaptopurine and its metabolites are directly or predominantly responsible for cell death.
Cơ Chế Tác Dụng : 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. [PubChem] Mercaptopurine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to thioinosinic acid (TIMP). This intracellular nucleotide inhibits several reactions involving inosinic acid (IMP), including the conversion of IMP to xanthylic acid (XMP) and the conversion of IMP to adenylic acid (AMP) via adenylosuccinate (SAMP). In addition, 6-methylthioinosinate (MTIMP) is formed by the methylation of TIMP. Both TIMP and MTIMP have been reported to inhibit glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway for purine ribonucleotide synthesis. Experiments indicate that radiolabeled mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine. Some mercaptopurine is converted to nucleotide derivatives of 6-thioguanine (6-TG) by the sequential actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase, converting TIMP to thioguanylic acid (TGMP).
Dược Động Học :
▧ Absorption :
Clinical studies have shown that the absorption of an oral dose of mercaptopurine in humans is incomplete and variable, averaging approximately 50% of the administered dose. The factors influencing absorption are unknown.
▧ Volume of Distribution :
The volume of distribution exceeded that of the total body water.
▧ Protein binding :
Plasma protein binding averages 19% over the concentration range 10 to 50 µg/mL (a concentration only achieved by intravenous administration of mercaptopurine at doses exceeding 5 to 10 mg/kg).
▧ Metabolism :
Hepatic. Degradation primarily by xanthine oxidase. The catabolism of mercaptopurine and its metabolites is complex. In humans, after oral administration of 35S-6-mercaptopurine, urine contains intact mercaptopurine, thiouric acid (formed by direct oxidation by xanthine oxidase, probably via 6-mercapto-8-hydroxypurine), and a number of 6-methylated thiopurines. The methylthiopurines yield appreciable amounts of inorganic sulfate.
▧ Half Life :
Triphasic: 45 minutes, 2.5 hours, and 10 hours.
Độc Tính : Signs and symptoms of overdosage may be immediate such as anorexia, nausea, vomiting, and diarrhea; or delayed such as myelosuppression, liver dysfunction, and gastroenteritis. The oral LD50 of mercaptopurine was determined to be 480 mg/kg in the mouse and 425 mg/kg in the rat.
Chỉ Định : For remission induction and maintenance therapy of acute lymphatic leukemia.
Tương Tác Thuốc :
  • Acenocoumarol Mercaptopurine may decrease the anticoagulant effect of acenocoumarol.
  • Allopurinol Allopurinol may increase the effect of thiopurine, mercaptopurine.
  • Aminosalicylic Acid Aminosalicylic acid may increase the toxicity of thiopurine, mercaptopurine.
  • Anisindione Mercaptopurine may decrease the anticoagulant effect of anisindione.
  • Atracurium The agent dereases the effect of the muscle relaxant
  • Dicoumarol Mercaptopurine may decrease the anticoagulant effect of dicumarol.
  • Doxacurium chloride The agent dereases the effect of the muscle relaxant
  • Febuxostat Coadministration of febuxostat with xanthine oxidase substrate drugs (azathioprine, mercaptopurine or theophylline) could increase plasma concentrations of these drugs, since these drugs are metabolized by xanthine oxidase, resulting in severe toxicity; hence their concomitant use is contraindicated. Since febuxostat does not inhibit or induce cytochrome P450 enzymes it lacks significant drug interactions with other drugs metabolized of these enzymes.
  • Mesalazine Mesalazine may increase the toxicity of thiopurine, mercaptopurine.
  • Metocurine The agent dereases the effect of the muscle relaxant
  • Mivacurium The agent dereases the effect of the muscle relaxant
  • Olsalazine Olsalazine may increase the toxicity of thiopurine, mercaptopurine.
  • Pancuronium The agent dereases the effect of the muscle relaxant
  • Sulfasalazine Sulfasalazine may increase the toxicity of thiopurine, mercaptopurine.
  • Tioguanine Complete cross resistance may occur.
  • Trastuzumab Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
  • Tubocurarine The agent dereases the effect of the muscle relaxant
  • Vecuronium The agent dereases the effect of the muscle relaxant
  • Warfarin Mercaptopurine may decrease the anticoagulant effect of warfarin.
Liều Lượng & Cách Dùng : Tablet - Oral - 50 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Leukerin
  • Công ty :
    Sản phẩm biệt dược : Purinethol
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01033
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=667490
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506988
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C02380
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D04931
ChemSpider
http://www.chemspider.com/Chemical-Structure.580869.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50200098
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0378-3547-52
PharmGKB
http://www.pharmgkb.org/drug/PA450379
Wikipedia
http://en.wikipedia.org/wiki/Mercaptopurine
RxList
http://www.rxlist.com/cgi/generic2/mercaptopurine.htm
Drugs.com
http://www.drugs.com/cdi/mercaptopurine.html
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