6,7-dihydro-3H-purine-6-thione

• ChemBase ID: 905
• Molecular Formular: C5H4N4S
• Molecular Mass: 152.17706
• Monoisotopic Mass: 152.01566715
• SMILES: S=c1nc[nH]c2nc[nH]c12
• Canonical SMILES: S=c1nc[nH]c2c1[nH]cn2
• InChI: InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
• InChIKey: GLVAUDGFNGKCSF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,7-dihydro-3H-purine-6-thione
• IUPAC Traditional name: 6-mercaptopurine
• Brand Name: Ismipur; Leukerin; Leupurin; Mercaleukim; Mercaleukin; Mern; Puri-Nethol; Purimethol; Purinethol
• Synonyms: Purinethol; 6-MP; Mercaptopurine Monohydrate; Mercapurin; 6 MP; MP; 6-Mercaptopurine; Mercaptopurine

Database IDs

• CAS Number: 50-44-2
• PubChem SID: 160964368; 46506988
• PubChem CID: 667490

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.498602
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.123077706
• LogD (pH = 7.4): -0.12507708
• Log P: -0.121789195
• Molar Refractivity: 43.6027 cm^3
• Polarizability: 15.407385 Å^3
• Polar Surface Area: 53.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.13
• LOG S: -2.32
• Solubility (Water): 7.35e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; 6.85 mg/mL
• Hydrophobicity(logP): -0.4

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: DNA/RNA synthesis

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB01033

• Drug Groups: approved
• Description: 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]
• Indication: For remission induction and maintenance therapy of acute lymphatic leukemia.
• Pharmacology: 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.
• Toxicity: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• 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.
• Half Life: Triphasic: 45 minutes, 2.5 hours, and 10 hours.
• 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).
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1305

Research Area: Infection
Biological Activity:
Mercaptopurine is used to treat leukemia. It is also used for pediatric non-Hodgkin’s lymphoma, polycythemia vera, psoriatic arthritis, and inflammatory bowel disease. It has demonstrated some in vitro effectiveness against Mycobacterium paratuberculosis 6-MP ribonucleotide inhibits purine nucleotide synthesis and metabolism. This alters the synthesis and function of RNA and DNA. Mercaptopurine interferes with nucleotide interconversion and glycoprotein synthesis. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Mercaptopurine