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Identification
- Summary
Mercaptopurine is an antineoplastic agent used to treat acute lymphocytic leukemia.
- Brand Names
- Purixan
- Generic Name
- Mercaptopurine
- DrugBank Accession Number
- DB01033
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Mercaptopurine (DB01033)
- Weight
- Average: 152.177
Monoisotopic: 152.015666838 - Chemical Formula
- C5H4N4S
- Synonyms
- 1,9-DIHYDRO-6H-PURINE-6-THIONE
- 6 MP
- 6-Mercaptopurine
- 6-MP
- 6-Thiohypoxanthine
- 6-Thioxopurine
- Mercaptopurina
- Mercaptopurine
- Mercaptopurine anhydrous
- Mercaptopurinum
- Mercapurin
Pharmacology
- Indication
For remission induction and maintenance therapy of acute lymphatic leukemia.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Acute lymphoblastic leukemia •••••••••••• Used in combination to treat Acute promyelocytic leukemia ••• ••••• Used in combination to manage Autoimmune hepatitis ••• ••••• Management of Crohn disease ••• ••••• Used in combination to treat Lymphoblastic lymphoma ••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
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.
- Mechanism of action
Mercaptopurine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to thioinosinic acid (TIMP). TIMP inhibits several reactions that involve inosinic acid (IMP), such as the conversion of IMP to xanthylic acid (XMP) and the conversion of IMP to adenylic acid (AMP) via adenylosuccinate (SAMP). Upon methylation, TIMP forms 6-methylthioinosinate (MTIMP) which inhibits glutamine-5-phosphoribosylpyrophosphate amidotransferase in addition to TIMP. Glutamine-5-phosphoribosylpyrophosphate amidotransferase is the first enzyme unique to the de novo pathway for purine ribonucleotide synthesis. According to experimental findings using radiolabeled mercaptopurine, mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine. In comparison, some mercaptopurine may be converted to nucleotide derivatives of 6-thioguanine (6-TG) via actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase that convert TIMP to thioguanylic acid (TGMP).
Target Actions Organism AHypoxanthine-guanine phosphoribosyltransferase inhibitorHumans AInosine-5'-monophosphate dehydrogenase 1 inhibitorHumans UAmidophosphoribosyltransferase inhibitorHumans UInosine-5'-monophosphate dehydrogenase inhibitorHumans - 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.
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- Route of elimination
Not Available
- Half-life
Triphasic: 45 minutes, 2.5 hours, and 10 hours.
- Clearance
Not Available
- Adverse Effects
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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.
- Pathways
Pathway Category Mercaptopurine Action Pathway Drug action Azathioprine Metabolism Pathway Drug metabolism Azathioprine Action Pathway Drug action Thioguanine Action Pathway Drug action Mercaptopurine Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Thiopurine S-methyltransferase TPMT*2 (G;G) / (C;G) G Allele ADR Directly Studied Patients with this genotype have reduced metabolism of mercaptopurine resulting in increased toxicity. Details Thiopurine S-methyltransferase TPMT*3A (A;A) / (A;G) A Allele ADR Directly Studied Patients with this genotype have reduced metabolism of mercaptopurine resulting in increased toxicity. Details Thiopurine S-methyltransferase TPMT*3C (G;G) / (A;G) G Allele ADR Directly Studied Patients with this genotype have reduced metabolism of mercaptopurine resulting in increased toxicity. Details Thiopurine S-methyltransferase TPMT*3B Not Available c.460G>A ADR Inferred Myelosuppression Details Thiopurine S-methyltransferase TPMT*4A Not Available G > A ADR Inferred Myelosuppression Details
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Mercaptopurine. Abatacept The risk or severity of adverse effects can be increased when Mercaptopurine is combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Mercaptopurine. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Mercaptopurine. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Mercaptopurine. - Food Interactions
- Drink plenty of fluids.
- Take on an empty stomach.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Mercaptopurine monohydrate E7WED276I5 6112-76-1 WFFQYWAAEWLHJC-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Leukerin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mercaptopurine Tablet 50 mg/1 Oral Teva 2005-04-27 2013-10-31 US 
Mercaptopurine Tablets USP Tablet 50 mg Oral Sterimax Inc 2013-11-27 Not applicable Canada 
Purinethol Tablet 50 mg/1 Oral Teva Select Brands 2004-07-30 2013-10-31 US Purinethol Tablet 50 mg/1 Oral Stason Pharmaceuticals, Inc. 2022-01-15 Not applicable US Purinethol Tablet 50 mg Oral TEVA Canada Limited 1954-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mercaptopurine Tablet 50 mg/1 Oral Amerincan Health Packaging 2009-12-16 2015-09-30 US 
Mercaptopurine Tablet 50 mg/1 Oral Hikma Pharmaceuticals USA Inc. 2004-02-13 Not applicable US 
Mercaptopurine Tablet 50 mg/1 Oral Avera McKennan Hospital 2015-03-01 2017-05-24 US 
Mercaptopurine Tablet 50 mg/1 Oral Physicians Total Care, Inc. 2005-05-23 Not applicable US 
Mercaptopurine Tablet 50 mg/1 Oral Remedy Repack 2011-11-03 2012-11-03 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image PURINETHOL 50 MG TABLET, 25 ADET Mercaptopurine (50 mg) Tablet Oral VLD DANIŞMANLIK TIBBİ ÜRÜNLER VE TANITIM HİZMETLERİ LTD. ŞTİ. 2018-05-29 Not applicable Turkey 
Categories
- ATC Codes
- L01BB02 — Mercaptopurine
- L01BB — Purine analogues
- L01B — ANTIMETABOLITES
- L01 — ANTINEOPLASTIC AGENTS
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- Drug Categories
- Antimetabolites
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Drugs for Obstructive Airway Diseases
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Immunologic Factors
- Immunosuppressive Agents
- Myelosuppressive Agents
- Narrow Therapeutic Index Drugs
- Noxae
- Nucleic Acid Synthesis Inhibitors
- Nucleoside Metabolic Inhibitor
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- OAT3/SLC22A8 Substrates with a Narrow Therapeutic Index
- Purine Analogues
- Purines
- Sulfhydryl Compounds
- Sulfur Compounds
- Thiopurine Analogs
- Toxic Actions
- Xanthine derivatives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as purinethiones. These are purines in which the purine moiety bears a thioketone.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyrimidines
- Sub Class
- Purines and purine derivatives
- Direct Parent
- Purinethiones
- Alternative Parents
- Pyrimidinethiones / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organosulfur compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
- Substituents
- Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Organosulfur compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- aryl thiol (CHEBI:2208)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- PKK6MUZ20G
- CAS number
- 50-44-2
- InChI Key
- GLVAUDGFNGKCSF-UHFFFAOYSA-N
- InChI
- InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
- IUPAC Name
- 6,7-dihydro-3H-purine-6-thione
- SMILES
- S=C1N=CNC2=C1NC=N2
References
- General References
- External Links
- Human Metabolome Database
- HMDB0015167
- KEGG Drug
- D04931
- KEGG Compound
- C02380
- PubChem Compound
- 667490
- PubChem Substance
- 46506988
- ChemSpider
- 580869
- BindingDB
- 50423778
- 103
- ChEBI
- 50667
- ChEMBL
- CHEMBL1425
- ZINC
- ZINC000004658290
- Therapeutic Targets Database
- DAP000147
- PharmGKB
- PA450379
- PDBe Ligand
- PM6
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Mercaptopurine
- PDB Entries
- 3bgd / 3ns1
- FDA label
- Download (44.1 KB)
- MSDS
- Download (73.8 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Childhood Acute Lymphoblastic Leukemia in Remission 1 somestatus stop reason just information to hide Not Available Completed Not Available Inflammatory Bowel Diseases (IBD) / Psoriasis 1 somestatus stop reason just information to hide Not Available Completed Treatment Ataxia-Telangiectasia (A-T) 1 somestatus stop reason just information to hide Not Available Completed Treatment Leukemias 1 somestatus stop reason just information to hide Not Available Recruiting Not Available Acute Lymphocytic Leukemia (ALL) / Chemotherapeutic Agent Toxicity / Gene Abnormality / Minimal Residual Disease 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amerisource Health Services Corp.
- DSM Corp.
- Gate Pharmaceuticals
- Medisca Inc.
- Mylan
- Par Pharmaceuticals
- Roxane Labs
- Stason Pharmaceuticals Inc.
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Pill Tablet Oral 50 mg Tablet Oral 50 mg/1 Tablet Oral Tablet Oral 50.000 mg Suspension Oral 20 mg/1mL Suspension Oral 20 MG/ML - Prices
Unit description Cost Unit Mercaptopurine powder 33.97USD g Purinethol 50 mg tablet 6.09USD tablet Mercaptopurine 50 mg tablet 4.17USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 313 dec °C PhysProp water solubility 6.85E+004 mg/L YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.01 HANSCH,C & LEO,AJ (1985) - Predicted Properties
Property Value Source Water Solubility 0.735 mg/mL ALOGPS logP -0.13 ALOGPS logP -0.12 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 11.09 Chemaxon pKa (Strongest Basic) 2.99 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 53.07 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 43.6 m3·mol-1 Chemaxon Polarizability 14.04 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8854 Blood Brain Barrier + 0.8946 Caco-2 permeable - 0.6556 P-glycoprotein substrate Non-substrate 0.7141 P-glycoprotein inhibitor I Non-inhibitor 0.9143 P-glycoprotein inhibitor II Non-inhibitor 0.9848 Renal organic cation transporter Non-inhibitor 0.8543 CYP450 2C9 substrate Non-substrate 0.8607 CYP450 2D6 substrate Non-substrate 0.8533 CYP450 3A4 substrate Non-substrate 0.7949 CYP450 1A2 substrate Inhibitor 0.7555 CYP450 2C9 inhibitor Non-inhibitor 0.6955 CYP450 2D6 inhibitor Non-inhibitor 0.8224 CYP450 2C19 inhibitor Non-inhibitor 0.7472 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6635 Ames test Non AMES toxic 0.5076 Carcinogenicity Non-carcinogens 0.9369 Biodegradation Not ready biodegradable 0.9972 Rat acute toxicity 2.3684 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9857 hERG inhibition (predictor II) Non-inhibitor 0.8734
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 124.4511657 predictedDarkChem Lite v0.1.0 [M-H]- 124.7038657 predictedDarkChem Lite v0.1.0 [M-H]- 124.4924657 predictedDarkChem Lite v0.1.0 [M-H]- 122.87714 predictedDeepCCS 1.0 (2019) [M-H]- 124.4511657 predictedDarkChem Lite v0.1.0 [M-H]- 124.7038657 predictedDarkChem Lite v0.1.0 [M-H]- 124.4924657 predictedDarkChem Lite v0.1.0 [M-H]- 122.87714 predictedDeepCCS 1.0 (2019) [M+H]+ 125.6654657 predictedDarkChem Lite v0.1.0 [M+H]+ 125.5032657 predictedDarkChem Lite v0.1.0 [M+H]+ 125.6557657 predictedDarkChem Lite v0.1.0 [M+H]+ 125.015976 predictedDeepCCS 1.0 (2019) [M+H]+ 125.6654657 predictedDarkChem Lite v0.1.0 [M+H]+ 125.5032657 predictedDarkChem Lite v0.1.0 [M+H]+ 125.6557657 predictedDarkChem Lite v0.1.0 [M+H]+ 125.015976 predictedDeepCCS 1.0 (2019) [M+Na]+ 125.1227657 predictedDarkChem Lite v0.1.0 [M+Na]+ 125.1937657 predictedDarkChem Lite v0.1.0 [M+Na]+ 125.0256657 predictedDarkChem Lite v0.1.0 [M+Na]+ 133.70946 predictedDeepCCS 1.0 (2019) [M+Na]+ 125.1227657 predictedDarkChem Lite v0.1.0 [M+Na]+ 125.1937657 predictedDarkChem Lite v0.1.0 [M+Na]+ 125.0256657 predictedDarkChem Lite v0.1.0 [M+Na]+ 133.70946 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway
- Specific Function
- Guanine phosphoribosyltransferase activity
- Gene Name
- HPRT1
- Uniprot ID
- P00492
- Uniprot Name
- Hypoxanthine-guanine phosphoribosyltransferase
- Molecular Weight
- 24579.155 Da
References
- Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors
- Specific Function
- Dna binding
- Gene Name
- IMPDH1
- Uniprot ID
- P20839
- Uniprot Name
- Inosine-5'-monophosphate dehydrogenase 1
- Molecular Weight
- 55405.365 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Catalyzes the formation of phosphoribosylamine from phosphoribosylpyrophosphate (PRPP) and glutamine
- Specific Function
- 4 iron, 4 sulfur cluster binding
- Gene Name
- PPAT
- Uniprot ID
- Q06203
- Uniprot Name
- Amidophosphoribosyltransferase
- Molecular Weight
- 57398.52 Da
References
- Sahasranaman S, Howard D, Roy S: Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67. doi: 10.1007/s00228-008-0478-6. Epub 2008 May 28. [Article]
- Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors
- Specific Function
- Dna binding
Components:
| Name | UniProt ID |
|---|---|
| Inosine-5'-monophosphate dehydrogenase 1 | P20839 |
| Inosine-5'-monophosphate dehydrogenase 2 | P12268 |
References
- Sahasranaman S, Howard D, Roy S: Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67. doi: 10.1007/s00228-008-0478-6. Epub 2008 May 28. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide, N-methylphthalazinium and phthalazine, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Participates in the bioactivation of prodrugs such as famciclovir, catalyzing the oxidation step from 6-deoxypenciclovir to penciclovir, which is a potent antiviral agent. Is probably involved in the regulation of reactive oxygen species homeostasis. May be a prominent source of superoxide generation via the one-electron reduction of molecular oxygen. May also catalyze nitric oxide (NO) production via the reduction of nitrite to NO with NADH or aldehyde as electron donor. May play a role in adipogenesis
- Specific Function
- 2 iron, 2 sulfur cluster binding
- Gene Name
- AOX1
- Uniprot ID
- Q06278
- Uniprot Name
- Aldehyde oxidase
- Molecular Weight
- 147916.735 Da
References
- Link [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine (also called mercaptopurine, 6-MP or its brand name Purinethol) and 6-thioguanine (also called tioguanine or 6-TG) using S-adenosyl-L-methionine as the methyl donor (PubMed:18484748, PubMed:657528). TPMT activity modulates the cytotoxic effects of thiopurine prodrugs. A natural substrate for this enzyme has yet to be identified
- Specific Function
- S-adenosyl-l-methionine binding
- Gene Name
- TPMT
- Uniprot ID
- P51580
- Uniprot Name
- Thiopurine S-methyltransferase
- Molecular Weight
- 28180.09 Da
References
- Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro)
- Specific Function
- 2 iron, 2 sulfur cluster binding
- Gene Name
- XDH
- Uniprot ID
- P47989
- Uniprot Name
- Xanthine dehydrogenase/oxidase
- Molecular Weight
- 146422.99 Da
References
- Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)
- Specific Function
- Organic anion transmembrane transporter activity
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Organic anion transporter 3
- Molecular Weight
- 59855.585 Da
References
- Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. [Article]
- Mori S, Takanaga H, Ohtsuki S, Deguchi T, Kang YS, Hosoya K, Terasaki T: Rat organic anion transporter 3 (rOAT3) is responsible for brain-to-blood efflux of homovanillic acid at the abluminal membrane of brain capillary endothelial cells. J Cereb Blood Flow Metab. 2003 Apr;23(4):432-40. [Article]
- Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [Article]
- El-Sheikh AA, Greupink R, Wortelboer HM, van den Heuvel JJ, Schreurs M, Koenderink JB, Masereeuw R, Russel FG: Interaction of immunosuppressive drugs with human organic anion transporter (OAT) 1 and OAT3, and multidrug resistance-associated protein (MRP) 2 and MRP4. Transl Res. 2013 Dec;162(6):398-409. doi: 10.1016/j.trsl.2013.08.003. Epub 2013 Sep 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds and xenobiotics from cells. Transports a range of endogenous molecules that have a key role in cellular communication and signaling, including cyclic nucleotides such as cyclic AMP (cAMP) and cyclic GMP (cGMP), bile acids, steroid conjugates, urate, and prostaglandins (PubMed:11856762, PubMed:12523936, PubMed:12835412, PubMed:12883481, PubMed:15364914, PubMed:15454390, PubMed:16282361, PubMed:17959747, PubMed:18300232, PubMed:26721430). Mediates the ATP-dependent efflux of glutathione conjugates such as leukotriene C4 (LTC4) and leukotriene B4 (LTB4) too. The presence of GSH is necessary for the ATP-dependent transport of LTB4, whereas GSH is not required for the transport of LTC4 (PubMed:17959747). Mediates the cotransport of bile acids with reduced glutathione (GSH) (PubMed:12523936, PubMed:12883481, PubMed:16282361). Transports a wide range of drugs and their metabolites, including anticancer, antiviral and antibiotics molecules (PubMed:11856762, PubMed:12105214, PubMed:15454390, PubMed:17344354, PubMed:18300232). Confers resistance to anticancer agents such as methotrexate (PubMed:11106685)
- Specific Function
- 15-hydroxyprostaglandin dehydrogenase (nad+) activity
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- ATP-binding cassette sub-family C member 4
- Molecular Weight
- 149525.33 Da
References
- Chen ZS, Lee K, Kruh GD: Transport of cyclic nucleotides and estradiol 17-beta-D-glucuronide by multidrug resistance protein 4. Resistance to 6-mercaptopurine and 6-thioguanine. J Biol Chem. 2001 Sep 7;276(36):33747-54. Epub 2001 Jul 10. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds, and xenobiotics from cells. Mediates ATP-dependent transport of endogenous metabolites such as cAMP and cGMP, folic acid and N-lactoyl-amino acids (in vitro) (PubMed:10893247, PubMed:12637526, PubMed:12695538, PubMed:15899835, PubMed:17229149, PubMed:25964343). Acts also as a general glutamate conjugate and analog transporter that can limit the brain levels of endogenous metabolites, drugs, and toxins (PubMed:26515061). Confers resistance to the antiviral agent PMEA (PubMed:12695538). Able to transport several anticancer drugs including methotrexate, and nucleotide analogs in vitro, however it does with low affinity, thus the exact role of ABCC5 in mediating resistance still needs to be elucidated (PubMed:10840050, PubMed:12435799, PubMed:12695538, PubMed:15899835). Acts as a heme transporter required for the translocation of cytosolic heme to the secretory pathway (PubMed:24836561). May play a role in energy metabolism by regulating the glucagon-like peptide 1 (GLP-1) secretion from enteroendocrine cells (By similarity)
- Specific Function
- Abc-type xenobiotic transporter activity
- Gene Name
- ABCC5
- Uniprot ID
- O15440
- Uniprot Name
- ATP-binding cassette sub-family C member 5
- Molecular Weight
- 160658.8 Da
References
- Wijnholds J, Mol CA, van Deemter L, de Haas M, Scheffer GL, Baas F, Beijnen JH, Scheper RJ, Hatse S, De Clercq E, Balzarini J, Borst P: Multidrug-resistance protein 5 is a multispecific organic anion transporter able to transport nucleotide analogs. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7476-81. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-dependent and purine-selective transporter (PubMed:10087507, PubMed:9435697). Exhibits the transport characteristics of the nucleoside transport system cif or N1 subtype (N1/cif) (selective for purine nucleosides and uridine) (PubMed:10087507, PubMed:21795683, PubMed:9435697). Plays a critical role in specific uptake and salvage of purine nucleosides in kidney and other tissues (PubMed:9435697). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable)
- Specific Function
- Azole transmembrane transporter activity
- Gene Name
- SLC28A2
- Uniprot ID
- O43868
- Uniprot Name
- Sodium/nucleoside cotransporter 2
- Molecular Weight
- 71925.565 Da
References
- Link [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-dependent, pyrimidine- and purine-selective (PubMed:11032837, PubMed:15861042, PubMed:16446384, PubMed:17140564, PubMed:21998139). Involved in the homeostasis of endogenous nucleosides (PubMed:11032837, PubMed:15861042). Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtype (N3/cib) (with marked transport of both thymidine and inosine) (PubMed:11032837). Employs a 2:1 sodium/nucleoside ratio (PubMed:11032837). Transports uridine (PubMed:21795683). Also able to transport gemcitabine, 3'-azido-3'-deoxythymidine (AZT), ribavirin and 3-deazauridine (PubMed:11032837, PubMed:17140564)
- Specific Function
- Nucleoside
- Gene Name
- SLC28A3
- Uniprot ID
- Q9HAS3
- Uniprot Name
- Solute carrier family 28 member 3
- Molecular Weight
- 76929.61 Da
References
- Link [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Uniporter involved in the facilitative transport of nucleosides and nucleobases, and contributes to maintaining their cellular homeostasis (PubMed:10722669, PubMed:10755314, PubMed:12527552, PubMed:14759222, PubMed:15037197, PubMed:17379602, PubMed:21795683, PubMed:26406980, PubMed:27995448, PubMed:35790189, PubMed:8986748). Functions as a Na(+)-independent transporter (PubMed:8986748). Involved in the transport of nucleosides such as adenosine, guanosine, inosine, uridine, thymidine and cytidine (PubMed:10722669, PubMed:10755314, PubMed:12527552, PubMed:14759222, PubMed:15037197, PubMed:17379602, PubMed:26406980, PubMed:8986748). Also transports purine nucleobases (hypoxanthine, adenine, guanine) and pyrimidine nucleobases (thymine, uracil) (PubMed:21795683, PubMed:27995448). Mediates basolateral nucleoside uptake into Sertoli cells, thereby regulating the transport of nucleosides in testis across the blood-testis barrier (By similarity). Regulates inosine levels in brown adipocytes tissues (BAT) and extracellular inosine levels, which controls BAT-dependent energy expenditure (PubMed:35790189)
- Specific Function
- Adenine transmembrane transporter activity
- Gene Name
- SLC29A1
- Uniprot ID
- Q99808
- Uniprot Name
- Equilibrative nucleoside transporter 1
- Molecular Weight
- 50218.805 Da
References
- Link [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Bidirectional uniporter involved in the facilitative transport of nucleosides and nucleobases, and contributes to maintaining their cellular homeostasis (PubMed:10722669, PubMed:12527552, PubMed:12590919, PubMed:16214850, PubMed:21795683, PubMed:9396714, PubMed:9478986). Functions as a Na(+)-independent, passive transporter (PubMed:9478986). Involved in the transport of nucleosides such as inosine, adenosine, uridine, thymidine, cytidine and guanosine (PubMed:10722669, PubMed:12527552, PubMed:12590919, PubMed:16214850, PubMed:21795683, PubMed:9396714, PubMed:9478986). Also able to transport purine nucleobases (hypoxanthine, adenine, guanine) and pyrimidine nucleobases (thymine, uracil) (PubMed:16214850, PubMed:21795683). Involved in nucleoside transport at basolateral membrane of kidney cells, allowing liver absorption of nucleoside metabolites (PubMed:12527552). Mediates apical nucleoside uptake into Sertoli cells, thereby regulating the transport of nucleosides in testis across the blood-testis-barrier (PubMed:23639800). Mediates both the influx and efflux of hypoxanthine in skeletal muscle microvascular endothelial cells to control the amount of intracellular hypoxanthine available for xanthine oxidase-mediated ROS production (By similarity)
- Specific Function
- Adenine transmembrane transporter activity
- Gene Name
- SLC29A2
- Uniprot ID
- Q14542
- Uniprot Name
- Equilibrative nucleoside transporter 2
- Molecular Weight
- 50112.335 Da
References
- Link [Link]
Drug created at June 13, 2005 13:24 / Updated at September 19, 2024 06:09