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    Chemistry

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    Also known as: 6-mercaptopurine, 50-44-2, Purinethol, Mercapurin, 6-thiopurine, Leukerin
    Molecular Formula
    C5H4N4S
    Molecular Weight
    152.18  g/mol
    InChI Key
    GLVAUDGFNGKCSF-UHFFFAOYSA-N
    FDA UNII
    PKK6MUZ20G
    Mercaptopurine
    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.
    Mercaptopurine anhydrous is a Nucleoside Metabolic Inhibitor. The mechanism of action of mercaptopurine anhydrous is as a Nucleic Acid Synthesis Inhibitor.
    1 2D Structure

    Mercaptopurine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3,7-dihydropurine-6-thione
    2.1.2 InChI
    InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
    2.1.3 InChI Key
    GLVAUDGFNGKCSF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=NC2=C(N1)C(=S)N=CN2
    2.2 Other Identifiers
    2.2.1 UNII
    PKK6MUZ20G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1,7-dihydro-6h-purine-6-thione

    2. 6 Mercaptopurine

    3. 6 Mercaptopurine Monohydrate

    4. 6 Thiohypoxanthine

    5. 6 Thiopurine

    6. 6-mercaptopurine

    7. 6-mercaptopurine Monohydrate

    8. 6-thiohypoxanthine

    9. 6-thiopurine

    10. 6h-purine-6-thione, 1,7-dihydro-

    11. Bw 57 323h

    12. Bw 57-323h

    13. Bw 57323h

    14. Leupurin

    15. Mecaptopurine Anhydrous

    16. Mercaptopurina Wellcome

    17. Puri-nethol

    18. Purimethol

    19. Purinethol

    2.3.2 Depositor-Supplied Synonyms

    1. 6-mercaptopurine

    2. 50-44-2

    3. Purinethol

    4. Mercapurin

    5. 6-thiopurine

    6. Leukerin

    7. Leupurin

    8. Mercaleukin

    9. 7h-purine-6-thiol

    10. 6-thioxopurine

    11. Puri-nethol

    12. Purinethiol

    13. Ismipur

    14. Mern

    15. 6-thiohypoxanthine

    16. 6-mercaptopurin

    17. 6-purinethiol

    18. 1,9-dihydro-6h-purine-6-thione

    19. Purimethol

    20. 6-mp

    21. Purine-6-thiol

    22. 3h-purine-6-thiol

    23. 6 Mp

    24. 9h-purine-6-thiol

    25. Mercaleukim

    26. 3,7-dihydropurine-6-thione

    27. 1,7-dihydro-6h-purine-6-thione

    28. Hypoxanthine, Thio-

    29. Mercaptopurine (6-mp)

    30. Mercaptopurine Anhydrous

    31. Mercaptopurin

    32. Mercaptopurina

    33. Mercaptopurinum

    34. Merkaptopuryna

    35. 6h-purine-6-thione, 1,7-dihydro-

    36. Xaluprine

    37. 6-merkaptopurin

    38. Purine, 6-mercapto-

    39. 9h-purine-6(1h)-thione

    40. Purine-6(1h)-thione

    41. Nci-c04886

    42. 7-mercapto-1,3,4,6-tetrazaindene

    43. 1h-purine, 6-mercapto-

    44. Nsc 755

    45. U-4748

    46. 1,9-dihydropurine-6-thione

    47. Purixan

    48. Mercaptopurine;6-mp

    49. Nsc755

    50. Nsc-755

    51. Mercaptopurine (inn)

    52. 3,7-dihydro-6h-purine-6-thione

    53. Purinethol (tn)

    54. Pkk6muz20g

    55. 1h-purine-6(7h)-thione.

    56. Chebi:2208

    57. Mercaptopurine (van)

    58. Dsstox_cid_810

    59. Mercaptopurin [german]

    60. Merkaptopuryna [polish]

    61. 6-merkaptopurin [czech]

    62. Dsstox_rid_75801

    63. Mercaptopurine [inn]

    64. Dsstox_gsid_20810

    65. Mercaptopurine (anhydrous)

    66. Mercaptopurinum [inn-latin]

    67. Mercaptopurina [inn-spanish]

    68. Thiohypoxanthine

    69. Purine-6-thiol, Monohydrate

    70. Cas-50-44-2

    71. 157930-11-5

    72. Smr000544948

    73. Mercaptopurine, 6-

    74. Ccris 2761

    75. Hsdb 3235

    76. Sr-05000001925

    77. 1194-62-3

    78. Einecs 200-037-4

    79. Unii-pkk6muz20g

    80. Ncimech_000025

    81. 9h-purin-6-yl Hydrosulfide

    82. A Thiopurine

    83. Mercaptopurine [usan:usp:inn]

    84. 157930-13-7

    85. Spectrum_000921

    86. Spectrum2_000060

    87. Spectrum3_000491

    88. Spectrum4_000857

    89. Spectrum5_000950

    90. M0063

    91. H-purine-6(1h)-thione

    92. Azathioprine Ep Impurity B

    93. Schembl3893

    94. Chembl1425

    95. Bspbio_001981

    96. Kbiogr_001493

    97. Kbiogr_002363

    98. Kbioss_001401

    99. Kbioss_002366

    100. Mercaptopurine [hsdb]

    101. Ag-670/31547064

    102. Mls001066623

    103. Mls001304020

    104. Mls001304953

    105. Mls006011869

    106. Divk1c_000493

    107. Spectrum1500387

    108. Spbio_000219

    109. 6-mercaptopurine [mi]

    110. Gtpl7226

    111. Schembl2790086

    112. 7h-purin-6-yl Hydrosulfide #

    113. 6-mercaptopurine [iarc]

    114. Dtxsid0020810

    115. Schembl12683725

    116. Chebi:50667

    117. Chebi:94796

    118. Hms501i15

    119. Kbio1_000493

    120. Kbio2_001401

    121. Kbio2_002363

    122. Kbio2_003969

    123. Kbio2_004931

    124. Kbio2_006537

    125. Kbio2_007499

    126. Kbio3_001481

    127. Kbio3_002842

    128. 7-mercapto-1,4,6-tetrazaindene

    129. Cmap_000033

    130. Ninds_000493

    131. 6,7-dihydro-3h-purine-6-thione

    132. Hms1920l07

    133. Hms2091b20

    134. Hms2236l06

    135. Hms3259n03

    136. Hms3369m05

    137. Hms3651g07

    138. Hms3713n10

    139. Hms3747a17

    140. Hms3872n13

    141. Pharmakon1600-01500387

    142. Act11542

    143. Discontinued, See M225450

    144. Zinc4658290

    145. Tox21_111158

    146. Tox21_202591

    147. Bdbm50423778

    148. Ccg-35344

    149. Ccg-39915

    150. Mfcd00233552

    151. Nsc759614

    152. Nsc817004

    153. S1305

    154. Sk5357

    155. Stk727062

    156. Stl257085

    157. 6-mercaptopurine, Analytical Standard

    158. Wln: T56 Bm Dn Fn Hnj Ish

    159. Akos000170222

    160. Akos000275858

    161. Akos005224624

    162. Akos008901311

    163. Akos016903205

    164. Tox21_111158_1

    165. Am81386

    166. Ccg-266232

    167. Cs-1499

    168. Db01033

    169. Nc00613

    170. Nsc-817004

    171. Idi1_000493

    172. Mercaptopurine Anhydrous [who-dd]

    173. Ncgc00091641-02

    174. Ncgc00091641-03

    175. Ncgc00091641-04

    176. Ncgc00091641-16

    177. Ncgc00094717-01

    178. Ncgc00094717-02

    179. Ncgc00094717-03

    180. Ncgc00094717-05

    181. Ncgc00094717-06

    182. Ncgc00188973-01

    183. Ncgc00188973-02

    184. Ncgc00260139-01

    185. Ac-11464

    186. As-13109

    187. Hy-13677

    188. Nci60_041653

    189. Smr004703503

    190. Sbi-0051437.p004

    191. Db-026398

    192. Azathioprine Impurity B [ep Impurity]

    193. Bb 0241023

    194. Ft-0621175

    195. Sw199090-2

    196. En300-61517

    197. 50m442

    198. C01756

    199. C02380

    200. D04931

    201. Ab00171799_05

    202. Ab00641894-03

    203. Ab00641894-04

    204. Ab00641894_05

    205. Ab00876276-13

    206. 233d552

    207. 462m721

    208. 599m524

    209. A828129

    210. Q418529

    211. Sr-05000001925-1

    212. Sr-05000001925-2

    213. W-105961

    214. Purine Antimetabolite: Inhibits Nucleic Acid Replication

    215. 1,9-dihydropurine-6-thione Discontinued, See M225450

    216. Mercaptopurine; 7h-purine-6-thiol; Azathioprine Bp Impurity B

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 152.18 g/mol
    Molecular Formula C5H4N4S
    XLogP30
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count0
    Exact Mass152.01566732 g/mol
    Monoisotopic Mass152.01566732 g/mol
    Topological Polar Surface Area85.2 Ų
    Heavy Atom Count10
    Formal Charge0
    Complexity190
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameMercaptopurine
    PubMed HealthMercaptopurine (By mouth)
    Drug ClassesAntineoplastic Agent, Antirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelMercaptopurine was synthesized and developed by Hitchings, Elion, and associates at the Wellcome Research Laboratories.Mercaptopurine, known chemically as 6H-purine-6-thione, 1,7-dihydro-, monohydrate, is an analogue of the purine bases adenine and h...
    Active IngredientMercaptopurine
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyRoxane; Prometheus Labs; Mylan

    2 of 4  
    Drug NamePurinethol
    PubMed HealthMercaptopurine (By mouth)
    Drug ClassesAntineoplastic Agent, Antirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelPURINETHOL (mercaptopurine) was synthesized and developed by Hitchings, Elion, and associates at the Wellcome Research Laboratories.Mercaptopurine, known chemically as 1,7-dihydro-6H-purine-6-thione monohydrate, is an analogue of the purine bases ade...
    Active IngredientMercaptopurine
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyTeva

    3 of 4  
    Drug NameMercaptopurine
    PubMed HealthMercaptopurine (By mouth)
    Drug ClassesAntineoplastic Agent, Antirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelMercaptopurine was synthesized and developed by Hitchings, Elion, and associates at the Wellcome Research Laboratories.Mercaptopurine, known chemically as 6H-purine-6-thione, 1,7-dihydro-, monohydrate, is an analogue of the purine bases adenine and h...
    Active IngredientMercaptopurine
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyRoxane; Prometheus Labs; Mylan

    4 of 4  
    Drug NamePurinethol
    PubMed HealthMercaptopurine (By mouth)
    Drug ClassesAntineoplastic Agent, Antirheumatic, Cytotoxic, Gastrointestinal Agent
    Drug LabelPURINETHOL (mercaptopurine) was synthesized and developed by Hitchings, Elion, and associates at the Wellcome Research Laboratories.Mercaptopurine, known chemically as 1,7-dihydro-6H-purine-6-thione monohydrate, is an analogue of the purine bases ade...
    Active IngredientMercaptopurine
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyTeva

    4.2 Therapeutic Uses

    Antimetabolites; Antimetabolites, Antineoplastic; Immunosuppressive Agents; Nucleic Acid Synthesis Inhibitors

    National Library of Medicine's Medical Subject Headings. Mercaptopurine. Online file (MeSH, 2016). Available from, as of December 5, 2016: https://www.nlm.nih.gov/mesh/2016/mesh_browser/MBrowser.html

    /CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Mercaptopurine is included in the database.

    NIH/NLM; ClinicalTrials.Gov. Available from, as of February 1, 2017: https://clinicaltrials.gov/ct2/results?term=MERCAPTOPURINE&Search=Search

    Mercaptopurine tablets are indicated for maintenance therapy of acute lymphatic (lymphocytic, lymophoblastic) leukemia as part of a combination regimen. The response to this agent depends upon the particular subclassification of acute lymphatic leukemia and the age of the patient (pediatric or adult). Mercaptopurine is not effective prophylaxis or treatment of central nervous system leukemia. Mercaptopurine is not effective in acute myelogenous leukemia, chronic lymphatic leukemia, the lymphomas (including Hodgkins Disease), or solid tumors. /Included in US product label/

    NIH; DailyMed. Current Medication Information for Mercaptopurine (Updated: October 2016). Available from, as of February 6, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c3b5b8b0-bc5c-4ce9-bbdc-febba60c2658

    MEDICATION (VET): Rarely used in veterinary medicine. Veterinary uses of mercaptopurine have included adjunctive therapy of lymphosarcoma, acute leukemias, and severe rheumatoid arthritis. It may have potential benefit in treating other autoimmune conditions (eg, unresponsive ulcerative colitis) as well.

    Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 928

    For more Therapeutic Uses (Complete) data for Mercaptopurine (9 total), please visit the HSDB record page.

    4.3 Drug Warning

    Tumor lysis syndrome with hyperuricemia and/or hyperuricosuria may occur as a result of rapid cell lysis in patients receiving mercaptopurine as antineoplastic therapy. Prophylactic use of a xanthine oxidase inhibitor such as allopurinol may be used to minimize these adverse effects, but reduction of mercaptopurine dosage is required.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1176

    VET: Like azathioprine, mercaptopurine is best avoided in cats. Additionally, with with caution in dog breeds that potentially have a low thiopurine methyltransferase (TPMT) activity (eg, giant Schnauzers).

    Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 929

    VET: At usual doses, GI effects (nausea, anorexia, vomiting, diarrhea) are most likely seen in small animals. However, bone marrow suppression, hepatotoxicity, pancreatitis, GI (including oral) ulceration, and dermatologic reactions are, potentially, possible.

    Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 929

    Drug fever rarely has been reported in patients receiving mercaptopurine. Other causes of pyrexia, such as sepsis, should be ruled out before attributing the effect to the drug in patients with acute leukemia.103 Other infrequently occurring adverse effects of mercaptopurine include fever, headache, and excessive weakness. Oligospermia has been reported.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1177

    For more Drug Warnings (Complete) data for Mercaptopurine (20 total), please visit the HSDB record page.

    4.4 Drug Indication

    For remission induction and maintenance therapy of acute lymphatic leukemia.

    FDA Label

    Xaluprine is indicated for the treatment of acute lymphoblastic leukaemia (ALL) in adults, adolescents and children.

    5 Pharmacology and Biochemistry
    5.1 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.

    5.2 MeSH Pharmacological Classification

    Antimetabolites

    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, Antineoplastic

    Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

    Immunosuppressive Agents

    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.)

    Nucleic Acid Synthesis Inhibitors

    Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    MERCAPTOPURINE ANHYDROUS
    5.3.2 FDA UNII
    PKK6MUZ20G
    5.3.3 Pharmacological Classes
    Nucleoside Metabolic Inhibitor [EPC]; Nucleic Acid Synthesis Inhibitors [MoA]
    5.4 ATC Code

    L01BB02

    L01BB02

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01B - Antimetabolites

    L01BB - Purine analogues

    L01BB02 - Mercaptopurine

    5.5 Absorption, Distribution and Excretion

    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.

    /MILK/ It is not known whether mercaptopurine is distributed into milk.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1178

    Mercaptopurine and its metabolites are distributed throughout total body water. The volume of distribution of mercaptopurine usually exceeds total body water content. Although the drug reportedly crosses the blood-brain barrier, CSF concentrations are not sufficient for the treatment of meningeal leukemia.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1178

    Mercaptopurine is excreted in urine as unchanged drug and metabolites. In one study in adults with normal renal function, about 11% of an oral dose was recovered in the urine within 6 hours.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1179

    The immunosuppressant azathioprine is increasingly being used in pregnancy. The human placenta is considered a relative barrier to the major metabolite, 6-mercaptopurine (6-MP), and likely explains the lack of proven teratogenicity in humans. The aim of this study was to determine how the human placenta restricts 6-MP transfer using the human placental perfusion model. After addition of 50 ng/mL (n=4) and 500 ng/mL (n=3) 6-MP into the maternal circulation, there was a biphasic decline in its concentration and a delay in fetal circulation appearance. Under equilibrative conditions, the fetal-to-maternal concentration ratio was >1.0 as a result of ion trapping. Binding to placental tissue and maternal pharmacokinetic parameters are the main factors that restrict placental transfer of 6-MP. Active transport is unlikely to play a significant role and drug interactions involving, or polymorphisms in, placental drug efflux transporters are not likely to put the fetus at risk of higher 6-MP exposure.

    PMID:21903160 Hutson JR et al; Reprod Toxicol 32 (3): 349-53 (2011)

    For more Absorption, Distribution and Excretion (Complete) data for Mercaptopurine (9 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    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.

    After oral administration of 35(S)-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.

    NIH; DailyMed. Current Medication Information for Mercaptopurine (Updated: October 2016). Available from, as of February 6, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c3b5b8b0-bc5c-4ce9-bbdc-febba60c2658

    Mercaptopurine is metabolized via 2 major pathways. Mercaptopurine is rapidly and extensively oxidized to 6-thiouric acid in the liver by the enzyme xanthine oxidase. Because xanthine oxidase is inhibited by allopurinol, concomitant use of this drug decreases the metabolism of mercaptopurine and its active metabolites and leads to toxicity. If allopurinol and mercaptopurine are used concomitantly, the dosage of mercaptopurine must be reduced to avoid toxicity. Another major catabolic pathway is thiol methylation of mercaptopurine to form the inactive metabolite methyl-6-MP. This reaction is catalyzed by the enzyme thiopurine S-methyltransferase (TPMT). Variability in TPMT activity in patients because of a genetic polymorphism in the TPMT gene causes interindividual differences in the metabolism of mercaptopurine and resulting systemic exposure to the drug and its active metabolites. Dethiolation can also occur, with large portions of the sulfur being excreted as inorganic sulfate.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1179

    ... In this study, we investigated the in vitro metabolism of 6-mercaptopurine (6MP) to 6-thiouric acid (6TUA) in pooled human liver cytosol. We discovered that 6MP is metabolized to 6TUA through sequential metabolism via the 6-thioxanthine (6TX) intermediate. The role of human AO and XO in the metabolism of 6MP was established using the specific inhibitors raloxifene and febuxostat. Both AO and XO were involved in the metabolism of the 6TX intermediate, whereas only XO was responsible for the conversion of 6TX to 6TUA. These findings were further confirmed using purified human AO and Escherichia coli lysate containing expressed recombinant human XO. Xanthine dehydrogenase (XDH), which belongs to the family of xanthine oxidoreductases and preferentially reduces nicotinamide adenine dinucleotide (NAD(+)), was shown to contribute to the overall production of the 6TX intermediate as well as the final product 6TUA in the presence of NAD(+) in human liver cytosol. In conclusion, we present evidence that three enzymes, AO, XO, and XDH, contribute to the production of 6TX intermediate, whereas only XO and XDH are involved in the conversion of 6TX to 6TUA in pooled HLC.

    PMID:24824603 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4109211 Choughule KV et al; Drug Metab Dispos 42 (8): 1334-40 (2014)

    The thiopurine antimetabolites, 6-mercaptopurine (6-MP) and 6-thioguanine (6-TG) are inactive pro-drugs that require intracellular metabolism for activation to cytotoxic metabolites. Thiopurine methyltransferase (TPMT) is one of the most important enzymes in this process metabolizing both 6-MP and 6-TG to different methylated metabolites including methylthioinosine monophosphate (meTIMP) and methylthioguanosine monophosphate (meTGMP), respectively, with different suggested pharmacological and cytotoxic properties. While meTIMP is a potent inhibitor of de novo purine synthesis (DNPS) and significantly contributes to the cytotoxic effects of 6-MP, meTGMP, does not add much to the effects of 6-TG, and the cytotoxicity of 6-TG seems to be more dependent on incorporation of thioguanine nucleotides (TGNs) into DNA rather than inhibition of DNPS. In order to investigate the role of TPMT in metabolism and thus, cytotoxic effects of 6-MP and 6-TG, we knocked down the expression of the gene encoding the TPMT enzyme using specifically designed small interference RNA (siRNA) in human MOLT4 leukemia cells. The knock-down was confirmed at RNA, protein, and enzyme function levels. Apoptosis was determined using annexin V and propidium iodide staining and FACS analysis. The results showed a 34% increase in sensitivity of MOLT4 cells to 1 uM 6-TG after treatment with TPMT-targeting siRNA, as compared to cells transfected with non-targeting siRNA, while the sensitivity of the cells toward 6-MP was not affected significantly by down-regulation of the TPMT gene. This differential contribution of the enzyme TPMT to the cytotoxicity of the two thiopurines is probably due to its role in formation of the meTIMP, the cytotoxic methylated metabolite of 6-MP, while in case of 6-TG methylation by TPMT substantially deactivates the drug.

    PMID:23811272 Karim H et al; Biochem Biophys Res Commun 437 (2): 280-6 (2013)

    6-Thiouric acid is the major metabolite of 6-mercaptopurine and is formed from this drug by the action of xanthine oxidase.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V26 257 (1981)

    5.7 Biological Half-Life

    Triphasic: 45 minutes, 2.5 hours, and 10 hours.

    Following IV administration of mercaptopurine (an IV preparation of the drug currently is not commercially available in the US), the elimination half-life of the drug is reportedly 21 minutes in pediatric patients and 47 minutes in adults.

    American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1178

    After an intravenous dose, the half-life of the drug in plasma is relatively short (about 50 minutes) due to uptake by cells, renal excretion, and rapid metabolic degradation.

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1235

    After iv administration of 6-mercaptopurine, the half-Iie for disappearance from the blood was about 9 min in rats and 14 min in mice.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V26 257 (1981)

    5.8 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).

    The pathogenesis of several neurodegenerative diseases often involves the microglial activation and associated inflammatory processes. Activated microglia release pro-inflammatory factors that may be neurotoxic. 6-Mercaptopurine (6-MP) is a well-established immunosuppressive drug. Common understanding of their immunosuppressive properties is largely limited to peripheral immune cells. However, the effect of 6-MP in the central nervous system, especially in microglia in the context of neuroinflammation is, as yet, unclear. Tumor necrosis factor-alpha (TNF-a) is a key cytokine of the immune system that initiates and promotes neuroinflammation. The present study aimed to investigate the effect of 6-MP on TNF-a production by microglia to discern the molecular mechanisms of this modulation. Lipopolysaccharide (LPS) was used to induce an inflammatory response in cultured primary microglia or murine BV-2 microglial cells. Released TNF-a was measured by enzyme-linked immunosorbent assay (ELISA). Gene expression was determined by real-time reverse transcription polymerase chain reaction (RT-PCR). Signaling molecules were analyzed by western blotting, and activation of NF-kB was measured by ELISA-based DNA binding analysis and luciferase reporter assay. Chromatin immunoprecipitation (ChIP) analysis was performed to examine NF-kB p65 and coactivator p300 enrichments and histone modifications at the endogenous TNF-a promoter. Treatment of LPS-activated microglia with 6-MP significantly attenuated TNF-a production. In 6-MP pretreated microglia, LPS-induced MAPK signaling, I?B-a degradation, NF-kB p65 nuclear translocation, and in vitro p65 DNA binding activity were not impaired. However, 6-MP suppressed transactivation activity of NF-?B and TNF-a promoter by inhibiting phosphorylation and acetylation of p65 on Ser276 and Lys310, respectively. ChIP analyses revealed that 6-MP dampened LPS-induced histone H3 acetylation of chromatin surrounding the TNF-a promoter, ultimately leading to a decrease in p65/coactivator-mediated transcription of TNF-a gene. Furthermore, 6-MP enhanced orphan nuclear receptor Nur77 expression. Using RNA interference approach, we further demonstrated that Nur77 upregulation contribute to 6-MP-mediated inhibitory effect on TNF-a production. Additionally, 6-MP also impeded TNF-a mRNA translation through prevention of LPS-activated PI3K/Akt/mTOR signaling cascades. These results suggest that 6-MP might have a therapeutic potential in neuroinflammation-related neurodegenerative disorders through downregulation of microglia-mediated inflammatory processes.

    PMID:27075886 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4831152 Huang HY et al; J Neuroinflammation 13 (1): 78 (2016)

    Mercaptopurine (6-MP) competes with hypoxanthine and guanine for the enzyme hyphoxanthine-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). Animal tumors that are resistant to mercaptopurine often have lost the ability to convert mercaptopurine to TIMP. However, it is clear that resistance to mercaptopurine may be acquired by other means as well, particularly in human leukemias. 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.

    NIH; DailyMed. Current Medication Information for Mercaptopurine (Updated: October 2016). Available from, as of February 6, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c3b5b8b0-bc5c-4ce9-bbdc-febba60c2658

    Inflammatory bowel disease is characterized by chronic intestinal inflammation. Azathioprine and its metabolite 6-mercaptopurine (6-MP) are effective immunosuppressive drugs that are widely used in patients with inflammatory bowel disease. ... Azathioprine and 6-MP have been shown to affect small GTPase Rac1 in T cells and endothelial cells, whereas the effect on macrophages and gut epithelial cells is unknown. Macrophages (RAW cells) and gut epithelial cells (Caco-2 cells) were activated by cytokines and the effect on Rac1 signaling was assessed in the presence or absence of 6-MP. Rac1 is activated in macrophages and epithelial cells, and treatment with 6-MP resulted in Rac1 inhibition. In macrophages, interferon-gamma induced downstream signaling through c-Jun-N-terminal Kinase (JNK) resulting in inducible nitric oxide synthase (iNOS) expression. iNOS expression was reduced by 6-MP in a Rac1-dependent manner. In epithelial cells, 6-MP efficiently inhibited tumor necrosis factor-a-induced expression of the chemokines CCL2 and interleukin-8, although only interleukin-8 expression was inhibited in a Rac1-dependent manner. In addition, activation of the transcription factor STAT3 was suppressed in a Rac1-dependent fashion by 6-MP, resulting in reduced proliferation of the epithelial cells due to diminished cyclin D1 expression. These data demonstrate that 6-MP affects macrophages and gut epithelial cells beneficially, in addition to T cells and endothelial cells. Furthermore, mechanistic insight is provided to support development of Rac1-specific inhibitors for clinical use in inflammatory bowel disease.

    PMID:25029617 Marinkovic G et al; Inflamm Bowel Dis 20 (9): 1487-95 (2014)

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