MERCAPTOPURINE ANHYDROUS

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H4N4S
Molecular Weight	152.177
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

S=C1NC=NC2=C1N=CN2

InChI

InChIKey=GLVAUDGFNGKCSF-UHFFFAOYSA-N

InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009053s032lbl.pdf

Mercaptopurine, marketed under the brand name Purinethol among others, is a medication used for cancer and autoimmune diseases. 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). PURINETHOL (mercaptopurine) is indicated for maintenance therapy of acute lymphatic (lymphocytic, lymphoblastic) 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).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Amidophosphoribosyltransferase 3 Target ID: CHEMBL2362992 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18506437 \| http://drugcentral.org/drugcard/1708?q=MERCAPTOPURINE	Inhibitor 8297
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18506437 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009053s032lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/17188583	Inhibitor 8297
prostaglandin biosynthetic process 23 Target ID: GO:0001516 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3247467	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute lymphoblastic leukemia 27 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009053s032lbl.pdf	Primary		Approved 8429	PURINETHOL Approved Use Mercaptopurine tablets are indicated for maintenance therapy of acute lymphatic (lymphocytic, lymphoblastic) 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 tablets are not effective for prophylaxis or treatment of central nervous system leukemia. Mercaptopurine tablets are not effective in acute myelogenous leukemia, chronic lymphatic leukemia, the lymphomas (including Hodgkins Disease), or solid tumors. Launch Date 1953

C_max

Value	Dose	Co-administered	Analyte	Population
69.5 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9048271	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		MERCAPTOPURINE ANHYDROUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
74 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3470165	75 mg/m² single, intravenous dose: 75 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		MERCAPTOPURINE ANHYDROUS plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
135.8 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9048271	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		MERCAPTOPURINE ANHYDROUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
200 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3470165	75 mg/m² single, intravenous dose: 75 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		MERCAPTOPURINE ANHYDROUS plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3470165	75 mg/m² single, intravenous dose: 75 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		MERCAPTOPURINE ANHYDROUS plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
81% DRUG LABEL https://nctr-crs.fda.gov/fdalabel/services/spl/set-ids/15904472-4c32-4224-95d3-eb131a7ff9c8/spl-doc?hl=mercaptopurine			MERCAPTOPURINE ANHYDROUS plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg 3 times / day multiple, oral Studied dose Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf https://pubmed.ncbi.nlm.nih.gov/19555631/	unhealthy, 37 years n = 1 Health Status: unhealthy Condition: hyperthyroidism Age Group: 37 years Sex: F Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf https://pubmed.ncbi.nlm.nih.gov/19555631/	Other AEs: Anorexia, Nausea... Other AEs: Anorexia Nausea Vomiting Myelosuppression Hepatic disease Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205919s000lbl.pdf https://pubmed.ncbi.nlm.nih.gov/19555631/
50 mg/m2/hour 1 times / 2 days multiple, intravenous Studied dose Dose: 50 mg/m2/hour, 1 times / 2 days Route: intravenous Route: multiple Dose: 50 mg/m2/hour, 1 times / 2 days Sources: https://pubmed.ncbi.nlm.nih.gov/1600597/	unhealthy, Median age 9.5 years n = 51 Health Status: unhealthy Condition: leukemia Age Group: Median age 9.5 years Population Size: 51 Sources: https://pubmed.ncbi.nlm.nih.gov/1600597/	Other AEs: ALT increased, AST increased... Other AEs: ALT increased (grade 3) AST increased (grade 3) Bilirubin increased (grade 3) Sources: https://pubmed.ncbi.nlm.nih.gov/1600597/
1125 mg/m2 1 times / day multiple, intravenous (mean) Studied dose Dose: 1125 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1125 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: https://pubmed.ncbi.nlm.nih.gov/8120558/	unhealthy, age range 2 to 17 years n = 23 Health Status: unhealthy Condition: acute leukemia Age Group: age range 2 to 17 years Sex: M+F Population Size: 23 Sources: https://pubmed.ncbi.nlm.nih.gov/8120558/	Other AEs: Pancytopenia, Neutropenic fever... Other AEs: Pancytopenia (100%) Neutropenic fever (91%) Bacteremia (65%) Candidemia (13%) Cytomegalovirus infection (4%) Bleeding (4%) Nausea (100%) Mucosal ulceration (52%) Diarrhea (26%) Typhlitis (4%) Alopecia (100%) Peeling of hands & feet on soles (52%) Papular skin eruption (30%) Conjunctivitis (13%) Death (8%) Sources: https://pubmed.ncbi.nlm.nih.gov/8120558/
1250 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 1250 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1250 mg/m2, 1 times / day Co-administed with:: cytarabine(500 mg/m2 IV; 4 days) Sources: https://pubmed.ncbi.nlm.nih.gov/8120558/	unhealthy, age range 4 to 14 years n = 12 Health Status: unhealthy Condition: acute leukemia Age Group: age range 4 to 14 years Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/8120558/	Sources: https://pubmed.ncbi.nlm.nih.gov/8120558/
50 mg/m2/hour 1 times / 3 weeks multiple, intravenous Studied dose Dose: 50 mg/m2/hour, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 50 mg/m2/hour, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/4038917/	unhealthy, median age 10 years n = 10 Health Status: unhealthy Condition: cancer Age Group: median age 10 years Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/4038917/	DLT: Mucositis... Dose limiting toxicities: Mucositis (grade 3, 30%) Sources: https://pubmed.ncbi.nlm.nih.gov/4038917/
35 mg/m2 1 times / day multiple, parenteral MTD Dose: 35 mg/m2, 1 times / day Route: parenteral Route: multiple Dose: 35 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9713314/	unhealthy, median age 60 years n = 7 Health Status: unhealthy Condition: colon cancer Age Group: median age 60 years Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/9713314/	DLT: Neutropenia, Thrombocytopenia... Other AEs: Neutropenia, Hyperbilirubinaemia... Dose limiting toxicities: Neutropenia (grade 3, 12.5%) Thrombocytopenia (grade 3, 12.5%) Other AEs: Neutropenia (grade 2, 75%) Hyperbilirubinaemia (50%) Sources: https://pubmed.ncbi.nlm.nih.gov/9713314/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 706 OATP1B1 788 BSEP 402 MRP4 204 MRP3 157 CYP2C19 1478 CYP1A2 1524	TPMT 5

Drug as perpetrator

Target	Modality	Activity
BSEP 403	inhibitor 3277 Sources: https://academic.oup.com/toxsci/article/136/1/216/1653420 Page: -	no [IC50 133 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://pubs.acs.org/doi/10.1021/tx300075j Page: -	no
CYP2C19 1553	inhibitor 3277 Sources: https://pubs.acs.org/doi/10.1021/tx300075j Page: -	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubs.acs.org/doi/10.1021/tx300075j Page: -	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubs.acs.org/doi/10.1021/tx300075j Page: -	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubs.acs.org/doi/10.1021/tx300075j Page: -	no
MRP3 207	inhibitor 3277 Sources: https://academic.oup.com/toxsci/article/136/1/216/1653420 Page: -	no
MRP4 238	inhibitor 3277 Sources: https://academic.oup.com/toxsci/article/136/1/216/1653420 Page: -	no
OATP1B1 803	inhibitor 3277 Sources: https://molpharm.aspetjournals.org/content/83/6/1257?with-ds=yes Page: -	no
OATP1B3 715	inhibitor 3277 Sources: https://molpharm.aspetjournals.org/content/83/6/1257?with-ds=yes Page: -	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
TPMT 5	substrate 3367 Sources: http://medreviews.com/sites/default/files/2018-02/RIGD_3suppl1_s30.pdf#page=8 Page: 8.0	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY556883	https://www.001chemical.com/chem/50-44-2
3B Scientific (Wuhan) Corp	3B3-010771	http://www.3bsc.com/index/pro_info.php?id=33264
AA Blocks	AA0038MP	http://www.aablocks.com/goods/Goods/detail?id=AA0038MP
AHH Chemical co.,ltd	MT-16617	http://www.ahhchemical.com/product/MT-16617.html
AK Scientific, Inc. (AKSCI)	6450AJ	http://www.aksci.com/item_detail.php?cat=6450AJ
AK Scientific, Inc. (AKSCI)	H348	http://www.aksci.com/item_detail.php?cat=H348
Aaron Chemicals	AR0039EH	http://www.aaronchem.com/50-44-2
AbMole Bioscience	M5771	http://www.abmole.com/products/mercaptopurine-(6-mp).html
Acadechem	ACDS-063904	http://www.acadechemical.com/product/138603
Achemica	ACMC-1AUNA	http://www.achemica.com/prodinfo/?id=23363
Achemo Scientific Limited	AC-13751	http://www.achemo.com/product_view.asp?ID=3641
Achemtek	0104-015751	http://www.achemtek.com/50-44-2
Adooq BioScience	A10568	https://www.adooq.com/mercaptopurine.html
Allbio Pharm Co., Ltd	AD04542	http://www.allbiopharm.com/product/n/AD04542
Ambeed	A262086	https://www.ambeed.com/products/50-44-2.html
Ambinter	Amb19871503	http://www.ambinter.com/reference/19871503
Ambinter	Amb22094177	http://www.ambinter.com/reference/22094177
Angene	AGN-PC-0OBCLT	http://www.angenechemical.com/productshow/AGN-PC-0OBCLT.html
Anward	ANW-30999	http://www.anward.com/pro_result/20361
Anward	ANW-57555	http://www.anward.com/pro_result/44006
ApexBio Technology	A2355	http://www.apexbt.com/mercaptopurine-6-mp.html
Aromalake	LS20858	http://www.aromalake.com/6-Mercaptopurine-p4173.html
Aronis	ARONIS27054	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=19951
Aurora Fine Chemicals LLC	A00.451.223	http://online.aurorafinechemicals.com/info?ID=A00.451.223
Aurora Fine Chemicals LLC	K00.363.564	http://online.aurorafinechemicals.com/info?ID=K00.363.564
Aurum Pharmatech LLC	W-5114	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5114
BLD Pharm	BD01223348	http://www.bldpharm.com/products/157930-11-5.html
BLD Pharm	BD33839	http://www.bldpharm.com/products/50-44-2.html
BioCrick	BCC1186	http://www.biocrick.com/Mercaptopurine-6-MP-BCC1186.html
BioSynth	W-105961	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-105961.html
Boerchem	BC202313	http://www.boerchem.com/?product_33963.html
CSNpharm	CSN16373	https://www.csnpharm.com/products/6-mercaptopurine.html
Capot Chemical	9680	http://www.capotchem.com/en/9680.htm
Capot Chemical	PubChem9680	http://www.capotchem.com/en/9680.htm
Chem Scene	CS-1499	http://www.chemscene.com/50-44-2.html
ChemMol	1201510	http://www.chemmol.com/chemmol/1201510.html
ChemMol	30101353	http://www.chemmol.com/chemmol/30101353.html
ChemMol	42303035	http://www.chemmol.com/chemmol/42303035.html
ChemMol	44025678	http://www.chemmol.com/chemmol/44025678.html
ChemMol	49401460	http://www.chemmol.com/chemmol/49401460.html
Chemspace	CSSB00000748415	https://chem-space.com/CSSB00000748415
Clearsynth	CS-O-30642	http://www.clearsynth.com/en/CSO30642.html
Debye Scientific	DB-026398	http://www.debyesci.com/DB-026398.html
Finetech	FT-0621175	http://www.finetechnology-ind.com/prod/detail/pub/50-44-2.html
Glentham Life Sciences	GP0789	http://www.glentham.com/products/product/GP0789/
Hairui	HR135280	http://www.hairuichem.com/en/product/50-44-2.html
Lab Network	LN00222396	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00222396
Matrix Scientific	147903	https://www.matrixscientific.com/147903.html
MedChem Express	HY-13677	https://www.medchemexpress.com/6-Mercaptopurine.html
Molcore	MC556883	https://www.molcore.com/product/50-44-2
OChem	11066	http://www.ocheminc.com/index.php?act=psearch&pid=233D552
OChem	10489	http://www.ocheminc.com/index.php?act=psearch&pid=462M721
OChem	3905	http://www.ocheminc.com/index.php?act=psearch&pid=50M442
OChem	3904	http://www.ocheminc.com/index.php?act=psearch&pid=599M524
Oakwood	219749	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=100748&ExtHyperLink=1
Oakwood	50540	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=196267&ExtHyperLink=1
Renno Tech	RP21622	http://www.rennotech.com/product_show.asp?id=27335
Selleck Chemicals	S1305	http://www.selleckchem.com/products/Mercaptopurine.html
Sigma-Aldrich	38171_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/38171?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S048247	http://www.sinfoobiotech.com/product/1051645
Smolecule	S548851	http://www.smolecule.com/products/s548851
Synthink Research Chemicals	SA17903	https://synthinkchemicals.com/product/azathioprine-ep-impurity-b/
TCI (Tokyo Chemical Industry)	M0063	http://www.tcichemicals.com/eshop/en/us/commodity/M0063/index.html
THE BioTek	bt-288262	https://www.thebiotek.com/product/inhibitors/bt-288262
Vitas-M Laboratory	BBL033743	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL033743&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
Yuhao Chemical	RT18294	http://www.chemyuhao.com/50-44-2.html
abcr GmbH	AB310793	http://www.abcr.com/shop/en/AB310793
eNovation Chemicals	D584258	https://www.enovationchem.com/ProductDetails.asp?ProductID=D584258
iChemical	EBD540779	http://www.ichemical.com/products/50-44-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-4811219863	https://mcule.com/MCULE-4811219863/

PubMed

Title	Date	PubMed
Pharmacokinetic considerations in the treatment of inflammatory bowel disease.	2001	11707060
Therapeutic drug monitoring of cytotoxic drugs.	2001	11564055
Intrathecal chemotherapy with antineoplastic agents in children.	2001	11354696
Severe life-threatening diarrhea caused by azathioprine but not by 6-mercaptopurine.	2001	11244253
Genotype-phenotype correlation for thiopurine S-methyltransferase in healthy Italian subjects.	2001 Apr	11372592
Thiopurine methyltransferase activity in the Jewish population of Israel.	2001 Apr	11372589
Preponderance of thiopurine S-methyltransferase deficiency and heterozygosity among patients intolerant to mercaptopurine or azathioprine.	2001 Apr 15	11304783
Cyclosporine in ulcerative colitis: state of the art.	2001 Apr-Jun	11475136
Prognostic value of day 14 blast percentage and the absolute blast index in bone marrow of children with acute lymphoblastic leukemia.	2001 Apr-May	11293286
Reversal of cytosine arabinoside (ara-C) resistance by the synergistic combination of 6-thioguanine plus ara-C plus PEG-asparaginase (TGAP) in human leukemia lines lacking or expressing p53 protein.	2001 Aug	11561778
[Metastatic Crohn's disease in childhood].	2001 Aug	11472671
Glucocorticoids and IL-10, but not 6-MP, 5-ASA or sulfasalazine block endothelial expression of MAdCAM-1: implications for inflammatory bowel disease therapy.	2001 Aug	11472325
Review article: the risk of lymphoma associated with inflammatory bowel disease and immunosuppressive treatment.	2001 Aug	11472312
Differing contribution of thiopurine methyltransferase to mercaptopurine versus thioguanine effects in human leukemic cells.	2001 Aug 1	11479220
Evolving medical therapies for ulcerative colitis.	2001 Dec	11696283
Langerhans' cell histiocytosis presenting with a para-aortic lesion and heart failure.	2001 Feb	11393100
A multicenter trial of 6-mercaptopurine and prednisone in children with newly diagnosed Crohn disease.	2001 Feb	11321377
Induction therapy of adult acute lymphocytic leukemia without the use of vincristine or prednisone.	2001 Feb	11253603
New developments in the immunosuppressive drug monitoring of cyclosporine, tacrolimus, and azathioprine.	2001 Feb	11239509
Intravenous cyclosporine in refractory pyoderma gangrenosum complicating inflammatory bowel disease.	2001 Feb	11233655
Tumor lysis syndrome in an infant with Langerhans cell histiocytosis successfully treated using continuous arteriovenous hemofiltration.	2001 Feb	11216709
Smooth muscle tumor developing in an immunocompromised child after therapy for leukemia.	2001 Feb	11216708
Tautomerism and infrared spectra of 2-thiopurine: an experimental matrix isolation and theoretical ab initio and density functional theory study.	2001 Feb	11206573
A novel protein complex distinct from mismatch repair binds thioguanylated DNA.	2001 Feb	11160874
Therapeutic drug monitoring of azathioprine and 6-mercaptopurine metabolites in Crohn disease.	2001 Jan	11218242
Further evidence that 6-MP taken by the father with IBD provides risk of congenital anomaly to the pregnancy.	2001 Jan	11197267
Results of a randomized phase III trial in children and adolescents with advanced stage diffuse large cell non Hodgkin's lymphoma: a Pediatric Oncology Group study.	2001 Jul	11699405
Pneumococcal arthritis affects performance status in patients with chronic GVHD of the skin following allogeneic bone marrow transplantation.	2001 Jul	11530813
Repetitious appearance and disappearance of different kinds of clonal cytogenetic abnormalities after allogeneic bone marrow transplantation.	2001 Jul	11530811
If at first you don't succeed...Try again?	2001 Jul	11467666
Mechanism of activation of an immunosuppressive drug: azathioprine. Quantum chemical study on the reaction of azathioprine with cysteine.	2001 Jul 4	11427067
Antimycobacterial activity of 9-sulfonylated/sulfenylated-6-mercaptopurine derivatives.	2001 Jul 9	11425535
Cost-utility of initial medical management for Crohn's disease perianal fistulae.	2001 Jun	11375946
6-Mercaptopurine for children newly diagnosed with Crohn's disease.	2001 Jun	11353560
Improved methods for determining the concentration of 6-thioguanine nucleotides and 6-methylmercaptopurine nucleotides in blood.	2001 Jun 5	11419732
Plasma pharmacokinetics and cerebrospinal fluid penetration of thioguanine in children with acute lymphoblastic leukemia: a collaborative Pediatric Oncology Branch, NCI, and Children's Cancer Group study.	2001 Mar	11320662
Fasting hypoglycemia is common during maintenance therapy for childhood acute lymphoblastic leukemia.	2001 Mar	11241057
High-throughput genotyping of thiopurine S-methyltransferase by denaturing HPLC.	2001 Mar	11238310
Effect of the glutathione/glutathione disulfide redox couple on thiopurine methyltransferase.	2001 Mar 15	11266655
Crohn's disease of the esophagus: clinical features and outcomes.	2001 May	11383583
Approach to corticosteroid-dependent and corticosteroid-refractory Crohn's disease.	2001 May	11380040
Treatment of refractory microscopic colitis with azathioprine and 6-mercaptopurine.	2001 May	11313319
Rational dosing of azathioprine and 6-mercaptopurine.	2001 May	11302950
Pitfalls in the determination of mutant alleles of the thiopurine methyltransferase gene.	2001 Nov	11681423
Azathioprine treatment and male fertility in inflammatory bowel disease.	2001 Nov	11677195
Diagnosis and treatment of perianal fistulas in Crohn disease.	2001 Nov 20	11712881
6-mercaptopurine metabolite levels in children with inflammatory bowel disease.	2001 Oct	11698762
Review article: the limitations of corticosteroid therapy in Crohn's disease.	2001 Oct	11563990
Use of azathioprine or 6-mercaptopurine for treatment of steroid-dependent lymphocytic and collagenous colitis.	2001 Sep	11569721
Neutropenia is not required for clinical remission during azathioprine therapy in inflammatory bowel disease.	2001 Sep	11564954

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Intestinal Arterial Insufficiency Initial Dosage: Oral: 2.5 mg/kg of body weight per day (100 to 200 mg in the average adult). This dose may be continued daily for several weeks or more in some patients. If, after 4 weeks at this dosage, there is no clinical improvement and no definite evidence of leukocyte or platelet depression, the dosage may be increased up to 5 mg/kg daily. A dosage of 2.5 mg/kg per day may result in a rapid fall in leukocyte count within 1 to 2 weeks in some adults with acute lymphatic leukemia and high total leukocyte counts. The total daily dosage may be given at one time. It is calculated to the nearest multiple of 25 mg. Maintenance Therapy: Once a complete hematologic remission is obtained, maintenance therapy is considered essential. A usual daily maintenance dose of mercaptopurine is 1.5 to 2.5 mg/kg per day as a single dose. Mercaptopurine should rarely be relied upon as a single agent for the maintenance of remissions induced in acute leukemia. Usual Adult Dose for Acute Lymphoblastic Leukemia Initial Dosage: Oral: 2.5 mg/kg of body weight per day (100 to 200 mg in the average adult). This dose may be continued daily for several weeks or more in some patients. If, after 4 weeks at this dosage, there is no clinical improvement and no definite evidence of leukocyte or platelet depression, the dosage may be increased up to 5 mg/kg daily. A dosage of 2.5 mg/kg per day may result in a rapid fall in leukocyte count within 1 to 2 weeks in some adults with acute lymphatic leukemia and high total leukocyte counts. The total daily dosage may be given at one time. It is calculated to the nearest multiple of 25 mg. Maintenance Therapy: Once a complete hematologic remission is obtained, maintenance therapy is considered essential. A usual daily maintenance dose of mercaptopurine is 1.5 to 2.5 mg/kg per day as a single dose. Mercaptopurine should rarely be relied upon as a single agent for the maintenance of remissions induced in acute leukemia. Usual Adult Dose for Crohn's Disease - Acute Oral: 1.0 to 1.5 mg/kg of body weight per day Usual Adult Dose for Crohn's Disease - Maintenance Oral: 1.0 to 1.5 mg/kg of body weight per day Usual Adult Dose for Ulcerative Colitis - Maintenance Oral: 1.0 to 1.5 mg/kg of body weight per day Usual Adult Dose for Inflammatory Bowel Disease Oral: 1.0 to 1.5 mg/kg of body weight per day

Route of Administration: Oral

In Vitro Use Guide

Mercaptopurine (10-500 ug/ml) inhibits in a dose-dependent manner the production of PGE2, PGF2 alpha, 6-keto-PGF1 alpha and TXB2 by unseparated spleen cells as well as that of 6-keto-PGF1 alpha by adherent peritoneal macrophages.

Name

Type

Language

MERCAPTOPURINE ANHYDROUS

Common Name

English

Mercaptopurine anhydrous [WHO-DD]

Common Name

English

6-MERCAPTOPURINE

Systematic Name

English

1,9-DIHYDRO-6H-PURINE-6-THIONE

Systematic Name

English

AZATHIOPRINE IMPURITY B [EP IMPURITY]

Common Name

English

6-MERCAPTOPURINE [MI]

Common Name

English

MERCAPTOPURINE [HSDB]

Common Name

English

mercaptopurine [INN]

Common Name

English

6-MERCAPTOPURINE [IARC]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1556