Details of the Drug

General Information of Drug (ID: DMTM2IK)

Drug Name

Mercaptopurine

Synonyms

6-mercaptopurine; Ismipur; Leukerin; Leupurin; Mercaleukim; Mercaleukin; Mercaptopurin; Mercaptopurina; Mercaptopurinum; Mercapurin; Merkaptopuryna; Mern; Purimethol; Purinethiol; Purinethol; Thiopurine; Leupu rin; Mercaptopurin [German]; Mercaptopurina Wellcome; Mercaptopurine anhydrous; Merkaptopuryna [Polish]; Puri Nethol; BW 57 323H; Glaxo Wellcome Brand of 6 Mercaptopurine; GlaxoSmithKline Brand of 6 Mercaptopurine; M0063; NCIMech_000025; PM6; Wellcome Brand of 6 Mercaptopurine; Glaxo Wellcome Brand of 6-Mercaptopurine; GlaxoSmithKline Brand of 6-Mercaptopurine; Mercaptopurina [INN-Spanish]; Mercaptopurine (INN); Mercaptopurine (VAN); Mercaptopurine (anhydrous); Mercaptopurinum [INN-Latin]; Puri-Nethol; Purineantimetabolite: inhibits nucleic acid replication; Purinethol (TN); U-4748; Wellcome Brand of 6-Mercaptopurine; AG-670/31547064; Purine-6-thiol; Leukerin, 99%-Carc; Purine-6(1H)-thione; Purinethol, 6-mercaptopurine, 6-MP, Mercaptopurine; 6 MP; 6 Mercaptopurine Monohydrate; 6 Thiohypoxanthine; 6 Thiopurine; 6-MERCAPTOPURINE MONOHYDRATE; 6-MP; 6-Mercaptopurin; 6-Merkaptopurin; 6-Merkaptopurin [Czech]; 6-Purinethiol; 6-Thiohypoxanthine; 6-Thiopurine; 6-Thioxopurine; Mercaptopurine (Purine analog)

Indication

Disease Entry	ICD 11	Status	REF
Acute lymphoblastic leukaemia	2A85	Approved	[1], [2]
Crohn disease	DD70	Phase 4	[3]

Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

152.18

Topological Polar Surface Area (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 15 mL/min/kg [5]
Elimination: 22% of drug is excreted from urine in the unchanged form [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 1 hour [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 16.42808 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.85% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1 L/kg [5]

Chemical Identifiers

Formula: C5H4N4S
IUPAC Name: 3,7-dihydropurine-6-thione
Canonical SMILES: C1=NC2=C(N1)C(=S)N=CN2
InChI: InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChIKey: GLVAUDGFNGKCSF-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 667490
ChEBI ID: CHEBI:2208
CAS Number: 50-44-2
DrugBank ID: DB01033
TTD ID: D09UZO
VARIDT ID: DR00145
INTEDE ID: DR1031
ACDINA ID: D00399

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Amidophosphoribosyltransferase (PPAT)	TTZFTY4	PUR1_HUMAN	Breaker	[7]
Inosine-5'-monophosphate dehydrogenase 1 (IMPDH1)	TTL7C8Q	IMDH1_HUMAN	Inhibitor	[8]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Equilibrative nucleobase transporter 1 (SLC43A3)	DTGBPR5	S43A3_HUMAN	Substrate	[9]
Equilibrative nucleoside transporter 2 (SLC29A2)	DTW78DQ	S29A2_HUMAN	Substrate	[10]
Equilibrative nucleoside transporter 1 (SLC29A1)	DTXD1TQ	S29A1_HUMAN	Substrate	[10]
Concentrative nucleoside transporter 2 (SLC28A2)	DT82KPY	S28A2_HUMAN	Substrate	[10]
Concentrative Na(+)-nucleoside cotransporter 3 (SLC28A3)	DT4YL5R	S28A3_HUMAN	Substrate	[11]
Multidrug resistance-associated protein 5 (ABCC5)	DTYVM24	MRP5_HUMAN	Substrate	[12]
Multidrug resistance-associated protein 4 (ABCC4)	DTCSGPB	MRP4_HUMAN	Substrate	[13]
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[14]
Organic anion transporter 3 (SLC22A8)	DTVP67E	S22A8_HUMAN	Substrate	[15]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 1A1 (CYP1A1)	DE6OQ3W	CP1A1_HUMAN	Substrate	[16]
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[16]
Thiopurine methyltransferase (TPMT)	DEFQ8VO	TPMT_HUMAN	Substrate	[17]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Mercaptopurine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Mercaptopurine and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[107]
Roflumilast	DMPGHY8	Moderate	Additive immunosuppressive effects by the combination of Mercaptopurine and Roflumilast.	Asthma [CA23]	[108]
Ofloxacin	DM0VQN3	Minor	Decreased absorption of Mercaptopurine due to intestinal mucosa variation caused by Ofloxacin.	Bacterial infection [1A00-1C4Z]	[109]
Sparfloxacin	DMB4HCT	Minor	Decreased absorption of Mercaptopurine due to intestinal mucosa variation caused by Sparfloxacin.	Bacterial infection [1A00-1C4Z]	[109]
Gemifloxacin	DMHT34O	Minor	Decreased absorption of Mercaptopurine due to intestinal mucosa variation caused by Gemifloxacin.	Bacterial infection [1A00-1C4Z]	[109]
Norfloxacin	DMIZ6W2	Minor	Decreased absorption of Mercaptopurine due to intestinal mucosa variation caused by Norfloxacin.	Bacterial infection [1A00-1C4Z]	[109]
ABT-492	DMJFD2I	Minor	Decreased absorption of Mercaptopurine due to intestinal mucosa variation caused by ABT-492.	Bacterial infection [1A00-1C4Z]	[109]
Levofloxacin	DMS60RB	Minor	Decreased absorption of Mercaptopurine due to intestinal mucosa variation caused by Levofloxacin.	Bacterial infection [1A00-1C4Z]	[109]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Mercaptopurine and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[110]
Anisindione	DM2C48U	Moderate	Antagonize the effect of Mercaptopurine when combined with Anisindione.	Coagulation defect [3B10]	[111]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Mercaptopurine and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[112]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Mercaptopurine and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[113]
Teriflunomide	DMQ2FKJ	Major	Additive immunosuppressive effects by the combination of Mercaptopurine and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[114]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Mercaptopurine and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[115]
Febuxostat	DMDEXQ0	Major	Decreased metabolism of Mercaptopurine caused by Febuxostat mediated inhibition of non-CYP450 enzyme.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[116]
Denosumab	DMNI0KO	Moderate	Additive myelosuppressive effects by the combination of Mercaptopurine and Denosumab.	Low bone mass disorder [FB83]	[117]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Mercaptopurine and Idelalisib.	Mature B-cell leukaemia [2A82]	[118]
Thalidomide	DM70BU5	Major	Additive thrombogenic effects by the combination of Mercaptopurine and Thalidomide.	Multiple myeloma [2A83]	[119]
Tecfidera	DM2OVDT	Moderate	Additive immunosuppressive effects by the combination of Mercaptopurine and Tecfidera.	Multiple sclerosis [8A40]	[120]
Siponimod	DM2R86O	Major	Additive immunosuppressive effects by the combination of Mercaptopurine and Siponimod.	Multiple sclerosis [8A40]	[107]
Fingolimod	DM5JVAN	Major	Additive immunosuppressive effects by the combination of Mercaptopurine and Fingolimod.	Multiple sclerosis [8A40]	[121]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Mercaptopurine and Ocrelizumab.	Multiple sclerosis [8A40]	[122]
Ozanimod	DMT6AM2	Major	Additive immunosuppressive effects by the combination of Mercaptopurine and Ozanimod.	Multiple sclerosis [8A40]	[108]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive immunosuppressive effects by the combination of Mercaptopurine and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[123]
Gatifloxacin	DMSL679	Minor	Decreased absorption of Mercaptopurine due to intestinal mucosa variation caused by Gatifloxacin.	Respiratory infection [CA07-CA4Z]	[109]
Canakinumab	DM8HLO5	Moderate	Additive immunosuppressive effects by the combination of Mercaptopurine and Canakinumab.	Rheumatoid arthritis [FA20]	[124]
Rilonacept	DMGLUQS	Moderate	Additive immunosuppressive effects by the combination of Mercaptopurine and Rilonacept.	Rheumatoid arthritis [FA20]	[124]
Golimumab	DMHZV7X	Major	Additive immunosuppressive effects by the combination of Mercaptopurine and Golimumab.	Rheumatoid arthritis [FA20]	[125]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Mercaptopurine and Leflunomide.	Rheumatoid arthritis [FA20]	[114]
Anthrax vaccine	DM9GSWY	Moderate	Antagonize the effect of Mercaptopurine when combined with Anthrax vaccine.	Sepsis [1G40-1G41]	[126]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Mercaptopurine and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[108]
Olsalazine	DMZW9HA	Moderate	Decreased metabolism of Mercaptopurine caused by Olsalazine mediated inhibition of non-CYP450 enzyme.	Ulcerative colitis [DD71]	[127]
Valganciclovir	DMS2IUH	Moderate	Additive myelosuppressive effects by the combination of Mercaptopurine and Valganciclovir.	Virus infection [1A24-1D9Z]	[107]
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⏷ Show the Full List of 33 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
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⏷ Show the Full List of 6 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Mercaptopurine 50 mg tablet	50 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

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