Details of the Drug

General Information of Drug (ID: DMLPAOB)

Drug Name
Allopurinol
Synonyms
Adenock; Ailural; Ailurial; Allohexal; Allohexan; Alloprin; Allopur; Allopurin; Allopurinolum; Allorin; Allozym; Allpargin; Allural; Aloprim; Alopurinol; Aloral; Alositol; Aluline; Anoprolin; Anzief; Apulonga; Apurin; Apurol; Atisuril; Bleminol; Bloxanth; Caplenal; Capurate; Cellidrin; Cosuric; Dabrosin; Dabroson; Embarin; Epidropal; Epuric; Foligan; Geapur; Gichtex; Gotax; Hamarin; Hexanuret; Jenapurinol; Ketanrift; Ledopur; Lopurin; Lysuron; Milurit; Milurite; Miniplanor; Monarch; Nektrohan; Novopurol; Progout; Pureduct; Purinol; Remid; Riball; Rimapurinol; Roucol; Sigapurol; Suspendol; Takanarumin; Tipuric; Urbol; Uribenz; Uricemil; Uridocid; Uriprim; Uripurinol; Uritas; Urobenyl; Urolit; Urosin; Urtias; Xanthomax; Xanturat; Xanturic; Zygout; Zyloprim; Zyloric; Dura Al; Pan Quimica; A 8003; BW 56158; Urtias 100; AL-100; Allo-Puren; Allohexal (TN); Allopurinol(I); Allosig (TN); Apo-Allopurinol; BW 56-158; Ketobun-A; Progout (TN); Puricos (TN); Quimica, Pan; Zyloprim (TN); Zyloric (TN); BW-56-158; B. W. 56-158; 4-HPP
Indication
Disease Entry ICD 11 Status REF
Gout FA25 Approved [1]
Hyperuricaemia 5C55.Y Approved [2]
Recurrent adult burkitt lymphoma 2A85.6 Approved [1]
Therapeutic Class
Antimetabolites
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 136.11
Logarithm of the Partition Coefficient (xlogp) -0.7
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Clearance
The clearance of drug is 10 to 20 mL/min []
Elimination
Approximately 80% of orally ingested allopurinol is found excreted in the urine as various metabolites, and about 20% of ingested allopurinol is excreted in the feces [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 1 - 2 hours []
Metabolism
The drug is metabolized via the purine salvage pathway [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 97.71233 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 0.97% [7]
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 0.58 L/kg [7]
Water Solubility
The ability of drug to dissolve in water is measured as 0.569 mg/mL [3]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Aplasia pure red cell Not Available GYPA OTABU4YV [8]
Reperfusion injury Not Available MPO OTOOXLIN [8]
Reperfusion injury Not Available ICAM1 OTTOIX77 [8]
subcutaneous tissue disorders rs2395029 HCP5 OTV0YRI8 [9]
Toxic epidermal necrolysis HLA-DQB1*02:02 HLA-DQB OTVVI3UI [10]
Toxic epidermal necrolysis HLA-C*08:01 HLA-C OTV38BUJ [10]
Toxic epidermal necrolysis HLA-A*33:03 HLA-A OTAH14LU [11]
⏷ Show the Full List of 7 ADR Information of This Drug
Chemical Identifiers
Formula
C5H4N4O
IUPAC Name
1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one
Canonical SMILES
C1=NNC2=C1C(=O)NC=N2
InChI
InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
InChIKey
OFCNXPDARWKPPY-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
135401907
ChEBI ID
CHEBI:40279
CAS Number
315-30-0
DrugBank ID
DB00437
TTD ID
D04KYY
VARIDT ID
DR00074
INTEDE ID
DR0066
ACDINA ID
D00020
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Xanthine dehydrogenase/oxidase (XDH) TT7RJY8 XDH_HUMAN Inhibitor [12]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic anion transporter 2 (SLC22A7) DT0OC1Q S22A7_HUMAN Substrate [13]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [14]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
RNA cytidine acetyltransferase (hALP)
Main DME 		DEZV4AP NAT10_HUMAN Substrate [15]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Angiopoietin-related protein 3 (ANGPTL3) OTCD5Z9W ANGL3_HUMAN Gene/Protein Processing [16]
Apolipoprotein B-100 (APOB) OTH0UOCZ APOB_HUMAN Gene/Protein Processing [16]
Apolipoprotein C-III (APOC3) OTW3520C APOC3_HUMAN Gene/Protein Processing [16]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [17]
Cyclic AMP-dependent transcription factor ATF-6 alpha (ATF6) OTAFHAVI ATF6A_HUMAN Gene/Protein Processing [16]
Cytochrome P450 4A11 (CYP4A11) OTPU5J0S CP4AB_HUMAN Gene/Protein Processing [18]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [16]
Endoplasmic reticulum chaperone BiP (HSPA5) OTFUIRAO BIP_HUMAN Gene/Protein Processing [16]
Glycophorin-A (GYPA) OTABU4YV GLPA_HUMAN Drug Response [8]
Heme oxygenase 1 (HMOX1) OTC1W6UX HMOX1_HUMAN Gene/Protein Processing [19]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Allopurinol
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Probenecid DMMFWOJ Minor Increased renal excretion of Allopurinol caused by Probenecid. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [20]
Coadministration of a Drug Treating the Disease Different from Allopurinol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Tamoxifen DMLB0EZ Minor Increased risk of hepatotoxicity by the combination of Allopurinol and Tamoxifen. Breast cancer [2C60-2C6Y] [21]
Anisindione DM2C48U Moderate Decreased metabolism of Allopurinol caused by Anisindione mediated inhibition of CYP450 enzyme. Coagulation defect [3B10] [22]
Didanosine DMI2QPE Major Decreased metabolism of Allopurinol caused by Didanosine mediated inhibition of non-CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [23]
Mercaptopurine DMTM2IK Major Decreased metabolism of Allopurinol caused by Mercaptopurine mediated inhibition of non-CYP450 enzyme. Mature B-cell lymphoma [2A85] [24]
Warfarin DMJYCVW Moderate Decreased metabolism of Allopurinol caused by Warfarin mediated inhibition of CYP450 enzyme. Supraventricular tachyarrhythmia [BC81] [22]
Azathioprine DMMZSXQ Major Decreased metabolism of Allopurinol caused by Azathioprine mediated inhibition of non-CYP450 enzyme. Transplant rejection [NE84] [24]
Chlorpropamide DMPHZQE Minor Decreased renal excretion of Allopurinol caused by Chlorpropamide. Type 2 diabetes mellitus [5A11] [25]
⏷ Show the Full List of 7 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
Sunset yellow FCF E00255 17730 Colorant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Carmellose sodium E00625 Not Available Disintegrant
Crospovidone E00626 Not Available Disintegrant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Vinylpyrrolidone E00668 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
⏷ Show the Full List of 11 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Allopurinol 100 mg tablet 100 mg Oral Tablet Oral
Allopurinol 300 mg tablet 300 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Allopurinol FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6795).
3 BDDCS applied to over 900 drugs
4 Reiter S, Simmonds HA, Webster DR, Watson AR: On the metabolism of allopurinol. Formation of allopurinol-1-riboside in purine nucleoside phosphorylase deficiency. Biochem Pharmacol. 1983 Jul 15;32(14):2167-74.
5 Schoenhard G, Oppermann J, Kohn FE: Metabolism and pharmacokinetic studies of misoprostol. Dig Dis Sci. 1985 Nov;30(11 Suppl):126S-128S. doi: 10.1007/bf01309397.
6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
9 Clinical Pharmacogenetics Implementation Consortium guidelines for human leukocyte antigen-B genotype and allopurinol dosing. Clin Pharmacol Ther. 2013 Feb;93(2):153-8. doi: 10.1038/clpt.2012.209. Epub 2012 Oct 17.
10 A study of HLA class I and class II 4-digit allele level in Stevens-Johnson syndrome and toxic epidermal necrolysis. Int J Immunogenet. 2011 Aug;38(4):303-9. doi: 10.1111/j.1744-313X.2011.01011.x. Epub 2011 May 4.
11 Positive and negative associations of HLA class I alleles with allopurinol-induced SCARs in Koreans. Pharmacogenet Genomics. 2011 May;21(5):303-7. doi: 10.1097/FPC.0b013e32834282b8.
12 Allopurinol: xanthine oxidase inhibitor. Tex Med. 1966 Jan;62(1):100-1.
13 Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14.
14 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.
15 Xanthine oxidase inhibition by allopurinol affects the reliability of urinary caffeine metabolic ratios as markers for N-acetyltransferase 2 and CYP1A2 activities. Eur J Clin Pharmacol. 1999 Jan;54(11):869-76.
16 Drug-induced hepatic steatosis in absence of severe mitochondrial dysfunction in HepaRG cells: proof of multiple mechanism-based toxicity. Cell Biol Toxicol. 2021 Apr;37(2):151-175. doi: 10.1007/s10565-020-09537-1. Epub 2020 Jun 14.
17 Allopurinol induces innate immune responses through mitogen-activated protein kinase signaling pathways in HL-60 cells. J Appl Toxicol. 2016 Sep;36(9):1120-8. doi: 10.1002/jat.3272. Epub 2015 Dec 7.
18 Allopurinol Protects Against Cholestatic Liver Injury in Mice Not Through Depletion of Uric Acid. Toxicol Sci. 2021 May 27;181(2):295-305. doi: 10.1093/toxsci/kfab034.
19 Systemic drugs inducing non-immediate cutaneous adverse reactions and contact sensitizers evoke similar responses in THP-1 cells. J Appl Toxicol. 2015 Apr;35(4):398-406. doi: 10.1002/jat.3033. Epub 2014 Aug 4.
20 Elion GB, Yu TF, Gutman AB, Hitchings GH "Renal clearance of oxipurinol, the chief metabolite of allopurinol." Am J Med 45 (1968): 69-77. [PMID: 5658870]
21 Shah KA, Levin J, Rosen N, Greenwald E, Zumoff B "Allopurinol hepatotoxicity potentiated by tamoxifen." N Y State J Med 82 (1982): 1745-6. [PMID: 6960280]
22 Lowenthal DT "The treatment of hyperuricemia." Am Fam Physician 14 (1976): 98-100. [PMID: 937167]
23 Boelaert JR, Dom GM, Huitema AD, Beijnen JH, Lange JM "The boosting of didanosine by allopurinol permits a halving of the didanosine dosage." AIDS 16 (2002): 2221-2223. [PMID: 12409745]
24 Berns A, Rubenfeld S, Rymzo WT "Hazard of combining allopurinol and thiopruine." N Engl J Med 286 (1972): 730-1. [PMID: 5061067]
25 Petitpierre B, Perrin L, Rudhardt M, et al "Behaviour of chlorpropamide in renal insufficiency and under the effect of associated drug therapy." Int J Clin Pharmacol 6 (1972): 120-4. [PMID: 4638970]