ContaminantDB: Allopurinol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:58:37 UTC

Update Date

2026-03-26 18:39:00 UTC

Accession Number

CHEM002503

Identification

Common Name

Allopurinol

Class

Small Molecule

Description

Allopurinol is only found in individuals that have used or taken this drug. It is a xanthine oxidase inhibitor that decreases uric acid production. It also acts as an antimetabolite on some simpler organisms. [PubChem] Allopurinol and its active metabolite, oxypurinol, inhibits the enzyme xanthine oxidase, blocking the conversion of the oxypurines hypoxanthine and xanthine to uric acid. Elevated concentrations of oxypurine and oxypurine inhibition of xanthine oxidase through negative feedback results in a decrease in the concentrations of uric acid in the serum and urine. Allopurinol also facilitates the incorporation of hypoxanthine and xanthine into DNA and RNA, leading to a feedback inhibition of de novo purin synthesis and a decrease in serum uric acid concentrations as a result of an increase in nucleotide concentration.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Antimetabolite
Drug
Enzyme Inhibitor
Free Radical Scavenger
Gout Suppressant
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,5-Dihydro-4H-pyrazolo(3,4-D)pyrimidin-4-one	ChEBI
1,5-Dihydro-4H-pyrazolo(3,4-D)pyrimidine-4-one	ChEBI
1H-Pyrazolo(3,4-D)pyrimidin-4-ol	ChEBI
4'-Hydroxypyrazolol(3,4-D)pyrimidine	ChEBI
4-HPP	ChEBI
4-Hydroxy-1H-pyrazolo(3,4-D)pyrimidine	ChEBI
4-Hydroxy-3,4-pyrazolopyrimidine	ChEBI
4-Hydroxypyrazolo(3,4-D)pyrimidine	ChEBI
4-Hydroxypyrazolopyrimidine	ChEBI
4-Hydroxypyrazolyl(3,4-D)pyrimidine	ChEBI
4H-Pyrazolo(3,4-D)pyrimidin-4-one	ChEBI
AL-100	ChEBI
Allopurinolum	ChEBI
Alopurinol	ChEBI
Zyloprim	ChEBI
Allopurinol alphapharm brand	HMDB
Allopurinol basf brand	HMDB
Allopurinol merz brand	HMDB
Allopurinol pharmafarm brand	HMDB
Allopurinol roche brand	HMDB
Allopurinol tad brand	HMDB
Allopurinol thiemann brand	HMDB
Allopurinol wellcome brand	HMDB
Ashbourne brand OF allopurinol	HMDB
Boots brand OF allopurinol	HMDB
Fawns and mcallan brand OF allopurinol	HMDB
Foligan	HMDB
Hamarin	HMDB
Hennig brand OF allopurinol	HMDB
Horner brand OF allopurinol	HMDB
Jenapharm brand OF allopurinol	HMDB
Milurit	HMDB
Milurite	HMDB
Quimica, pan	HMDB
Remid	HMDB
Rima brand OF allopurinol	HMDB
Rimapurinol	HMDB
Rougier brand OF allopurinol	HMDB
Thiemann brand OF allopurinol	HMDB
Urtias	HMDB
Xanturic	HMDB
Allohexan	HMDB
Allopurinol horner brand	HMDB
Allopurinol merckle brand	HMDB
Allopurinol multipharma brand	HMDB
Allopurinol nicholas brand	HMDB
Allopurinol novopharm brand	HMDB
Allopurinol r.a.n. brand	HMDB
Allopurinol rima brand	HMDB
Allural	HMDB
Amrad brand OF allopurinol	HMDB
Atisuril	HMDB
Clonmel brand OF allopurinol	HMDB
Embarin	HMDB
Glaxo wellcome brand OF allopurinol	HMDB
ICN brand OF allopurinol	HMDB
Merz brand OF allopurinol	HMDB
Multipharma brand OF allopurinol	HMDB
Nicholas brand OF allopurinol	HMDB
Purinol	HMDB
Rhône-poulenc rorer brand OF allopurinol	HMDB
Rosen brand OF allopurinol	HMDB
Suspendol	HMDB
TAD brand OF allopurinol	HMDB
Tipuric	HMDB
Uripurinol	HMDB
Wellcome brand OF allopurinol	HMDB
Xanthomax	HMDB
APS brand OF allopurinol	HMDB
Alloprin	HMDB
Allopurinol ashbourne brand	HMDB
Allopurinol clonmel brand	HMDB
Allopurinol douglas brand	HMDB
Allopurinol hennig brand	HMDB
Allopurinol hexal brand	HMDB
Allopurinol rosen brand	HMDB
Allopurinol gepepharm brand	HMDB
Allpargin	HMDB
Alphapharm brand OF allopurinol	HMDB
Apulonga	HMDB
Apurin	HMDB
BASF brand OF allopurinol	HMDB
Bleminol	HMDB
Boehringer mannheim brand OF allopurinol	HMDB
Byk gulden brand OF allopurinol	HMDB
Capurate	HMDB
Dorsch brand OF allopurinol	HMDB
Douglas brand OF allopurinol	HMDB
Hexal brand OF allopurinol	HMDB
Jenapurinol	HMDB
Merckle brand OF allopurinol	HMDB
Novopurol	HMDB
Pan quimica	HMDB
Pureduct	HMDB
Rhône poulenc rorer brand OF allopurinol	HMDB
Roche brand OF allopurinol	HMDB
Roucol	HMDB
Urosin	HMDB
Gepepharm brand OF allopurinol	HMDB
Allohexal	HMDB
Allopurin	HMDB
Allopurinol aps brand	HMDB
Allopurinol amrad brand	HMDB
Allopurinol azupharma brand	HMDB
Allopurinol bicther brand	HMDB
Allopurinol boots brand	HMDB
Allopurinol dorsch brand	HMDB
Allopurinol icn brand	HMDB
Allopurinol jenapharm brand	HMDB
Allopurinol pinewood brand	HMDB
Allopurinol protea brand	HMDB
Allopurinol rougier brand	HMDB
Allorin	HMDB
Azupharma brand OF allopurinol	HMDB
Bicther brand OF allopurinol	HMDB
Caplenal	HMDB
Cellidrin	HMDB
Henning berlin brand OF allopurinol	HMDB
Lopurin	HMDB
Lysuron	HMDB
Novopharm brand OF allopurinol	HMDB
Pharmafarm brand OF allopurinol	HMDB
Pinewood brand OF allopurinol	HMDB
Progout	HMDB
Protea brand OF allopurinol	HMDB
R.A.N. brand OF allopurinol	HMDB
Reig jofre brand OF allopurinol	HMDB
Uribenz	HMDB
Uridocid	HMDB
Zygout	HMDB
Zyloric	HMDB

Chemical Formula

C₅H₄N₄O

Average Molecular Mass

136.112 g/mol

Monoisotopic Mass

136.039 g/mol

CAS Registry Number

315-30-0

IUPAC Name

1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one

Traditional Name

ALLO

SMILES

O=C1N=CN=C2NNC=C12

InChI Identifier

InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)

InChI Key

OFCNXPDARWKPPY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidines. These are aromatic heterocyclic compounds containing a pyrazolo[3,4-d]pyrimidine ring system, which consists of a pyrazole ring fused to but and not sharing a nitrogen atom with a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrazolopyrimidines

Sub Class

Pyrazolo[3,4-d]pyrimidines

Direct Parent

Pyrazolo[3,4-d]pyrimidines

Alternative Parents

Substituents

Pyrazolo[3,4-d]pyrimidine
Pyrimidone
Pyrimidine
Azole
Pyrazole
Vinylogous amide
Heteroaromatic compound
Azacycle
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterobicyclic compound (CHEBI:40279 )
nucleobase analogue (CHEBI:40279 )
a small molecule (CPD-9024 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

gout suppressant

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	350°C
Boiling Point	Not Available
Solubility	569 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	5.88 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.8	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	2.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.85 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	54.24 m³·mol⁻¹	ChemAxon
Polarizability	11.67 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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0550-8900000000-225d53e43d6b82e006bf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-4900000000-5d6d365d7525c7325e01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-4900000000-ea448e075f973faea5ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000l-8900000000-98d308813f954ccc66e0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0006-9300000000-a0c962d1b7e8e76fd526	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0006-9100000000-d692c85314f5809e4758	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-01ox-9000000000-2662f35a8efe21c51958	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0900000000-4f38b316b66733e5ca8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0900000000-547b3dac7e9b0d01ef66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0900000000-43ea9e7d5a0f94da482f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-1900000000-fee6f9103fdd4cb1b6ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01p9-1900000000-eb9ece2b9b724a6af483	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03dr-2900000000-85aef327ef1281780d05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-01ox-9000000000-06c0452042d1533a15b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0006-9100000000-11cfb21dda6f6d415de0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-000l-8900000000-fe81b51b6b51c24c773c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0006-9300000000-fa9960ae057885ac4068	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-01p9-1900000000-5d1b0178a6ae7719b325	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-000i-0900000000-9a825177a0acbf892733	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-03dr-2900000000-906c0f13426783f2ef86	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-1eb7584dbb0630e49004	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-4e5cd23deb565d2f87e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-07wc-9200000000-214c548ad4d15f5bfbf4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-b7681f9e17751c711d37	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2900000000-a7c487c6207a07bf2903	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-af7211d0cc75dda0b005	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-7900000000-f5a7601a354a9d25428f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Approximately 80-90% absorbed from the gastrointestinal tract.

Mechanism of Toxicity

Allopurinol inhibits the enzyme xanthine oxidase, blocking the conversion of the oxypurines hypoxanthine and xanthine to uric acid. Elevated concentrations of oxypurine and oxypurine inhibition of xanthine oxidase through negative feedback results in a decrease in the concentrations of uric acid in the blood and urine. Allopurinol also facilitates the incorporation of hypoxanthine and xanthine into DNA and RNA, resulting in further reductions of serum uric acid concentrations.

Metabolism

Hepatic Route of Elimination: Approximately 20% of the ingested allopurinol is excreted in the feces. Half Life: 1-3 hours

Toxicity Values

LD₅₀=214 mg/kg (in mice)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of hyperuricemia associated with primary or secondary gout. Also indicated for the treatment of primary or secondary uric acid nephropathy, with or without the symptoms of gout, as well as chemotherapy-induced hyperuricemia and recurrent renal calculi.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

LD₅₀=214 mg/kg (in mice)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00437

HMDB ID

HMDB0014581

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Druey, J. and Schmidt, P.; US. Patent 2868,803; January 13,1959; assigned to Ciba Pharmaceutical Products Inc.
Hitchings, G.H. and Falco, EA.; U.S. Patent 3,474,098; October 21,1969; assigned to Bur-
roughs Wellcome & Co.
Cresswell, R.M.and Mentha, J.W.; US.Patent4,146,713; March27,1979; assigned to Bur-
roughs Wellcome & Co.

MSDS

Link

General References

1. Pacher P, Nivorozhkin A, Szabo C: Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114.

2. George J, Struthers AD: Role of urate, xanthine oxidase and the effects of allopurinol in vascular oxidative stress. Vasc Health Risk Manag. 2009;5(1):265-72. Epub 2009 Apr 8.

3. Suzuki I, Yamauchi T, Onuma M, Nozaki S: Allopurinol, an inhibitor of uric acid synthesis--can it be used for the treatment of metabolic syndrome and related disorders? Drugs Today (Barc). 2009 May;45(5):363-78. doi: 10.1358/dot.2009.45.5.1370460.

4. Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. doi: 10.1038/nrrheum.2009.236.

5. Schlesinger N: Diagnosing and treating gout: a review to aid primary care physicians. Postgrad Med. 2010 Mar;122(2):157-61. doi: 10.3810/pgm.2010.03.2133.

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11333159

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16650385

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24395556

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24590210

10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24591375

11. https://www.ncbi.nlm.nih.gov/pubmed/?term=7602118

Allopurinol (CHEM002503)

Structure for CHEM002503: Allopurinol