ChemFOnt: Showing chemical card for Allopurinol (CFc000008945)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:55 UTC

Chemfont ID

CFc000008945

Molecule Identification

Common Name

Allopurinol

Definition

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.

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 Weight

136.1115

Monoisotopic Molecular Weight

136.03851077

IUPAC Name

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

Traditional Name

ALLO

CAS Registry Number

315-30-0

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 10102915)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014581)

Process

Not Available

Role

Biological role

Free radical scavenger (HMDB: HMDB0014581)
Antimetabolite (HMDB: HMDB0014581)

Modulator

Inhibitor

EC 1.17.3.2 (xanthine oxidase) inhibitor (HMDB: HMDB0014581)

Industrial application

Gout suppressant (HMDB: HMDB0014581)

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014581

DrugBank ID

DB00437

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2010

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Allopurinol

METLIN ID

Not Available

PubChem Compound

2094

PDB ID

Not Available

ChEBI ID

40279

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Allopurinol (CFc000008945)

MOL for CFc000008945 (Allopurinol)

3D MOL for CFc000008945 (Allopurinol)

3D SDF for CFc000008945 (Allopurinol)

3D-SDF for CFc000008945 (Allopurinol)

PDB for CFc000008945 (Allopurinol)

3D PDB for CFc000008945 (Allopurinol)

SMILES for CFc000008945 (Allopurinol)

INCHI for CFc000008945 (Allopurinol)

Structure for CFc000008945 (Allopurinol)

3D Structure for CFc000008945 (Allopurinol)