Compound: allopurinol
SMILES: Oc1ncnc2c1cn[nH]2
InChIKey: OFCNXPDARWKPPY-UHFFFAOYSA-N
Synonyms: allopurinol, 315-30-0, 1H-Pyrazolo[3,4-d]pyrimidin-4-ol, Zyloric, Suspendol, Takanarumin, Allopur, Bloxanth, Uriprim, Xanturat, Urbol, Ketobun-A, Nektrohan, Adenock, Aluline, Dabrosin, Urobenyl, 4-Hydroxypyrazolo[3,4-d]pyrimidine, 1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one, Allopurinol(I), Allopurinolum, 4-HPP, Alopurinol, 1H-Pyrazolo(3,4-d)pyrimidin-4-ol, 4-Hydroxypyrazolopyrimidine, NSC-1390, 4-Hydroxy-1H-pyrazolo(3,4-d)pyrimidine, 4-Hydroxy-3,4-pyrazolopyrimidine, Sigapurol, 4-Hydroxypyrazolo(3,4-d)pyrimidine, 4-Hydroxypyrazolyl(3,4-d)pyrimidine, 4H-Pyrazolo(3,4-d)pyrimidin-4-one, 4'-Hydroxypyrazolol(3,4-d)pyrimidine, BW 56-158, AL-100, BW-56-158, 1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidin-4-one, 1,5-Dihydropyrazolo[3,4-d]pyrimidin-4-one, 1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidine-4-one, Uricto, CHEBI:40279, 4H-Pyrazolo(3,4-d)pyrimidin-4-one, 1,5-dihydro-, 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,5-dihydro-, 63CZ7GJN5I, Xanthomax-100, Xanthomax-300, NSC-101655, Aluline 100, Aluline 300, Hamarin 100, Hamarin 300, Zyloric-300, DTXSID4022573, NSC1390, 1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one, 1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one, NSC101655, BW-56158, 4-Hydroxy-1H-pyrazolo[3,4-d]pyrimidine, DTXCID502573, DUZALLO COMPONENT ALLOPURINOL, Milurite, Allohexan, 4-Hydroxypyrazolyl[3,4-d]pyrimidine, Pan Quimica, 4'-Hydroxypyrazolol[3,4-d]pyrimidine, 1,2-dihydropyrazolo(3,4-d)pyrimidin-4-one, 1,5-dihydropyrazolo(3,4-d)pyrimidin-4-one, 1H,2H,4H-pyrazolo(3,4-d)pyrimidin-4-one, allopurinolo, Zurinol, RefChem:54100, 4'-HPP, M04AA01, 1,5-Dihydro-4H-pyrazolo(3,4-d)pryimidin-4-one, 206-250-9, Zyloprim, Lopurin, Urosin, Atisuril, Epidropal, Uricemil, Anzief, Urolit, Anoprolin, Miniplanor, Ailural, Allozym, Alositol, Cosuric, Gichtex, Ledopur, Progout, Aloral, Apurol, Riball, 1H-Pyrazolo[3,4-d]pyrimidin-4(5H)-one, Ketanrift, Monarch, Hexanuret, Epuric, 180749-06-8, 180749-08-0, Dura Al, 73334-58-4, Urtias 100, 1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one, 2H-Pyrazolo[3,4-d]pyrimidin-4-ol, Alopurinol [INN-Spanish], Allopurinolum [INN-Latin], 180749-09-1, 1H-pyrazolo[3,4-d]pyrimidin-4(2H)-one, MFCD00599413, 916980-04-6, Zyloprim (TN), 1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one, B. W. 56-158, 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,2-dihydro-, 180749-07-9, 184789-03-5, MLS000069453, SMR000059083, 291279-53-3, 1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one, 4-Oxopyrazolo[3,4-d]pyrimidine, NCGC00015094-02, NCGC00094580-04, Uritas, 1,5-Dihydro-pyrazolo[3,4-d]pyrimidin-4-one, 4H-pyrazolo[3,4-d]pyrimidin-4-one, 1,7-dihydro-, F3329-0375, NSC 1390, pyrazolo[5,4-d]pyrimidin-4-ol, 4H-Pyrazolo[3, 1,5-dihydro-, Ailurial, WLN: T56 BMN GN INJ FQ, CAS-315-30-0, CCRIS 626, NSC 101655, HSDB 3004, SR-05000001983, EINECS 206-250-9, UNII-63CZ7GJN5I, Allohexal;, ATH008, Allopurinol RS, Zyloprim;, 1H-Pyrazolo[3,4-d]pyrimidin-4-ol (9CI), Allopurinol CRS, Allosig;, Progout;, 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,7-dihydro- (9CI), Xanthione oxidase, 4-Hydroxypyrazol[3,4-D]pyrimidine, Prestwick_511, Allopurinol [USAN:USP:INN:BAN:JAN], Allopurinol (Standard), Allopurinol (Zyloprim), Spectrum_000026, 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 2,5-dihydro- (9CI), 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 2,7-dihydro- (9CI), Allopurinol - EP grade, ALLOPURINOL [MI], Opera_ID_1680, Spectrum2_000098, Spectrum3_000289, Spectrum4_000135, Spectrum5_000768, ALLOPURINOL [INN], ALLOPURINOL [JAN], Lopac-A-8003, 1,4-d]pyrimidin-4-one, ALLOPURINOL [HSDB], ALLOPURINOL [USAN], Epitope ID:226980, A 8003, cid_2094, SCHEMBL4627, SCHEMBL4628, A1BD4, ALLOPURINOL [MART.], CHEMBL1467, NCIOpen2_001825, Lopac0_000102, SCHEMBL25803, ALLOPURINOL [USP-RS], ALLOPURINOL [WHO-DD], ALLOPURINOL [WHO-IP], BSPBio_001798, KBioGR_000550, KBioSS_000386, MLS001148183, US9138393, Allopurinol, US9144538, Allopurinol, DivK1c_000685, SCHEMBL167561, SCHEMBL626453, SPECTRUM1500108, SPBio_000056, ALLOPURINOLUM [WHO-IP], GTPL6795, orb1310380, orb3025936, SCHEMBL1128219, SCHEMBL3739112, SCHEMBL5550199, SCHEMBL6034419, SCHEMBL7400319, SCHEMBL7400321, SCHEMBL7403740, Allopurinol (JP18/USP/INN), SCHEMBL28672687, SCHEMBL29693720, BDBM35440, HMS502C07, HY-B0219R, KBio1_000685, KBio2_000386, KBio2_002954, KBio2_005522, KBio3_001298, ALLOPURINOL [EP IMPURITY], ALLOPURINOL [ORANGE BOOK], NINDS_000685, ALLOPURINOL [EP MONOGRAPH], BDBM181133, GLXC-07785, HMS1920A15, HMS2091G15, HMS2234M09, HMS3259K13, HMS3260E06, HMS3371I11, HMS3651O13, HMS3714L22, HMS5079O22, Pharmakon1600-01500108, ALLOPURINOL [USP MONOGRAPH], SMSSF-0109038, HY-B0219, MSK10865, STR05189, Tox21_110082, Tox21_200922, Tox21_500102, 4-Hydroxy-pyrazolo[3,4-d]pyrimidin, AC-019, BBL009959, BDBM50016784, BDBM50140241, CCG-38916, EBC-03149, MFCD08276167, NSC755858, s1630, SBB004202, SC1118, SC2251, STK378584, STK711106, 1,2,5,7-tetraaza-5H-inden-4-ol, AKOS000267490, AKOS000269759, AKOS024255717, Tox21_110082_1, Allopurinol, xanthine oxidase inhibitor, CCG-204197, CCG-221406, CCG-266128, DB00437, FA17288, LP00102, NC00492, NSC-755858, SB10164, SDCCGSBI-0050090.P005, IDI1_000685, NCGC00015094-01, NCGC00015094-03, NCGC00015094-04, NCGC00015094-05, NCGC00015094-06, NCGC00015094-07, NCGC00015094-08, NCGC00015094-18, NCGC00015094-22, NCGC00091134-01, NCGC00091134-02, NCGC00091134-03, NCGC00094580-01, NCGC00094580-02, NCGC00094580-05, NCGC00188948-01, NCGC00258476-01, NCGC00260787-01, FA160361, FA162226, TS-00028, SBI-0050090.P004, DB-065332, DB-261136, DB-272461, DB-272465, DB-272466, DB-272469, A0907, EU-0100102, NS00000618, ST45179105, SW199406-4, T0692, 1,5-dihydropyrazolo[3,4-d]-pyrimidin-4-one, EN300-34144, VU0611037-1, BIM-0061756.0001, D00224, F18007, 1,5Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one, AB00173448-03, AB00173448-04, AB00173448_05, AB01274719-01, AB01274719_02, 1,7-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one, AB-323/25048497, F069190, Q412486, SR-01000075595, 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 2,5-dihydro-, SR-01000075595-1, SR-05000001983-1, SR-05000001983-2, BRD-K86307448-001-16-7, BRD-K86307448-001-17-5, BRD-K86307448-001-19-1, F2173-0394, Z104486670, 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,2-dihydro- (9CI), 4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE, 2,7-DIHYDRO-, Allopurinol, British Pharmacopoeia (BP) Reference Standard, Allopurinol, European Pharmacopoeia (EP) Reference Standard, Allopurinol, United States Pharmacopeia (USP) Reference Standard, 1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one Synonym:  Allopurinol, Allopurinol, Pharmaceutical Secondary Standard; Certified Reference Material, InChI=1/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10, 691008-24-9
Theoretical properties:
molecular_formula: C5H4N4O
molecular_weight: 136.11 g/mol
exact_mass: 136.03851076 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 10
topological_polar_surface_area: 70.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: FLUFFY WHITE TO OFF-WHITE POWDER
color: FLUFFY WHITE TO OFF-WHITE POWDER
odor: SLIGHT
melting_point: greater than 662 °F (NTP, 1992)
solubility: less than 1 mg/mL at 64 °F (NTP, 1992)
Descriptions:
pubchem: Allopurinol is a bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring. It has a role as an antimetabolite, an EC 1.17.3.2 (xanthine oxidase) inhibitor, a gout suppressant and a radical scavenger. It is an organic heterobicyclic compound and a nucleobase analogue. It derives from a hydride of a 1H-pyrazolo[4,3-d]pyrimidine.
chebi: A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.
chembl: ALLOPURINOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Allopurinol is a medication used to decrease high blood uric acid levels. It is specifically used to prevent gout, prevent specific types of kidney stones and for the high uric acid levels that can occur with chemotherapy. It is taken orally (by mouth) or intravenously (injected into a vein).
Common side effects when used orally include itchiness and rash. Common side effects when used by injection include vomiting and kidney problems. While not recommended historically, starting allopurinol during an attack of gout appears to be safe. In those already on the medication, it should be continued even during an acute gout attack. While use during pregnancy does not appear to result in harm, this use has not been well studied. Allopurinol is in the xanthine oxidase inhibitor family of medications.
Allopurinol was approved for medical use in the United States in 1966. It is on the World Health Organization's List of Essential Medicines. Allopurinol is available as a generic medication. In 2023, it was the 45th most commonly prescribed medication in the United States, with more than 14 million prescriptions.