allopurinol indications/contra

Stem definitionDrug idCAS RN
124 315-30-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • zyloprim
  • allopurinol
  • tautomeric mixture of 1H-pyrazolo[3,4-d]pyrimidin-4-ol and 1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
  • allopurinol sodium
A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.
  • Molecular weight: 136.11
  • Formula: C5H4N4O
  • CLOGP: 0.63
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 74.69
  • ALOGS: -0.79
  • ROTB: 0

Drug dosage:

DoseUnitRoute
0.40 g O
0.40 g P

Approvals:

DateAgencyCompanyOrphan
Aug. 19, 1966 FDA PROMETHEUS LABS

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms 4841.03 40.09 896 3839 6999 3374125
Stevens-Johnson syndrome 1346.05 40.09 305 4430 6467 3374657
Toxic epidermal necrolysis 1236.52 40.09 265 4470 4280 3376844
Acute kidney injury 1073.67 40.09 396 4339 49287 3331837
Pyrexia 678.20 40.09 330 4405 80785 3300339
Rash 633.35 40.09 302 4433 70519 3310605
Eosinophilia 597.68 40.09 149 4586 4724 3376400
Rash maculo-papular 512.71 40.09 137 4598 5730 3375394
Renal failure 458.15 40.09 192 4543 32748 3348376
Dermatitis exfoliative 371.84 40.09 91 4644 2652 3378472
Thrombocytopenia 333.44 40.09 157 4578 35111 3346013
Pruritus 325.43 40.09 169 4566 46664 3334460
Renal impairment 323.93 40.09 127 4608 18134 3362990
Pancytopenia 306.26 40.09 123 4612 18697 3362427
Drug interaction 305.45 40.09 162 4573 46650 3334474
Skin exfoliation 299.38 40.09 97 4638 7940 3373184
Hepatitis 262.85 40.09 92 4643 9533 3371591
Drug eruption 262.72 40.09 79 4656 5046 3376078
Erythema multiforme 260.47 40.09 71 4664 3182 3377942
Toxic skin eruption 246.67 40.09 67 4668 2961 3378163
Rhabdomyolysis 235.82 40.09 97 4638 15632 3365492
Erythema 231.83 40.09 115 4620 28695 3352429
Gout 230.90 40.09 65 4670 3282 3377842
Dilatation intrahepatic duct acquired 227.18 40.09 36 4699 80 3381044
Agranulocytosis 221.90 40.09 70 4665 5242 3375882
Alanine aminotransferase increased 219.17 40.09 104 4631 23536 3357588
Sepsis 204.96 40.09 110 4625 32263 3348861
Anaemia 202.61 40.09 131 4604 54202 3326922
Rash erythematous 201.66 40.09 72 4663 7890 3373234
Hyperkalaemia 201.56 40.09 79 4656 11215 3369909

Pharmacologic Action:

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SourceCodeDescription
ATC M04AA01 MUSCULO-SKELETAL SYSTEM
ANTIGOUT PREPARATIONS
ANTIGOUT PREPARATIONS
Preparations inhibiting uric acid production
ATC M04AA51 MUSCULO-SKELETAL SYSTEM
ANTIGOUT PREPARATIONS
ANTIGOUT PREPARATIONS
Preparations inhibiting uric acid production
CHEBI has role CHEBI:35845 gout suppressant
FDA EPC N0000175698 Xanthine Oxidase Inhibitor
FDA MoA N0000000206 Xanthine Oxidase Inhibitors
MeSH PA D000963 Antimetabolites
MeSH PA D000975 Antioxidants
MeSH PA D018501 Antirheumatic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D016166 Free Radical Scavengers
MeSH PA D006074 Gout Suppressants
MeSH PA D009676 Noxae

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Hyperuricemia indication 35885006 DOID:1920
Articular gout indication 48440001 DOID:13189
Gout indication 90560007 DOID:13189
Uric acid renal calculus indication 274401005
Calcium renal calculus indication 427649000
Chemotherapy-Induced Hyperuricemia indication
Uric Acid Nephropathy Gout indication
Recurrent Calcium Renal Calculi indication
Dehydration contraindication 34095006
Chronic heart failure contraindication 48447003
Hypersensitivity angiitis contraindication 60555002 DOID:9809
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Deficiency of adenine phosphoribosyltransferase off-label use 124274002 DOID:0060350
Deficiency of ribose-phosphate pyrophosphokinase off-label use 124343001
Neonatal Phosphoribosylpyrophosphate Synthetase Superactivity off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.52 acidic
pKa2 9.43 acidic
pKa3 1.45 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
200MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 8283369 Nov. 26, 2028 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE
200MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 8357713 Nov. 26, 2028 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE
300MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 8283369 Nov. 26, 2028 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE
300MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 8357713 Nov. 26, 2028 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE
200MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 8546437 April 29, 2029 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE
300MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 8546437 April 29, 2029 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE
200MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 8084483 Aug. 17, 2029 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE
300MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 8084483 Aug. 17, 2029 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE
200MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 9216179 Aug. 1, 2031 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE
300MG DUZALLO IRONWOOD PHARMS INC N209203 Aug. 18, 2017 RX TABLET ORAL 9216179 Aug. 1, 2031 TREATMENT OF HYPERURICEMIA ASSOCIATED WITH GOUT IN PATIENTS WHO HAVE NOT ACHIEVED TARGET SERUM URIC ACID LEVELS WITH A MEDICALLY APPROPRIATE DAILY DOSE OF ALLOPURINOL ALONE

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Xanthine dehydrogenase/oxidase Enzyme INHIBITOR Ki 5.15 CHEMBL CHEMBL
Hypoxanthine-guanine phosphoribosyltransferase Enzyme WOMBAT-PK
Xanthine dehydrogenase/oxidase Enzyme Ki 6 CHEMBL
Xanthine dehydrogenase/oxidase Enzyme IC50 6.12 CHEMBL

External reference:

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IDSource
CHEBI:40279 CHEBI
DB00437 DRUGBANK_ID
4017895 VUID
N0000146247 NUI
C0002144 UMLSCUI
6795 IUPHAR_LIGAND_ID
D00224 KEGG_DRUG
428673RC2Z UNII
17795-21-0 SECONDARY_CAS_RN
1731 INN_ID
1816 MMSL
519 RXNORM
25246002 SNOMEDCT_US
387135004 SNOMEDCT_US
4150 MMSL
d00023 MMSL
4017895 VANDF
N0000005830 NDFRT
N0000146247 NDFRT
001084 NDDF
8256 MMSL
CHEMBL1467 ChEMBL_ID
CHEMBL1200477 ChEMBL_ID
D000493 MESH_DESCRIPTOR_UI
2094 PUBCHEM_CID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Allopurinol sodium HUMAN PRESCRIPTION DRUG LABEL 1 0143-9533 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 12 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0378-0137 TABLET 100 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0378-0181 TABLET 300 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0591-5543 TABLET 100 mg ORAL NDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0591-5544 TABLET 300 mg ORAL NDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0603-2115 TABLET 100 mg ORAL ANDA 12 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0603-2116 TABLET 300 mg ORAL ANDA 12 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0615-1592 TABLET 100 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0615-1593 TABLET 300 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0904-6266 TABLET, COATED 100 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0904-6267 TABLET, COATED 300 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0904-6571 TABLET 100 mg ORAL ANDA 12 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 0904-6572 TABLET 300 mg ORAL ANDA 12 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 10544-545 TABLET 100 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 10544-547 TABLET 300 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 10544-911 TABLET 300 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 16714-041 TABLET 100 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 16714-042 TABLET 300 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 16729-134 TABLET 100 mg ORAL ANDA 12 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 16729-135 TABLET 300 mg ORAL ANDA 12 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 21695-246 TABLET 300 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 21695-836 TABLET 100 mg ORAL ANDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 33261-597 TABLET 300 mg ORAL NDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 33261-810 TABLET 100 mg ORAL NDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 35356-856 TABLET 100 mg ORAL ANDA 12 sections
ALLOPURINOL HUMAN PRESCRIPTION DRUG LABEL 1 42549-500 TABLET 100 mg ORAL ANDA 12 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 43063-079 TABLET 100 mg ORAL ANDA 12 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 43063-774 TABLET 300 mg ORAL NDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 43063-793 TABLET 100 mg ORAL NDA 11 sections
Allopurinol HUMAN PRESCRIPTION DRUG LABEL 1 43353-088 TABLET 300 mg ORAL ANDA 12 sections