allopurinol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	124	315-30-0

Description:

Molecule	Description
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 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

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

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.40	g	O
0.40	g	P

ADMET properties:

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Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	97.71 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	53 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	12 %	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	11 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.97 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.80 mg/mL	Bocci G, Oprea TI, Benet LZ
t_half (Half-life)	0.80 hours	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.58 L/kg	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Aug. 19, 1966	FDA	PROMETHEUS LABS

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms	2181.74	9.98	1161	129293	32675	63325893
Acute kidney injury	958.02	9.98	1839	128615	261576	63096992
Drug ineffective	512.96	9.98	853	129601	1043912	62314656
Febrile neutropenia	470.42	9.98	860	129594	117589	63240979
Toxic epidermal necrolysis	445.88	9.98	389	130065	24945	63333623
Anaemia	409.70	9.98	1429	129025	292001	63066567
Stevens-Johnson syndrome	377.78	9.98	352	130102	24598	63333970
Renal failure	361.39	9.98	767	129687	116885	63241683
Pemphigus	360.54	9.98	3	130451	183723	63174845
Hyperkalaemia	356.81	9.98	496	129958	53707	63304861

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms	1249.75	10.77	1280	220356	31732	34703563
Drug ineffective	642.64	10.77	1203	220433	455548	34279747
Acute kidney injury	450.53	10.77	3388	218248	301600	34433695
Drug abuse	405.38	10.77	70	221566	99026	34636269
Toxicity to various agents	355.91	10.77	449	221187	199913	34535382
Gout	314.78	10.77	491	221145	18762	34716533
Off label use	267.01	10.77	1566	220070	417958	34317337
Tumour lysis syndrome	242.05	10.77	408	221228	16651	34718644
Hyperkalaemia	215.71	10.77	942	220694	68447	34666848
Stevens-Johnson syndrome	206.07	10.77	400	221236	18239	34717056

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms	3370.18	9.68	2419	302079	61825	79378065
Acute kidney injury	1473.04	9.68	4838	299660	514566	78925324
Drug ineffective	990.56	9.68	1633	302865	1079280	78360610
Toxic epidermal necrolysis	613.51	9.68	803	303695	43778	79396112
Hyperkalaemia	585.63	9.68	1327	303171	113071	79326819
Anaemia	575.86	9.68	3273	301225	441742	78998148
Febrile neutropenia	553.03	9.68	2038	302460	228961	79210929
Renal failure	549.00	9.68	1852	302646	199116	79240774
Tumour lysis syndrome	502.04	9.68	535	303963	23404	79416486
Stevens-Johnson syndrome	493.79	9.68	676	303822	38490	79401400

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
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:35221	antimetabolite
CHEBI has role	CHEBI:35634	xanthine oxidase inhibitors
CHEBI has role	CHEBI:35845	gout suppressants
CHEBI has role	CHEBI:48578	free radical scavengers
FDA EPC	N0000175698	Xanthine Oxidase Inhibitor
FDA MoA	N0000000206	Xanthine Oxidase Inhibitors
MeSH PA	D000963	Antimetabolites
MeSH PA	D000975	Antioxidants

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
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
Uric Acid Nephropathy Gout	indication
Chemotherapy-Induced Hyperuricemia	indication
Recurrent Calcium Renal Calculi	indication
Adjunctive treatment for bipolar disorder	off-label use	13746004	DOID:3312
Deficiency of adenine phosphoribosyltransferase	off-label use	124274002	DOID:0060350

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🐶 Veterinary Drug Use

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🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (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 strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
200MG;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	TABLET	ORAL	10183012	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;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	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;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	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;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	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;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	TABLET	ORAL	8357713	Dec. 22, 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;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	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
200MG;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	TABLET	ORAL	9956205	Dec. 28, 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;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	TABLET	ORAL	10183012	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;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	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;200MG	DUZALLO	IRONWOOD PHARMS INC	N209203	Aug. 18, 2017	DISCN	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

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Xanthine dehydrogenase/oxidase	Enzyme	P47989	XDH_HUMAN	INHIBITOR	Ki	5.15	CHEMBL	CHEMBL
Adenosine receptor A2a	GPCR	P29274	AA2AR_HUMAN		Kd	4.11	CHEMBL
Hypoxanthine-guanine phosphoribosyltransferase	Enzyme	P00492	HPRT_HUMAN				WOMBAT-PK
Xanthine dehydrogenase/oxidase	Enzyme		XDH_BOVIN		Ki	6	CHEMBL
Xanthine dehydrogenase/oxidase	Enzyme		XDH_RAT		IC50	6.12	CHEMBL
Shiga toxin subunit A	Ribosomal protein		STXA_SHIDY		IC50	4.62	CHEMBL

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External reference:

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ID	Source
001084	NDDF
005000	NDDF
135401907	PUBCHEM_CID
1590	MMSL
1731	INN_ID
17795-21-0	SECONDARY_CAS_RN
1816	MMSL
203600	RXNORM
25246002	SNOMEDCT_US
387135004	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0378-0137	TABLET	100 mg	ORAL	ANDA	20 sections
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0378-0137	TABLET	100 mg	ORAL	ANDA	20 sections
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0378-0181	TABLET	300 mg	ORAL	ANDA	20 sections
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0378-0181	TABLET	300 mg	ORAL	ANDA	20 sections
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0591-5543	TABLET	100 mg	ORAL	NDA	20 sections
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0591-5543	TABLET	100 mg	ORAL	NDA	20 sections
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0591-5544	TABLET	300 mg	ORAL	NDA	20 sections
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0591-5544	TABLET	300 mg	ORAL	NDA	20 sections
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0603-2115	TABLET	100 mg	ORAL	ANDA	12 sections
Allopurinol	HUMAN PRESCRIPTION DRUG LABEL	1	0603-2115	TABLET	100 mg	ORAL	ANDA	12 sections

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