allopurinol
Trade name: zyloprim
Approved
Aug 19, 1966
Allopurinol riboside is a metabolite of allopurinol, a xanthine oxidase inhibitor indicated for the management of patients with leukemia, lymphoma, and solid tumor malignancies who are receiving cancer therapy which causes elevations of serum and urinary uric acid levels and who cannot tolerate oral therapy. Allopurinol riboside is not an inhibitor of xanthine oxidase. Allopurinol riboside is commonly thought to be directly synthesized by purine nucleoside phosphorylase (PNP) in vivo. Allopurinol riboside competitively inhibits the action of PNP on inosine in vitro. Allopurinol riboside potently inhibits growth in vitro of promastigotes of Leishmania species. Patients with American cutaneous leishmaniasis who received allopurinol riboside had clinical improvement. In addition, allopurinol riboside demonstrated some effectivity against Trypanosoma cruzi infections in animals. — NCATS
Clinical trial activity
174 trials · 179 clinical orgs · 29 marketing orgs
Earliest trial started Sep 1, 1995 (NCT00004755)
Timeline
1960s
- Aug 19, 1966
Casper Pharma LLC — Earliest FDA Approval
- Aug 19, 1966
Casper Pharma LLC — NDA Secondary Org
- Aug 19, 1966
Casper Pharma LLC — NDA Organization
1980s
- Jun 10, 1980
Abbott — NDA Secondary Org
- Sep 28, 1984
Watson Pharmaceuticals — NDA Secondary Org
- Dec 10, 1985
Puracap Pharmaceutical — Marketing Organization
- Dec 24, 1985
Mutual Pharmaceutical — Marketing Organization
- Dec 31, 1985
Fosun — Marketing Organization
- Dec 31, 1985
Sandoz — Marketing Organization
- Dec 31, 1985
AiPing Pharm Inc — Marketing Organization
- Oct 24, 1986
Mylan — Marketing Organization
- Apr 2, 1987
Dr. Reddy's Laboratories — Marketing Organization
1990s
2000s
- Jan 1, 2003
Earliest Phase 1 Sponsor(trial)
- Jun 27, 2003
Endo Pharmaceuticals — Marketing Organization
- Jun 27, 2003
Vintage — Marketing Organization
- Aug 26, 2004
West-Ward Pharmaceutical — Marketing Organization
- Aug 26, 2004
Hikma — Marketing Organization
- Sep 8, 2005
Apotex — Marketing Organization
- Sep 8, 2005
Chartwell Pharmaceuticals — Marketing Organization
- Aug 30, 2007
Sun Pharmaceuticals — Marketing Organization
- Sep 11, 2007
Northstar Healthcare — Marketing Organization
2010s
- Mar 16, 2011
IPCA Laboratories Ltd. — Marketing Organization
- May 6, 2013
Accord Research — Marketing Organization
- Jul 28, 2016
Indoco Remedies — Marketing Organization
- Aug 18, 2017
Ironwood Pharmaceuticals — Marketing Organization
- Aug 18, 2017
Ironwood Pharmaceuticals — NDA Secondary Org
- Oct 12, 2017
Zydus Discovery DMCC — Marketing Organization
- Mar 12, 2019
Unichem — Marketing Organization
2020s
- Jan 26, 2022
Gland Pharma Ltd — Marketing Organization
- Mar 7, 2022
Harman Finochem — Marketing Organization
- Aug 3, 2023
Hetero Labs Ltd — Marketing Organization
- Dec 14, 2023
Lupin — Marketing Organization
Indications
Studied for
- Acute Coronary Syndrome · Phase 4
- Acute Kidney Injury · Phase 4
- Angina Pectoris · Phase 2/Phase 3
- Angina, Stable · Phase 4
- Arthritis · Phase 1/Phase 2
- Arthritis, Gouty · Phase 2
- Ascites · Phase 2/Phase 3
- Bipolar Disorder · Phase 4
- Blood Pressure · Phase 2
- Burkitt Lymphoma · Phase 2
- Cardiomyopathy, Dilated · Phase 1/Phase 2
- Cardiovascular Diseases · Phase 4
- Chronic Kidney Disease-Mineral and Bone Disorder · Phase 4
- Colitis, Ulcerative · Phase 3
- Coronary Artery Disease · Phase 4
- Deficiency Diseases · Phase 4
- Diabetes Mellitus · Phase 4
- Diabetes Mellitus, Type 1 · Phase 4
- Diabetes Mellitus, Type 2 · Phase 4
- Diabetic Nephropathies · Phase 4
- Diabetic Neuropathies · Phase 3
- Essential Hypertension · Phase 2
- Fallopian Tube Neoplasms · Phase 2
- Fasting · Phase 1
- Fetal Hypoxia · Phase 3
- Fibrosis · Phase 2/Phase 3
- Graft vs Host Disease · Phase 1
- Hamartoma · Phase 2
- Hand-Foot Syndrome · Phase 2
- Healthy Volunteers · Phase 1
- Heart Disease Risk Factors · Phase 1
- Heart Diseases · Phase 4
- Heart Failure · Phase 4
- Heart Failure, Diastolic · Phase 2
- Hematologic Diseases · Phase 2
- Hepatic Encephalopathy · Phase 2/Phase 3
- HIV Infections · Phase 3
- Hypertension · Phase 4
- Hypertrophy, Left Ventricular · Phase 4
- Hyperuricemia · Phase 4
- Hypoxia-Ischemia, Brain · Phase 3
- Infant, Newborn, Diseases · Phase 3
- Inflammation · Phase 3
- Inflammatory Bowel Diseases · Phase 1
- Ischemic Stroke · Phase 4
- Kidney Calculi · Phase 4
- Kidney Diseases · Phase 4
- Kidney Failure, Chronic · Phase 4
- Kidney Transplantation · Phase 4
- Leishmaniasis · Phase 2
- Leukemia, Biphenotypic, Acute · Phase 2
- Leukemia, Lymphocytic, Chronic, B-Cell · Phase 3
- Leukemia-Lymphoma, Adult T-Cell · Phase 1/Phase 2
- Leukemia, Myelogenous, Chronic, BCR-ABL Positive · Phase 2
- Leukemia, Myeloid · Phase 2
- Leukemia, Myeloid, Acute · Phase 2
- Leukemia, Myeloid, Chronic, Atypical, BCR-ABL Negative · Phase 1/Phase 2
- Leukemia, Myeloid, Chronic-Phase · Phase 2
- Leukemia, Plasma Cell · Phase 2
- Leukemia, Prolymphocytic · Phase 2
- Liver Cirrhosis · Phase 2/Phase 3
- Liver Diseases · Phase 2
- Lymphoma, B-Cell · Phase 2
- Lymphoma, B-Cell, Marginal Zone · Phase 2
- Lymphoma, Follicular · Phase 2
- Lymphoma, Mantle-Cell · Phase 2
- Lymphoma, Non-Hodgkin · Phase 3
- Lymphoma, T-Cell · Phase 2
- Mania · Phase 4
- Metabolic Syndrome · Phase 2
- Multiple Myeloma · Phase 2
- Musculoskeletal Diseases · Phase 3
- Mutation · Phase 2
- Myelodysplastic Syndromes · Phase 2
- Myeloproliferative Disorders · Phase 2
- Myocardial Ischemia · Phase 4
- Neoplasms · Phase 3
- Neoplasms, Plasma Cell · Phase 2
- Neuroprotection · Phase 3
- Obesity · Phase 3
- Ovarian Neoplasms · Phase 2
- Peripheral Arterial Disease · Phase 4
- Peritonitis · Phase 2/Phase 3
- Precursor B-Cell Lymphoblastic Leukemia-Lymphoma · Phase 2
- Precursor Cell Lymphoblastic Leukemia-Lymphoma · Phase 2
- Prediabetic State · Phase 3
- Prehypertension · Phase 2/Phase 3
- Primary Myelofibrosis · Phase 2
- Psychotic Disorders · Phase 4
- Renal Insufficiency · Phase 4
- Renal Insufficiency, Chronic · Phase 4
- Reperfusion Injury · Phase 3
- Salts · Early Phase 1
- Sarcopenia · Phase 4
- Schizophrenia · Phase 4
- Sleep Apnea, Obstructive · Phase 2
- Small Cell Lung Carcinoma · Phase 1/Phase 2
- Sprains and Strains · Phase 3
- Tuberculosis · Phase 1
- Tumor Lysis Syndrome · Phase 3
- Uric Acid · Phase 3
- Urination Disorders · Phase 2
- Urolithiasis · Phase 4
- Varicose Veins · Phase 2/Phase 3
- Vasoconstriction · Phase 1
- Vasodilation · Phase 1
Mechanism of action
- Xanthine dehydrogenaseINHIBITOR
XDH inhibitor
Combination products
duzallo
with lesinurad
Approval history
- approvedPriority reviewAug 19, 1966
Chemistry & pharmacology
SMILES
Oc1ncnc2[nH]ncc12- Mol. weight
- 136.11 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral, Parenteral
- Availability
- Prescription Only
Oral
Yes
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL1467 ↗
- WikipediaAllopurinol ↗
- NCATSWZS8452SEC ↗
- ChEMBLCHEMBL1200477 ↗
- NCATS63CZ7GJN5I ↗
Also known as
- 1,5-dihydro-4h-pyrazolo(3,4-d)pyrimidin-4-one
- 1,5-dihydro-4h-pyrazolo(3,4-d)pyrimidin-4-one
- 1,5-dihydro-4h-pyrazolo(3,4-d)pyrimidine-4-one
- 1,5-dihydro-4h-pyrazolo(3,4-d)pyrimidine-4-one
- 1h-pyrazolo(3,4-d)pyrimidin-4-ol
- 1h-pyrazolo(3,4-d)pyrimidin-4-ol
- 4-hpp
- 4-hpp
- 4h-pyrazolo(3,4-d)pyrimidin-4-one
- 4h-pyrazolo(3,4-d)pyrimidin-4-one
- 4-hydroxy-1h-pyrazolo(3,4-d)pyrimidine
- 4-hydroxy-1h-pyrazolo(3,4-d)pyrimidine
- 4-hydroxy-3,4-pyrazolopyrimidine
- 4-hydroxy-3,4-pyrazolopyrimidine
- 4-hydroxypyrazolo(3,4-d)pyrimidine
- 4-hydroxypyrazolo(3,4-d)pyrimidine
- 4'-hydroxypyrazolol(3,4-d)pyrimidine
- 4'-hydroxypyrazolol(3,4-d)pyrimidine
- 4-hydroxypyrazolopyrimidine
- 4-hydroxypyrazolopyrimidine
- 4-hydroxypyrazolyl(3,4-d)pyrimidine
- 4-hydroxypyrazolyl(3,4-d)pyrimidine
- allopurinol
- allopurinol
- allopurinol
- allopurinol
- allopurinol
- allopurinol
- allopurinol
- allopurinol
- allopurinol
- allopurinol sodium
- allopurinol sodium
- allopurinol sodium
- allopurinol sodium
- allopurinolum
- allopurinolum
- aloprim
- aloprim
- alopurinol
- alopurinol
- aloral
- aloral
- aluline 100
- aluline 100
- aluline 300
- aluline 300
- bw-56158
- bw-56158
- bw-56-158
- bw-56-158
- caplenal
- caplenal
- cosuric
- cosuric
- hamarin 100
- hamarin 100
- hamarin 300
- hamarin 300
- ledopur
- ledopur
- lopurin
- lopurin
- tautomeric mixture of 1h-pyrazolo[3,4-d]pyrimidin-4-ol and 1,5-dihydro-4h-pyrazolo[3,4-d]pyrimidin-4-one
- uricto
- uricto
- xanthomax-100
- xanthomax-100
- xanthomax-300
- xanthomax-300
- zyloprim
- zyloprim
- zyloprim
- zyloprim
- zyloprim
- zyloprim
- zyloprim
- zyloric
- zyloric
- zyloric-300
- zyloric-300
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07089888 | Phase 3 | Aug 4, 2025 | Crystalys Therapeutics |
| NCT07089875 | Phase 3 | Aug 1, 2025 | Crystalys Therapeutics |
| NCT06276556 | Phase 2/Phase 3 (Phase 3) | Apr 22, 2024 | Jiangsu Atom Bioscience and Pharmaceutical Co., Ltd. |
| NCT06056570 | Phase 1/Phase 2 (Phase 2) | Oct 31, 2023 | Urica Therapeutics Inc. |
| NCT05943821 | Phase 3 | Sep 1, 2023 | Poznan University |
| NCT05818085 | Phase 2/Phase 3 (Phase 3) | Aug 11, 2023 | Jiangsu Atom Bioscience and Pharmaceutical Co., Ltd. |
| NCT05888233 | Phase 2 | Aug 2, 2023 | Department of Veteran Affairs |
| NCT07033533 | Phase 1/Phase 2 (Phase 2) | Jun 1, 2023 | Tanta University |
| NCT07177898 | N/A | May 14, 2023 | King Edward Medical University, Narowal Medical College |
| NCT05805605 | Phase 2 | May 1, 2023 | University of Minnesota |
| NCT05586971 | Phase 3 | Jan 31, 2023 | LG |
| NCT05536349 | Phase 2 | Dec 20, 2022 | Loxo Oncology, The Leukemia and Lymphoma Society, University of Texas at Houston |
| NCT05511766 | Phase 2/Phase 3 (Phase 3) | Nov 15, 2022 | Alexandria University, Tanta University |
| NCT05545670 | Phase 2/Phase 3 (Phase 3) | Oct 1, 2022 | Tanta University |
| NCT05540184 | Phase 4 | Sep 30, 2022 | Beni Suef University, Cairo University |
| NCT05253833 | Phase 2 | Aug 12, 2022 | Arthrosi Therapeutics |
| NCT05474560 | N/A | Aug 1, 2022 | Ain Shams University |
| NCT04875702 | N/A | Jun 30, 2022 | Harvard University |
| NCT05828836 | Phase 2/Phase 3 (Phase 3) | Jun 15, 2022 | Tanta University |
| NCT05049863 | Phase 1/Phase 2 (Phase 2) | Mar 31, 2022 | Washington University in St. Louis |
Organizations
Research & Development (179)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Ardea Biosciences | For profit | 11 | 10 | 4 | 2009 |
| University of Minnesota | Academic/Hospital | 9 | 7 | 5 | 2007 |
| AstraZeneca | For profit | 8 | 7 | 3 | 2005 |
| National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK) | Government | 8 | 3 | 4 | 2003 |
| National Heart, Lung, and Blood Institute (NHLBI) | Government | 7 | 1 | 4 | 2003 |
| University of Dundee | Academic/Hospital | 7 | 7 | 1 | 2008 |
| National Cancer Institute (NCI) | Government | 6 | 4 | 1 | 1999 |
| Takeda | For profit | 6 | 6 | 2 | 2002 |
| Harvard University | Academic/Hospital | 5 | 3 | 3 | 1995 |
| University of Texas at Houston | Academic/Hospital | 5 | 5 | 1 | 2009 |
| British Heart Foundation | Academic/Hospital | 4 | 0 | 1 | 2011 |
| Parexel | For profit | 4 | 0 | 1 | 2019 |
| Tanta University | Academic/Hospital | 4 | 4 | 2 | 2022 |
| Utrecht University | Academic/Hospital | 4 | 3 | 2 | 2006 |
| Arthrosi Therapeutics | For profit | 3 | 3 | 2 | 2019 |
| Baylor University | Academic/Hospital | 3 | 0 | 1 | 2003 |
| Department of Veteran Affairs | Government | 3 | 2 | 2 | 1998 |
| Instituto Nacional de Cardiologia Ignacio Chavez | Academic/Hospital | 3 | 3 | 2 | 2010 |
| National Institute of Allergy and Infectious Diseases (NIAID) | Government | 3 | 3 | 3 | 1995 |
| Sanofi | For profit | 3 | 2 | 2 | 2004 |
Marketing (37)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Abbott | For profit | NDA2 | Jun 10, 1980 |
| Accord Research | For profit | MKTG | May 6, 2013 |
| AiPing Pharm Inc | For profit | MKTG | Dec 31, 1985 |
| Apotex | For profit | MKTG | Sep 8, 2005 |
| Casper Pharma LLC | For profit | NDA2 | Aug 19, 1966 |
| Casper Pharma LLC | For profit | NDA | Aug 19, 1966 |
| Chartwell Pharmaceuticals | For profit | MKTG | Sep 8, 2005 |
| Dr. Reddy's Laboratories | For profit | SYN | Apr 2, 1987 |
| Dr. Reddy's Laboratories | For profit | MKTG | Apr 2, 1987 |
| Endo Pharmaceuticals | For profit | MKTG | Jun 27, 2003 |
| Fosun | For profit | MKTG | Dec 31, 1985 |
| Gland Pharma Ltd | For profit | MKTG | Jan 26, 2022 |
| Harman Finochem | For profit | MKTG | Mar 7, 2022 |
| Hetero Labs Ltd | For profit | MKTG | Aug 3, 2023 |
| Hikma | For profit | SYN | Aug 26, 2004 |
| Hikma | For profit | MKTG | Aug 26, 2004 |
| IPCA Laboratories Ltd. | For profit | MKTG | Mar 16, 2011 |
| Indoco Remedies | For profit | SYN | Jul 28, 2016 |
| Indoco Remedies | For profit | MKTG | Jul 28, 2016 |
| Ironwood Pharmaceuticals | For profit | MKTG | Aug 18, 2017 |
| Ironwood Pharmaceuticals | For profit | NDA2 | Aug 18, 2017 |
| Lupin | For profit | MKTG | Dec 14, 2023 |
| Mutual Pharmaceutical | For profit | MKTG | Dec 24, 1985 |
| Mylan | For profit | NDA2 | May 17, 1996 |
| Mylan | For profit | MKTG | Oct 24, 1986 |
| Northstar Healthcare | Academic/Hospital | MKTG | Sep 11, 2007 |
| Puracap Pharmaceutical | For profit | MKTG | Dec 10, 1985 |
| Sandoz | For profit | MKTG | Dec 31, 1985 |
| Sun Pharmaceuticals | For profit | MKTG | Aug 30, 2007 |
| Sun Pharmaceuticals | For profit | SYN | Jan 9, 1987 |
| Superpharm | For profit | MKTG | — |
| Unichem | For profit | SYN | Mar 12, 2019 |
| Unichem | For profit | MKTG | Mar 12, 2019 |
| Vintage | For profit | MKTG | Jun 27, 2003 |
| Watson Pharmaceuticals | For profit | NDA2 | Sep 28, 1984 |
| West-Ward Pharmaceutical | For profit | MKTG | Aug 26, 2004 |
| Zydus Discovery DMCC | For profit | MKTG | Oct 12, 2017 |