Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H11NO7P2 |
Molecular Weight | 283.1123 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(CC1=CN=CC=C1)(P(O)(O)=O)P(O)(O)=O
InChI
InChIKey=IIDJRNMFWXDHID-UHFFFAOYSA-N
InChI=1S/C7H11NO7P2/c9-7(16(10,11)12,17(13,14)15)4-6-2-1-3-8-5-6/h1-3,5,9H,4H2,(H2,10,11,12)(H2,13,14,15)
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/mtm/risedronate.html
http://www.wikidoc.org/index.php/Risedronate
http://www.rxlist.com/actonel-drug.htm
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/mtm/risedronate.html
http://www.wikidoc.org/index.php/Risedronate
http://www.rxlist.com/actonel-drug.htm
Risedronic acid is a pyridinyl bisphosphonate that inhibits osteoclast-mediated bone resorption and modulates bone metabolism. The action of risedronate on bone tissue is based partly on its affinity for hydroxyapatite, which is part of the mineral matrix of bone. Risedronate also targets farnesyl pyrophosphate (FPP) synthase. It is FDA approved for the treatment of postmenopausal osteoporosis, osteoporosis in men, glucocorticoid-induced osteoporosis and Paget’s disease. Calcium, antacids, or oral medications containing divalent cations interfere with the absorption of Risedronic acid. Common adverse reactions include rash, abdominal pain, constipation, diarrhea, indigestion, nausea, backache, urinary tract infectious disease and influenza-like illness.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Hydroxyapatite crystals Sources: https://www.ncbi.nlm.nih.gov/pubmed/25568655 |
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Target ID: CHEMBL1782 |
3.9 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ACTONEL Approved UseACTONEL is indicated for the treatment and prevention of osteoporosis and Paget’s disease of bone in men and women. Launch Date1998 |
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Primary | ACTONEL Approved UseACTONEL is indicated for the treatment and prevention of glucocorticoid-induced osteoporosis in men and women who are either initiating or continuing systemic glucocorticoid treatment (daily dosage of ≥ 7.5 mg prednisone or equivalent) for chronic diseases. Launch Date1998 |
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Primary | ACTONEL Approved UseACTONEL is indicated for treatment of Paget’s disease of bone in men and women. Launch Date1998 |
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Primary | ACTONEL Approved UseACTONEL is indicated for treatment to increase bone mass in men with osteoporosis. Launch Date1998 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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2.05 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/14999521 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
RISEDRONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.49 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/14999521 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
RISEDRONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.61 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/14999521 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
RISEDRONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.362 |
unhealthy, 41.6±15.7 n = 60 Health Status: unhealthy Condition: Glucocorticoid-induced bone mineral density loss prevention Age Group: 41.6±15.7 Sex: M+F Population Size: 60 Sources: Page: p.362 |
Disc. AE: Skin rash, Gastrointestinal upset... AEs leading to discontinuation/dose reduction: Skin rash (1.7%) Sources: Page: p.362Gastrointestinal upset (1.7%) |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.9 |
unhealthy, 50 - 86 n = 613 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 86 Sex: F Population Size: 613 Sources: Page: p.9 |
Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea (0.3%) Sources: Page: p.9 |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.9 |
unhealthy, 50 - 86 n = 616 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 86 Sex: F Population Size: 616 Sources: Page: p.9 |
Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (0.2%) Sources: Page: p.9 |
75 mg 1 times / day multiple, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: Page: p.9 |
unhealthy, 50 - 86 n = 616 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 86 Sex: F Population Size: 616 Sources: Page: p.9 |
Disc. AE: Vomiting, Diarrhea... AEs leading to discontinuation/dose reduction: Vomiting (1%) Sources: Page: p.9Diarrhea (1%) |
150 mg 1 times / month multiple, oral Recommended Dose: 150 mg, 1 times / month Route: oral Route: multiple Dose: 150 mg, 1 times / month Sources: Page: p.10 |
unhealthy, 50 - 88 n = 650 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 88 Sex: F Population Size: 650 Sources: Page: p.10 |
Disc. AE: Abdominal pain upper, Diarrhea... AEs leading to discontinuation/dose reduction: Abdominal pain upper (2.5%) Sources: Page: p.10Diarrhea (0.8%) Vomiting (0.3%) |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.10 |
unhealthy, 50 - 88 n = 642 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 88 Sex: F Population Size: 642 Sources: Page: p.10 |
Disc. AE: Abdominal pain upper, Vomiting... AEs leading to discontinuation/dose reduction: Abdominal pain upper (1.4%) Sources: Page: p.10Vomiting (0.3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastrointestinal upset | 1.7% Disc. AE |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.362 |
unhealthy, 41.6±15.7 n = 60 Health Status: unhealthy Condition: Glucocorticoid-induced bone mineral density loss prevention Age Group: 41.6±15.7 Sex: M+F Population Size: 60 Sources: Page: p.362 |
Skin rash | 1.7% Disc. AE |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.362 |
unhealthy, 41.6±15.7 n = 60 Health Status: unhealthy Condition: Glucocorticoid-induced bone mineral density loss prevention Age Group: 41.6±15.7 Sex: M+F Population Size: 60 Sources: Page: p.362 |
Diarrhea | 0.3% Disc. AE |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.9 |
unhealthy, 50 - 86 n = 613 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 86 Sex: F Population Size: 613 Sources: Page: p.9 |
Vomiting | 0.2% Disc. AE |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.9 |
unhealthy, 50 - 86 n = 616 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 86 Sex: F Population Size: 616 Sources: Page: p.9 |
Diarrhea | 1% Disc. AE |
75 mg 1 times / day multiple, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: Page: p.9 |
unhealthy, 50 - 86 n = 616 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 86 Sex: F Population Size: 616 Sources: Page: p.9 |
Vomiting | 1% Disc. AE |
75 mg 1 times / day multiple, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: Page: p.9 |
unhealthy, 50 - 86 n = 616 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 86 Sex: F Population Size: 616 Sources: Page: p.9 |
Vomiting | 0.3% Disc. AE |
150 mg 1 times / month multiple, oral Recommended Dose: 150 mg, 1 times / month Route: oral Route: multiple Dose: 150 mg, 1 times / month Sources: Page: p.10 |
unhealthy, 50 - 88 n = 650 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 88 Sex: F Population Size: 650 Sources: Page: p.10 |
Diarrhea | 0.8% Disc. AE |
150 mg 1 times / month multiple, oral Recommended Dose: 150 mg, 1 times / month Route: oral Route: multiple Dose: 150 mg, 1 times / month Sources: Page: p.10 |
unhealthy, 50 - 88 n = 650 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 88 Sex: F Population Size: 650 Sources: Page: p.10 |
Abdominal pain upper | 2.5% Disc. AE |
150 mg 1 times / month multiple, oral Recommended Dose: 150 mg, 1 times / month Route: oral Route: multiple Dose: 150 mg, 1 times / month Sources: Page: p.10 |
unhealthy, 50 - 88 n = 650 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 88 Sex: F Population Size: 650 Sources: Page: p.10 |
Vomiting | 0.3% Disc. AE |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.10 |
unhealthy, 50 - 88 n = 642 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 88 Sex: F Population Size: 642 Sources: Page: p.10 |
Abdominal pain upper | 1.4% Disc. AE |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: Page: p.10 |
unhealthy, 50 - 88 n = 642 Health Status: unhealthy Condition: Postmenopausal osteoporosis Age Group: 50 - 88 Sex: F Population Size: 642 Sources: Page: p.10 |
PubMed
Title | Date | PubMed |
---|---|---|
Alendronate is a specific, nanomolar inhibitor of farnesyl diphosphate synthase. | 2000 Jan 1 |
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Bisphosphonates for the treatment of postmenopausal osteoporosis: clinical studies of etidronate and alendronate. | 2001 Dec |
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Anabolic agents for treating postmenopausal osteoporosis. | 2001 Dec |
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Inhibition of bone resorption by alendronate and risedronate does not require osteoclast apoptosis. | 2001 Dec |
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Risedronate pharmacokinetics and intra- and inter-subject variability upon single-dose intravenous and oral administration. | 2001 Feb |
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Treatment of osteoporosis with bisphosphonates. | 2001 Feb |
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Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. | 2001 Feb |
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Comparison insight dual X-ray absorptiometry (DXA), histomorphometry, ash weight, and morphometric indices for bone evaluation in an animal model (the orchidectomized rat) of male osteoporosis. | 2001 Jan |
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Effect of high doses of oral risedronate (20 mg/day) on serum parathyroid hormone levels and urinary collagen cross-link excretion in postmenopausal women with spinal osteoporosis. | 2001 Jan |
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[Fluorides and bisphosphonates in the treatment of osteoporosis]. | 2001 Jul |
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Role of bisphosphonates and calcitonin in the prevention and treatment of osteoporosis. | 2001 Jul |
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The use of scintigraphy to demonstrate the rapid esophageal transit of the oval film-coated placebo risedronate tablet compared to a round uncoated placebo tablet when administered with minimal volumes of water. | 2001 Jul 17 |
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Maintenance of cortical bone in human parathyroid hormone(1-84)-treated ovariectomized rats. | 2001 Mar |
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Once-a-week alendronate (Fosamax). | 2001 Mar 19 |
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Prevention and treatment of osteoporosis. | 2001 Mar-Apr |
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Effect of combined risedronate and hormone replacement therapies on bone mineral density in postmenopausal women. | 2001 May |
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Effects of suppressed bone turnover by bisphosphonates on microdamage accumulation and biomechanical properties in clinically relevant skeletal sites in beagles. | 2001 May |
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The effect of risedronate on the risk of hip fracture in elderly women. | 2001 May 31 |
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The effect of risedronate on the risk of hip fracture in elderly women. | 2001 May 31 |
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Bisphosphonate treatment suppresses not only stochastic remodeling but also the targeted repair of microdamage. | 2001 Nov |
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Role of alendronate and risedronate in preventing and treating osteoporosis. | 2001 Nov |
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[Economic aspects of osteoporosis therapy. What does a prevented fracture cost?]. | 2001 Nov 22 |
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Osteoporosis in men. | 2001 Nov-Dec |
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Risedronate increases bone density and reduces vertebral fracture risk within one year in men on corticosteroid therapy. | 2001 Oct |
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Maintenance of cancellous bone in ovariectomized, human parathyroid hormone [hPTH(1-84)]-treated rats by estrogen, risedronate, or reduced hPTH. | 2001 Oct |
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Risedronate: a new oral bisphosphonate. | 2001 Sep |
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Pharmacologic therapy for the treatment and prevention of osteoporosis. | 2001 Sep |
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Evaluation and treatment of postmenopausal osteoporosis. | 2001 Sep 25 |
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[Optimizing treatment of osteoporosis. Rapidly effective therapy lowers fracture risk in 1 year up to 70%]. | 2001 Sep 6 |
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Risedronate reduces the risk of first vertebral fracture in osteoporotic women. | 2002 |
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The underuse of therapy in the secondary prevention of hip fractures. | 2002 |
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Development of bisphosphonates. | 2002 |
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Risedronate for the prevention of fractures in postmenopausal osteoporosis. | 2002 Apr |
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[Episcleritis secondary to risedronate]. | 2002 Apr 27 |
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Antiresorptive treatment of postmenopausal osteoporosis: comparison of study designs and outcomes in large clinical trials with fracture as an endpoint. | 2002 Feb |
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Medical treatment of osteoporosis--increasing options. | 2002 Jan |
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Bone quality: getting closer to a definition. | 2002 Jul |
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Risedronate preserves trabecular architecture and increases bone strength in vertebra of ovariectomized minipigs as measured by three-dimensional microcomputed tomography. | 2002 Jul |
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Risedronate for the prevention and treatment of corticosteroid-induced osteoporosis. | 2002 Mar |
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Upper gastrointestinal tract safety of risedronate: a pooled analysis of 9 clinical trials. | 2002 Mar |
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[Risedronate, a new diphosphonate in osteoporosis and Paget's disease]. | 2002 Mar 2 |
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Risedronate: a new oral bisphosphonate. | 2002 May |
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Do bisphosphonates reduce the risk of osteoporotic fractures? An evaluation of the evidence to date. | 2002 May 28 |
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The potential of parathyroid hormone as a therapy for osteoporosis. | 2002 May-Jun |
Patents
Sample Use Guides
Treatment of Postmenopausal Osteoporosis: 5 mg daily, 35 mg once-a-week, 75 mg two consecutive days each month, 150 mg once-a-month.
Prevention of Postmenopausal Osteoporosis: 5 mg daily, 35 mg once-a-week.
Men with Osteoporosis: 35 mg once-a-week.
Glucocorticoid-Induced Osteoporosis: 5 mg daily.
Paget’s Disease: 30 mg daily for 2 month.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21357292
The antimalarial activities of risedronate, one of the most potent bisphosphonates clinically used to treat bone resorption diseases, against blood stages of Plasmodium falciparum (50% inhibitory concentration [IC50] of 20.3±1.0 μM).
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QM05BA07
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M05BB07
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C443
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Risedronate
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Risedronic acid
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)