Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H10NO7P2.Na |
Molecular Weight | 305.0941 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].OC(CC1=CN=CC=C1)(P(O)(O)=O)P(O)([O-])=O
InChI
InChIKey=DRFDPXKCEWYIAW-UHFFFAOYSA-M
InChI=1S/C7H11NO7P2.Na/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);/q;+1/p-1
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 |
---|---|---|
Hormone replacement therapy and prevention of vertebral fractures: a meta-analysis of randomised trials. | 2001 |
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Risedronate: a review of its pharmacological properties and clinical use in resorptive bone disease. | 2001 |
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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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[Therapy of osteoporosis. Risk factors alone are not an indication]. | 2001 Dec 6 |
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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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[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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[Bisphosphonate treatment prevents hip fractures in 70-79 year old women with osteoporotic vertebral fractures]. | 2001 Jul 14 |
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Ocular adverse effects of alendronic acid. | 2001 Jun |
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(31)P NMR of apicomplexans and the effects of risedronate on Cryptosporidium parvum growth. | 2001 Jun 15 |
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Risedronate: clinical usage. | 2001 May |
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[Therapy of osteoporosis from the viewpoint of evidence-based medicine]. | 2001 May 15 |
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Absolute vs. relative numbers in evaluating drug therapy. | 2001 May 15 |
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[Bisphosphonates in osteoporosis. Significantly reduces risk of fracture]. | 2001 May 3 |
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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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The effect of risedronate on the risk of hip fracture in elderly women. | 2001 May 31 |
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[Alternatives to hormonal treatment for the prevention of postmenopausal osteoporosis: the bisphosphonates]. | 2001 Nov |
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Bisphosphonate treatment suppresses not only stochastic remodeling but also the targeted repair of microdamage. | 2001 Nov |
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The role of serial bone mineral density testing for osteoporosis. | 2001 Nov |
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Role of alendronate and risedronate in preventing and treating osteoporosis. | 2001 Nov |
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A method to assess the proportion of treatment effect explained by a surrogate endpoint. | 2001 Nov 15 |
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[Economic aspects of osteoporosis therapy. What does a prevented fracture cost?]. | 2001 Nov 22 |
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Risedronate treatment and extended fracture protection in postmenopausal women. | 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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Alendronate for the treatment of osteoporosis in men. | 2001 Oct |
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Paget's disease of the spine and its management. | 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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Nitrogen-containing bisphosphonates induce apoptosis of Caco-2 cells in vitro by inhibiting the mevalonate pathway: a model of bisphosphonate-induced gastrointestinal toxicity. | 2001 Oct |
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[Osteoporosis. Fracture as alarm signal]. | 2001 Oct 11 |
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Pharmacologic therapy for the treatment and prevention of osteoporosis. | 2001 Sep |
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Vgamma2Vdelta2 T-cell receptor-mediated recognition of aminobisphosphonates. | 2001 Sep 1 |
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Evaluation and treatment of postmenopausal osteoporosis. | 2001 Sep 25 |
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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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Direct effects of bisphosphonates on breast cancer cells. | 2002 |
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[Osteoporosis - Evidence based therapy]. | 2002 Apr |
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Risedronate for the prevention of fractures in postmenopausal osteoporosis. | 2002 Apr |
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Therapies to improve bone mineral density and reduce the risk of fracture: clinical trial results. | 2002 Jan |
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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 |
|
Sequential treatment with basic fibroblast growth factor and PTH is more efficacious than treatment with PTH alone for increasing vertebral bone mass and strength in osteopenic ovariectomized rats. | 2002 Jul |
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Activity of bisphosphonates against Trypanosoma brucei rhodesiense. | 2002 Jul 4 |
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[Risedronate: clinical usage]. | 2002 Mar |
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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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The cost utility of bisphosphonate treatment in established osteoporosis. | 2002 May |
|
Do bisphosphonates reduce the risk of osteoporotic fractures? An evaluation of the evidence to date. | 2002 May 28 |
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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C443
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C67439
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FDA ORPHAN DRUG |
229106
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1926958
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ALTERNATIVE |
ACTIVE MOIETY
SUBSTANCE RECORD