Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | CH2Cl2O6P2.2Na |
| Molecular Weight | 288.856 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].OP([O-])(=O)C(Cl)(Cl)P(O)([O-])=O
InChI
InChIKey=HJKBJIYDJLVSAO-UHFFFAOYSA-L
InChI=1S/CH4Cl2O6P2.2Na/c2-1(3,10(4,5)6)11(7,8)9;;/h(H2,4,5,6)(H2,7,8,9);;/q;2*+1/p-2
| Molecular Formula | CH2Cl2O6P2 |
| Molecular Weight | 242.877 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Clodronate (also known as clodronic acid) is a drug used to treat a high level of calcium in the blood caused by changes in the body that happen with cancer. Clodronate is approved in some countries and is sold under trade trade name bonefos for oral use. Bonefos is indicated in the management of osteolytic lesions, hypercalcemia and bone pain associated with skeletal metastases in patients with carcinoma of the breast or multiple myeloma. Bonefos is also indicated for the maintenance of clinically acceptable serum calcium levels in patients with hypercalcemia of malignancy initially treated with an intravenous bisphosphonate. Bonefos forms complexes with divalent metal ions, and therefore simultaneous administration with food, antacids and mineral supplements may impair absorption. It was suggested, that the mechanism of action of clodronate was involved osteoclast apoptosis.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P05141 Gene ID: 292.0 Gene Symbol: SLC25A5 Target Organism: Homo sapiens (Human) |
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Target ID: P12236 Gene ID: 293.0 Gene Symbol: SLC25A6 Target Organism: Homo sapiens (Human) |
|||
Target ID: P12235 Gene ID: 291.0 Gene Symbol: SLC25A4 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Bonefos Approved UseBonefos tablets are indicated in the management of osteolytic lesions, hypercalcaemia and bone pain associated with skeletal metastases in patients with carcinoma of the breast or multiple myeloma. Bonefos tablets are also indicated for the maintenance of clinically acceptable serum calcium levels in patients with hypercalcaemia of malignancy initially treated with an intravenous bisphosphonate. |
|||
| Primary | Bonefos Approved UseBonefos tablets are indicated in the management of osteolytic lesions, hypercalcaemia and bone pain associated with skeletal metastases in patients with carcinoma of the breast or multiple myeloma. Bonefos tablets are also indicated for the maintenance of clinically acceptable serum calcium levels in patients with hypercalcaemia of malignancy initially treated with an intravenous bisphosphonate. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The difluoromethylenesulfonic acid group as a monoanionic phosphate surrogate for obtaining PTP1B inhibitors. | 2002-07 |
|
| Dissociation of angiogenesis and osteoclastogenesis during endochondral bone formation in neonatal mice. | 2002-06 |
|
| Bisphosphonate prodrugs. | 2002-06 |
|
| Role of resident alveolar macrophages in leukocyte traffic into the alveolar air space of intact mice. | 2002-06 |
|
| Correction of the nonlinear dose response improves the viability of adenoviral vectors for gene therapy of Fabry disease. | 2002-05-20 |
|
| The bisphosphonate zoledronic acid impairs Ras membrane [correction of impairs membrane] localisation and induces cytochrome c release in breast cancer cells. | 2002-05-06 |
|
| Alendronate inhibits invasion of PC-3 prostate cancer cells by affecting the mevalonate pathway. | 2002-05-01 |
|
| Complete healing of severe osteoradionecrosis with treatment combining pentoxifylline, tocopherol and clodronate. | 2002-05 |
|
| Effects of topical administration of clodronate on alveolar bone resorption in rats with experimental periodontitis. | 2002-05 |
|
| Macrophages are necessary for maximal nuclear factor-kappa B activation in response to endotoxin. | 2002-05 |
|
| Further insight into mechanism of action of clodronate: inhibition of mitochondrial ADP/ATP translocase by a nonhydrolyzable, adenine-containing metabolite. | 2002-05 |
|
| Is there a dose response relationship for clodronate in the treatment of tumour induced hypercalcaemia? | 2002-04-22 |
|
| [Bisphosphonate therapy in Paget disease?]. | 2002-03-22 |
|
| Bisphosphonates inhibit stromelysin-1 (MMP-3), matrix metalloelastase (MMP-12), collagenase-3 (MMP-13) and enamelysin (MMP-20), but not urokinase-type plasminogen activator, and diminish invasion and migration of human malignant and endothelial cell lines. | 2002-03 |
|
| Disodium chlodronate prevents bone resorption in experimental periodontitis in rats. | 2002-03 |
|
| Reductions in bone mass, structure, and strength in axial and appendicular skeletons associated with increased turnover after ovariectomy in mature cynomolgus monkeys and preventive effects of clodronate. | 2002-03 |
|
| Prospective evaluation of the peptide-bound collagen type I cross-links N-telopeptide and C-telopeptide in predicting bone metastases status. | 2002-02-01 |
|
| Bisphosphonate space measurement and dosage requirement for intravenous clodronate treatment of Paget's disease. | 2002-02 |
|
| Clodronate in myelofibrosis: a case report. | 2002-02 |
|
| Electrospray ionization mass spectrometry and tandem mass spectrometry of clodronate and related bisphosphonate and phosphonate compounds. | 2002-02 |
|
| Rapid recovery of platelet count following administration of liposome-encapsulated clodronate in a mouse model of immune thrombocytopenia. | 2002-02 |
|
| Does postmenopausal hormone replacement therapy affect cardiac autonomic regulation in osteoporotic women? | 2002-01-16 |
|
| Reduction of instability-induced bone resorption using bisphosphonates: high doses are needed in rats. | 2002-01 |
|
| Bisphosphonates suppress bone resorption by a direct effect on early osteoclast precursors without affecting the osteoclastogenic capacity of osteogenic cells: the role of protein geranylgeranylation in the action of nitrogen-containing bisphosphonates on osteoclast precursors. | 2002-01 |
|
| The role of perivascular and meningeal macrophages in experimental allergic encephalomyelitis. | 2002-01 |
|
| Recent advances in breast cancer (the Twenty-fourth San Antonio Breast Cancer Symposium, December, 2001). | 2002 |
|
| Treatment of complex regional pain syndrome type I. | 2002 |
|
| Actions of bisphosphonates in animal models of breast cancer. | 2002 |
|
| Development of bisphosphonates. | 2002 |
|
| The present and future role of bisphosphonates in the management of patients with breast cancer. | 2002 |
|
| Direct effects of bisphosphonates on breast cancer cells. | 2002 |
|
| Bisphosphonates for breast cancer. | 2002 |
|
| Clinical and biochemical response to single infusion of clodronate in active rheumatoid arthritis--a double blind placebo controlled study. | 2001-12 |
|
| Effects of long-term administration of clodronate on growing rat bone. | 2001-12 |
|
| [Parenteral disodium-clodronate in patients with rheumatoid arthritis. A two-month open clinical study]. | 2001-12 |
|
| Novel therapeutic approaches to cancer patients with bone metastasis. | 2001-12 |
|
| Inhibition of bone resorption by alendronate and risedronate does not require osteoclast apoptosis. | 2001-12 |
|
| Long-term impact of chemotherapy-induced ovarian failure on bone mineral density (BMD) in premenopausal breast cancer patients. The effect of adjuvant clodronate treatment. | 2001-12 |
|
| The cellular uptake and metabolism of clodronate in RAW 264 macrophages. | 2001-11 |
|
| Suppression of T cells results in long-term survival of mouse heart xenografts in C6-deficient rats. | 2001-11 |
|
| Meningeal and perivascular macrophages of the central nervous system play a protective role during bacterial meningitis. | 2001-10-15 |
|
| Critical role of Kupffer cell-derived IL-10 for host defense in septic peritonitis. | 2001-10-01 |
|
| Bisphosphonates in the treatment of metastatic breast cancer. | 2001-10 |
|
| Comparison of the effects of intravenous pamidronate and oral clodronate on symptoms and bone resorption in patients with metastatic bone disease. | 2001-10 |
|
| Paget's disease of the spine and its management. | 2001-10 |
|
| Nitrogen-containing bisphosphonates induce apoptosis of Caco-2 cells in vitro by inhibiting the mevalonate pathway: a model of bisphosphonate-induced gastrointestinal toxicity. | 2001-10 |
|
| The molecular mechanism of action of the antiresorptive and antiinflammatory drug clodronate: evidence for the formation in vivo of a metabolite that inhibits bone resorption and causes osteoclast and macrophage apoptosis. | 2001-09 |
|
| [Bisphosphonates in the treatment of breast carcinoma]. | 2001-08 |
|
| Strategies for management of prostate cancer-related bone pain. | 2001 |
|
| Bisphosphonates in multiple myeloma. | 2001 |
Patents
Sample Use Guides
A daily dose of 1600 mg should be taken as a single dose. When higher daily doses are used, the part of the dose exceeding 1600 mg should be taken separately (as a second dose) as recommended below.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: It was found that due to high bisphosphonate-bone binding affinity, bone surface exposure to clodronate for 3 min. had maximal resorption inhibition. The mechanism of action of both clodronate and zoledronic acid involved osteoclast apoptosis, whereas pamidronate had only minor apoptotic effect at dosages, which readily inhibited resorption. Zoledronic acid was not metabolised into an intracellular ATP-analogue in vitro in contrast to clodronate
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:50:43 GMT 2025
by
admin
on
Mon Mar 31 18:50:43 GMT 2025
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| Record UNII |
Y05R4GCQ1H
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| Record Status |
Validated (UNII)
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| Record Version |
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C443
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C87474
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100000088587
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |