Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H10N2O7P2 |
Molecular Weight | 272.0896 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(CN1C=CN=C1)(P(O)(O)=O)P(O)(O)=O
InChI
InChIKey=XRASPMIURGNCCH-UHFFFAOYSA-N
InChI=1S/C5H10N2O7P2/c8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7/h1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14)
Zoledronic acid (Reclast, Aclasta, Zometa) is an intravenous, highly potent amino-bisphosphonate approved worldwide, including in the USA, EU and Japan for use in patients with primary or secondary osteoporosis or low bone mass (approved indications vary between countries). Its high affinity to and long half-life in bone, and long duration of action allow for once-yearly administration, which has the potential to improve adherence to therapy. Zoledronic acid once yearly for up to 3 years improved bone mineral density (BMD) at several skeletal sites, reduced fracture risk and bone turnover, and/or preserved bone structure and mass relative to placebo in clinical studies in patients with primary or secondary osteoporosis. While additional benefits were seen when treatment was continued for up to 6 years, as evidenced by a reduced risk of vertebral fractures and higher BMD relative to 3 years’ therapy, there was the minimal advantage of treatment beyond 6 years. Therefore, in patients with low fracture risk, treatment discontinuation should be considered after approximately 5 years’ therapy. Zoledronic acid administered annually or once in 2 years was also effective in preventing bone loss in patients with low bone mass. Zoledronic acid was generally well tolerated, with the most common adverse events (AEs) being transient, mild-to-moderate post-infusion symptoms, which decreased with subsequent infusions.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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[Bisphosphonates in the treatment of breast carcinoma]. | 2001 Aug |
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Metastatic bone disease and tumour-induced hypercalcaemia: the role of bisphosphonates. | 2001 Jun |
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Bisphosphonates in the treatment of metastatic breast cancer. | 2001 Oct |
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The use of zoledronic acid, a novel, highly potent bisphosphonate, for the treatment of hypercalcemia of malignancy. | 2002 |
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The new bisphosphonate, Zometa (zoledronic acid), decreases skeletal complications in both osteolytic and osteoblastic lesions: a comparison to pamidronate. | 2002 |
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U.S. Food and Drug Administration drug approval summaries: imatinib mesylate, mesna tablets, and zoledronic acid. | 2002 |
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Actions of bisphosphonates in animal models of breast cancer. | 2002 |
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Development of bisphosphonates. | 2002 |
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FDA approves ZOMETA for treatment of cancer-related bone complications. | 2002 Apr |
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Is there a dose response relationship for clodronate in the treatment of tumour induced hypercalcaemia? | 2002 Apr 22 |
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Bisphosphonates: biological response modifiers in breast cancer. | 2002 Aug |
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Highly potent geminal bisphosphonates. From pamidronate disodium (Aredia) to zoledronic acid (Zometa). | 2002 Aug 15 |
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Advances in the biology and treatment of myeloma bone disease. | 2002 Dec |
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The anti-tumour activity of bisphosphonates. | 2002 Dec |
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Disease modifying and anti-nociceptive effects of the bisphosphonate, zoledronic acid in a model of bone cancer pain. | 2002 Dec |
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Monosodium [1-hydroxy-2-(1H-imidazol-3-ium-4-yl)ethane-1,1-diyl]bis(phosphonate) tetrahydrate (monosodium isozoledronate). | 2002 Dec |
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Pharmacological treatments for prostate cancer. | 2002 Dec |
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The role of osteoclastic activity in prostate cancer skeletal metastases. | 2002 Feb |
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Distinct mechanisms of bisphosphonate action between osteoblasts and breast cancer cells: identity of a potent new bisphosphonate analogue. | 2002 Feb |
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The effects of local administration of Zoledronate solution on the tooth movement and periodontal ligament. | 2002 Jul |
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New drugs 2002, part III. | 2002 Jul |
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Osteoporosis: challenges and new opportunities for therapy. | 2002 Jul |
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Bisphosphonates for cancer patients: why, how, and when? | 2002 Jul |
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Novel therapeutic options for osteoporosis. | 2002 Jul |
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Zoledronate once-yearly increases bone mineral density--implications for osteoporosis. | 2002 Jul |
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An investigation of bone resorption and Dictyostelium discoideum growth inhibition by bisphosphonate drugs. | 2002 Jul 4 |
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Electrolyte abnormalities with zoledronic acid therapy. | 2002 Jul-Aug |
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Zoledronic acid. A bisphosphonate for hypercalcemia of malignancy and osteolytic metastases. | 2002 Jul-Aug |
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Bisphosphonates influence the proliferation and the maturation of normal human osteoblasts. | 2002 Jun |
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Bisphosphonates and osteoporosis. | 2002 Jun 27 |
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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 Mar |
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Treatment of malignant hypercalcaemia. | 2002 May |
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The bisphosphonate zoledronic acid impairs Ras membrane [correction of impairs membrane] localisation and induces cytochrome c release in breast cancer cells. | 2002 May 6 |
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Pharmacokinetics and pharmacodynamics of zoledronic acid in cancer patients with bone metastases. | 2002 Nov |
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Severe increase in creatinine with hypocalcaemia in thalidomide-treated myeloma patients receiving zoledronic acid infusions. | 2002 Nov |
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Pamidronate causes apoptosis of plasma cells in vivo in patients with multiple myeloma. | 2002 Nov |
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Bisphosphonates inhibit angiogenesis in vitro and testosterone-stimulated vascular regrowth in the ventral prostate in castrated rats. | 2002 Nov 15 |
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Development and validation of a highly sensitive RIA for zoledronic acid, a new potent heterocyclic bisphosphonate, in human serum, plasma and urine. | 2002 Nov 7 |
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The use of bisphosphonates in patients with breast cancer. | 2002 Nov-Dec |
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Bisphosphonate therapy in multiple myeloma: past, present, future. | 2002 Nov-Dec |
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Zoledronic acid. | 2002 Nov-Dec |
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Gateways to clinical trials. | 2002 Oct |
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Zoledronic acid: new preparation. Just a me-too: no advance in hypercalcemia of malignancy. | 2002 Oct |
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Intravenous zoledronic acid in postmenopausal women with low bone mineral density. | 2002 Oct |
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The IL-6 receptor super-antagonist Sant7 enhances antiproliferative and apoptotic effects induced by dexamethasone and zoledronic acid on multiple myeloma cells. | 2002 Oct |
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Use of zoledronate to treat osteoblastic versus osteolytic lesions in a severe-combined-immunodeficient mouse model. | 2002 Oct 1 |
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A randomized, placebo-controlled trial of zoledronic acid in patients with hormone-refractory metastatic prostate carcinoma. | 2002 Oct 2 |
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Novel antiangiogenic effects of the bisphosphonate compound zoledronic acid. | 2002 Sep |
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American Society of Clinical Oncology clinical practice guidelines: the role of bisphosphonates in multiple myeloma. | 2002 Sep 1 |
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[Bisphosphonates in bone metastases. Fewer fractures, less pain]. | 2002 Sep 26 |
Patents
Sample Use Guides
The maximum recommended dose of Zometa in hypercalcemia of malignancy is 4 mg. The 4 mg dose must be given as a single-dose intravenous infusion over no less than 15 minutes.
Route of Administration:
Intravenous
For the transfection of the T24 human bladder cancer cells, pCMV6 empty vector (OriGene, Rockville, MD, USA) and pCMV6 TAp73 vector were transfected into cells using Lipofectamine™ 2000 (Invitrogen Life Technologies). After 6 h, the medium was refreshed and cultured for 48 h. Then the cells were treated with ZA (200 μM).
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NDF-RT |
N0000175579
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WHO-ATC |
M05BA08
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FDA ORPHAN DRUG |
130899
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NCI_THESAURUS |
C443
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NDF-RT |
N0000007707
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1546014
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118072-93-8
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7254
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M11658
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118072-93-8
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SUB00176MIG
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118072-93-8
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C80120
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SUB12624MIG
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DB00399
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68740
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)