Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | 2C5H10N2O7P2.5H2O |
| Molecular Weight | 634.2556 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.O.O.OC(CN1C=CN=C1)(P(O)(O)=O)P(O)(O)=O.OC(CN2C=CN=C2)(P(O)(O)=O)P(O)(O)=O
InChI
InChIKey=AZZILOGHCMYHQY-UHFFFAOYSA-N
InChI=1S/2C5H10N2O7P2.5H2O/c2*8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7;;;;;/h2*1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14);5*1H2
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C5H10N2O7P2 |
| Molecular Weight | 272.0896 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1782 |
4.1 nM [IC50] | ||
Target ID: CHEMBL4769 |
97.0 µM [IC50] | ||
Target ID: CHEMBL3510 |
92.0 nM [IC50] | ||
Target ID: CHEMBL205 |
62.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Zometa Approved UseINDICATIONS AND USAGE
Hypercalcemia of Malignancy. Zometa® (zoledronic acid for injection) is indicated for the treatment of hypercalcemia of malignancy. Vigorous saline hydration, an integral part of hypercalcemia therapy, should be initiated promptly and an attempt should be made to restore the urine output to about 2 L/day throughout treatment. Mild or asymptomatic hypercalcemia may be treated with conservative measures (i.e., saline hydration, with or without loop diuretics). Patients should be hydrated dequately throughout the treatment, but overhydration, especially in those patients who have cardiac failure, must be avoided. Diuretic therapy should not be employed prior to correction of hypovolemia. The safety and efficacy of Zometa in the treatment of hypercalcemia associated with hyperparathyroidism or with other non-tumor-related conditions has not been established.
Multiple Myeloma and Bone Metastases of Solid Tumors. Zometa is indicated for the treatment of patients with multiple myeloma and patients with documented bone metastases from solid tumors, in conjunction with standard antineoplastic therapy. Prostate cancer should have progressed after treatment with at least one hormonal therapy Launch Date2001 |
|||
| Primary | Zometa Approved UseINDICATIONS AND USAGE
Hypercalcemia of Malignancy. Zometa® (zoledronic acid for injection) is indicated for the treatment of hypercalcemia of malignancy. Vigorous saline hydration, an integral part of hypercalcemia therapy, should be initiated promptly and an attempt should be made to restore the urine output to about 2 L/day throughout treatment. Mild or asymptomatic hypercalcemia may be treated with conservative measures (i.e., saline hydration, with or without loop diuretics). Patients should be hydrated dequately throughout the treatment, but overhydration, especially in those patients who have cardiac failure, must be avoided. Diuretic therapy should not be employed prior to correction of hypovolemia. The safety and efficacy of Zometa in the treatment of hypercalcemia associated with hyperparathyroidism or with other non-tumor-related conditions has not been established.
Multiple Myeloma and Bone Metastases of Solid Tumors. Zometa is indicated for the treatment of patients with multiple myeloma and patients with documented bone metastases from solid tumors, in conjunction with standard antineoplastic therapy. Prostate cancer should have progressed after treatment with at least one hormonal therapy Launch Date2001 |
|||
| Primary | Zometa Approved UseINDICATIONS AND USAGE
Hypercalcemia of Malignancy. Zometa® (zoledronic acid for injection) is indicated for the treatment of hypercalcemia of malignancy. Vigorous saline hydration, an integral part of hypercalcemia therapy, should be initiated promptly and an attempt should be made to restore the urine output to about 2 L/day throughout treatment. Mild or asymptomatic hypercalcemia may be treated with conservative measures (i.e., saline hydration, with or without loop diuretics). Patients should be hydrated dequately throughout the treatment, but overhydration, especially in those patients who have cardiac failure, must be avoided. Diuretic therapy should not be employed prior to correction of hypovolemia. The safety and efficacy of Zometa in the treatment of hypercalcemia associated with hyperparathyroidism or with other non-tumor-related conditions has not been established.
Multiple Myeloma and Bone Metastases of Solid Tumors. Zometa is indicated for the treatment of patients with multiple myeloma and patients with documented bone metastases from solid tumors, in conjunction with standard antineoplastic therapy. Prostate cancer should have progressed after treatment with at least one hormonal therapy Launch Date2001 |
|||
| Primary | Zometa Approved UseINDICATIONS AND USAGE
Hypercalcemia of Malignancy. Zometa® (zoledronic acid for injection) is indicated for the treatment of hypercalcemia of malignancy. Vigorous saline hydration, an integral part of hypercalcemia therapy, should be initiated promptly and an attempt should be made to restore the urine output to about 2 L/day throughout treatment. Mild or asymptomatic hypercalcemia may be treated with conservative measures (i.e., saline hydration, with or without loop diuretics). Patients should be hydrated dequately throughout the treatment, but overhydration, especially in those patients who have cardiac failure, must be avoided. Diuretic therapy should not be employed prior to correction of hypovolemia. The safety and efficacy of Zometa in the treatment of hypercalcemia associated with hyperparathyroidism or with other non-tumor-related conditions has not been established.
Multiple Myeloma and Bone Metastases of Solid Tumors. Zometa is indicated for the treatment of patients with multiple myeloma and patients with documented bone metastases from solid tumors, in conjunction with standard antineoplastic therapy. Prostate cancer should have progressed after treatment with at least one hormonal therapy Launch Date2001 |
|||
| Primary | Zometa Approved UseINDICATIONS AND USAGE
Hypercalcemia of Malignancy. Zometa® (zoledronic acid for injection) is indicated for the treatment of hypercalcemia of malignancy. Vigorous saline hydration, an integral part of hypercalcemia therapy, should be initiated promptly and an attempt should be made to restore the urine output to about 2 L/day throughout treatment. Mild or asymptomatic hypercalcemia may be treated with conservative measures (i.e., saline hydration, with or without loop diuretics). Patients should be hydrated dequately throughout the treatment, but overhydration, especially in those patients who have cardiac failure, must be avoided. Diuretic therapy should not be employed prior to correction of hypovolemia. The safety and efficacy of Zometa in the treatment of hypercalcemia associated with hyperparathyroidism or with other non-tumor-related conditions has not been established.
Multiple Myeloma and Bone Metastases of Solid Tumors. Zometa is indicated for the treatment of patients with multiple myeloma and patients with documented bone metastases from solid tumors, in conjunction with standard antineoplastic therapy. Prostate cancer should have progressed after treatment with at least one hormonal therapy Launch Date2001 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
264 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21563999 |
4 mg single, intravenous dose: 4 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ZOLEDRONIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
420 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21563999 |
4 mg single, intravenous dose: 4 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ZOLEDRONIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
39 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21563999 |
4 mg single, intravenous dose: 4 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ZOLEDRONIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
16 mg 1 times / 4 weeks multiple, intravenous Highest studied dose Dose: 16 mg, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 16 mg, 1 times / 4 weeks Sources: |
unhealthy, 40-79 years Health Status: unhealthy Age Group: 40-79 years Sex: M+F Sources: |
|
16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
Other AEs: Skeletal pain, Fever... Other AEs: Skeletal pain (30%) Sources: Fever (20%) Anorexia (20%) Diarrhea (20%) Constipation (10%) Nausea (20%) Myalgia (20%) Arthralgia (10%) Anemia (30%) Rigors (20%) Coughing (20%) Leg edema (10%) Urinary tract infection (10%) Fatigue (40%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Arthralgia | 10% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Constipation | 10% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Leg edema | 10% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Urinary tract infection | 10% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Anorexia | 20% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Coughing | 20% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Diarrhea | 20% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Fever | 20% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Myalgia | 20% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Nausea | 20% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Rigors | 20% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Anemia | 30% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Skeletal pain | 30% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
| Fatigue | 40% | 16 mg single, intravenous Highest studied dose Dose: 16 mg Route: intravenous Route: single Dose: 16 mg Sources: |
unhealthy, 54 years (range: 34–73 years) Health Status: unhealthy Age Group: 54 years (range: 34–73 years) Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The use of bisphosphonates in patients with breast cancer. | 2003-01-07 |
|
| Bisphosphonate therapy in multiple myeloma: past, present, future. | 2002-12-04 |
|
| Advances in the biology and treatment of myeloma bone disease. | 2002-12 |
|
| The anti-tumour activity of bisphosphonates. | 2002-12 |
|
| Disease modifying and anti-nociceptive effects of the bisphosphonate, zoledronic acid in a model of bone cancer pain. | 2002-12 |
|
| Monosodium [1-hydroxy-2-(1H-imidazol-3-ium-4-yl)ethane-1,1-diyl]bis(phosphonate) tetrahydrate (monosodium isozoledronate). | 2002-12 |
|
| Pharmacological treatments for prostate cancer. | 2002-12 |
|
| Zoledronic acid improves the mechanical properties of normal and healing bone. | 2002-11-26 |
|
| Zoledronic acid. | 2002-11-19 |
|
| Bisphosphonates inhibit angiogenesis in vitro and testosterone-stimulated vascular regrowth in the ventral prostate in castrated rats. | 2002-11-15 |
|
| Development and validation of a highly sensitive RIA for zoledronic acid, a new potent heterocyclic bisphosphonate, in human serum, plasma and urine. | 2002-11-07 |
|
| Pharmacokinetics and pharmacodynamics of zoledronic acid in cancer patients with bone metastases. | 2002-11 |
|
| Severe increase in creatinine with hypocalcaemia in thalidomide-treated myeloma patients receiving zoledronic acid infusions. | 2002-11 |
|
| Pamidronate causes apoptosis of plasma cells in vivo in patients with multiple myeloma. | 2002-11 |
|
| A randomized, placebo-controlled trial of zoledronic acid in patients with hormone-refractory metastatic prostate carcinoma. | 2002-10-02 |
|
| Use of zoledronate to treat osteoblastic versus osteolytic lesions in a severe-combined-immunodeficient mouse model. | 2002-10-01 |
|
| Gateways to clinical trials. | 2002-10 |
|
| Zoledronic acid: new preparation. Just a me-too: no advance in hypercalcemia of malignancy. | 2002-10 |
|
| Intravenous zoledronic acid in postmenopausal women with low bone mineral density. | 2002-10 |
|
| The IL-6 receptor super-antagonist Sant7 enhances antiproliferative and apoptotic effects induced by dexamethasone and zoledronic acid on multiple myeloma cells. | 2002-10 |
|
| [Bisphosphonates in bone metastases. Fewer fractures, less pain]. | 2002-09-26 |
|
| American Society of Clinical Oncology clinical practice guidelines: the role of bisphosphonates in multiple myeloma. | 2002-09-01 |
|
| Novel antiangiogenic effects of the bisphosphonate compound zoledronic acid. | 2002-09 |
|
| Electrolyte abnormalities with zoledronic acid therapy. | 2002-08-20 |
|
| Highly potent geminal bisphosphonates. From pamidronate disodium (Aredia) to zoledronic acid (Zometa). | 2002-08-15 |
|
| Bisphosphonates: biological response modifiers in breast cancer. | 2002-08 |
|
| Adaptive dose finding for phase I clinical trials of drugs used for chemotherapy of cancer. | 2002-07-15 |
|
| Zoledronic acid. A bisphosphonate for hypercalcemia of malignancy and osteolytic metastases. | 2002-07-09 |
|
| An investigation of bone resorption and Dictyostelium discoideum growth inhibition by bisphosphonate drugs. | 2002-07-04 |
|
| The effects of local administration of Zoledronate solution on the tooth movement and periodontal ligament. | 2002-07 |
|
| New drugs 2002, part III. | 2002-07 |
|
| Osteoporosis: challenges and new opportunities for therapy. | 2002-07 |
|
| Bisphosphonates for cancer patients: why, how, and when? | 2002-07 |
|
| Novel therapeutic options for osteoporosis. | 2002-07 |
|
| Zoledronate once-yearly increases bone mineral density--implications for osteoporosis. | 2002-07 |
|
| Bisphosphonates and osteoporosis. | 2002-06-27 |
|
| Novel approaches to the management of bone metastases in patients with breast cancer. | 2002-06 |
|
| Bisphosphonates influence the proliferation and the maturation of normal human osteoblasts. | 2002-06 |
|
| The bisphosphonate zoledronic acid impairs Ras membrane [correction of impairs membrane] localisation and induces cytochrome c release in breast cancer cells. | 2002-05-06 |
|
| Treatment of malignant hypercalcaemia. | 2002-05 |
|
| FDA approves ZOMETA for treatment of cancer-related bone complications. | 2002-04 |
|
| The role of osteoclastic activity in prostate cancer skeletal metastases. | 2002-02 |
|
| Distinct mechanisms of bisphosphonate action between osteoblasts and breast cancer cells: identity of a potent new bisphosphonate analogue. | 2002-02 |
|
| The use of zoledronic acid, a novel, highly potent bisphosphonate, for the treatment of hypercalcemia of malignancy. | 2002 |
|
| The new bisphosphonate, Zometa (zoledronic acid), decreases skeletal complications in both osteolytic and osteoblastic lesions: a comparison to pamidronate. | 2002 |
|
| U.S. Food and Drug Administration drug approval summaries: imatinib mesylate, mesna tablets, and zoledronic acid. | 2002 |
|
| The role of bisphosphonates in breast cancer management: review article. | 2002 |
|
| FDA grants priority review for ZOMETA. | 2001-10 |
|
| Bisphosphonates in the treatment of metastatic breast cancer. | 2001-10 |
|
| Metastatic bone disease and tumour-induced hypercalcaemia: the role of bisphosphonates. | 2001-06 |
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).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:53:58 GMT 2025
by
admin
on
Mon Mar 31 18:53:58 GMT 2025
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| Record UNII |
1K9U67HDID
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| Record Status |
Validated (UNII)
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| Record Version |
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SUB178554
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100000164225
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| Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
