Zoledronic acid
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MedKoo CAT#: 100950

CAS#: 165800-06-6 (hydrate)

Description: Zoledronic acid is a synthetic imidazole bisphosphonate analog of pyrophosphate with anti-bone-resorption activity. A third-generation bisphosphonate, zoledronic acid binds to hydroxyapatite crystals in the bone matrix, slowing their dissolution and inhibiting the formation and aggregation of these crystals. This agent also inhibits farnesyl pyrophosphate synthase, an enzyme involved in terpenoid biosynthesis. Inhibition of this enzyme prevents the biosynthesis of isoprenoid lipids, donor substrates of farnesylation and geranylgeranylation during the post-translational modification of small GTPase signalling proteins, which are important in the process of osteoclast turnover.


Chemical Structure

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Zoledronic acid
CAS# 165800-06-6 (hydrate)

Theoretical Analysis

MedKoo Cat#: 100950
Name: Zoledronic acid
CAS#: 165800-06-6 (hydrate)
Chemical Formula: C5H12N2O8P2
Exact Mass: 271.99632
Molecular Weight: 290.1
Elemental Analysis: C, 22.07; H, 3.70; N, 10.30; O, 41.16; P, 22.77

Price and Availability

Size Price Availability Quantity
500.0mg USD 90.0 Ready to ship
1.0g USD 150.0 Ready to ship
2.0g USD 250.0 Ready to ship
5.0g USD 550.0 Ready to ship
10.0g USD 950.0 Ready to ship
20.0g USD 1650.0 Ready to ship
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Related CAS #: 165800-06-6 (hydrate)   118072-93-8 (anhydrous)  

Synonym: Zoledronic acid; CGP 42446; CGP42446A; ZOL 446; zoledronate; zoledronate. brand name: Zometa; Reclast.

IUPAC/Chemical Name: (1-hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyl)diphosphonic acid hydrate

InChi Key: FUXFIVRTGHOMSO-UHFFFAOYSA-N

InChi Code: InChI=1S/C5H10N2O7P2.H2O/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);1H2

SMILES Code: OC(P(O)(O)=O)(P(O)(O)=O)CN1C=CN=C1.[H]O[H]

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined.

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined.

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Zoledronic acid monohydrate (Zoledronate monohydrate) is a third-generation bisphosphonate (BP), with potent anti-resorptive activity.
In vitro activity: In the present paper this study shows that by using ZOL (Zoledronic acid) that inhibition of the mevalonate pathway at the stage of farnesylation (FDP synthase) compromises the growth of the CB-MA9 cells, particularly when the cells require membrane dependent cell-cell interactions in 3D colony culture. ZOL was also found to effectively inhibit the formation and size of cobblestone like structures which form when HSCs or MA9 cells migrate burrowing underneath the stromal layer. Reference: Heliyon. 2020 Jun; 6(6): e04020. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7283156/
In vivo activity: In the SKOV3ip1 mouse model, restraint stress increased tumor growth by 4.07-fold (mean difference 0.834 g) and nodule counts by 3.54-fold (mean difference 14.14), while ZA (Zoledronic acid) significantly abrogated this effect (Figure 5b; p < 0.001). In the HeyT30 model, stress significantly increased tumor growth by 2.0-fold (mean difference 1.769 g), and nodule counts by 2.5-fold (mean difference 4.5). Similarly to the SKOV3ip1 model, ZA treatment prevented the effects of stress on tumor growth and nodule development in the HeyT30 model (Figure 5c; p < 0.05). Reference: Cancers (Basel). 2020 Sep; 12(9): 2671. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7563308/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.01 0.03
PBS (pH 7.2) 1.6 5.52
Water 1.0 3.45

Preparing Stock Solutions

The following data is based on the product molecular weight 290.1 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Chiarella E, Codispoti B, Aloisio A, Cosentino EG, Scicchitano S, Montalcini Y, Lico D, Morrone G, Mesuraca M, Bond HM. Zoledronic acid inhibits the growth of leukemic MLL-AF9 transformed hematopoietic cells. Heliyon. 2020 Jun 5;6(6):e04020. doi: 10.1016/j.heliyon.2020.e04020. PMID: 32529062; PMCID: PMC7283156. 2. Huang XL, Huang LY, Cheng YT, Li F, Zhou Q, Wu C, Shi QH, Guan ZZ, Liao J, Hong W. Zoledronic acid inhibits osteoclast differentiation and function through the regulation of NF-κB and JNK signalling pathways. Int J Mol Med. 2019 Aug;44(2):582-592. doi: 10.3892/ijmm.2019.4207. Epub 2019 May 23. PMID: 31173157; PMCID: PMC6605660. 3. Colon-Echevarria CB, Ortiz T, Maldonado L, Hidalgo-Vargas MJ, Pérez-Morales J, Aquino-Acevedo AN, Herrera-Noriega R, Bonilla-Claudio M, Castro EM, Armaiz-Pena GN. Zoledronic Acid Abrogates Restraint Stress-Induced Macrophage Infiltration, PDGF-AA Expression, and Ovarian Cancer Growth. Cancers (Basel). 2020 Sep 18;12(9):2671. doi: 10.3390/cancers12092671. PMID: 32962103; PMCID: PMC7563308. 4. Yang X, Xu X, Chen J, Wang Q, Wang G, Ai X, Wang X, Pan J. Zoledronic acid regulates the synthesis and secretion of IL-1β through Histone methylation in macrophages. Cell Death Discov. 2020 Jun 11;6:47. doi: 10.1038/s41420-020-0273-4. PMID: 32566254; PMCID: PMC7289826.
In vitro protocol: 1. Chiarella E, Codispoti B, Aloisio A, Cosentino EG, Scicchitano S, Montalcini Y, Lico D, Morrone G, Mesuraca M, Bond HM. Zoledronic acid inhibits the growth of leukemic MLL-AF9 transformed hematopoietic cells. Heliyon. 2020 Jun 5;6(6):e04020. doi: 10.1016/j.heliyon.2020.e04020. PMID: 32529062; PMCID: PMC7283156. 2. Huang XL, Huang LY, Cheng YT, Li F, Zhou Q, Wu C, Shi QH, Guan ZZ, Liao J, Hong W. Zoledronic acid inhibits osteoclast differentiation and function through the regulation of NF-κB and JNK signalling pathways. Int J Mol Med. 2019 Aug;44(2):582-592. doi: 10.3892/ijmm.2019.4207. Epub 2019 May 23. PMID: 31173157; PMCID: PMC6605660.
In vivo protocol: 1. Colon-Echevarria CB, Ortiz T, Maldonado L, Hidalgo-Vargas MJ, Pérez-Morales J, Aquino-Acevedo AN, Herrera-Noriega R, Bonilla-Claudio M, Castro EM, Armaiz-Pena GN. Zoledronic Acid Abrogates Restraint Stress-Induced Macrophage Infiltration, PDGF-AA Expression, and Ovarian Cancer Growth. Cancers (Basel). 2020 Sep 18;12(9):2671. doi: 10.3390/cancers12092671. PMID: 32962103; PMCID: PMC7563308. 2. Yang X, Xu X, Chen J, Wang Q, Wang G, Ai X, Wang X, Pan J. Zoledronic acid regulates the synthesis and secretion of IL-1β through Histone methylation in macrophages. Cell Death Discov. 2020 Jun 11;6:47. doi: 10.1038/s41420-020-0273-4. PMID: 32566254; PMCID: PMC7289826.

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Jayaram R, O'Donnell PW, Puleo DA. Systems for local, sustained release of zoledronic acid as a potential treatment for metastatic bone disease. Mater Sci Eng C Mater Biol Appl. 2021 Jan;118:111395. doi: 10.1016/j.msec.2020.111395. Epub 2020 Aug 22. PMID: 33255000.

1: Albani-Campanario M, Buendía-Díaz G, Flores-Islas Mde L, Maquita-Nakano C, Ochoa-Cervantes J. [Zoledronic acid-based uveitis: a case report and a bibliography review]. Ginecol Obstet Mex. 2012 May;80(5):355-9. Review. Spanish. PubMed PMID: 23301428.

2: Huang WW, Huang C, Liu J, Zheng HY, Lin L. Zoledronic acid as an adjuvant therapy in patients with breast cancer: a systematic review and meta-analysis. PLoS One. 2012;7(7):e40783. doi: 10.1371/journal.pone.0040783. Epub 2012 Jul 26. Review. PubMed PMID: 22844410; PubMed Central PMCID: PMC3406041.

3: Zhang J, Wang R, Zhao YL, Sun XH, Zhao HX, Tan L, Chen DC, Hai-Bin X. Efficacy of intravenous zoledronic acid in the prevention and treatment of osteoporosis: a meta-analysis. Asian Pac J Trop Med. 2012 Sep;5(9):743-8. doi: 10.1016/S1995-7645(12)60118-7. Review. PubMed PMID: 22805729.

4: Hadji P, Coleman R, Gnant M, Green J. The impact of menopause on bone, zoledronic acid, and implications for breast cancer growth and metastasis. Ann Oncol. 2012 Nov;23(11):2782-90. doi: 10.1093/annonc/mds169. Epub 2012 Jun 22. Review. PubMed PMID: 22730099; PubMed Central PMCID: PMC3477882.

5: Carter JA, Botteman MF. Health-economic review of zoledronic acid for the management of skeletal-related events in bone-metastatic prostate cancer. Expert Rev Pharmacoecon Outcomes Res. 2012 Aug;12(4):425-37. doi: 10.1586/erp.12.31. Epub 2012 Apr 27. Review. PubMed PMID: 22540167.

6: Dranitsaris G, Hatzimichael E. Interpreting results from oncology clinical trials: a comparison of denosumab to zoledronic acid for the prevention of skeletal-related events in cancer patients. Support Care Cancer. 2012 Jul;20(7):1353-60. doi: 10.1007/s00520-012-1461-4. Epub 2012 Apr 27. Review. PubMed PMID: 22539050; PubMed Central PMCID: PMC3360851.

7: Gnant M. Zoledronic acid in the treatment of early-stage breast cancer: is there a final verdict? Curr Oncol Rep. 2012 Feb;14(1):35-43. doi: 10.1007/s11912-011-0209-5. Review. PubMed PMID: 22113793.

8: Yan T, Yin W, Zhou Q, Zhou L, Jiang Y, Du Y, Shao Z, Lu J. The efficacy of zoledronic acid in breast cancer adjuvant therapy: a meta-analysis of randomised controlled trials. Eur J Cancer. 2012 Jan;48(2):187-95. doi: 10.1016/j.ejca.2011.10.021. Epub 2011 Nov 17. Review. PubMed PMID: 22100904.

9: Hamilton E, Clay TM, Blackwell KL. New perspectives on zoledronic acid in breast cancer: potential augmentation of anticancer immune response. Cancer Invest. 2011 Oct;29(8):533-41. doi: 10.3109/07357907.2011.605413. Epub 2011 Aug 15. Review. PubMed PMID: 21843051.

10: Lipton A. Zoledronic acid: multiplicity of use across the cancer continuum. Expert Rev Anticancer Ther. 2011 Jul;11(7):999-1012. doi: 10.1586/era.11.71. Review. PubMed PMID: 21806323.



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