Neridronic acid
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MedKoo CAT#: 326681

CAS#: 79778-41-9 (free acid)

Description: Neridronic acid, also known neridronate, is a bisphosphonate. In Italy it is used to treat Osteogenesis imperfecta and Paget's disease of bone. Neridronic acid treatment has been reported to be effective also in other skeletal diseases such as osteoporosis, algodystrophy, hypercalcemia of malignancy and bone metastasis. Neridronic acid has been developed only for parenteral use, and it is the only one used as intramuscular injection.

Chemical Structure

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Neridronic acid
CAS# 79778-41-9 (free acid)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326681
Name: Neridronic acid
CAS#: 79778-41-9 (free acid)
Chemical Formula: C6H17NO7P2
Exact Mass: 277.05
Molecular Weight: 277.150
Elemental Analysis: C, 26.00; H, 6.18; N, 5.05; O, 40.41; P, 22.35

Price and Availability

Size Price Availability Quantity
10mg USD 190
20mg USD 350
50mg USD 550
100mg USD 950
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Related CAS #: 80729-79-9 (sodium)   79778-41-9 (free acid)    

Synonym: Neridronate; Neridronic acid; Nerixia.

IUPAC/Chemical Name: (6-Amino-1-hydroxyhexylidene)diphosphonic acid

InChi Key: PUUSSSIBPPTKTP-UHFFFAOYSA-N

InChi Code: InChI=1S/C6H17NO7P2/c7-5-3-1-2-4-6(8,15(9,10)11)16(12,13)14/h8H,1-5,7H2,(H2,9,10,11)(H2,12,13,14)

SMILES Code: OC(P(O)(O)=O)(P(O)(O)=O)CCCCCN

Appearance: 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: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Neridronic acid, also known neridronate, is a bisphosphonate.
In vitro activity: In order to allow a better delivery of neridronate (a N-containing bisphosphonate with relatively poor activity), liposomes were evaluated in vitro on cancer cell lines (MDA-MB-231, U87-MG and Caco2). The influence of neridronate (free or liposomal) on cell viability or proliferation after treatment was evaluated using the MTT method, as well as cell migration and invasion assays; these techniques showed a drastic improvement of the action of neridronate on MDA-MB-231 cells with an EC(50) 50 times lower when neridronate was encapsulated. Reference: Int J Pharm. 2010 Jan 4;383(1-2):116-22. https://pubmed.ncbi.nlm.nih.gov/19748562/
In vivo activity: The effects of the amino-bisphosphonate neridronate on endothelial cell functions involved in angiogenesis, namely, proliferation and morphogenesis on Matrigel were tested in vitro, whereas its effects on angiogenesis were studied in vivo, by using the chick embryo chorioallantoic membrane (CAM) assay. In vivo, when tested in the CAM assay, neridronate again displayed the capability to inhibit FGF-2-induced angiogenesis. Reference: Clin Rheumatol. 2007 Jul;26(7):1094-8. https://pubmed.ncbi.nlm.nih.gov/17106617/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 5.0 18.04

Preparing Stock Solutions

The following data is based on the product molecular weight 277.15 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. Chebbi I, Migianu-Griffoni E, Sainte-Catherine O, Lecouvey M, Seksek O. In vitro assessment of liposomal neridronate on MDA-MB-231 human breast cancer cells. Int J Pharm. 2010 Jan 4;383(1-2):116-22. doi: 10.1016/j.ijpharm.2009.09.011. Epub 2009 Sep 11. PMID: 19748562. 2. Corrado A, Cantatore FP, Grano M, Colucci S. Neridronate and human osteoblasts in normal, osteoporotic and osteoarthritic subjects. Clin Rheumatol. 2005 Sep;24(5):527-34. doi: 10.1007/s10067-005-1100-2. Epub 2005 Aug 10. PMID: 16091841.
In vitro protocol: 1. Chebbi I, Migianu-Griffoni E, Sainte-Catherine O, Lecouvey M, Seksek O. In vitro assessment of liposomal neridronate on MDA-MB-231 human breast cancer cells. Int J Pharm. 2010 Jan 4;383(1-2):116-22. doi: 10.1016/j.ijpharm.2009.09.011. Epub 2009 Sep 11. PMID: 19748562. 2. Corrado A, Cantatore FP, Grano M, Colucci S. Neridronate and human osteoblasts in normal, osteoporotic and osteoarthritic subjects. Clin Rheumatol. 2005 Sep;24(5):527-34. doi: 10.1007/s10067-005-1100-2. Epub 2005 Aug 10. PMID: 16091841.
In vivo protocol: 1. Ribatti D, Nico B, Mangieri D, Maruotti N, Longo V, Vacca A, Cantatore FP. Neridronate inhibits angiogenesis in vitro and in vivo. Clin Rheumatol. 2007 Jul;26(7):1094-8. doi: 10.1007/s10067-006-0455-3. Epub 2006 Nov 15. PMID: 17106617.

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1: Varenna M, Zucchi F, Failoni S, Becciolini A, Berruto M. Intravenous neridronate in the treatment of acute painful knee osteoarthritis: a randomized controlled study. Rheumatology (Oxford). 2015 Oct;54(10):1826-32. doi: 10.1093/rheumatology/kev123. Epub 2015 May 20. PubMed PMID: 25998450.

2: D'Eufemia P, Finocchiaro R, Villani C, Zambrano A, Lodato V, Palombaro M, Properzi E, Celli M. Serum brain-type creatine kinase increases in children with osteogenesis imperfecta during neridronate treatment. Pediatr Res. 2014 May;75(5):626-30. doi: 10.1038/pr.2014.20. Epub 2014 Feb 11. PubMed PMID: 24518563.

3: Viapiana O, Gatti D, Idolazzi L, Fracassi E, Adami S, Troplini S, Povino MR, Rossini M. Bisphosphonates vs infliximab in ankylosing spondylitis treatment. Rheumatology (Oxford). 2014 Jan;53(1):90-4. doi: 10.1093/rheumatology/ket321. Epub 2013 Sep 24. PubMed PMID: 24067888.

4: Varenna M, Adami S, Rossini M, Gatti D, Idolazzi L, Zucchi F, Malavolta N, Sinigaglia L. Treatment of complex regional pain syndrome type I with neridronate: a randomized, double-blind, placebo-controlled study. Rheumatology (Oxford). 2013 Mar;52(3):534-42. doi: 10.1093/rheumatology/kes312. Epub 2012 Nov 30. PubMed PMID: 23204550.

5: Saari AL, Hyvönen H, Lahtinen M, Ylisirniö M, Turhanen P, Kolehmainen E, Peräniemi S, Vepsäläinen J. Systematic study of the physicochemical properties of a homologous series of aminobisphosphonates. Molecules. 2012 Sep 12;17(9):10928-45. doi: 10.3390/molecules170910928. PubMed PMID: 22971579.

6: Forni GL, Perrotta S, Giusti A, Quarta G, Pitrolo L, Cappellini MD, D'Ascola DG, Borgna Pignatti C, Rigano P, Filosa A, Iolascon G, Nobili B, Baldini M, Rosa A, Pinto V, Palummeri E. Neridronate improves bone mineral density and reduces back pain in β-thalassaemia patients with osteoporosis: results from a phase 2, randomized, parallel-arm, open-label study. Br J Haematol. 2012 Jul;158(2):274-82. doi: 10.1111/j.1365-2141.2012.09152.x. Epub 2012 May 10. PubMed PMID: 22571408.

7: Gatti D, Viapiana O, Adami S, Idolazzi L, Fracassi E, Rossini M. Bisphosphonate treatment of postmenopausal osteoporosis is associated with a dose dependent increase in serum sclerostin. Bone. 2012 Mar;50(3):739-42. doi: 10.1016/j.bone.2011.11.028. Epub 2011 Dec 10. PubMed PMID: 22178539.

8: Maines E, Monti E, Doro F, Morandi G, Cavarzere P, Antoniazzi F. Children and adolescents treated with neridronate for osteogenesis imperfecta show no evidence of any osteonecrosis of the jaw. J Bone Miner Metab. 2012 Jul;30(4):434-8. doi: 10.1007/s00774-011-0331-3. Epub 2011 Nov 8. PubMed PMID: 22065238.

9: Semler O, Beccard R, Palmisano D, Demant A, Fricke O, Schoenau E, Koerber F. Reshaping of vertebrae during treatment with neridronate or pamidronate in children with osteogenesis imperfecta. Horm Res Paediatr. 2011;76(5):321-7. doi: 10.1159/000331128. Epub 2011 Sep 27. PubMed PMID: 21952409.

10: Rossini M, Viapiana O, Kalpakcioglu B, Dhangana R, Gatti D, Braga V, Fracassi E, Adami S. Long-term effects of neridronate and its discontinuation in patients with primary hyperparathyroidism. Calcif Tissue Int. 2011 Jul;89(1):21-8. doi: 10.1007/s00223-011-9489-x. Epub 2011 May 13. PubMed PMID: 21567168.

11: Merlotti D, Rendina D, Gennari L, Mossetti G, Gianfrancesco F, Martini G, De Filippo G, Avanzati A, Franci B, Campagna MS, Strazzullo P, Nuti R. Comparison of intravenous and intramuscular neridronate regimens for the treatment of Paget disease of bone. J Bone Miner Res. 2011 Mar;26(3):512-8. doi: 10.1002/jbmr.237. PubMed PMID: 20814970.

12: Ironside MS, Duer MJ, Reid DG, Byard S. Bisphosphonate protonation states, conformations, and dynamics on bone mineral probed by solid-state NMR without isotope enrichment. Eur J Pharm Biopharm. 2010 Sep;76(1):120-6. doi: 10.1016/j.ejpb.2010.05.013. Epub 2010 Jun 8. PubMed PMID: 20554022.

13: Carda S, Invernizzi M, Sainaghi PP, Cisari C. Acute pseudogout following intravenous neridronate for osteoporosis. J Rheumatol. 2010 May;37(5):1076. doi: 10.3899/jrheum.091016. PubMed PMID: 20439533.

14: D'Eufemia P, Finocchiaro R, Celli M, Raccio I, Zambrano A, Tetti M, Smacchia P, Iacobini M. Taurine deficiency in thalassemia major-induced osteoporosis treated with neridronate. Biomed Pharmacother. 2010 Apr;64(4):271-4. doi: 10.1016/j.biopha.2009.06.014. Epub 2009 Oct 23. PubMed PMID: 20359847.

15: Nicolin V, Narducci P, Bareggi R. Role of neridronate on MCF-7 estrogen dependent breast cancer model of bone metastasis: a preliminary study. Invest New Drugs. 2011 Feb;29(1):189-91. doi: 10.1007/s10637-009-9325-6. Epub 2009 Oct 2. PubMed PMID: 19798468.

16: Benucci M, Saviola G, Baiardi P, Abdi-Ali L, Povino MR, Dolenti S, Campostrini L, Sacco S, Manfredi M, Rossini M. Effects of monthly intramuscular neridronate in rheumatic patients in chronic treatment with low-dose glucocorticoids. Clin Exp Rheumatol. 2009 Jul-Aug;27(4):567-73. PubMed PMID: 19772786.

17: Gatti D, Viapiana O, Idolazzi L, Fracassi E, Adami S. Neridronic acid for the treatment of bone metabolic diseases. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1305-11. doi: 10.1517/17425250903029190. Review. PubMed PMID: 19761412.

18: Chebbi I, Migianu-Griffoni E, Sainte-Catherine O, Lecouvey M, Seksek O. In vitro assessment of liposomal neridronate on MDA-MB-231 human breast cancer cells. Int J Pharm. 2010 Jan 4;383(1-2):116-22. doi: 10.1016/j.ijpharm.2009.09.011. Epub 2009 Sep 11. PubMed PMID: 19748562.

19: Gennari L, Merlotti D, Mossetti G, Rendina D, De Paola V, Martini G, Nuti R. The use of intravenous aminobisphosphonates for the treatment of Paget's disease of bone. Mini Rev Med Chem. 2009 Aug;9(9):1052-63. Review. PubMed PMID: 19689402.

20: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Apr;31(3):183-226. PubMed PMID: 19536362.