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MedKoo Cat#: 574839 | Name: Pamidronic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pamidronic acid is a synthetic organophosphonic compound which can have its action reversed by hydroxyapatite. [(18)F]AlF-NOTA-pamidronic acid showed promising cellular uptake in Saos-2.

Chemical Structure

Pamidronic acid
Pamidronic acid
CAS#40391-99-9

Theoretical Analysis

MedKoo Cat#: 574839

Name: Pamidronic acid

CAS#: 40391-99-9

Chemical Formula: C3H11NO7P2

Exact Mass: 235.0011

Molecular Weight: 235.07

Elemental Analysis: C, 15.33; H, 4.72; N, 5.96; O, 47.64; P, 26.35

Price and Availability

Size Price Availability Quantity
250mg USD 430.00 2 Weeks
1g USD 550.00 2 Weeks
5g USD 875.00 2 Weeks
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Synonym
Pamidronic acid
IUPAC/Chemical Name
(3-Amino-1-hydroxypropane-1,1-diyl)diphosphonic acid
InChi Key
WRUUGTRCQOWXEG-UHFFFAOYSA-N
InChi Code
InChI=1S/C3H11NO7P2/c4-2-1-3(5,12(6,7)8)13(9,10)11/h5H,1-2,4H2,(H2,6,7,8)(H2,9,10,11)
SMILES Code
OC(P(O)(O)=O)(P(O)(O)=O)CCN
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
Shelf Life
>3 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:
Pamidronic acid is a drug used to treat a broad spectrum of bone absorption diseases.
In vitro activity:
As expected, pamidronate disodium 1, 5, and 10 μg/ml were unfavorable for BMMSC growth (P < .05), whereas 0.1 and 0.5 μg/mL did not affect BMMSC growth (P ≥ .05). BMMSCs treated with pamidronate disodium 0.5 μg/mL had lower ALP activity, ALP staining, and ARS staining (P < .05), and BMMSCs treated with low concentrations (<0.5 μg/mL) of pamidronate disodium had the same levels of ALP activity, ALP staining, and ARS staining as the control (0 μg/mL). Pamidronate disodium 0.5 μg/mL decreased the expression of genes and proteins involved in Wnt and β-catenin signaling. Reference: J Oral Maxillofac Surg. 2017 Oct;75(10):2135-2143. https://pubmed.ncbi.nlm.nih.gov/28412267/
In vivo activity:
Micro-CT and histology analyses indicated that PAM treatment for 2 or 10 weeks could completely prevent or reverse osteoarthritic subchondral bone loss and cartilage surface erosion. Immunohistochemistry and western blot analysis indicated that expression of OPG and RANKL increased, although RANKL expression increased more significantly than that of OPG. Therefore the ratio of OPG to RANKL was lower in the ACLT rabbit group. However, the ratio of OPG to RANKL in the PAM group was significantly higher than that in the ACLT group. Additionally, expression of MMP-9 and TLR-4 were upregulated in the ACLT group and downregulated in the PAM treated groups. Reference: BMC Musculoskelet Disord. 2014 Nov 6;15:370. https://pubmed.ncbi.nlm.nih.gov/25377946/
Solvent mg/mL mM
Solubility
DMSO 1.0 4.25
Water 30.5 129.75
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 235.07 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. Xu Y, Sun J, Yang X, Yu Y, Mai H, Li Z. Pamidronate Disodium Leads to Bone Necrosis via Suppression of Wnt/β-Catenin Signaling in Human Bone Marrow Mesenchymal Stem Cells In Vitro. J Oral Maxillofac Surg. 2017 Oct;75(10):2135-2143. doi: 10.1016/j.joms.2017.03.016. Epub 2017 Mar 22. PMID: 28412267. 2. Viereck V, Emons G, Lauck V, Frosch KH, Blaschke S, Gründker C, Hofbauer LC. Bisphosphonates pamidronate and zoledronic acid stimulate osteoprotegerin production by primary human osteoblasts. Biochem Biophys Res Commun. 2002 Mar 1;291(3):680-6. doi: 10.1006/bbrc.2002.6510. PMID: 11855844. 3. Lv Y, Xia JY, Chen JY, Zhao H, Yan HC, Yang HS, Li Q, Fan YX, Guo KJ, Chen XY. Effects of pamidronate disodium on the loss of osteoarthritic subchondral bone and the expression of cartilaginous and subchondral osteoprotegerin and RANKL in rabbits. BMC Musculoskelet Disord. 2014 Nov 6;15:370. doi: 10.1186/1471-2474-15-370. PMID: 25377946; PMCID: PMC4240862. 4. Kapitola J, Zák J. Effect of pamidronate on bone blood flow in oophorectomized rats. Physiol Res. 1998;47(4):237-40. PMID: 9803469.
In vitro protocol:
1. Xu Y, Sun J, Yang X, Yu Y, Mai H, Li Z. Pamidronate Disodium Leads to Bone Necrosis via Suppression of Wnt/β-Catenin Signaling in Human Bone Marrow Mesenchymal Stem Cells In Vitro. J Oral Maxillofac Surg. 2017 Oct;75(10):2135-2143. doi: 10.1016/j.joms.2017.03.016. Epub 2017 Mar 22. PMID: 28412267. 2. Viereck V, Emons G, Lauck V, Frosch KH, Blaschke S, Gründker C, Hofbauer LC. Bisphosphonates pamidronate and zoledronic acid stimulate osteoprotegerin production by primary human osteoblasts. Biochem Biophys Res Commun. 2002 Mar 1;291(3):680-6. doi: 10.1006/bbrc.2002.6510. PMID: 11855844.
In vivo protocol:
1. Lv Y, Xia JY, Chen JY, Zhao H, Yan HC, Yang HS, Li Q, Fan YX, Guo KJ, Chen XY. Effects of pamidronate disodium on the loss of osteoarthritic subchondral bone and the expression of cartilaginous and subchondral osteoprotegerin and RANKL in rabbits. BMC Musculoskelet Disord. 2014 Nov 6;15:370. doi: 10.1186/1471-2474-15-370. PMID: 25377946; PMCID: PMC4240862. 2. Kapitola J, Zák J. Effect of pamidronate on bone blood flow in oophorectomized rats. Physiol Res. 1998;47(4):237-40. PMID: 9803469.
1: Fauzi MSA, Sabri MSA, Halim AAA, Abidin SAIZ. Combinatorial effects of hydroxyapatite and Tualang honey on medication-related osteonecrosis of the jaw (MRONJ): An in vitro study. J Stomatol Oral Maxillofac Surg. 2024 Jul 30:101999. doi: 10.1016/j.jormas.2024.101999. Epub ahead of print. PMID: 39089510. 2: Cheng T, Wang N, Wen R, Wang S, Zhang H, Cheng M. Discovery of non- sulfonamide carbonic anhydrase IX inhibitors through structure-based virtual screening. Phys Chem Chem Phys. 2024 Mar 13;26(11):8767-8774. doi: 10.1039/d3cp05846h. PMID: 38420672. 3: Sun Z, Xiao L, Chen Y, Wang J, Zeng F, Zhang H, Zhang J, Yang K, Hu YJ. Constructive On-DNA Abramov Reaction and Pudovik Reaction for DEL Synthesis. ACS Med Chem Lett. 2023 Mar 10;14(4):473-478. doi: 10.1021/acsmedchemlett.3c00022. PMID: 37077381; PMCID: PMC10107919. 4: Hassan H, Othman MF, Abdul Razak HR, Zakaria ZA, Ahmad Saad FF, Osman MA, Yi LH, Ashhar Z, Idris J, Abdul Hamid MHN, Safee ZM. Preparation, Optimisation, and In Vitro Evaluation of [18F]AlF-NOTA-Pamidronic Acid for Bone Imaging PET. Molecules. 2022 Nov 17;27(22):7969. doi: 10.3390/molecules27227969. PMID: 36432069; PMCID: PMC9696850. 5: Rattanawonsakul K, Bullock G, Bolt R, Claeyssens F, Atkins S, Hearnden V. In vitro Effect of Geranylgeraniol (GGOH) on Bisphosphonate-Induced Cytotoxicity of Oral Mucosa Cells. Front Oral Health. 2022 Jun 20;3:892615. doi: 10.3389/froh.2022.892615. PMID: 35795156; PMCID: PMC9251184. 6: Bullock G, Miller CA, McKechnie A, Hearnden V. A Review Into the Effects of Pamidronic Acid and Zoledronic Acid on the Oral Mucosa in Medication-Related Osteonecrosis of the Jaw. Front Oral Health. 2022 Feb 9;2:822411. doi: 10.3389/froh.2021.822411. PMID: 35224540; PMCID: PMC8865370. 7: Guk Y, Zyma A, Kincha-Polishchuk T, Chewerda A, Skuratov O. [DRUG CORRECTION OF THE STRUCTURAL AND FUNCTIONAL STATUS OF BONE TISSUE IN PATIENTS WITH FIBROUS DYSPLASIA]. Georgian Med News. 2021 Jul-Aug;(316-317):46-52. Russian. PMID: 34511443. 8: Mathavan S, Kue CS, Kumar S. Identification of potential candidate genes for lip and oral cavity cancer using network analysis. Genomics Inform. 2021 Mar;19(1):e4. doi: 10.5808/gi.20062. Epub 2021 Mar 15. PMID: 33840168; PMCID: PMC8042300. 9: Holmen Olofsson G, Pedersen SR, Aehnlich P, Svane IM, Idorn M, Thor Straten P. The capacity of CD4+ Vγ9Vδ2 T cells to kill cancer cells correlates with co-expression of CD56. Cytotherapy. 2021 Jul;23(7):582-589. doi: 10.1016/j.jcyt.2021.02.003. Epub 2021 Mar 28. PMID: 33785258. 10: Mady MF, Rehman A, Kelland MA. Synthesis and Antiscaling Evaluation of Novel Hydroxybisphosphonates for Oilfield Applications. ACS Omega. 2021 Feb 25;6(9):6488-6497. doi: 10.1021/acsomega.1c00379. PMID: 33718740; PMCID: PMC7948439. 11: Roztoczyńska D, Wójcik M, Konturek A, Nogieć A, Hubalewska-Dydejczyk A, Starzyk J. Bilateral slipped capital femoral epiphysis as first manifestation of primary hyperparathyroidism in a 15-year-old boy. Pediatr Endocrinol Diabetes Metab. 2020;26(4):220-224. English. doi: 10.5114/pedm.2020.100805. PMID: 33554497. 12: Sin HK, Wong PN, Lo KY, Lo MW, Chan SF, Lo KC, Wong YY, Ho LY, Kwok WT, Chan KC, Wong AK, Mak SK. Treatment of Severe Tumoral Calcinosis with Teriparatide in a Dialysis Patient after Total Parathyroidectomy. Case Rep Nephrol. 2021 Jan 6;2021:6695906. doi: 10.1155/2021/6695906. PMID: 33505741; PMCID: PMC7808806. 13: Pijnenburg L, Salem JE, Lebrun-Vignes B, Sibilia J, Javier RM, Arnaud L. Atrial fibrillation in patients treated with intravenous zoledronic or pamidronic acid: a pharmacoepidemiological study. Eur J Endocrinol. 2021 Mar;184(3):437-444. doi: 10.1530/EJE-20-0650. PMID: 33449911. 14: Ashhar Z, Yusof NA, Ahmad Saad FF, Mohd Nor SM, Mohammad F, Bahrin Wan Kamal WH, Hassan MH, Ahmad Hassali H, Al-Lohedan HA. Preparation, Characterization, and Radiolabeling of [68Ga]Ga-NODAGA-Pamidronic Acid: A Potential PET Bone Imaging Agent. Molecules. 2020 Jun 9;25(11):2668. doi: 10.3390/molecules25112668. PMID: 32526838; PMCID: PMC7321328. 15: Bullock G, Miller C, McKechnie A, Hearnden V. Synthetic Hydroxyapatite Inhibits Bisphosphonate Toxicity to the Oral Mucosa In Vitro. Materials (Basel). 2020 May 1;13(9):2086. doi: 10.3390/ma13092086. PMID: 32369961; PMCID: PMC7254283. 16: Zhuravleva IY, Polienko YF, Karpova EV, Timchenko TP, Vasilieva MB, Baratova LA, Shatskaya SS, Kuznetsova EV, Nichay NR, Beshchasna N, Bogachev-Prokophiev AV. Treatment with bisphosphonates to mitigate calcification of elastin- containing bioprosthetic materials. J Biomed Mater Res A. 2020 May;108(7):1579-1588. doi: 10.1002/jbm.a.36927. Epub 2020 Apr 9. PMID: 32176416. 17: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Pamidronate. 2018 Oct 31. PMID: 30000439. 18: Tatara MR, Krupski W, Majer-Dziedzic B. Bone mineral density changes of lumbar spine and femur in osteoporotic patient treated with bisphosphonates and beta-hydroxy-beta-methylbutyrate (HMB): Case report. Medicine (Baltimore). 2017 Oct;96(41):e8178. doi: 10.1097/MD.0000000000008178. PMID: 29019883; PMCID: PMC5662306. 19: Erfani M, Rahmani N, Doroudi A, Shafiei M. Preparation and evaluation of rhenium-188-pamidronate as a palliative treatment in bone metastasis. Nucl Med Biol. 2017 Jun;49:1-7. doi: 10.1016/j.nucmedbio.2017.02.001. Epub 2017 Feb 24. PMID: 28279906. 20: Meckel M, Bergmann R, Miederer M, Roesch F. Bone targeting compounds for radiotherapy and imaging: *Me(III)-DOTA conjugates of bisphosphonic acid, pamidronic acid and zoledronic acid. EJNMMI Radiopharm Chem. 2017;1(1):14. doi: 10.1186/s41181-016-0017-1. Epub 2016 Sep 23. Erratum in: EJNMMI Radiopharm Chem. 2018 Nov 26;3:13. doi: 10.1186/s41181-018-0049-9. PMID: 29564390; PMCID: PMC5843815.