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MedKoo Cat#: 328607 | Name: Minodronic Acid Monohydrate
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Description:

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

Minodronic Acid Monohydrate (also known as Bonoteo, YM-529, and YH-529) is a nitrogen-containing bisphosphonate that has a greater inhibitory effect on bone resorption. Mindodronic Acid is used for the treatment of osteoporosis.

Chemical Structure

Minodronic Acid Monohydrate
Minodronic Acid Monohydrate
CAS#155648-60-5(monohydrate)

Theoretical Analysis

MedKoo Cat#: 328607

Name: Minodronic Acid Monohydrate

CAS#: 155648-60-5(monohydrate)

Chemical Formula: C9H14N2O8P2

Exact Mass: 0.0000

Molecular Weight: 340.16

Elemental Analysis: C, 31.78; H, 4.15; N, 8.24; O, 37.63; P, 18.21

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 weeks
250mg USD 600.00 2 Weeks
1g USD 1,250.00 2 Weeks
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Related CAS #
155648-60-5(monohydrate) 180064-38-4 (acid)
Synonym
Minodronic Acid Monohydrate; ONO-5920; YM-529; YH-529; BPH-261; ONO 5920; YM 529; YH 529; BPH 261; ONO5920; YM529; YH529; BPH261; Bonoteo
IUPAC/Chemical Name
(1-hydroxy-2-(imidazo[1,2-a]pyridin-3-yl)ethane-1,1-diyl)bis(phosphonic acid) hydrate
InChi Key
GPAPAOGRNKUFGH-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H12N2O7P2.H2O/c12-9(19(13,14)15,20(16,17)18)5-7-6-10-8-3-1-2-4-11(7)8;/h1-4,6,12H,5H2,(H2,13,14,15)(H2,16,17,18);1H2
SMILES Code
OC(P(O)(O)=O)(P(O)(O)=O)CC1=CN=C2C=CC=CN21.[H]O[H]
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
>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
Related CAS# 180064-38-4(Minodronic Acid) 155648-60-5(Minodronic Acid Monohydrate)
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Minodronic Acid Monohydrate (also known as Bonoteo, YM-529, and YH-529) is a nitrogen-containing bisphosphonate that has a greater inhibitory effect on bone resorption.
In vitro activity:
In an osteoclast culture with 1 µM minodronic acid, 65% of minodronic acid was bound to bone, and C-terminal cross-linking telopeptide release was inhibited by 96%. Cultured osteoclasts without minodronic acid treatment formed ruffled borders and bone resorption lacunae and had rich cytoplasm, whereas those treated with 1 µM minodronic acid were not multinucleated, stained densely with toluidine blue, and were detached from the bone surface. Reference: J Bone Miner Metab. 2018 Jan;36(1):54-63. https://pubmed.ncbi.nlm.nih.gov/28243795/
In vivo activity:
This study employed model mice of spontaneous skin inflammation, specifically overexpressing human caspase-1 in the epidermis. The effects of minodronate and anti-RANKL antibody on bone structure, histology, and femur blood flow were studied. Minodronate improved bone density by decreasing osteoclasts, but anti-RANKL antibody did not improve. In the dermatitis model, the blood flow in the bone marrow was decreased, and minodronate restored this parameter. Reference: Int J Mol Sci. 2020 May 20;21(10):3620. https://pubmed.ncbi.nlm.nih.gov/32443893/

Preparing Stock Solutions

The following data is based on the product molecular weight 340.16 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. Tanaka M, Hosoya A, Mori H, Kayasuga R, Nakamura H, Ozawa H. Minodronic acid induces morphological changes in osteoclasts at bone resorption sites and reaches a level required for antagonism of purinergic P2X2/3 receptors. J Bone Miner Metab. 2018 Jan;36(1):54-63. doi: 10.1007/s00774-017-0814-y. Epub 2017 Feb 27. PMID: 28243795. 2. Yasukawa M, Nakazawa T, Kawaguchi T, Kawai N, Tsujimura T, Tojo T, Taniguchi S. Minodronic Acid in Combination with γδT Cells Induces Apoptosis of Non-small Cell Lung Carcinoma Cell Lines. Anticancer Res. 2016 Nov;36(11):5883-5886. doi: 10.21873/anticanres.11174. PMID: 27793912. 3. Mizutani K, Isono K, Matsushima Y, Okada K, Umaoka A, Iida S, Habe K, Hagimori K, Yamazaki H, Yamanaka K. Inflammatory Skin-Derived Cytokines Accelerate Osteoporosis in Mice with Persistent Skin Inflammation. Int J Mol Sci. 2020 May 20;21(10):3620. doi: 10.3390/ijms21103620. PMID: 32443893; PMCID: PMC7279417. 4. Kasukawa Y, Miyakoshi N, Suzuki M, Tsuchie H, Sato C, Kawano T, Akagawa M, Ono Y, Shimada Y. Analgesic effects of minodronate in a rat chronic pain model. Biomed Res. 2018;39(5):261-268. doi: 10.2220/biomedres.39.261. PMID: 30333433.
In vitro protocol:
1. Tanaka M, Hosoya A, Mori H, Kayasuga R, Nakamura H, Ozawa H. Minodronic acid induces morphological changes in osteoclasts at bone resorption sites and reaches a level required for antagonism of purinergic P2X2/3 receptors. J Bone Miner Metab. 2018 Jan;36(1):54-63. doi: 10.1007/s00774-017-0814-y. Epub 2017 Feb 27. PMID: 28243795. 2. Yasukawa M, Nakazawa T, Kawaguchi T, Kawai N, Tsujimura T, Tojo T, Taniguchi S. Minodronic Acid in Combination with γδT Cells Induces Apoptosis of Non-small Cell Lung Carcinoma Cell Lines. Anticancer Res. 2016 Nov;36(11):5883-5886. doi: 10.21873/anticanres.11174. PMID: 27793912.
In vivo protocol:
1. Mizutani K, Isono K, Matsushima Y, Okada K, Umaoka A, Iida S, Habe K, Hagimori K, Yamazaki H, Yamanaka K. Inflammatory Skin-Derived Cytokines Accelerate Osteoporosis in Mice with Persistent Skin Inflammation. Int J Mol Sci. 2020 May 20;21(10):3620. doi: 10.3390/ijms21103620. PMID: 32443893; PMCID: PMC7279417. 2. Kasukawa Y, Miyakoshi N, Suzuki M, Tsuchie H, Sato C, Kawano T, Akagawa M, Ono Y, Shimada Y. Analgesic effects of minodronate in a rat chronic pain model. Biomed Res. 2018;39(5):261-268. doi: 10.2220/biomedres.39.261. PMID: 30333433.
1: Tanaka M, Mori H, Kawabata K, Mashiba T. Minodronic acid ameliorates vertebral bone strength by increasing bone mineral density in 9-month treatment of ovariectomized cynomolgus monkeys. Bone. 2016 Jul;88:157-64. doi: 10.1016/j.bone.2016.05.001. Epub 2016 May 4. PubMed PMID: 27155564. 2: Kitamura N, Shiraiwa H, Inomata H, Nozaki T, Ikumi N, Sugiyama K, Nagasawa Y, Karasawa H, Iwata M, Matsukawa Y, Takei M. Efficacy and safety of minodronic acid hydrate in patients with steroid-induced osteoporosis. Int J Rheum Dis. 2016 Mar 1. doi: 10.1111/1756-185X.12844. [Epub ahead of print] PubMed PMID: 26929019. 3: Imai A, Matsunami K, Ichigo S, Takagi H. Minodronic acid suppresses gonadotropin-releasing hormone agonist-induced bone remodeling biomarkers: a retrospective pilot study. Gynecol Endocrinol. 2016;32(3):250-2. doi: 10.3109/09513590.2015.1112783. Epub 2015 Nov 20. PubMed PMID: 26503621. 4: Zhou Y, He X, Li H, Ni Y, Xu M, Sattar H, Chen H, Li W. Pharmacokinetics and tolerability of minodronic acid tablets in healthy Chinese subjects and food and age effects on the pharmacokinetics. Clin Ther. 2015 Apr 1;37(4):869-76. doi: 10.1016/j.clinthera.2015.01.015. Epub 2015 Mar 5. PubMed PMID: 25748293. 5: Tanaka M, Matsugaki A, Ishimoto T, Nakano T. Evaluation of crystallographic orientation of biological apatite in vertebral cortical bone in ovariectomized cynomolgus monkeys treated with minodronic acid and alendronate. J Bone Miner Metab. 2016 Mar;34(2):234-41. doi: 10.1007/s00774-015-0658-2. Epub 2015 Apr 3. PubMed PMID: 25837430. 6: Iwamoto J, Seki A, Sato Y. Effect of combined teriparatide and monthly minodronic acid therapy on cancellous bone mass in ovariectomized rats: a bone histomorphometry study. Bone. 2014 Jul;64:88-94. doi: 10.1016/j.bone.2014.04.003. Epub 2014 Apr 13. PubMed PMID: 24727162. 7: Tanaka M, Mori H, Kayasuga R, Ochi Y, Yamada H, Kawada N, Kawabata K. Effect of intermittent and daily regimens of minodronic Acid on bone metabolism in an ovariectomized rat model of osteoporosis. Calcif Tissue Int. 2014 Aug;95(2):166-73. doi: 10.1007/s00223-014-9876-1. Epub 2014 Jun 6. PubMed PMID: 24903232. 8: Yang Y, Liu C, Zhang Y, Zhou L, Zhong D, Chen X. On-cartridge derivatization coupled with solid-phase extraction for the ultra-sensitive determination of minodronic acid in human plasma by LC-MS/MS method. J Pharm Biomed Anal. 2015 Oct 10;114:408-15. doi: 10.1016/j.jpba.2015.05.038. Epub 2015 Jun 18. PubMed PMID: 26117452. 9: Kimoto A, Tanaka M, Nozaki K, Mori M, Fukushima S, Mori H, Shiroya T, Nakamura T. Intermittent minodronic acid treatment with sufficient bone resorption inhibition prevents reduction in bone mass and strength in ovariectomized rats with established osteopenia comparable with daily treatment. Bone. 2013 Jul;55(1):189-97. doi: 10.1016/j.bone.2013.02.013. Epub 2013 Feb 26. PubMed PMID: 23486179. 10: Tanaka M, Mori H, Kawabata K. Attenuation of Antiresorptive Action in Withdrawal of Minodronic Acid for Three Months After Treatment for Twelve Months in Ovariectomized Rats. Calcif Tissue Int. 2015 Oct;97(4):402-11. doi: 10.1007/s00223-015-0017-2. Epub 2015 Jun 6. PubMed PMID: 26048283.

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