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Clodronic Acid, also known as Clodronate, is an organochlorine compound that is a bisphosphonate. It is characterized by the replacement of both hydrogens in methylene chloride with phosphonic acid groups. Clodronic Acid inhibits bone resorption and soft tissue calcification, making it a valuable compound in the medical field.

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  • 10596-23-3 Structure
  • Basic information

    1. Product Name: CLODRONIC ACID
    2. Synonyms: CLODRONIC ACID;Disodium diphosphonate;Clodronic;(Dichloromethylene)bis(phosphonic acid);ARC-69931;Dichloromethylenebis(phosphonic acid);Dichloromethylenebisphosphonic acid;Aids071014
    3. CAS NO:10596-23-3
    4. Molecular Formula: CH4Cl2O6P2
    5. Molecular Weight: 244.89
    6. EINECS: 234-212-1
    7. Product Categories: N/A
    8. Mol File: 10596-23-3.mol
    9. Article Data: 8
  • Chemical Properties

    1. Melting Point: 249-251°
    2. Boiling Point: 474.7°Cat760mmHg
    3. Flash Point: 240.9°C
    4. Appearance: /
    5. Density: 2.306g/cm3
    6. Vapor Pressure: 2.55E-10mmHg at 25°C
    7. Refractive Index: 1.598
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: N/A
    10. PKA: 0.75±0.10(Predicted)
    11. CAS DataBase Reference: CLODRONIC ACID(CAS DataBase Reference)
    12. NIST Chemistry Reference: CLODRONIC ACID(10596-23-3)
    13. EPA Substance Registry System: CLODRONIC ACID(10596-23-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 10596-23-3(Hazardous Substances Data)

10596-23-3 Usage

Uses

Used in Pharmaceutical Industry:
Clodronic Acid is used as a regulator for calcium levels in the body. It plays a crucial role in the treatment of osteoporosis by inhibiting bone resorption and maintaining healthy bone density. Additionally, its ATP-analogs can interfere with cell signaling pathways, providing potential therapeutic benefits.
Used in Treatment of Hypercalcemia:
Clodronic Acid is used as an adjunct in the treatment of severe hypercalcemia associated with malignancy. It helps to regulate calcium levels in the blood, which can become dangerously high in certain cancer patients.
Used in Management of Skeletal Metastases:
Clodronic Acid is used in the management of osteolytic lesions and bone pain associated with skeletal metastases. It helps to slow down the progression of bone damage and alleviate pain caused by the spread of cancer to the bones.
Used in Osteoporosis Treatment:
Clodronic Acid is used as a therapeutic agent for osteoporosis, helping to increase bone mineral density and reduce the risk of fractures. Its ability to inhibit bone resorption makes it an effective treatment option for this condition.

Check Digit Verification of cas no

The CAS Registry Mumber 10596-23-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,5,9 and 6 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 10596-23:
(7*1)+(6*0)+(5*5)+(4*9)+(3*6)+(2*2)+(1*3)=93
93 % 10 = 3
So 10596-23-3 is a valid CAS Registry Number.
InChI:InChI=1/CH4Cl2O6P2/c2-1(3,10(4,5)6)11(7,8)9/h(H2,4,5,6)(H2,7,8,9)

10596-23-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name clodronic acid

1.2 Other means of identification

Product number -
Other names dichloromethanediphosphonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10596-23-3 SDS

10596-23-3Related news

ArticlesEffects of zoledronic acid versus CLODRONIC ACID (cas 10596-23-3) on skeletal morbidity in patients with newly diagnosed multiple myeloma (MRC Myeloma IX): secondary outcomes from a randomised controlled trial08/17/2019

SummaryBackgroundBisphosphonates are the standard of care for reducing the risk of skeletal-related events in patients with bone lesions from multiple myeloma. The MRC Myeloma IX study was designed to compare the effects of zoledronic acid versus clodronic acid in newly diagnosed patients with m...detailed

ArticlesFirst-line treatment with zoledronic acid as compared with CLODRONIC ACID (cas 10596-23-3) in multiple myeloma (MRC Myeloma IX): a randomised controlled trial08/16/2019

SummaryBackgroundBisphosphonates reduce the risk of skeletal events in patients with malignant bone disease, and zoledronic acid has shown potential anticancer effects in preclinical and clinical studies. We aimed to establish whether bisphosphonates can affect clinical outcomes in patients with...detailed

Determination of impurities in CLODRONIC ACID (cas 10596-23-3) by anion-exchange chromatography08/15/2019

A validated ion chromatographic method for the determination of anionic impurities in clodronic acid or disodium clodronate is described. Separations are performed by using an anion-exchange column (IonPac AS5) and a sodium hydroxide gradient. Impurities are detected by suppressed conductivity w...detailed

Clinical efficacy of CLODRONIC ACID (cas 10596-23-3) in horses diagnosed with navicular syndrome: A field study using objective and subjective lameness evaluation08/14/2019

Navicular syndrome, a common cause of equine forelimb lameness, is associated with pathological changes in the navicular bone. Consequently, administration of bisphosphonates (BPs) has been advocated in order to modify the rate of bone turnover. The present study aimed to assess the clinical eff...detailed

10596-23-3Relevant articles and documents

Bisphosphonate prodrugs: Synthesis and in vitro evaluation of novel clodronic acid dianhydrides as bioreversible prodrugs of clodronate

Ahlmark, Marko,Veps?l?inen, Jouko,Taipale, Hannu,Niemi, Riku,J?rvinen, Tomi

, p. 1473 - 1476 (1999)

P,P'-Diacetyl, P,P'-dibutyroyl, P,P'-dipivaloyl, and P,P'-dibenzoyl (dichloromethylene)bisphosphonic acid dianhydride disodium salts (2a-d) were synthesized and evaluated as novel bioreversible prodrugs of clodronate. The anhydrides were prepared by reacting anhydrous tetrasodium clodronate with a large excess of the corresponding acid anhydride. The dianhydrides 2a-d alone were more lipophilic than the parent clodronate, as determined by drug partitioning between 1-octanol and phosphate buffer at pH 7.4. They also were stable toward chemical hydrolysis in aqueous solutions (pH 7.4 and 2.0). The half-lives for chemical degradation in a buffer solution at 37 °C varied from 0.7 to 286 h and from 15 to 790 h at pH 2.0 and 7.4, respectively. The dianhydrides 2a,b,d underwent complete enzymatic hydrolysis to clodronate in 80% serum at 37 °C after 1 min, although 2c had a half-life of 3.3 h. The aqueous solubility of clodronate decreased considerably in the presence of Ca2+ ions. This is most probably due to formation of poorly water-soluble chelates, which may also hinder the oral absorption of clodronate. However, Ca2+ ions did not have an effect on the aqueous solubility of clodronic acid dianhydrides, and therefore, these prodrugs may improve oral absorption of the parent drug. In conclusion, these novel dianhydride derivatives may be potentially useful prodrugs of clodronate which, due to their lipophilicity and lack of Ca2+ chelating, increase its bioavailability after oral administration.

Bisphosphonate-Generated ATP-Analogs Inhibit Cell Signaling Pathways

Malwal, Satish R.,O'Dowd, Bing,Feng, Xinxin,Turhanen, Petri,Shin, Christopher,Yao, Jiaqi,Kim, Boo Kyung,Baig, Noman,Zhou, Tianhui,Bansal, Sandhya,Khade, Rahul L.,Zhang, Yong,Oldfield, Eric

supporting information, p. 7568 - 7578 (2018/05/31)

Bisphosphonates are a major class of drugs used to treat osteoporosis, Paget's disease, and cancer. They have been proposed to act by inhibiting one or more targets including protein prenylation, the epidermal growth factor receptor, or the adenine nucleotide translocase. Inhibition of the latter is due to formation in cells of analogs of ATP: the isopentenyl ester of ATP (ApppI) or an AppXp-type analog of ATP, such as AMP-clodronate (AppCCl2p). We screened both ApppI as well as AppCCl2p against a panel of 369 kinases finding potent inhibition of some tyrosine kinases by AppCCl2p, attributable to formation of a strong hydrogen bond between tyrosine and the terminal phosphonate. We then synthesized bisphosphonate preprodrugs that are converted in cells to other ATP-analogs, finding low nM kinase inhibitors that inhibited cell signaling pathways. These results help clarify our understanding of the mechanisms of action of bisphosphonates, potentially opening up new routes to the development of bone resorption, anticancer, and anti-inflammatory drug leads.

Transition state in DNA polymerase β Catalysis: Rate-Limiting chemistry altered by base-pair configuration

Oertell, Keriann,Chamberlain, Brian T.,Wu, Yue,Ferri, Elena,Kashemirov, Boris A.,Beard, William A.,Wilson, Samuel H.,McKenna, Charles E.,Goodman, Myron F.

, p. 1842 - 1848 (2014/04/17)

Kinetics studies of dNTP analogues having pyrophosphate-mimicking β,β-pCXYp leaving groups with variable X and Y substitution reveal striking differences in the chemical transition-state energy for DNA polymerase β that depend on all aspects of base-pairing configurations, including whether the incoming dNTP is a purine or pyrimidine and if base-pairings are right (T*A and G*C) or wrong (T*G and G*T). Br?nsted plots of the catalytic rate constant (log(kpol)) versus pKa4 for the leaving group exhibit linear free energy relationships (LFERs) with negative slopes ranging from -0.6 to -2.0, consistent with chemical rate-determining transition-states in which the active-site adjusts to charge-stabilization demand during chemistry depending on base-pair configuration. The Br?nsted slopes as well as the intercepts differ dramatically and provide the first direct evidence that dNTP base recognition by the enzyme-primer-template complex triggers a conformational change in the catalytic region of the active-site that significantly modifies the rate-determining chemical step.

2-MeS-β,γ-CCl2-ATP is a potent agent for reducing intraocular pressure

Eliahu, Shay,Martín-Gil, Alba,Perez De Lara, María Jesús,Pintor, Jesús,Camden, Jean,Weisman, Gary A.,Lecka, Joanna,Sévigny, Jean,Fischer, Bilha

experimental part, p. 3305 - 3319 (2010/09/06)

Extracellular nucleotides can modify the production or drainage of the aqueous humor via activation of P2 receptors and therefore affect the intraocular pressure (IOP). We have synthesized slowly hydrolyzable nucleoside di- and triphosphate analogues, 1, and 8-14. Analogues 8-14 were completely resistant to hydrolysis by alkaline phosphatase over 30 min at 37 °C. In human blood serum, analogues 8-14 exhibited high stability, e.g., analogues 9 and 10-14 were only 15% and 0% degraded after 24 h, respectively. Moreover, analogues 8-14 were highly stable at pH 1.4 (t1/2 1 h-30 days). Analogues 8-14 were agonists of the P2Y1 receptor (EC50 0.57-9.54 μM). Ocular administration of most analogues into rabbits reduced IOP, e.g., analogue 9 reduced IOP by 32% (EC50 95.5 nM). Analogue 9 was more effective at reducing IOP than several common glaucoma drugs and represents a promising alternative to timolol maleate, which cannot be used for the treatment of patients suffering from asthma or cardiac problems.

Tablet with improved bioavailability containing dichloromethylenediphosphonic acid as the active substance

-

, (2008/06/13)

The invention concerns tablets with improved bioavailability of the active substance dichloromethylenediphosphonic acid or of a physiologically tolerated salt thereof and with a content of microcrystalline cellulose as a pharmaceutical auxiliary substance, pharmaceutical packs containing these tablets, the use of the active substance dichloromethylenediphosphonic acid together with microcrystalline cellulose for the production of a tablet with improved bioavailability and the process for producing the tablet.

Oral compositions

-

, (2008/06/13)

Oral compositions providing antitartar and antigingivitis benefits containing an antitartar agent and a stannous salt.

Oral composition for calculus retardation

-

, (2008/06/13)

Oral compositions, such as toothpaste, mouthwash, and the like, containing certain polyphosphonic acids and their salts which retard dental calculus formation without damaging tooth structure.

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