Clodronic acid

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Clodronic acid
Clodronic acid.png
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Legal status
Legal status
Identifiers
  • (Dichloro-phosphono-methyl)phosphonic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.031.090 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula CH4Cl2O6P2
Molar mass 244.88 g·mol−1
3D model (JSmol)
  • ClC(Cl)(P(=O)(O)O)P(=O)(O)O
  • InChI=1S/CH4Cl2O6P2/c2-1(3,10(4,5)6)11(7,8)9/h(H2,4,5,6)(H2,7,8,9) Yes check.svgY
  • Key:ACSIXWWBWUQEHA-UHFFFAOYSA-N Yes check.svgY
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Clodronic acid (INN) or clodronate disodium (Na2CH2Cl2O6P2) (USAN) is a first generation (non-nitrogenous) bisphosphonate. It is an anti-osteoporotic drug approved for the prevention and treatment of osteoporosis in post-menopausal women and men to reduce vertebral fractures, hyperparathyroidism, hypercalcemia in malignancy, multiple myeloma and fracture related pain because of its anti-inflammatory effects shown as a reduction in inflammatory markers like IL-1β, IL-6, and TNF-α. [1]

Contents

Medical uses

A study comparing the analgesic effect of clodronic acid versus acetaminophen in osteoporotic vertebral fractures showed that clodronic acid provided more analgesia than 3 grams/day of acetaminophen. [2]

Clodronic acid is also used in experimental medicine to selectively deplete macrophages.

Clodronic acid is approved for human use in Canada and Australia, the United Kingdom, where it is marketed as Bonefos, Loron, Clodron and in Italy as Clasteon, Difosfonal, Osteostab and several generics. In other countries is prescribed as a bone resorption inhibitor and antihypercalcemic agent. It is not approved for use in the United States, because it has too many adverse effects.

Veterinary uses

Clodronic acid is approved for use in horses under the trade name Osphos, for treatment of bone resorptive processes of navicular syndrome. It is given by intramuscular injection at one point in time, with the total dose divided into 2-3 sites on the horse. Clinical effects (e.g. improvement of lameness) after a single treatment can be seen up to 6 months post-treatment.

Adverse effects

Clodronic acid has been shown to have several adverse effects. These include: [3]

References

  1. Pennanen N, Lapinjoki S, Urtti A, Mönkkönen J (June 1995). "Effect of liposomal and free bisphosphonates on the IL-1 beta, IL-6 and TNF alpha secretion from RAW 264 cells in vitro". Pharmaceutical Research. 12 (6): 916–22. doi:10.1023/A:1016281608773. PMID   7667201. S2CID   46332840.
  2. Rovetta G, Monteforte P, Balestra V (2000). "Intravenous clodronate for acute pain induced by osteoporotic vertebral fracture". Drugs Under Experimental and Clinical Research. 26 (1): 25–30. PMID   10761534.
  3. U.S. Food and Drug Administration. "FDA Provides Equine Veterinarians with Important Information about TILDREN and OSPHOS for Navicular Syndrome in Horses". Food and Drug Administration . Archived from the original on February 24, 2015. Retrieved 3 January 2015.