Ibandronic acid

Ibandronic acid is a bisphosphonate medication used in the prevention and treatment of osteoporosis and metastasis-associated skeletal fractures in people with cancer.[1] It may also be used to treat hypercalcemia (elevated blood calcium levels). It is typically formulated as its sodium salt ibandronate sodium.

Ibandronic acid
Clinical data
Trade namesBoniva, Bonviva, Bondronat, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability0.6%
Protein binding90.9 to 99.5%
(concentration-dependent)
MetabolismNil
Elimination half-life10 to 60 hours
ExcretionKidney
Identifiers
IUPAC name
  • Hydroxy-[1-hydroxy-3-[methyl(pentyl)amino]-1-phosphonopropyl]phosphinate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.214.537
Chemical and physical data
FormulaC9H23NO7P2
Molar mass319.231 g·mol−1
3D model (JSmol)
SMILES
  • O=P(O)(O)C(O)(CCN(CCCCC)C)P(=O)(O)O
InChI
  • InChI=1S/C9H23NO7P2/c1-3-4-5-7-10(2)8-6-9(11,18(12,13)14)19(15,16)17/h11H,3-8H2,1-2H3,(H2,12,13,14)(H2,15,16,17) Y
  • Key:MPBVHIBUJCELCL-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

It was patented in 1986 by Boehringer Mannheim and approved for medical use in 1996.[2]

Medical uses

Ibandronate is indicated for the treatment and prevention of osteoporosis in post-menopausal women.[3] In May 2003, the U.S. Food and Drug Administration (FDA) approved Ibandronate as a daily treatment for post-menopausal osteoporosis. The basis for this approval was a three-year, randomized, double-blind, placebo-controlled trial women with post-menopausal osteoporosis. Every participant also received daily oral doses of calcium and 400IUs [international units] of vitamin D. At the study's conclusion, both doses significantly reduced the occurrence risk of new vertebral fractures by 50–52 percent when compared to the effects of the placebo drug.

Ibandronate is efficacious for the prevention of metastasis-related bone fractures in multiple myeloma, breast cancer, and certain other cancers.[4]

Adverse effects

In 2008, the U.S Food and Drug Administration (FDA) issued a communication warning of the possibility of severe and sometimes incapacitating bone, joint or muscle pain.[5] A study conducted by the American Society of Bone and Mineral Research concluded that long-term use of bisphosphonates, including Boniva, may increase the risk of a rare but serious fracture of the femur. [6] The drug also has been associated with osteonecrosis of the jaw, relatively rare but serious condition.[7]

Pharmacology
Relative potency[8]
Bisphosphonate Relative potency
Etidronate 1
Tiludronate 10
Pamidronate 100
Alendronate 100-500
Ibandronate 500-1000
Risedronate 1000
Zoledronate 5000

Brand names

Ibandronic acid is marketed under the trade names Boniva in the US, Bondronat in Europe, Bonviva in Asia, Bandrone in India, Ibandrix in Ecuador, Adronil in Pakistan, Bondrova in Bangladesh and Bonprove in Egypt, Fosfonat in Mexico.

References
  1. Bauss F, Schimmer RC (March 2006). "Ibandronate: the first once-monthly oral bisphosphonate for treatment of postmenopausal osteoporosis". Therapeutics and Clinical Risk Management. 2 (1): 3–18. PMC 1661644. PMID 18360577.
  2. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 523. ISBN 9783527607495.
  3. "boniva". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
  4. Sittig HB (2012). "Pathogenesis and bisphosphonate treatment of skeletal events and bone pain in metastatic cancer: focus on ibandronate". Onkologie. 35 (6): 380–7. doi:10.1159/000338947. PMID 22722461. S2CID 8413102.
  5. "Information for Healthcare Professionals: Bisphosphonates (marketed as Actonel, Actonel+Ca, Aredia, Boniva, Didronel, Fosamax, Fosamax+D, Reclast, Skelid, and Zometa)". U.S. Food and Drug Administration. Retrieved 27 October 2010.
  6. "Drugs Commonly Prescribed for Osteoporosis Patients are Effective at Reducing Risk of Hip and Spine Fractures, But Panel Says May be Related to Unusual Thigh Bone Fractures When Used Long Term". Journal of Bone and Mineral Research=27 October 2010.
  7. "Osteonecrosis of the jaw (ONJ) and drug treatments for osteoporosis" (PDF). nos.org.uk. The National Osteoporosis Society.
  8. Tripathi KD (2013-09-30). Essentials of medical pharmacology (Seventh ed.). New Delhi. ISBN 9789350259375. OCLC 868299888.
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