Ibandronic acid

Last updated

Ibandronic acid
Ibandronic acid.svg
Clinical data
Trade names Boniva, Bonviva, Bondronat, others
AHFS/Drugs.com Monograph
License data
Pregnancy
category
  • AU:B3
Routes of
administration
By mouth, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 0.6%
Protein binding 90.9 to 99.5%
(concentration-dependent)
Metabolism Nil
Elimination half-life 10 to 60 hours
Excretion Kidney
Identifiers
  • 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 InfoCard 100.214.537 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H23NO7P2
Molar mass 319.231 g·mol−1
3D model (JSmol)
  • O=P(O)(O)C(O)(CCN(CCCCC)C)P(=O)(O)O
  • 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) Yes check.svgY
  • Key:MPBVHIBUJCELCL-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Ibandronic acid is a bisphosphonate medication used in the prevention and treatment of osteoporosis and metastasis-associated skeletal fractures in people with cancer. [4] It may also be used to treat hypercalcemia (elevated blood calcium levels). It is typically formulated as its sodium salt ibandronate sodium.[ medical citation needed ]

Contents

It was patented in 1986 by Boehringer Mannheim and approved for medical use in 1996. [5]

Medical uses

Ibandronate is indicated for the treatment and prevention of osteoporosis in post-menopausal women. [6] In May 2003, the US Food and Drug Administration (FDA) approved ibandronate as a daily treatment for post-menopausal osteoporosis.[ medical citation needed ] The basis for this approval was a three-year, randomized, double-blind, placebo-controlled trial women with post-menopausal osteoporosis.[ medical citation needed ] Each participant also received daily oral doses of calcium and 400IUs [international units] of vitamin D.[ medical citation needed ] 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.[ medical citation needed ]

Ibandronate is efficacious for the prevention of metastasis-related bone fractures in multiple myeloma, breast cancer, and certain other cancers. [7]

Adverse effects

In 2008, the US Food and Drug Administration (FDA) issued a communication warning of the possibility of severe and sometimes incapacitating bone, joint or muscle pain. [8] 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. [9] The drug also has been associated with osteonecrosis of the jaw, a relatively rare but serious condition. [10]

Pharmacology

Mechanism of action

Nitrogen containing bisphosphonates, which include ibandronate, pamidronate and alendronate exert their effects on osteoclasts mainly by inhibiting the synthesis of isoprenoid lipids such as isopentenyl diphosphate (IPP), farnesyl diphosphate (FPP), and geranylgeranyl diphosphate (GGPP) via the mevalonate pathway. These isoprenoids are used in posttranslational modifcation(prenylation) of small GTPases such as Ras, Rho, and Rac. These prenylated GTPases are necessary for various cellular processes including osteoclast morphology, endosome trafficking, and apoptosis. [11]

Relative potency [12]
BisphosphonateRelative potency
Etidronate 1
Tiludronate 10
Pamidronate 100
Alendronate 100-500
Ibandronate500-1000
Risedronate 1000
Zoledronate 5000

Society and culture

Brand names

Ibandronic acid is sold under the brand names Boniva, Bondronat, Bonviva, Bandrone, Ibandrix, Adronil, Bondrova, Bonprove, and Fosfonat.

Related Research Articles

<span class="mw-page-title-main">Osteoporosis</span> Skeletal disorder

Osteoporosis is a systemic skeletal disorder characterized by low bone mass, micro-architectural deterioration of bone tissue leading to more porous bone, and consequent increase in fracture risk.

<span class="mw-page-title-main">Bisphosphonate</span> Pharmaceutical drugs for preventing bone loss

Bisphosphonates are a class of drugs that prevent the loss of bone density, used to treat osteoporosis and similar diseases. They are the most commonly prescribed drugs used to treat osteoporosis. They are called bisphosphonates because they have two phosphonate groups. They are thus also called diphosphonates.

<span class="mw-page-title-main">Paget's disease of bone</span> Disease affecting bone remodeling

Paget's disease of bone is a condition involving cellular remodeling and deformity of one or more bones. The affected bones show signs of dysregulated bone remodeling at the microscopic level, specifically excessive bone breakdown and subsequent disorganized new bone formation. These structural changes cause the bone to weaken, which may result in deformity, pain, fracture or arthritis of associated joints.

<span class="mw-page-title-main">Teriparatide</span> Pharmaceutical drug for treating osteoporosis

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<span class="mw-page-title-main">Alendronic acid</span> Chemical compound

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Zoledronic acid, also known as zoledronate and sold under the brand name Zometa among others, by Novartis among others, is a medication used to treat a number of bone diseases. These include osteoporosis, high blood calcium due to cancer, bone breakdown due to cancer, Paget's disease of bone and Duchenne muscular dystrophy (DMD). It is given by injection into a vein.

<span class="mw-page-title-main">Osteopenia</span> Abnormally low bone mineral density

Osteopenia, known as "low bone mass" or "low bone density", is a condition in which bone mineral density is low. Because their bones are weaker, people with osteopenia may have a higher risk of fractures, and some people may go on to develop osteoporosis. In 2010, 43 million older adults in the US had osteopenia. Unlike osteoporosis, osteopenia does not usually cause symptoms, and losing bone density in itself does not cause pain.

<span class="mw-page-title-main">Risedronic acid</span> Chemical compound

Risedronic acid, often used as its sodium salt risedronate sodium, is a bisphosphonate. It slows down the cells which break down bone. It's used to treat or prevent osteoporosis, and treat Paget's disease of bone. It is taken by mouth.

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<span class="mw-page-title-main">Bone resorption</span> Breakdown of bone tissue to be absorbed into the blood

Bone resorption is resorption of bone tissue, that is, the process by which osteoclasts break down the tissue in bones and release the minerals, resulting in a transfer of calcium from bone tissue to the blood.

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<span class="mw-page-title-main">Medication-related osteonecrosis of the jaw</span> Medical condition

Medication-related osteonecrosis of the jaw is progressive death of the jawbone in a person exposed to a medication known to increase the risk of disease, in the absence of a previous radiation treatment. It may lead to surgical complication in the form of impaired wound healing following oral and maxillofacial surgery, periodontal surgery, or endodontic therapy.

<span class="mw-page-title-main">Bone metastasis</span> Medical condition

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<span class="mw-page-title-main">Discovery and development of bisphosphonates</span> Drugs used to treat bone disorders

Bisphosphonates are an important class of drugs originally commercialised in the mid to late 20th century. They are used for the treatment of osteoporosis and other bone disorders that cause bone fragility and diseases where bone resorption is excessive. Osteoporosis is common in post-menopausal women and patients in corticosteroid treatment where biphosphonates have been proven a valuable treatment and also used successfully against Paget's disease, myeloma, bone metastases and hypercalcemia. Bisphosphonates reduce breakdown of bones by inhibiting osteoclasts, they have a long history of use and today there are a few different types of bisphosphonate drugs on the market around the world.

References

  1. "Bondronat EPAR". European Medicines Agency (EMA). 25 June 1996. Retrieved 28 August 2024.
  2. "Bonviva EPAR". European Medicines Agency (EMA). 23 February 2004. Retrieved 28 August 2024.
  3. "Iasibon EPAR". European Medicines Agency (EMA). 21 January 2011. Retrieved 30 August 2024.
  4. 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.
  5. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 523. ISBN   9783527607495.
  6. "Boniva". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
  7. 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.
  8. "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.
  9. Shane E, Burr D, Ebeling PR, Abrahamsen B, Adler RA, Brown TD, et al. (American Society for Bone and Mineral Research) (November 2010). "Atypical subtrochanteric and diaphyseal femoral fractures: report of a task force of the American Society for Bone and Mineral Research". Journal of Bone and Mineral Research. 25 (11): 2267–2294. doi: 10.1002/jbmr.253 . PMID   20842676. S2CID   15194275.{{cite journal}}: CS1 maint: overridden setting (link); Lay summary in: "JBMR Publishes ASBMR Task Force Report on Atypical Femoral Fractures". Journal of Bone and Mineral Research. 14 September 2010. Archived from the original on 9 April 2016. Retrieved 27 October 2010.
  10. "Osteonecrosis of the jaw (ONJ) and drug treatments for osteoporosis" (PDF). United Kingdom: The National Osteoporosis Society. Archived from the original (PDF) on 17 June 2017. Retrieved 14 August 2018.
  11. Rogers MJ, Gordon S, Benford HL, Coxon FP, Luckman SP, Monkkonen J, et al. (June 2000). "Cellular and molecular mechanisms of action of bisphosphonates". Cancer. 88 (12 Suppl): 2961–2978. doi:10.1002/1097-0142(20000615)88:12+<2961::AID-CNCR12>3.0.CO;2-L. PMID   10898340.
  12. Tripathi KD (30 September 2013). Essentials of Medical Pharmacology (Seventh ed.). New Delhi: Jaypee Brothers Medical Publisher. ISBN   9789350259375. OCLC   868299888.