Ibandronic acid

Ibandronic acid

Systematic (IUPAC) name
{1-Hydroxy-3-[methyl(pentyl)amino]propane-1,1-diyl}bis(phosphonic acid)
Clinical data
AHFS/Drugs.com	International Drug Names
Licence data	EMA:Link, US FDA:link
Pregnancy category	US: C (Risk not ruled out)
Legal status	℞ (Prescription only)
Routes of administration	Oral, intravenous
Pharmacokinetic data
Bioavailability	0.6%
Protein binding	90.9 to 99.5% (concentration-dependent)
Metabolism	Nil
Biological half-life	10 to 60 hours
Excretion	Renal
Identifiers
CAS Number	114084-78-5 Y
ATC code	M05BA06 (WHO)
PubChem	CID: 60852
IUPHAR/BPS	3059
DrugBank	DB00710 N
ChemSpider	54839 Y
UNII	UMD7G2653W Y
KEGG	D08056 Y
ChEMBL	CHEMBL997 Y
Chemical data
Formula	C9H23NO7P2
Molecular mass	319.229 g/mol
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)

Ibandronic acid (INN) or ibandronate sodium (USAN) is a potent bisphosphonate drug developed by Hoffman La Roche and used in the prevention and treatment of osteoporosis and metastasis-associated skeletal fractures in people with cancer. It may also be used to treat hypercalcemia (elevated blood calcium levels). Global sales in 2008 were 1.1B CHF ($1.0B USD at 01/01/2009 exchange rates).

Medical uses

Ibandronate is indicated for the treatment and prevention of osteoporosis in post-menopausal women. 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.

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 and/or muscle pain. 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.

Brand names

Ibandronic acid is marketed under the trade names Boniva in the USA, Bondronat in Europe, Bonviva in Asia,Ibandrix in Ecuador and Bondrova in Pakistan.

External links

• Ibandronate bound to proteins in the PDB
• Boniva Osteoporosis Treatment by GlaxoSmithKline and Roche Laboratories
• Boniva adverse events reported to the FDA