Pamidronic acid

Chemical compound

AU: B3

Routes of
administrationIntravenousATC code

M05BA03 (WHO)

UK: POM (Prescription only)
US: ℞-only

Pharmacokinetic dataBioavailabilityn/aProtein binding54%MetabolismNilElimination half-life28 ± 7 hoursExcretionRenalIdentifiers

IUPAC name

(3-amino-1-hydroxypropane-1,1-diyl)bis(phosphonic acid)

CAS Number

40391-99-9^Y

PubChem CID

4674

IUPHAR/BPS

7259

DrugBank

DB00282^Y

ChemSpider

4512^Y

UNII

OYY3447OMC

KEGG

D07281^Y

ChEMBL

ChEMBL834^Y

CompTox Dashboard (EPA)

DTXSID4023414

ECHA InfoCard100.049.897

Chemical and physical dataFormulaC₃H₁₁NO₇P₂Molar mass235.069 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=P(O)(O)C(O)(CCN)P(=O)(O)O

InChI

InChI=1S/C3H11NO7P2/c4-2-1-3(5,12(6,7)8)13(9,10)11/h5H,1-2,4H2,(H2,6,7,8)(H2,9,10,11)^Y
Key:WRUUGTRCQOWXEG-UHFFFAOYSA-N^Y

(verify)

Pamidronic acid or pamidronate disodium or APD (marketed as Aredia among others), is a nitrogen-containing bisphosphonate used to prevent osteoporosis.

It was patented in 1971 and approved for medical use in 1987.^[1]

Medical uses

It is used to prevent bone loss, and treat osteoporosis. It is also used to strengthen bone in Paget's disease, to prevent bone loss due to steroid use, and in certain cancers with high propensity to bone, such as multiple myeloma. Due to its ability to sequester calcium in bone, it is also used to treat high calcium levels. It is also used as an experimental treatment of the bone disorder osteogenesis imperfecta. It has been studied in the treatment of complex regional pain syndrome.^[2]

Administration

Intravenous, usually 90 mg monthly. 30 mg, 60 mg, 90 mg and for hospitals, 120 mg vials are available, mixed with mannitol.

Side effects

Common side effects include bone pain, low calcium levels, nausea, and dizziness. Osteonecrosis of the jaw is a rare complication which has been associated with the use of bisphosphonates, including pamidronate.^[3]

Pamidronate activates human γδ T cells in vitro and in vivo, which may lead to flu-like symptoms upon administration.

Pharmacology

Relative potency^[4]
Bisphosphonate	Relative potency
Etidronate	1
Tiludronate	10
Pamidronate	100
Alendronate	100-500
Ibandronate	500-1000
Risedronate	1000
Zoledronate	5000

References

^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 523. ISBN 9783527607495.
^ Kubalek I, Fain O, Paries J, Kettaneh A, Thomas M (December 2001). "Treatment of reflex sympathetic dystrophy with pamidronate: 29 cases". Rheumatology. 40 (12): 1394–1397. doi:10.1093/rheumatology/40.12.1394. PMID 11752511.
^ Zarychanski R, Elphee E, Walton P, Johnston J (January 2006). "Osteonecrosis of the jaw associated with pamidronate therapy". American Journal of Hematology. 81 (1): 73–75. doi:10.1002/ajh.20481. PMID 16369966. S2CID 11830192.
^ Tripathi KD (2013-09-30). Essentials of medical pharmacology (Seventh ed.). New Delhi: Jaypee Brothers Medical Publishers Pvt. Limited. ISBN 9789350259375. OCLC 868299888.