ContaminantDB: Pamidronate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-07-15 20:42:44 UTC

Update Date

2026-05-14 16:34:23 UTC

Accession Number

CHEM002110

Identification

Common Name

Pamidronate

Class

Small Molecule

Description

Pamidronate is only found in individuals that have used or taken this drug.Pamidronate, marketed as pamidronate disodium pentahydrate under the brand name Aredia, is a bisphosphonate. The mechanism of action of pamidronate is inhibition of bone resorption. Pamidronate adsorbs to calcium phosphate (hydroxyapatite) crystals in bone and may directly block dissolution of this mineral component of bone. In vitro studies also suggest that inhibition of osteoclast activity contributes to inhibition of bone resorption. Pamidronate also targets farnesyl pyrophosphate (FPP) synthase. Nitrogen-containing bisphosphonates (such as pamidronate, alendronate, risedronate, ibandronate and zoledronate) appear to act as analogues of isoprenoid diphosphate lipids, thereby inhibiting FPP synthase, an enzyme in the mevalonate pathway. Inhibition of this enzyme in osteoclasts prevents the biosynthesis of isoprenoid lipids (FPP and GGPP) that are essential for the post-translational farnesylation and geranylgeranylation of small GTPase signalling proteins. This activity inhibits osteoclast activity and reduces bone resorption and turnover. In postmenopausal women, it reduces the elevated rate of bone turnover, leading to, on average, a net gain in bone mass.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anti-Inflammatory Agent
Antineoplastic Agent
Bisphosphonate
Bone Density Conservation Agent
Drug
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Pamidronic acid	Kegg
Ribodroat	Kegg
Pamidronate disodium	HMDB
(3-Amino-1-hydroxypropylidene)-1,1-biphosphonate	HMDB
Novartis brand OF pamidronate disodium salt	HMDB
Amino-1-hydroxypropane-1,1-diphosphonate	HMDB
Pamidronate calcium	HMDB
(3-Amino-1-hydroxypropylidene)-1,1-bisphosphonate	HMDB
Aredia	HMDB
1-Hydroxy-3-aminopropane-1,1-diphosphonic acid	HMDB
Amidronate	HMDB
Aminohydroxypropylidene diphosphonate	HMDB
Pamidronate monosodium	HMDB
AHPrBP	HMDB
APD	HMDB
Aminopropanehydroxydiphosphonate	HMDB
1 Hydroxy 3 aminopropane 1,1 diphosphonic acid	HMDB
Amino 1 hydroxypropane 1,1 diphosphonate	HMDB

Chemical Formula

C₃H₁₁NO₇P₂

Average Molecular Mass

235.070 g/mol

Monoisotopic Mass

235.001 g/mol

CAS Registry Number

40391-99-9

IUPAC Name

(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid

Traditional Name

pamidronate

SMILES

NCCC(O)(P(O)(O)=O)P(O)(O)=O

InChI Identifier

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)

InChI Key

WRUUGTRCQOWXEG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Bisphosphonates

Direct Parent

Bisphosphonates

Alternative Parents

Substituents

Bisphosphonate
Organophosphonic acid
1,3-aminoalcohol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Pamidronate Pathway	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1.58e+01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	15.8 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-4.5	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	0.67	ChemAxon
pKa (Strongest Basic)	9.86	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	161.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	42.62 m³·mol⁻¹	ChemAxon
Polarizability	17.34 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9010000000-c609aeb84dc854acef5e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fl0-9530000000-3dcc66dec182929ad44c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0590000000-70afb6f8f6bd4fa8dc0c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f80-4900000000-d984e8b630279adf9117	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lr-9220000000-23665351b55d84521171	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f89-2590000000-b548987abea136813705	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uyi-5940000000-2fa45eefdeb643c06194	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-9000000000-57907eeacb268739b125	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001r-9070000000-60834fd1c274bf3a378e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0690000000-46aca5e6c3a2ca2b76cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-4a70bd6f6de42e1622e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-0090000000-2ee377abd33f38d7b1d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-9020000000-13ae78878ab3e85dd77f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-818b4c1881e12ac6419e	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Parenteral (intravenous). Plasma concentration rises rapidly upon IV administration.

Mechanism of Toxicity

The mechanism of action of pamidronate is inhibition of bone resorption. Pamidronate adsorbs to calcium phosphate (hydroxyapatite) crystals in bone and may directly block dissolution of this mineral component of bone. In vitro studies also suggest that inhibition of osteoclast activity contributes to inhibition of bone resorption. Pamidronate also targets farnesyl pyrophosphate (FPP) synthase. Nitrogen-containing bisphosphonates (such as pamidronate, alendronate, risedronate, ibandronate and zoledronate) appear to act as analogues of isoprenoid diphosphate lipids, thereby inhibiting FPP synthase, an enzyme in the mevalonate pathway. Inhibition of this enzyme in osteoclasts prevents the biosynthesis of isoprenoid lipids (FPP and GGPP) that are essential for the post-translational farnesylation and geranylgeranylation of small GTPase signalling proteins. This activity inhibits osteoclast activity and reduces bone resorption and turnover. In postmenopausal women, it reduces the elevated rate of bone turnover, leading to, on average, a net gain in bone mass.

Metabolism

Pamidronate is not metabolized and is exclusively eliminated by renal excretion. Route of Elimination: Pamidronate is not metabolized and is exclusively eliminated by renal excretion. Half Life: The mean ± SD elimination half-life is 28 ± 7 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Pamidronate is in a class of drugs called bisphosphonates. Pamidronate reduces breakdown of the bones. Pamidronate is used in the treatment of Paget's disease of bone; to reduce high levels of calcium in the blood associated with malignancy (cancer); and to reduce the breakdown of bone due to metastases of breast cancer or multiple myeloma. For the treatment of moderate or severe hypercalcemia associated with malignancy

Minimum Risk Level

Not Available

Health Effects

Rare cases of uveitis, iritis, scleritis, and episcleritis have been reported, including one case of scleritis, and one case of uveitis upon separate rechallenges.

Symptoms

Side effects include an allergic reaction, kidney problems, seizures, low levels of calcium, magnesium, or phosphorus in the blood

Treatment

If overdosage occurs, symptomatic hypocalcemia could also result; such patients should be treated with short-term intravenous calcium. (4)

Concentrations

Not Available

External Links

DrugBank ID

DB00282

HMDB ID

HMDB0014427

FooDB ID