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Showing metabocard for Pamidronate (HMDB0014427)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:37 UTC
HMDB IDHMDB0014427
Secondary Accession Numbers
  • HMDB14427
Metabolite Identification
Common NamePamidronate
DescriptionPamidronate 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. [Wikipedia ]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.
Structure
Data?1582753178
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014427 (Pamidronate)

282
  Mrv0541 02231214342D          

 13 12  0  0  0  0            999 V2000
    2.8075   -1.0743    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2492    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345   -1.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950   -0.3598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.1633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6490   -0.9637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.8993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    0.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6208    1.3955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095    0.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2527    0.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  1  8  2  0  0  0  0
  1 11  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2  9  2  0  0  0  0
  2 11  1  0  0  0  0
  3 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for HMDB0014427 (Pamidronate)

HMDB0014427
     RDKit          3D
Pamidronate
 24 23  0  0  0  0  0  0  0  0999 V2000
    3.1621    0.6284   -0.3611 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0311   -0.2456   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8150    0.6192    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4431   -0.1131    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -0.6824    1.6459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840    1.1268    0.5337 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.8571    0.5404    1.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4113    1.3798   -1.0088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1952    2.5871    1.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543   -1.3209   -0.8268 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0213   -1.5448   -1.9334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -2.8311   -0.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4406   -0.8948   -1.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9110    0.0496   -0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5622    1.0739    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2788   -0.6670    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006   -1.0093   -0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773    1.3919    0.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7258    1.1825   -0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -1.3701    1.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0354    2.1815   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    2.5459    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5521   -2.9242    0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9035   -1.7039   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  8 21  1  0
  9 22  1  0
 12 23  1  0
 13 24  1  0
M  END
Download

3D SDF for HMDB0014427 (Pamidronate)

282
  Mrv0541 02231214342D          

 13 12  0  0  0  0            999 V2000
    2.8075   -1.0743    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2492    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345   -1.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950   -0.3598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.1633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6490   -0.9637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.8993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    0.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6208    1.3955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095    0.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2527    0.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  1  8  2  0  0  0  0
  1 11  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2  9  2  0  0  0  0
  2 11  1  0  0  0  0
  3 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014427

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C3H11NO7P2

> <MOLECULAR_WEIGHT>
235.0695

> <EXACT_MASS>
235.001074735

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
17.338067565065554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid

> <ALOGPS_LOGP>
-1.41

> <JCHEM_LOGP>
-4.536482727267307

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.4320105727980836

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6686214006842395

> <JCHEM_PKA_STRONGEST_BASIC>
9.855403863984701

> <JCHEM_POLAR_SURFACE_AREA>
161.31

> <JCHEM_REFRACTIVITY>
42.6188

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.58e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pamidronate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0014427 (Pamidronate)

HMDB0014427
     RDKit          3D
Pamidronate
 24 23  0  0  0  0  0  0  0  0999 V2000
    3.1621    0.6284   -0.3611 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0311   -0.2456   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8150    0.6192    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4431   -0.1131    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -0.6824    1.6459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7840    1.1268    0.5337 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.8571    0.5404    1.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4113    1.3798   -1.0088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1952    2.5871    1.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543   -1.3209   -0.8268 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0213   -1.5448   -1.9334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -2.8311   -0.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4406   -0.8948   -1.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9110    0.0496   -0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5622    1.0739    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2788   -0.6670    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006   -1.0093   -0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773    1.3919    0.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7258    1.1825   -0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -1.3701    1.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0354    2.1815   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    2.5459    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5521   -2.9242    0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9035   -1.7039   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  8 21  1  0
  9 22  1  0
 12 23  1  0
 13 24  1  0
M  END
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PDB for HMDB0014427 (Pamidronate)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 282                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0       5.241  -2.005   0.000  0.00  0.00           P+0
HETATM    2  P   UNK     0       7.908  -0.465   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0       7.344  -2.569   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.471  -0.672   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.907  -2.775   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.242   0.305   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       8.678  -1.799   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.241  -3.545   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       7.641   1.051   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       4.892   2.605   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.574  -1.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.804   0.098   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.072   1.615   0.000  0.00  0.00           C+0
CONECT    1    4    5    8   11                                             
CONECT    2    6    7    9   11                                             
CONECT    3   11                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    1                                                            
CONECT    9    2                                                            
CONECT   10   13                                                            
CONECT   11    1    2    3   12                                             
CONECT   12   11   13                                                       
CONECT   13   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0014427 (Pamidronate)

COMPND    HMDB0014427
HETATM    1  N1  UNL     1       3.162   0.628  -0.361  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.031  -0.246  -0.008  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.815   0.619   0.033  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.443  -0.113   0.381  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.278  -0.682   1.646  1.00  0.00           O  
HETATM    6  P1  UNL     1      -1.784   1.127   0.534  1.00  0.00           P  
HETATM    7  O2  UNL     1      -2.857   0.540   1.395  1.00  0.00           O  
HETATM    8  O3  UNL     1      -2.411   1.380  -1.009  1.00  0.00           O  
HETATM    9  O4  UNL     1      -1.195   2.587   1.117  1.00  0.00           O  
HETATM   10  P2  UNL     1      -0.954  -1.321  -0.827  1.00  0.00           P  
HETATM   11  O5  UNL     1       0.021  -1.545  -1.933  1.00  0.00           O  
HETATM   12  O6  UNL     1      -1.193  -2.831  -0.059  1.00  0.00           O  
HETATM   13  O7  UNL     1      -2.441  -0.895  -1.561  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.911   0.050  -0.803  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.562   1.074   0.490  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.279  -0.667   0.975  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.001  -1.009  -0.812  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.977   1.392   0.816  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.726   1.182  -0.925  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.451  -1.370   1.545  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.035   2.182  -1.441  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.888   2.546   2.040  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.552  -2.924   0.685  1.00  0.00           H  
HETATM   24  H11 UNL     1      -2.904  -1.704  -1.916  1.00  0.00           H  
CONECT    1    2   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5    6   10
CONECT    5   20
CONECT    6    7    7    8    9
CONECT    8   21
CONECT    9   22
CONECT   10   11   11   12   13
CONECT   12   23
CONECT   13   24
END
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SMILES for HMDB0014427 (Pamidronate)

NCCC(O)(P(O)(O)=O)P(O)(O)=O
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INCHI for HMDB0014427 (Pamidronate)

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)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC3H11NO7P2
Average Molecular Weight235.0695
Monoisotopic Molecular Weight235.001074735
IUPAC Name(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid
Traditional Namepamidronate
CAS Registry Number40391-99-9
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 KeyWRUUGTRCQOWXEG-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassBisphosphonates
Direct ParentBisphosphonates
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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility15.8 g/LNot Available
LogP-4.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00282 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00282 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00282
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4512
KEGG Compound IDC07395
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPamidronic acid
METLIN IDNot Available
PubChem Compound4674
PDB ID210
ChEBI ID160401
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zarychanski R, Elphee E, Walton P, Johnston J: Osteonecrosis of the jaw associated with pamidronate therapy. Am J Hematol. 2006 Jan;81(1):73-5. [PubMed:16369966 ]

Enzymes

Enzyme Details
1. Farnesyl pyrophosphate synthase
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate.
Gene Name:
FDPS
Uniprot ID:
P14324
Molecular weight:
48275.03
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Bergstrom JD, Bostedor RG, Masarachia PJ, Reszka AA, Rodan G: Alendronate is a specific, nanomolar inhibitor of farnesyl diphosphate synthase. Arch Biochem Biophys. 2000 Jan 1;373(1):231-41. [PubMed:10620343 ]
  3. Dunford JE, Thompson K, Coxon FP, Luckman SP, Hahn FM, Poulter CD, Ebetino FH, Rogers MJ: Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. J Pharmacol Exp Ther. 2001 Feb;296(2):235-42. [PubMed:11160603 ]
  4. Notarnicola M, Messa C, Cavallini A, Bifulco M, Tecce MF, Eletto D, Di Leo A, Montemurro S, Laezza C, Caruso MG: Higher farnesyl diphosphate synthase activity in human colorectal cancer inhibition of cellular apoptosis. Oncology. 2004;67(5-6):351-8. [PubMed:15713990 ]
  5. Riebeling C, Forsea AM, Raisova M, Orfanos CE, Geilen CC: The bisphosphonate pamidronate induces apoptosis in human melanoma cells in vitro. Br J Cancer. 2002 Jul 29;87(3):366-71. [PubMed:12177810 ]
  6. Zhang PL, Lun M, Siegelmann-Danieli N, Blasick TM, Brown RE: Pamidronate resistance and associated low ras levels in breast cancer cells: a role for combinatorial therapy. Ann Clin Lab Sci. 2004 Summer;34(3):263-70. [PubMed:15487700 ]