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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:27 UTC
HMDB IDHMDB0014848
Secondary Accession Numbers
  • HMDB14848
Metabolite Identification
Common NameIbandronate
DescriptionIbandronate, also known as ibandronic acid or R484, belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms. Ibandronate is a drug which is used for the treatment and prevention of osteoporosis in postmenopausal women. Ibandronate is a very strong basic compound (based on its pKa). In humans, ibandronate is involved in ibandronate action pathway. Ibandronate is indicated for the treatment and prevention of osteoporosis in post-menopausal women. Ibandronate is a potentially toxic compound. Ibandronic acid or ibandronate sodium is a bisphosphonate medication used in the prevention and treatment of osteoporosis and metastasis-associated skeletal fractures in people with cancer. In May 2003, the U.S. Food and Drug Administration (FDA) approved Ibandronate as a daily treatment for 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. In 2008, the U.S Food and Drug Administration (FDA) issued a communication warning of the possibility of severe and sometimes incapacitating bone, joint or muscle pain. The basis for this approval was a three-year, randomized, double-blind, placebo-controlled trial women with post-menopausal osteoporosis. 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. It was patented in 1986 by Boehringer Mannheim and approved for medical use in 1996. Ibandronic acid is marketed under the trade names Boniva in the USA, Bondronat in Europe, Bonviva in Asia, Bandrone in India, Ibandrix in Ecuador, Adronil in Pakistan, Bondrova in Bangladesh and Bonprove in Egypt. Ibandronate is efficacious for the prevention of metastasis-related bone fractures in multiple myeloma, breast cancer, and certain other cancers. It may also be used to treat hypercalcemia (elevated blood calcium levels). The drug also has been associated with osteonecrosis of the jaw, relatively rare but serious condition.
Structure
Data?1582753227
Synonyms
ValueSource
Ibandronic acidGenerator
BondronatHMDB
Ibandronate sodium monohydrateHMDB
R484HMDB
(1-Hydroxy-3-(methylpentylamino)propylidene)bisphosphonateHMDB
1-Hydroxy-3-(methylpentylamino)propylidenebisphosphonateHMDB
BonvivaHMDB
BonivaHMDB
Ibandronic acid, sodium salt, monohydrateHMDB
Ibandronate sodiumHMDB
Ibandronate sodium anhydrousHMDB
Chemical FormulaC9H23NO7P2
Average Molecular Weight319.2289
Monoisotopic Molecular Weight319.094975119
IUPAC Name{1-hydroxy-3-[methyl(pentyl)amino]-1-phosphonopropyl}phosphonic acid
Traditional Nameibandronate
CAS Registry Number114084-78-5
SMILES
CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O
InChI Identifier
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)
InChI KeyMPBVHIBUJCELCL-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
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility13.4 g/LNot Available
LogP-2.1Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility13.4 g/LALOGPS
logP0.26ALOGPS
logP-2.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)9.93ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area138.53 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity71.16 m³·mol⁻¹ChemAxon
Polarizability29.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available173.99631661259
DarkChem[M-H]-PredictedNot Available168.09731661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Ibandronate,1TMS,#12452.6646https://arxiv.org/abs/1905.12712
Ibandronate,1TMS,#22434.6309https://arxiv.org/abs/1905.12712
Ibandronate,1TBDMS,#12709.827https://arxiv.org/abs/1905.12712
Ibandronate,1TBDMS,#22692.0994https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08gl-9130000000-f1a145132fe5a1d4852e2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0233-9113000000-5576d5d18472e7b11a4a2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1089000000-b2afb60f04d1d70760142016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0080-7790000000-037f20f19b338e3a638b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c3-9120000000-6b11acb03cc3d07ff6112016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-1159000000-86d2ef11326a8e83cda42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-4694000000-cd166d728f1d865e6ce52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9000000000-d06bd55271aea4ebdb182016-08-03View Spectrum
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 DB00710 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00710 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 IDDB00710
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54839
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIbandronic acid
METLIN IDNot Available
PubChem Compound60852
PDB IDBFQ
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Epstein S, Zaidi M: Biological properties and mechanism of action of ibandronate: application to the treatment of osteoporosis. Bone. 2005 Oct;37(4):433-40. [PubMed:16046205 ]

Enzymes

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. Chapurlat RD, Delmas PD: Drug insight: Bisphosphonates for postmenopausal osteoporosis. Nat Clin Pract Endocrinol Metab. 2006 Apr;2(4):211-9; quiz following 238. [PubMed:16932286 ]
  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. Rondeau JM, Bitsch F, Bourgier E, Geiser M, Hemmig R, Kroemer M, Lehmann S, Ramage P, Rieffel S, Strauss A, Green JR, Jahnke W: Structural basis for the exceptional in vivo efficacy of bisphosphonate drugs. ChemMedChem. 2006 Feb;1(2):267-73. [PubMed:16892359 ]