Raloxifene (CED0002655)

Record Information
Version1.0
Creation Date2016-05-22 03:45:46 UTC
Update Date2026-08-22 08:14:28 UTC
Accession NumberCHEM016860
Identification
Common NameRaloxifene
ClassSmall Molecule
Description
Raloxifene is an organic compound with the formula C28H27NO4S and an average molecular weight of 473.58 g/mol. Raloxifene belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. This compound is found in or released from 20 recorded sources, including household cleaning and consumer products such as bleaching agents, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Other sources include electrical and electronic equipment—specifically electrodes, antennas, adjustable resistors, line transmission systems, and electrically stimulated smoking devices—as well as building and construction materials like tents or canopies and ladders. Additionally, it is associated with food preservation, the preparation of vinegar, and healthcare products involving sex hormones and modulators of the genital system. The recorded exposure route is oral. At the molecular level, raloxifene interacts with four recorded protein targets, acting as an agonist or binder of estrogen receptor (ESR1), estrogen receptor beta (ESR2), trefoil factor 1 (TFF1), and serpin B9 (SERPINB9). In clinical applications, it is used as a treatment for osteoporosis (PMC12068388, PMC3074486, PMC3126968, PMC3825671, PMC4092345, PMC7064359) and breast cancer (PMC12722357, PMC3702660), and it has a therapeutic effect on breast cancer (PMC2686344). However, the compound is also associated with an increase in stroke (PMC4906542, PMC7589419, PMC8395200).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(2-(4-Hydroxyphenyl)-6-hydroxybenzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)methanoneChEBI
KeoxifeneChEBI
LY 139481ChEBI
RaloxifenoChEBI
RaloxifenumChEBI
EvidenKegg
RaxetoKegg
LY-139481HMDB
RALHMDB
Raloxifene hydrochlorideHMDB
EvistaHMDB
Keoxifene hydrochlorideHMDB
Raloxifene HCLHMDB
Chemical FormulaC28H27NO4S
Average Molecular Mass473.583 g/mol
Monoisotopic Mass473.166 g/mol
CAS Registry Number84449-90-1
IUPAC Name2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-ol
Traditional Nameraloxifene
SMILESOC1=CC=C(C=C1)C1=C(C(=O)C2=CC=C(OCCN3CCCCC3)C=C2)C2=C(S1)C=C(O)C=C2
InChI IdentifierInChI=1S/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2
InChI KeyGZUITABIAKMVPG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • 3-aroylthiophene
  • Benzothiophene
  • 1-benzothiophene
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Thiophene carboxylic acid or derivatives
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Piperidine
  • Heteroaromatic compound
  • Thiophene
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00051 g/LALOGPS
logP5.45ALOGPS
logP5.69ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)8.89ChemAxon
pKa (Strongest Basic)7.95ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity135.48 m³·mol⁻¹ChemAxon
Polarizability52.55 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006t-9112200000-194dfc7c577ba3e76b98Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0udj-9010136000-3bb502413414534da20bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0035900000-dcf0b4afb1abd2691c7cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-6600900000-ea14790ae9aed263379bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000900000-f184aabcb2eb146ebe92Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000900000-3d3c761b7ff900186d5fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0231900000-0fc53037915f41184d0bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000900000-6e89a56db5f01a157640Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-1800900000-cfc74f58ad18897ca1beNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-8900000000-6cbb38555e813af5fa9cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000900000-76a62cda029e256d3f18Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014j-0494000000-d01ec5346aa038f5719aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0230900000-0fc53037915f41184d0bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0007900000-9eb122a555c8e7444904Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014j-0494000000-6cde9fd49faae3fb307dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000900000-3015478097ea6bee8d7aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9000000000-f3e7a5afa55ea1305028Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0007900000-2bda40c3103c3604b7c1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0059000000-1bf6aa63d8858df8932fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dr-0190000000-7ee2becffb54ed42c6e2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01p6-0092000000-86616f94829b2c365c93Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03du-0091000000-886acbada930a41a9869Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9100000000-03b23ac05bb6b5f98ec7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01q9-9300000000-7c279bc68f900179fba3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-6600900000-9ba65d43eeb355328141Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0035900000-6f22a70cc04594a33700Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0114900000-e8c217b2f20574044c33Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xs-4984400000-a2731ab247793dc0402eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014u-7296000000-82a010336a5451ab7f97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1012900000-c3bc16da6ed53c190cf7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03kc-2149500000-8a3b4929414c1ff5dc90Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00l6-5596000000-26179eaf5995f4a2067bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0000900000-9c89a06f300f4a812722Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0102900000-550388024e0bfc143d92Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-6189200000-abab8747d3a68b3d2299Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0000900000-9e8bacd05d7357b7b866Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03k9-1922800000-e36773363a3d095e59d1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01x0-9600000000-115f15d66eaef7d00f1aNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1269.0Log mg/kg[710:2300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
breast cancerhas_therapeutic_effect_onNot AvailablePMC2686344
breast canceris_treatment_forNot AvailablePMC12722357 , PMC12722357 , PMC3702660
osteoporosisis_treatment_forNot AvailablePMC12068388 , PMC12068388 , PMC3074486 , PMC3126968 , PMC3825671 , PMC4092345 , PMC7064359
strokeassociated_withincreasePMC4906542 , PMC7589419 , PMC8395200
pulmonary embolismassociated_withNot AvailablePMC10532995
estrogen receptor-positive breast canceris_treatment_forNot AvailablePMC12409151
Exposure Sources
Source IDSourceSectorReference
325Sex hormones and modulators of the genital systemHealthcare, pharmaceuticals & veterinary productsNot Available
498LaddersBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)0.0778492
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)0.467095
Click to view 3D structureEstrogen receptorP06211Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureEstrogen receptor betaQ62986Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structurePhenazine biosynthesis protein PhzB 2Q02L47Pseudomonas aeruginosaPredicted (SEA)0.155698
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)25.301
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)39.3917
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)40.248
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)70.1422
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)104.318
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)89.6045
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)51.8476
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)43.362
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)28.4928
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)28.4928
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)22.8098
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)47.0988
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)69.7529
Tyrosine-protein kinase Fyn structureClick to view 3D structureTyrosine-protein kinase FynP06241HumansPredicted (SEA)89.9937
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)110.779
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)103.072
Click to view 3D structureTransient receptor potential cation channel subfamily V member 3Q8K424Mus musculusPredicted (SEA)3.11397
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)12.6894
D(1A) dopamine receptor structureClick to view 3D structureD(1A) dopamine receptorP21728HumansPredicted (SEA)49.9792
Histamine H3 receptor structureClick to view 3D structureHistamine H3 receptorQ9Y5N1HumansPredicted (SEA)33.9423
Concentrations
Not Available
External Links
DrugBank IDDB00481
HMDB IDHMDB0014624
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRaloxifene
Chemspider ID4859
ChEBI ID8772
PubChem Compound ID5035
Kegg Compound IDC07228
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Balfour JA, Goa KL: Raloxifene. Drugs Aging. 1998 Apr;12(4):335-41; discussion 342.
2. Khovidhunkit W, Shoback DM: Clinical effects of raloxifene hydrochloride in women. Ann Intern Med. 1999 Mar 2;130(5):431-9.
3. Cummings SR, Eckert S, Krueger KA, Grady D, Powles TJ, Cauley JA, Norton L, Nickelsen T, Bjarnason NH, Morrow M, Lippman ME, Black D, Glusman JE, Costa A, Jordan VC: The effect of raloxifene on risk of breast cancer in postmenopausal women: results from the MORE randomized trial. Multiple Outcomes of Raloxifene Evaluation. JAMA. 1999 Jun 16;281(23):2189-97.
4. Bryant HU, Glasebrook AL, Yang NN, Sato M: An estrogen receptor basis for raloxifene action in bone. J Steroid Biochem Mol Biol. 1999 Apr-Jun;69(1-6):37-44.
5. Clemett D, Spencer CM: Raloxifene: a review of its use in postmenopausal osteoporosis. Drugs. 2000 Aug;60(2):379-411.
6. Barrett-Connor E: Raloxifene: risks and benefits. Ann N Y Acad Sci. 2001 Dec;949:295-303.
7. Heringa M: Review on raloxifene: profile of a selective estrogen receptor modulator. Int J Clin Pharmacol Ther. 2003 Aug;41(8):331-45.
8. Authors unspecified: A STARring role for raloxifene? Lancet Oncol. 2006 Jun;7(6):443.
9. Diez-Perez A: Selective estrogen receptor modulators (SERMS). Arq Bras Endocrinol Metabol. 2006 Aug;50(4):720-34.
10. Silverman SL: New selective estrogen receptor modulators (SERMs) in development. Curr Osteoporos Rep. 2010 Sep;8(3):151-3. doi: 10.1007/s11914-010-0025-0.