raloxifene indications/contra

Stem definitionDrug idCAS RN
antiestrogens or estrogen receptor modulators, clomifene and tamoxifen derivatives 2351 84449-90-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • raloxifene
  • keoxifene
  • raloxifene hydrochloride
  • evista
  • raloxifene HCl
A second generation selective estrogen receptor modulator (SERM) used to prevent osteoporosis in postmenopausal women. It has estrogen agonist effects on bone and cholesterol metabolism but behaves as a complete estrogen antagonist on mammary gland and uterine tissue.
  • Molecular weight: 473.59
  • Formula: C28H27NO4S
  • CLOGP: 6.86
  • LIPINSKI: 1
  • HAC: 5
  • HDO: 2
  • TPSA: 70
  • ALOGS: -5.97
  • ROTB: 7

Drug dosage:

DoseUnitRoute
60 mg O

Approvals:

DateAgencyCompanyOrphan
Dec. 9, 1997 FDA LILLY

FDA Adverse Event Reporting System

scroll-->
MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Breast cancer 592.03 28.22 144 2373 7973 3375369
Deep vein thrombosis 458.06 28.22 145 2372 21244 3362098
Endometrial cancer 448.93 28.22 74 2443 505 3382837
Pulmonary embolism 373.93 28.22 133 2384 27755 3355587
Bone density decreased 303.80 28.22 61 2456 1352 3381990
Breast cancer female 233.28 28.22 49 2468 1362 3381980
Fall 229.77 28.22 117 2400 58766 3324576
Fracture 223.52 28.22 54 2463 2852 3380490
Spinal compression fracture 213.83 28.22 49 2468 2053 3381289
Hip fracture 213.02 28.22 59 2458 5356 3377986
Retinal vein thrombosis 205.96 28.22 35 2482 291 3383051
Cerebral infarction 171.54 28.22 55 2462 8245 3375097
Retinal vein occlusion 154.11 28.22 32 2485 837 3382505
Spinal fracture 151.27 28.22 39 2478 2681 3380661
Transient ischaemic attack 142.71 28.22 50 2467 9821 3373521
Muscle spasms 136.02 28.22 64 2453 26839 3356503
Hot flush 131.86 28.22 44 2473 7457 3375885
Body height decreased 129.46 28.22 30 2487 1316 3382026
Thoracic vertebral fracture 128.76 28.22 26 2491 589 3382753
Cerebrovascular accident 119.56 28.22 64 2453 35224 3348118
Femur fracture 116.70 28.22 40 2477 7348 3375994
Compression fracture 114.41 28.22 26 2491 1044 3382298
Oestrogen receptor assay positive 110.60 28.22 19 2498 169 3383173
Pain in extremity 109.85 28.22 68 2449 49144 3334198
Breast cancer in situ 108.83 28.22 21 2496 373 3382969
Oedema peripheral 107.14 28.22 59 2458 34302 3349040
Pelvic fracture 106.70 28.22 26 2491 1416 3381926
Visual acuity reduced 101.56 28.22 38 2479 8976 3374366
Lumbar vertebral fracture 97.87 28.22 22 2495 840 3382502
Thrombosis 94.88 28.22 41 2476 14049 3369293

Pharmacologic Action:

scroll-->
SourceCodeDescription
ATC G03XC01 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
OTHER SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
Selective estrogen receptor modulators
FDA EPC N0000175826 Estrogen Agonist/Antagonist
MeSH PA D050071 Bone Density Conservation Agents
MeSH PA D004965 Estrogen Antagonists
MeSH PA D020847 Estrogen Receptor Modulators
MeSH PA D006727 Hormone Antagonists
MeSH PA D006730 Hormones, Hormone Substitutes, and Hormone Antagonists
MeSH PA D020845 Selective Estrogen Receptor Modulators
CHEBI has role CHEBI:50646 bone density conservation agent
CHEBI has role CHEBI:50739 estrogen receptor modulator
CHEBI has role CHEBI:50837 estrogen antagonist

Drug Use (View source of the data)

scroll-->
DiseaseRelationSNOMED_IDDOID
Postmenopausal osteoporosis indication 102447009
Prevention of Breast Carcinoma indication
Lupus anticoagulant disorder contraindication 19267009 DOID:2988
Hypertensive disorder contraindication 38341003 DOID:10763
Thrombosis of retinal vein contraindication 46085004 DOID:1727
Chronic heart failure contraindication 48447003
Atrial fibrillation contraindication 49436004 DOID:0060224
Thrombophlebitis contraindication 64156001 DOID:3875
Deep venous thrombosis contraindication 128053003
Impaired renal function disorder contraindication 197663003
Cerebrovascular accident contraindication 230690007 DOID:6713
Pulmonary thromboembolism contraindication 233935004
Thrombophilia contraindication 234467004 DOID:2452
Disease of liver contraindication 235856003 DOID:409
Transient ischemic attack contraindication 266257000 DOID:224
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Smokes tobacco daily contraindication 449868002
Prevention of Glucocorticoid-Induced Osteoporosis off-label use

Acid dissociation constants calculated using MoKa v3.0.0

scroll-->
Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.13 acidic
pKa2 8.6 acidic
pKa3 9.15 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

scroll-->
TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Estrogen receptor Nuclear hormone receptor ANTAGONIST IC50 9.40 WOMBAT-PK IUPHAR
Estrogen receptor beta Nuclear hormone receptor MODULATOR EC50 8 WOMBAT-PK CHEMBL
D(1A) dopamine receptor GPCR Ki 5.71 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 6.41 DRUG MATRIX
Adenosine receptor A2a GPCR Ki 5.93 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 6.20 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 5.72 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 6.55 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 6.38 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.21 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.77 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.27 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 6.97 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.83 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 6.32 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 6.19 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 5.63 DRUG MATRIX
Acetylcholinesterase Enzyme IC50 6.40 DRUG MATRIX
Cytochrome P450 2C9 Enzyme IC50 5.70 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.44 DRUG MATRIX
Substance-K receptor GPCR Ki 5.88 DRUG MATRIX
Interleukin-6 Cytokine IC50 8.05 WOMBAT-PK
G-protein coupled estrogen receptor 1 GPCR EC50 6.50 WOMBAT-PK
5-hydroxytryptamine receptor 1D GPCR Ki 6.52 WOMBAT-PK
Aldehyde oxidase Enzyme IC50 8.54 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 6.30 WOMBAT-PK
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Enzyme Ki 9 WOMBAT-PK
Phospholipase D2 Enzyme IC50 5.47 CHEMBL
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor EC50 4.93 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.42 CHEMBL
Phospholipase D1 Enzyme IC50 5.40 CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 7.16 CHEMBL
Bile acid receptor Nuclear hormone receptor IC50 4.94 CHEMBL
Mu-type opioid receptor GPCR Ki 6.32 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 5.83 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 6.07 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 6.63 DRUG MATRIX
Cruzipain Enzyme IC50 4.48 CHEMBL
Estrogen receptor Transcription factor IC50 8.73 CHEMBL
Estrogen receptor Transcription factor Ki 9.43 CHEMBL
C-8 sterol isomerase Enzyme Ki 7.18 CHEMBL
Estrogen receptor beta Transcription factor Ki 8.56 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 5.66 CHEMBL

External reference:

scroll-->
IDSource
DB00481 DRUGBANK_ID
2820 IUPHAR_LIGAND_ID
4024098 VUID
N0000022103 NUI
C0244404 UMLSCUI
D02217 KEGG_DRUG
CHEMBL81 ChEMBL_ID
4F86W47BR6 UNII
82640-04-8 SECONDARY_CAS_RN
419530003 SNOMEDCT_US
4024098 VANDF
N0000022103 NDFRT
72143 RXNORM
109029006 SNOMEDCT_US
d04261 MMSL
83711 MMSL
007282 NDDF
CHEMBL1116 ChEMBL_ID
5035 PUBCHEM_CID
D020849 MESH_DESCRIPTOR_UI
5388 INN_ID
CHEBI:8772 CHEBI
RAL PDB_CHEM_ID

Pharmaceutical products:

scroll-->
ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Evista HUMAN PRESCRIPTION DRUG LABEL 1 0002-4165 TABLET 60 mg ORAL NDA 19 sections
Evista HUMAN PRESCRIPTION DRUG LABEL 1 0002-4184 TABLET 60 mg ORAL NDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-7290 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0179-0151 TABLET 60 mg ORAL NDA authorized generic 20 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0179-0212 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0179-0220 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0440-5295 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene HUMAN PRESCRIPTION DRUG LABEL 1 0591-2367 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 31722-256 TABLET 60 mg ORAL ANDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-726 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-253 TABLET, FILM COATED 60 mg ORAL ANDA 20 sections
Raloxifene hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43598-505 TABLET, FILM COATED 60 mg ORAL ANDA 20 sections
Evista HUMAN PRESCRIPTION DRUG LABEL 1 49999-458 TABLET 60 mg ORAL NDA 19 sections
Raloxifene hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50228-306 TABLET, FILM COATED 60 mg ORAL ANDA 20 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 52343-137 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Evista HUMAN PRESCRIPTION DRUG LABEL 1 54868-4170 TABLET 60 mg ORAL NDA 19 sections
Evista HUMAN PRESCRIPTION DRUG LABEL 1 55289-266 TABLET 60 mg ORAL NDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60687-266 TABLET 60 mg ORAL ANDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-057 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65862-709 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 66993-417 TABLET 60 mg ORAL NDA authorized generic 20 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 66993-661 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
raloxifene hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68462-393 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 69097-825 TABLET 60 mg ORAL ANDA 19 sections
Raloxifene hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 69189-0418 TABLET 60 mg ORAL NDA authorized generic 19 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 69189-0678 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections
Raloxifene HUMAN PRESCRIPTION DRUG LABEL 1 69189-2367 TABLET, FILM COATED 60 mg ORAL ANDA 20 sections
Raloxifene Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 76282-256 TABLET, FILM COATED 60 mg ORAL ANDA 19 sections