toremifene Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antiestrogens or estrogen receptor modulators, clomifene and tamoxifen derivatives 2709 89778-26-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • FC1157a
  • FC-1157a
  • FC 1157a
  • fareston
  • toremifene
  • chlortamoxifen
  • toremifene citrate
A first generation selective estrogen receptor modulator (SERM). Like TAMOXIFEN, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue.
  • Molecular weight: 405.97
  • Formula: C26H28ClNO
  • CLOGP: 6.53
  • LIPINSKI: 1
  • HAC: 2
  • HDO: 0
  • TPSA: 12.47
  • ALOGS: -6
  • ROTB: 9

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
60 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.38 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 8.20 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
May 29, 1997 FDA PROSTRAKAN INC

FDA Adverse Event Reporting System (Female)

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
Osteonecrosis of jaw 78.43 35.53 25 538 34377 46651122
Osteomyelitis 49.81 35.53 16 547 22367 46663132

FDA Adverse Event Reporting System (Male)

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

Pharmacologic Action:

SourceCodeDescription
ATC L02BA02 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ENDOCRINE THERAPY
HORMONE ANTAGONISTS AND RELATED AGENTS
Anti-estrogens
FDA MoA N0000000168 Selective Estrogen Receptor Modulators
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018931 Antineoplastic Agents, Hormonal
MeSH PA D050071 Bone Density Conservation Agents
MeSH PA D020847 Estrogen Receptor Modulators
MeSH PA D006727 Hormone Antagonists
MeSH PA D020845 Selective Estrogen Receptor Modulators
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:50646 anti-osteoporotics
CHEBI has role CHEBI:50837 oestrogen antagonist
CHEBI has role CHEBI:149553 anti-coronaviral agents
FDA EPC N0000175826 Estrogen Agonist/Antagonist

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Metastatic Breast Carcinoma indication
Torsades de pointes contraindication 31722008
Hypokalemia contraindication 43339004
Hypercalcemia contraindication 66931009 DOID:12678
Leukopenia contraindication 84828003 DOID:615
Prolonged QT interval contraindication 111975006
Hypomagnesemia contraindication 190855004
Endometrial hyperplasia contraindication 237072009
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Thromboembolic disorder contraindication 371039008
Breastfeeding (mother) contraindication 413712001
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.61 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Estrogen receptor Nuclear hormone receptor MODULATOR WOMBAT-PK CHEMBL
Estrogen-related receptor gamma Nuclear hormone receptor WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 5.38 CHEMBL

External reference:

IDSource
D00967 KEGG_DRUG
89778-27-8 SECONDARY_CAS_RN
4021088 VANDF
4024102 VANDF
C0600382 UMLSCUI
CHEBI:9635 CHEBI
T0R PDB_CHEM_ID
CHEMBL1200675 ChEMBL_ID
CHEMBL1655 ChEMBL_ID
D017312 MESH_DESCRIPTOR_UI
5698 INN_ID
DB00539 DRUGBANK_ID
7NFE54O27T UNII
56008 PUBCHEM_CID
4325 IUPHAR_LIGAND_ID
155082 RXNORM
11447 MMSL
305699 MMSL
5603 MMSL
d04137 MMSL
006098 NDDF
007222 NDDF
387057008 SNOMEDCT_US
387588002 SNOMEDCT_US
96378009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fareston HUMAN PRESCRIPTION DRUG LABEL 1 42747-327 TABLET 60 mg ORAL NDA 27 sections
Toremifene Citrate Human Prescription Drug Label 1 64980-404 TABLET 60 mg ORAL ANDA 28 sections
toremifene citrate Human Prescription Drug Label 1 69539-152 TABLET 60 mg ORAL ANDA 26 sections
toremifene citrate Human Prescription Drug Label 1 72205-050 TABLET 60 mg ORAL ANDA 26 sections