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Toremifene Citrate

PubChem CID
3005572
Structure
Toremifene Citrate_small.png
Molecular Formula
Synonyms
  • TOREMIFENE CITRATE
  • 89778-27-8
  • Fareston
  • FC 1157a
  • Toremifene citrate [USAN]
Molecular Weight
598.1 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
Toremifene citrate is a stilbenoid. It has a role as an anticoronaviral agent.
Toremifene Citrate is the citrate salt of a nonsteroidal triphenylethylene antiestrogen. Chemically related to tamoxifen, toremifene is a selective estrogen receptor modulator (SERM). This agent binds competitively to estrogen receptors, thereby interfering with estrogen activity. Toremifene also has intrinsic estrogenic properties, which is manifested depending on the tissue or species. (NCI04)
TOREMIFENE CITRATE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1996 and has 3 approved and 2 investigational indications. This drug has a black box warning from the FDA.
See also: Toremifene (has active moiety).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Toremifene Citrate.png

1.2 3D Status

Conformer generation is disallowed since mixture or salt

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C26H28ClNO.C6H8O7/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-16H,17-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

IWEQQRMGNVVKQW-OQKDUQJOSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CN(C)CCOC1=CC=C(C=C1)/C(=C(/CCCl)\C2=CC=CC=C2)/C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C32H36ClNO8
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 KEGG ID

2.3.9 NCI Thesaurus Code

2.3.10 NSC Number

2.3.11 RXCUI

2.3.12 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Citrate, Toremifene
  • Fareston
  • FC 1157a
  • FC-1157a
  • FC1157a
  • Toremifene
  • Toremifene Citrate
  • Toremifene Citrate (1:1)
  • Toremifene, (E)-Isomer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
598.1 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
14
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
597.2129448 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
597.2129448 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
145 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
42
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
710
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Solubility

4.4 [ug/mL] (The mean of the results at pH 7.4)

3.2.2 Collision Cross Section

203 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Human drug -> Discontinued
Human drug -> Prescription; Active ingredient (TOREMIFENE CITRATE)
Human drugs -> Endocrine therapy -> Human pharmacotherapeutic group -> EMA Drug Category

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
406.193
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

406.194641 100

408.191315 31.78

407.196716 29.54

409.193878 6.30

205.099274 1.32

Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

First line hormone treatment of hormone-dependent metastatic breast cancer in postmenopausal patients. Fareston is not recommended for patients with estrogen receptor negative tumours.

7.2 FDA Approved Drugs

7.3 FDA Orange Book

7.4 FDA National Drug Code Directory

7.5 Drug Labels

Drug and label
Active ingredient and drug

7.6 Cancer Drugs

Drug Name
Fareston (Toremifene)
Brand Name(s)

Acapodene

Fareston

FDA Approved
Yes
Drug Use

Toremifene citrate is approved to treat:

• Breast cancer that has spread to other parts of the body. It is used in postmenopausal women whose cancer is estrogen receptor positive (ER+) or when it is not known if the cancer is ER+ or estrogen receptor negative (ER-).

7.7 Clinical Trials

7.7.1 ClinicalTrials.gov

7.7.2 EU Clinical Trials Register

7.8 EMA Drug Information

Medicine
Category
Human drugs
Therapeutic area
Breast Neoplasms
Active Substance
toremifene
INN/Common name
toremifene
Pharmacotherapeutic Classes
Endocrine therapy
Status
This medicine is authorized for use in the European Union
Company
Orion Corporation
Market Date
1996-02-14

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Antineoplastic Agents, Hormonal
Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)
Bone Density Conservation Agents
Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)
Selective Estrogen Receptor Modulators
A structurally diverse group of compounds distinguished from ESTROGENS by their ability to bind and activate ESTROGEN RECEPTORS but act as either an agonist or antagonist depending on the tissue type and hormonal milieu. They are classified as either first generation because they demonstrate estrogen agonist properties in the ENDOMETRIUM or second generation based on their patterns of tissue specificity. (Horm Res 1997;48:155-63) (See all compounds classified as Selective Estrogen Receptor Modulators.)

8.2 FDA Pharmacological Classification

Non-Proprietary Name
TOREMIFENE CITRATE
Pharmacological Classes
Selective Estrogen Receptor Modulators [MoA]; Estrogen Agonist/Antagonist [EPC]

8.3 ATC Code

L02BA02

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Human drugs -> Endocrine therapy -> Human pharmacotherapeutic group -> EMA Drug Category
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Corrosive
Irritant
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]

H318 (92.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H400 (92.7%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (92.7%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, P391, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (97.6%)

Eye Dam. 1 (92.7%)

Aquatic Acute 1 (92.7%)

Aquatic Chronic 1 (92.7%)

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Chemical Co-Occurrences in Literature

13.4 Chemical-Gene Co-Occurrences in Literature

13.5 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 Chemical Co-Occurrences in Patents

14.3 Chemical-Disease Co-Occurrences in Patents

14.4 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 KEGG: Drug

17.5 KEGG: USP

17.6 KEGG: ATC

17.7 KEGG: Target-based Classification of Drugs

17.8 KEGG: Drug Groups

17.9 KEGG: Drug Classes

17.10 ChemIDplus

17.11 ChEMBL Target Tree

17.12 UN GHS Classification

17.13 CCSBase Classification

17.14 EPA DSSTox Classification

17.15 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Burnham Center for Chemical Genomics
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    (Z)-1,2-diphenyl-1-[4-[2-(dimethylamino)etoxy]phenyl]-4-chloro-1-butencitrate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.189.661
    (Z)-1,2-diphenyl-1-[4-[2-(dimethylamino)etoxy]phenyl]-4-chloro-1-butencitrate (EC: 663-344-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/194584
  7. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  9. ChEBI
  10. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  11. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  12. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  13. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  14. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  15. DailyMed
  16. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  17. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  18. EU Clinical Trials Register
  19. FDA Orange Book
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  20. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Therapeutic category of drugs in Japan
    http://www.genome.jp/kegg-bin/get_htext?br08301.keg
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  21. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  22. National Drug Code (NDC) Directory
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  23. NCI Cancer Drugs
  24. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  25. Wikidata
  26. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Antineoplastic Agents, Hormonal
    https://www.ncbi.nlm.nih.gov/mesh/68018931
    Bone Density Conservation Agents
    https://www.ncbi.nlm.nih.gov/mesh/68050071
    Selective Estrogen Receptor Modulators
    https://www.ncbi.nlm.nih.gov/mesh/68020845
  27. PubChem
  28. GHS Classification (UNECE)
  29. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  30. NCBI
CONTENTS