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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014813
Secondary Accession Numbers
  • HMDB14813
Metabolite Identification
Common NameTamoxifen
DescriptionTamoxifen is only found in individuals that have used or taken this drug. It is one of the selective estrogen receptor modulators with tissue-specific activities. Tamoxifen acts as an anti-estrogen (inhibiting agent) in the mammary tissue, but as an estrogen (stimulating agent) in cholesterol metabolism, bone density, and cell proliferation in the endometrium. [PubChem]Tamoxifen binds to estrogen receptors (ER), inducing a conformational change in the receptor. This results in a blockage or change in the expression of estrogen dependent genes. The prolonged binding of tamoxifen to the nuclear chromatin of these results in reduced DNA polymerase activity, impaired thymidine utilization, blockade of estradiol uptake, and decreased estrogen response. It is likely that tamoxifen interacts with other coactivators or corepressors in the tissue and binds with different estrogen receptors, ER-alpha or ER-beta, producing both estrogenic and antiestrogenic effects.
Structure
Data?1582753223
Synonyms
ValueSource
(Z)-2-(4-(1,2-Diphenyl-1-butenyl)phenoxy)-N,N-dimethylethanamineChEBI
(Z)-2-(Para-(1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethylamineChEBI
1-p-beta-Dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-eneChEBI
1-Para-beta-dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-eneChEBI
Apo-tamoxChEBI
CitofenChEBI
CrisafenoChEBI
DiemonChEBI
Gen-tamoxifenChEBI
IstubolChEBI
NoltamChEBI
NourytamChEBI
OncomoxChEBI
RetaximChEBI
TamofenChEBI
TamoneChEBI
TamoxastaChEBI
TamoxifeneChEBI
TamoxifenoChEBI
TamoxifenumChEBI
trans-TamoxifenChEBI
ValodexChEBI
ZemideChEBI
TamoplexKegg
1-p-b-Dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-eneGenerator
1-p-Β-dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-eneGenerator
1-Para-b-dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-eneGenerator
1-Para-β-dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-eneGenerator
Tamoxifen citrateHMDB
NolvadexHMDB
NovaldexHMDB
Savient brand OF tamoxifen citrateHMDB
Citrate, tamoxifenHMDB
TomaxithenHMDB
SoltamoxHMDB
ZitazoniumHMDB
Chemical FormulaC26H29NO
Average Molecular Weight371.5146
Monoisotopic Molecular Weight371.224914555
IUPAC Name(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine
Traditional Nametamoxifen
CAS Registry Number10540-29-1
SMILES
CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
InChI KeyNKANXQFJJICGDU-QPLCGJKRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Diphenylmethane
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point97 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.001 g/LNot Available
LogP7.1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM197.130932474
[M+H]+Not Available197.208http://allccs.zhulab.cn/database/detail?ID=AllCCS00001399
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.001 g/LALOGPS
logP5.93ALOGPS
logP6.35ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity128.43 m³·mol⁻¹ChemAxon
Polarizability44.19 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.71731661259
DarkChem[M-H]-189.7231661259
DeepCCS[M+H]+196.76430932474
DeepCCS[M-H]-194.39830932474
DeepCCS[M-2H]-228.69730932474
DeepCCS[M+Na]+203.92530932474
AllCCS[M+H]+194.832859911
AllCCS[M+H-H2O]+191.932859911
AllCCS[M+NH4]+197.532859911
AllCCS[M+Na]+198.332859911
AllCCS[M-H]-198.332859911
AllCCS[M+Na-2H]-198.132859911
AllCCS[M+HCOO]-198.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TamoxifenCC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C13797.3Standard polar33892256
TamoxifenCC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C12804.1Standard non polar33892256
TamoxifenCC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C12726.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tamoxifen GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9144000000-3359f7eb514ced73f0222017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tamoxifen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen , positive-QTOFsplash10-004i-3972000000-38c8a6cb6c6f2505438b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen LC-ESI-QFT , positive-QTOFsplash10-00di-9006000000-8443975759913521d9cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 40V, Positive-QTOFsplash10-004i-0890000000-7d32643701e60529d39b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 40V, Positive-QTOFsplash10-004i-0890000000-fd906e590fdf543b68992021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 35V, Positive-QTOFsplash10-00di-9006000000-f84f79502277004ac0402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 30V, Positive-QTOFsplash10-00di-0349000000-4205fab50150d73f24d62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 10V, Positive-QTOFsplash10-00di-0009000000-a245a8f75fd67b24d1252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 20V, Positive-QTOFsplash10-00di-0009000000-cf65e058d06ec3f0c2d22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 15V, Positive-QTOFsplash10-00di-0009000000-e2e1640918ad010e0f152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 50V, Positive-QTOFsplash10-004i-0980000000-655d348a80f2ddaa21132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 30V, Positive-QTOFsplash10-00di-9002000000-1725fbd9626a212cad692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 45V, Positive-QTOFsplash10-00di-9000000000-b52da730d05051dbfa6c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 75V, Positive-QTOFsplash10-00di-9000000000-fdf49fca2d2b0e8c78d12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 60V, Positive-QTOFsplash10-00di-9000000000-a8956f34f19e5a62993c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 40V, Positive-QTOFsplash10-00dl-9100000000-1fb3454c775df7c7ed052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 20V, Positive-QTOFsplash10-00di-9116000000-3913ede2827c623648212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 10V, Positive-QTOFsplash10-00di-9000000000-c281f0985f57fc8287372021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 90V, Positive-QTOFsplash10-00di-9100000000-60d346ff207483b51e772021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tamoxifen 50V, Positive-QTOFsplash10-004i-0980000000-ac0d9364dc824e030b742021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamoxifen 10V, Positive-QTOFsplash10-00di-1249000000-300a60fd4d5ac611b49c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamoxifen 20V, Positive-QTOFsplash10-00di-9464000000-b29d0ae97047e89de42d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamoxifen 40V, Positive-QTOFsplash10-0600-9561000000-bb923af5238f4028d8b12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamoxifen 10V, Negative-QTOFsplash10-00di-1029000000-e34a1955366e5613bde82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamoxifen 20V, Negative-QTOFsplash10-006t-1095000000-1eb06b0cfd7f34bf98082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tamoxifen 40V, Negative-QTOFsplash10-000t-2190000000-7cebd77678fb7be2a3e52016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00675 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00675 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 IDDB00675
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2015313
KEGG Compound IDC07108
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTamoxifen
METLIN IDNot Available
PubChem Compound2733526
PDB IDNot Available
ChEBI ID41774
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jordan VC: Fourteenth Gaddum Memorial Lecture. A current view of tamoxifen for the treatment and prevention of breast cancer. Br J Pharmacol. 1993 Oct;110(2):507-17. [PubMed:8242225 ]
  2. Howell A, Cuzick J, Baum M, Buzdar A, Dowsett M, Forbes JF, Hoctin-Boes G, Houghton J, Locker GY, Tobias JS: Results of the ATAC (Arimidex, Tamoxifen, Alone or in Combination) trial after completion of 5 years' adjuvant treatment for breast cancer. Lancet. 2005 Jan 1-7;365(9453):60-2. [PubMed:15639680 ]
  3. Steiner AZ, Terplan M, Paulson RJ: Comparison of tamoxifen and clomiphene citrate for ovulation induction: a meta-analysis. Hum Reprod. 2005 Jun;20(6):1511-5. Epub 2005 Apr 21. [PubMed:15845599 ]
  4. Jordan VC: Tamoxifen (ICI46,474) as a targeted therapy to treat and prevent breast cancer. Br J Pharmacol. 2006 Jan;147 Suppl 1:S269-76. [PubMed:16402113 ]
  5. van Bommel EF, Hendriksz TR, Huiskes AW, Zeegers AG: Brief communication: tamoxifen therapy for nonmalignant retroperitoneal fibrosis. Ann Intern Med. 2006 Jan 17;144(2):101-6. [PubMed:16418409 ]
  6. Graumann K, Jungbauer A: Agonistic and synergistic activity of tamoxifen in a yeast model system. Biochem Pharmacol. 2000 Jan 15;59(2):177-85. [PubMed:10810452 ]
  7. (). FDA label . .

Enzymes

General function:
Involved in flavin-containing monooxygenase activity
Specific function:
In contrast with other forms of FMO it does not seem to be a drug-metabolizing enzyme.
Gene Name:
FMO5
Uniprot ID:
P49326
Molecular weight:
32480.04
Reactions
Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Catalyzes the N-oxidation of certain primary alkylamines to their oximes via an N-hydroxylamine intermediate. Inactive toward certain tertiary amines, such as imipramine or chloropromazine. Can catalyze the S-oxidation of methimazole. The truncated form is catalytically inactive.
Gene Name:
FMO2
Uniprot ID:
Q99518
Molecular weight:
53643.29
Reactions
Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides.
Gene Name:
FMO4
Uniprot ID:
P31512
Molecular weight:
63342.055
Reactions
Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
Gene Name:
FMO3
Uniprot ID:
P31513
Molecular weight:
60032.975
Reactions
Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name:
FMO1
Uniprot ID:
Q01740
Molecular weight:
60310.285
Reactions
Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails