Tamoxifen metabolism (Homo sapiens)

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1-5Alternate pathwayMCF-7 cell proliferationMain pathwaySulfationDeaminationAlcohol metabolismSulfationSulfationSULT1E1cis-4-hydroxytamoxifen-N-glucuronidePAPtrans-4-SulfoxytamoxifenCYP2A6UGT1A8PAPScis-4-hydroxytamoxifenSULT2A1SULT2A1CYP2C9N-desmethyltamoxifenUGT1A10CYP3A4UGT1A4alpha-hydroxy-N-desmethyltamoxifentrans-4-hydroxytamoxifen-N-glucuronidecis-tamoxifen-4-O-glucuronideCYP1A2cis-4-hydroxy-N-desmethyltamoxifentrans-tamoxifen-4-O-glucuronideSULT1A1UGT1A4PAPSCYP3A4CYP3A5CYP2C8trans-tamoxifenFMO1CYP3A4MetaboliteCYP3A4CYP3A4Tamoxifen-N-oxideCYP2C19CYP3A4SULT1A1CYP2C19CYP2D6UGT2B7deamino-hydroxytamoxifenCYP2C19CYP2D6cis-N-desmethyltamoxifen-O-glucuronidetamoxifen-N-glucuronideFMO3CYP2C9alpha-hydroxytamoxifenUGT1A4CYP2E1N,N-didesmethyltamoxifenSULT2A1CYP1B1SULT1E1trans-N-desmethyltamoxifen-O-glucuronideCYP2D6CYP2D6UGT2B15CYP3A5PAPtrans-4-SulfoxytamoxifenCYP3A4CYP1A14-hydroxy-N-desmethyltamoxifenSSRItrans-4-hydroxytamoxifen


Description

Tamoxifen (TMX), sold under the brand name Nolvadex among others, is a medication that is used to prevent breast cancer in women and treat breast cancer in women and men.[1] It is also being studied for other types of cancer[1]. Tamoxifen is currently used for the treatment of both early and advanced estrogen receptor (ER)-positive (ER+) breast cancer in pre- and post-menopausal women[2]. Additionally, it is the most common hormone treatment for male breast cancer.

[1]: https://www.cancer.gov/about-cancer/treatment/drugs/tamoxifencitrate

[2]: Jordan, V. Craig. "A current view of tamoxifen for the treatment and prevention of breast cancer." British journal of pharmacology 110.2 (1993): 507-517.

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Bibliography

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  1. Ogura K, Ishikawa Y, Kaku T, Nishiyama T, Ohnuma T, Muro K, Hiratsuka A; ''Quaternary ammonium-linked glucuronidation of trans-4-hydroxytamoxifen, an active metabolite of tamoxifen, by human liver microsomes and UDP-glucuronosyltransferase 1A4.''; Biochem Pharmacol, 2006 PubMed Europe PMC Scholia
  2. Jordan VC; ''New insights into the metabolism of tamoxifen and its role in the treatment and prevention of breast cancer.''; Steroids, 2007 PubMed Europe PMC Scholia
  3. Jordan VC; ''Chemoprevention of breast cancer with selective oestrogen-receptor modulators.''; Nat Rev Cancer, 2007 PubMed Europe PMC Scholia
  4. Kaku T, Ogura K, Nishiyama T, Ohnuma T, Muro K, Hiratsuka A; ''Quaternary ammonium-linked glucuronidation of tamoxifen by human liver microsomes and UDP-glucuronosyltransferase 1A4.''; Biochem Pharmacol, 2004 PubMed Europe PMC Scholia
  5. Lazarus P, Blevins-Primeau AS, Zheng Y, Sun D; ''Potential role of UGT pharmacogenetics in cancer treatment and prevention: focus on tamoxifen.''; Ann N Y Acad Sci, 2009 PubMed Europe PMC Scholia
  6. Jordan VC; ''Fourteenth Gaddum Memorial Lecture. A current view of tamoxifen for the treatment and prevention of breast cancer.''; Br J Pharmacol, 1993 PubMed Europe PMC Scholia

History

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CompareRevisionActionTimeUserComment
135040view11:17, 1 August 2024EgonwAdded the reference listed in the description to the bibliography
134408view20:35, 21 July 2024EweitzEconomize layout
126229view06:28, 17 April 2023EgonwLicense is CCZero
114497view07:32, 18 January 2021EgonwCorrected PubChem CID for the trans/E stereoisomer.
106824view13:30, 17 September 2019MaintBotHMDB identifier normalization
92400view08:27, 1 June 2017DeSlModified description
92388view18:24, 31 May 2017EgonwOntology Term : 'xenobiotic metabolic pathway' added !
85084view22:40, 12 April 2016EgonwAdded a few metabolite identifiers.
79986view16:34, 29 April 2015ZariCorrected Ensembl Id for CYP2A6,UGT2B15
69462view19:18, 8 July 2013EgonwAdded two missing identifiers.
69461view19:13, 8 July 2013EgonwReplaced an outdated HMDB identifier with the 3.5 one.
68966view17:40, 8 July 2013MaintBotUpdated to 2013 gpml schema
67683view11:48, 26 June 2013DdiglesOntology Term : 'breast cancer pathway' added !
59176view18:43, 22 February 2013MaintBotUpdated Ensembl and UniProt data source
57002view13:40, 19 January 2013EgonwCorrected to the correct PubChem-compound data source.
48234view05:46, 17 May 2012MaintBotUpdating PubChem xrefs
48212view05:28, 17 May 2012MaintBotAutomatic update of PubChem xrefs
45101view22:07, 6 October 2011KhanspersOntology Term : 'estrogen-receptor positive breast cancer' added !
41135view23:38, 1 March 2011MaintBotRemoved redundant pathway information and comments
38734view21:31, 23 September 2010Khansperschanged arrow types
33408view14:49, 30 November 2009MaintBotRemoved group label
32747view23:23, 3 September 2009MaintBotModified categories
29331view12:42, 24 April 2009Pieter GiesbertzAdded compound identifiers
29330view12:25, 24 April 2009Pieter GiesbertzAdded compound identifiers
29329view11:13, 24 April 2009Pieter GiesbertzSpecify description
29328view11:11, 24 April 2009Pieter GiesbertzSpecify description
29327view11:06, 24 April 2009Pieter GiesbertzSpecify description
29295view12:14, 22 April 2009Pieter GiesbertzAdded literature references
29294view11:34, 22 April 2009Pieter GiesbertzSpecify description
29293view11:24, 22 April 2009Pieter GiesbertzSpecify description
29292view10:55, 22 April 2009Pieter GiesbertzPeriodical save, work in progress
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29137view13:01, 6 April 2009Pieter GiesbertzPeriodical save, work in progress
29136view12:40, 6 April 2009Pieter GiesbertzPeriodical save, work in progress
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29134view12:11, 6 April 2009Pieter GiesbertzPeriodical save, work in progress
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29131view10:10, 6 April 2009Pieter GiesbertzSpecify description
29130view10:04, 6 April 2009Pieter GiesbertzPeriodical save, work in progress
29129view09:53, 6 April 2009Pieter GiesbertzPeriodical save, work in progress
29128view09:39, 6 April 2009Pieter GiesbertzPeriodical save, work in progress
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29126view09:23, 6 April 2009Pieter GiesbertzSpecify description

External references

DataNodes

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NameTypeDatabase referenceComment
4-hydroxy-N-desmethyltamoxifenMetabolite3035980 (PubChem-compound)
CYP1A1GeneProductENSG00000140465 (Ensembl)
CYP1A2GeneProductENSG00000140505 (Ensembl)
CYP1B1GeneProductENSG00000138061 (Ensembl)
CYP2A6GeneProductENSG00000255974 (Ensembl)
CYP2C19GeneProductENSG00000165841 (Ensembl)
CYP2C8GeneProductENSG00000138115 (Ensembl)
CYP2C9GeneProductENSG00000138109 (Ensembl)
CYP2D6GeneProductENSG00000100197 (Ensembl)
CYP2E1GeneProductENSG00000130649 (Ensembl)
CYP3A4GeneProductENSG00000160868 (Ensembl)
CYP3A5GeneProductENSG00000106258 (Ensembl)
FMO1GeneProductENSG00000010932 (Ensembl)
FMO3GeneProductENSG00000007933 (Ensembl)
MetaboliteMetaboliteCHEBI:25212 (ChEBI)
N,N-didesmethyltamoxifenMetabolite3036172 (PubChem-compound)
N-desmethyltamoxifenMetabolite3032890 (PubChem-compound)
PAPMetaboliteHMDB0000061 (HMDB)
PAPSMetabolite10214 (PubChem-compound)
SSRIMetaboliteCHEBI:50949 (ChEBI)
SULT1A1GeneProductENSG00000196502 (Ensembl)
SULT1E1GeneProductENSG00000109193 (Ensembl)
SULT2A1GeneProductENSG00000105398 (Ensembl)
Tamoxifen-N-oxideMetabolite3033895 (PubChem-compound)
UGT1A10GeneProduct54575 (Entrez Gene)
UGT1A4GeneProduct54657 (Entrez Gene)
UGT1A8GeneProduct54576 (Entrez Gene)
UGT2B15GeneProductENSG00000196620 (Ensembl)
UGT2B7GeneProduct7364 (Entrez Gene)
alpha-hydroxy-N-desmethyltamoxifenMetabolite10474509 (PubChem-compound)
alpha-hydroxytamoxifenMetaboliteHMDB0060585 (HMDB)
cis-4-hydroxy-N-desmethyltamoxifenMetabolite
cis-4-hydroxytamoxifen-N-glucuronideMetabolite
cis-4-hydroxytamoxifenMetabolite449459 (PubChem-compound)
cis-N-desmethyltamoxifen-O-glucuronideMetabolite
cis-tamoxifen-4-O-glucuronideMetabolite
deamino-hydroxytamoxifenMetabolite3033897 (PubChem-compound)
tamoxifen-N-glucuronideMetabolite5460873 (PubChem-compound)
trans-4-SulfoxytamoxifenMetabolite
trans-4-hydroxytamoxifen-N-glucuronideMetabolite
trans-4-hydroxytamoxifenMetabolite449459 (PubChem-compound)
trans-N-desmethyltamoxifen-O-glucuronideMetabolite
trans-tamoxifen-4-O-glucuronideMetabolite
trans-tamoxifenMetaboliteHMDB0014813 (HMDB)

Annotated Interactions

No annotated interactions

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