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-{{short description|Photopharmacological agent}}
+{{Short description|A light-activated prodrug of methotrexate}}
-'''Phototrexate''' is a [[Photopharmacology|photopharmacological agent]]<ref name="VelemaSzymanski2014">{{cite journal|last1=Velema|first1=Willem A.|last2=Szymanski|first2=Wiktor|last3=Feringa|first3=Ben L.|title=Photopharmacology: Beyond Proof of Principle|journal=Journal of the American Chemical Society|volume=136|issue=6|year=2014|pages=2178–2191|issn=0002-7863|doi=10.1021/ja413063e}}</ref><ref name="BroichhagenFrank2015">{{cite journal|last1=Broichhagen|first1=Johannes|last2=Frank|first2=James Allen|last3=Trauner|first3=Dirk|title=A Roadmap to Success in Photopharmacology|journal=Accounts of Chemical Research|volume=48|issue=7|year=2015|pages=1947–1960|issn=0001-4842|doi=10.1021/acs.accounts.5b00129}}</ref> that behaves as light-regulated inhibitor of the [[dihydrofolate reductase]] (DHFR).<ref name="MateraGomila2018">{{cite journal|last1=Matera|first1=Carlo|last2=Gomila|first2=Alexandre M. J.|last3=Camarero|first3=Núria|last4=Libergoli|first4=Michela|last5=Soler|first5=Concepció|last6=Gorostiza|first6=Pau|title=Photoswitchable Antimetabolite for Targeted Photoactivated Chemotherapy|journal=Journal of the American Chemical Society|volume=140|issue=46|year=2018|pages=15764–15773|issn=0002-7863|doi=10.1021/jacs.8b08249}}</ref><ref name="MashitaKowada2019">{{cite journal|last1=Mashita|first1=Takato|last2=Kowada|first2=Toshiyuki|last3=Takahashi|first3=Hiroto|last4=Matsui|first4=Toshitaka|last5=Mizukami|first5=Shin|title=Light‐Wavelength‐Based Quantitative Control of Dihydrofolate Reductase Activity by Using a Photochromic Isostere of an Inhibitor|journal=ChemBioChem|year=2019|issn=1439-4227|doi=10.1002/cbic.201800816}}</ref> It is a [[Photoisomerization|photoisomerizable]] structural analogue of the [[chemotherapy]] agent [[methotrexate]]. Pharmacological effects of phototrexate can be switched on and off by [[Ultraviolet|UVA]] and visible [[light]], respectively. Phototrexate is almost inactive in its [[Cis–trans isomerism|''trans'']] configuration while it behaves as a potent [[antifolate]] in its ''cis'' configuration. It can also spontaneously self-deactivate in the dark.
+'''Phototrexate''' is a [[prodrug]] of [[methotrexate]], designed to be activated by light. It is part of a class of drugs known as [[photopharmacology]], which involves the use of light to control the activity of pharmaceutical agents. This approach allows for spatial and temporal control of drug activation, potentially reducing side effects and increasing therapeutic efficacy.
-[[File:Cis-Phototrexate skeletal.svg|thumb|left|''cis''-Phototrexate]]
+==Mechanism of Action==
-{{clear left}}
+Phototrexate is an inactive form of methotrexate that becomes active upon exposure to specific wavelengths of light. Methotrexate itself is a well-known [[antimetabolite]] and [[antifolate]] drug that inhibits the enzyme [[dihydrofolate reductase]] (DHFR), leading to a decrease in [[tetrahydrofolate]] and subsequent inhibition of [[DNA synthesis]], [[RNA synthesis]], and [[protein synthesis]]. By using light to activate phototrexate, it is possible to target the drug's effects to specific tissues or cells, minimizing systemic exposure and reducing potential side effects.
-==See also==
+==Applications==
-* [[Cancer]]
+Phototrexate is primarily being investigated for its potential use in treating [[cancer]] and [[autoimmune diseases]]. In cancer therapy, the ability to activate the drug in a localized area could allow for higher concentrations of the active drug in the tumor while sparing healthy tissues. In autoimmune diseases, such as [[rheumatoid arthritis]], targeted activation could reduce the immunosuppressive effects on the entire body.
-== References ==
+==Advantages of Photopharmacology==
-{{reflist}}
+The use of light to control drug activity offers several advantages:
-[[Category:Dihydrofolate reductase inhibitors]]
+==Challenges and Considerations==
-[[Category:Chemotherapy]]
+While photopharmacology offers promising advantages, there are challenges to its implementation:
-{{antineoplastic-drug-stub}}
+==Future Directions==
-{{dictionary-stub1}}
+Research is ongoing to improve the efficacy and safety of phototrexate and other photopharmacological agents. Advances in light delivery systems, such as [[optical fibers]] and [[biocompatible]] light sources, are being explored to enhance the clinical applicability of these therapies.

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2024-02-22T15:56:18Z

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{{short description|Photopharmacological agent}}
{{Infobox drug
| drug_name = ''trans''-Phototrexate
| IUPAC_name = (2''S'')-2-[(4-[(2,4-Diaminoquinazolin-6-yl)diazenyl]benzoyl)amino]pentanedioic acid
| image = Phototrexate skeletal.svg
| alt =
| caption =

| pronounce =
| tradename =
| Drugs.com =
| MedlinePlus =
| pregnancy_AU = 
| pregnancy_AU_comment =
| pregnancy_US = 
| pregnancy_category=
| routes_of_administration =
| legal_AU = 
| legal_AU_comment =
| legal_BR = 
| legal_BR_comment =
| legal_CA = 
| legal_DE = 
| legal_NZ = 
| legal_UK = 
| legal_US = 
| legal_UN = 
| legal_status = 

| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action=
| excretion =

| CAS_number =
| class =
| ATCvet =
| ATC_prefix = None
| ATC_suffix =
| PubChem =
| DrugBank =

| chemical_formula =
| C=20 | H=19 | N=7 | O=5
| molecular_weight =
| smiles = C1(=NC(=NC2=C1C=C(C=C2)N=NC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N)N
| StdInChI=1S/C20H19N7O5/c21-17-13-9-12(5-6-14(13)24-20(22)25-17)27-26-11-3-1-10(2-4-11)18(30)23-15(19(31)32)7-8-16(28)29/h1-6,9,15H,7-8H2,(H,23,30)(H,28,29)(H,31,32)(H4,21,22,24,25)/t15-/m0/s1
| StdInChIKey = IODLJULYGHWOLC-HNNXBMFYSA-N
}}

'''Phototrexate''' is a [[Photopharmacology|photopharmacological agent]]<ref name="VelemaSzymanski2014">{{cite journal|last1=Velema|first1=Willem A.|last2=Szymanski|first2=Wiktor|last3=Feringa|first3=Ben L.|title=Photopharmacology: Beyond Proof of Principle|journal=Journal of the American Chemical Society|volume=136|issue=6|year=2014|pages=2178–2191|issn=0002-7863|doi=10.1021/ja413063e}}</ref><ref name="BroichhagenFrank2015">{{cite journal|last1=Broichhagen|first1=Johannes|last2=Frank|first2=James Allen|last3=Trauner|first3=Dirk|title=A Roadmap to Success in Photopharmacology|journal=Accounts of Chemical Research|volume=48|issue=7|year=2015|pages=1947–1960|issn=0001-4842|doi=10.1021/acs.accounts.5b00129}}</ref> that behaves as light-regulated inhibitor of the [[dihydrofolate reductase]] (DHFR).<ref name="MateraGomila2018">{{cite journal|last1=Matera|first1=Carlo|last2=Gomila|first2=Alexandre M. J.|last3=Camarero|first3=Núria|last4=Libergoli|first4=Michela|last5=Soler|first5=Concepció|last6=Gorostiza|first6=Pau|title=Photoswitchable Antimetabolite for Targeted Photoactivated Chemotherapy|journal=Journal of the American Chemical Society|volume=140|issue=46|year=2018|pages=15764–15773|issn=0002-7863|doi=10.1021/jacs.8b08249}}</ref><ref name="MashitaKowada2019">{{cite journal|last1=Mashita|first1=Takato|last2=Kowada|first2=Toshiyuki|last3=Takahashi|first3=Hiroto|last4=Matsui|first4=Toshitaka|last5=Mizukami|first5=Shin|title=Light‐Wavelength‐Based Quantitative Control of Dihydrofolate Reductase Activity by Using a Photochromic Isostere of an Inhibitor|journal=ChemBioChem|year=2019|issn=1439-4227|doi=10.1002/cbic.201800816}}</ref> It is a [[Photoisomerization|photoisomerizable]] structural analogue of the [[chemotherapy]] agent [[methotrexate]]. Pharmacological effects of phototrexate can be switched on and off by [[Ultraviolet|UVA]] and visible [[light]], respectively. Phototrexate is almost inactive in its [[Cis–trans isomerism|''trans'']] configuration while it behaves as a potent [[antifolate]] in its ''cis'' configuration. It can also spontaneously self-deactivate in the dark.

[[File:Cis-Phototrexate skeletal.svg|thumb|left|''cis''-Phototrexate]]
{{clear left}}

==See also==
* [[Cancer]]
* [[Psoriasis]]
* [[Psoriatic arthritis]]

== References ==
{{reflist}}

[[Category:Dihydrofolate reductase inhibitors]]
[[Category:Chemotherapy]]

{{antineoplastic-drug-stub}}
{{dictionary-stub1}}

Phototrexate - Revision history

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