CX157: Difference between revisions

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			{{short description\|Chemical compound}}
	{{Drugbox		{{Drugbox
			\| verifiedrevid = 396516252
	\| IUPAC_name = 3-fluoro-7-(2,2,2-trifluoroethoxy)phenoxathiine 10,10-dioxide		\| IUPAC_name = 3-fluoro-7-(2,2,2-trifluoroethoxy)phenoxathiine 10,10-dioxide
	\| image = CX157 structure.svg		\| image = CX157 structure.svg

			<!--Clinical data-->
			\| tradename =
		⚫	\| pregnancy_category =
		⚫	\| legal_status = Uncontrolled
		⚫	\| routes_of_administration = Oral

			<!--Pharmacokinetic data-->
		⚫	\| bioavailability =
		⚫	\| metabolism =
		⚫	\| elimination_half-life =
		⚫	\| excretion =

			<!--Identifiers-->
		⚫	\| CAS_number = 205187-53-7
			\| CAS_number_Ref = {{cascite\|correct\|CAS}}
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = O6L62LZJ0Q
		⚫	\| ATC_prefix = none
		⚫	\| ATC_suffix =
		⚫	\| PubChem = 18687754
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\| ChemSpiderID = 13701383

			<!--Chemical data-->
			\| C = 14 \| H = 8 \| F = 4 \| O = 4 \| S = 1
		⚫	\| smiles = FC(F)(F)COc2cc3Oc1cc(F)ccc1S(=O)(=O)c3cc2
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C14H8F4O4S/c15-8-1-3-12-10(5-8)22-11-6-9(21-7-14(16,17)18)2-4-13(11)23(12,19)20/h1-6H,7H2		\| StdInChI = 1S/C14H8F4O4S/c15-8-1-3-12-10(5-8)22-11-6-9(21-7-14(16,17)18)2-4-13(11)23(12,19)20/h1-6H,7H2
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = PDIMOTRDGUQMNY-UHFFFAOYSA-N		\| StdInChIKey = PDIMOTRDGUQMNY-UHFFFAOYSA-N
⚫	\| CAS_number =
⚫	\| ATC_prefix = none
⚫	\| ATC_suffix =
⚫	\| PubChem = 18687754
⚫	\| ChemSpiderID = 13701383
	\| chemical_formula = C<sub>14</sub>H<sub>8</sub>F<sub>4</sub>O<sub>4</sub>S
	\| molecular_weight = 348.27 g/mol
⚫	\| smiles = FC(F)(F)COc2cc3Oc1cc(F)ccc1S(=O)(=O)c3cc2
⚫	\| bioavailability =
⚫	\| metabolism =
⚫	\| elimination_half-life =
⚫	\| excretion =
⚫	\| pregnancy_category =
⚫	\| legal_status = Uncontrolled
⚫	\| routes_of_administration = Oral
	}}		}}

	'''~~Tyrima~~''' ('''~~CX157~~''') is a ] and ] (RIMA).<ref>{{cite conference \|~~author~~=Fielding R, Mielach F, Free J, Pande A \|title=Pharmacokinetics and oral bioavailability of CX157, a reversible selective MAO-A inhibitor, in primates \|year=2007 \|conference=2007 AAPS Annual Meeting & Exposition \|url=http://www.aapsj.org/abstracts/AM_2007/AAPS2007-001233.PDF \|accessdate=2009-06-14}}</ref> It is ~~currently~~ in phase II ]s for the treatment of ].<ref>{{ClinicalTrialsGov\|NCT00739908}}</ref>		'''CX157''' (proposed trade name '''TriRima''', formerly '''Tyrima''') is a ] and ] (RIMA).<ref>{{cite conference \|vauthors=Fielding R, Mielach F, Free J, Pande A \|title=Pharmacokinetics and oral bioavailability of CX157, a reversible selective MAO-A inhibitor, in primates \|year=2007 \|conference=2007 AAPS Annual Meeting & Exposition \|url=http://www.aapsj.org/abstracts/AM_2007/AAPS2007-001233.PDF \|accessdate=2009-06-14 \|archive-url=https://web.archive.org/web/20110526192425/http://www.aapsj.org/abstracts/AM_2007/AAPS2007-001233.PDF \|archive-date=2011-05-26 \|url-status=dead }}</ref> As of 2007 it was in ] ]s for the treatment of ].<ref>{{ClinicalTrialsGov\|NCT00739908}\|A Study of CX157 (TriRima) for the Treatment of Depression (CX157-200)}}</ref> In 2013, work on the drug was terminated.

	== See also ==
⚫	* ] ~~(RIMA)~~
	* ] (MAOI)

	== References ==		==References==
	{{Reflist\|2}}		{{Reflist\|2}}


			{{Monoamine metabolism modulators}}
	{{Antidepressants}}
	{{Anxiolytics}}
	{{Adrenergics}}
	{{Dopaminergics}}
	{{Serotonergics}}

		⚫	]
	]		]
			]
			]
			]
			]
			]

Latest revision as of 00:11, 5 November 2022

Chemical compound Pharmaceutical compound

CX157
Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 3-fluoro-7-(2,2,2-trifluoroethoxy)phenoxathiine 10,10-dioxide
CAS Number	205187-53-7
PubChem CID	18687754
ChemSpider	13701383
UNII	O6L62LZJ0Q
CompTox Dashboard (EPA)	DTXSID40174517
Chemical and physical data
Formula	C₁₄H₈F₄O₄S
Molar mass	348.27 g·mol
3D model (JSmol)	Interactive image
SMILES FC(F)(F)COc2cc3Oc1cc(F)ccc1S(=O)(=O)c3cc2
InChI InChI=1S/C14H8F4O4S/c15-8-1-3-12-10(5-8)22-11-6-9(21-7-14(16,17)18)2-4-13(11)23(12,19)20/h1-6H,7H2 Key:PDIMOTRDGUQMNY-UHFFFAOYSA-N
(verify)

CX157 (proposed trade name TriRima, formerly Tyrima) is a selective and reversible inhibitor of MAO-A (RIMA). As of 2007 it was in phase II clinical trials for the treatment of depression. In 2013, work on the drug was terminated.

References

Fielding R, Mielach F, Free J, Pande A (2007). Pharmacokinetics and oral bioavailability of CX157, a reversible selective MAO-A inhibitor, in primates (PDF). 2007 AAPS Annual Meeting & Exposition. Archived from the original (PDF) on 2011-05-26. Retrieved 2009-06-14.
Clinical trial number NCT00739908} for "A Study of CX157 (TriRima) for the Treatment of Depression (CX157-200)" at ClinicalTrials.gov

Monoamine metabolism modulators

Non-specific

AAADTooltip Aromatic L-amino acid decarboxylase

Substrates→Products: L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAOTooltip Monoamine oxidase

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR): Epinephrine (adrenaline)→DHMA
Metanephrine→MHPG/VMA
Norepinephrine (noradrenaline)→DHMA
Normetanephrine→MHPG/VMA
Dopamine→DOPAC
3-Methoxytyramine→HVA
Serotonin→5-HIAA

Inhibitors: Non-selective: Benmoxin
Caroxazone
Echinopsidine
Furazolidone
Guineesine
Hydralazine
Indantadol
Iproclozide
Iproniazid
Isocarboxazid
Isoniazid
Linezolid
Mebanazine
Metfendrazine
Nialamide
Octamoxin
Paraxazone
Phenelzine
Pheniprazine
Phenoxypropazine
Pivhydrazine
Procarbazine
Safrazine
Tranylcypromine

Inhibitors: MAO-A-selective: Amiflamine
Bazinaprine
Befloxatone
Brofaromine
Cimoxatone
Clorgiline
CX157 (Tyrima)
Eprobemide
Esuprone
Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine)
Methylene blue
Metralindole
Minaprine
Moclobemide
Pirlindole
Sercloremine
Tetrindole
Toloxatone

Inhibitors: MAO-B selective: Adarigiline
Almoxatone
D-Deprenyl
Desmethylselegiline
Ethanol
Ladostigil
Lazabemide
Milacemide
Mofegiline
Nicotine
Pargyline
Rasagiline
Safinamide
Selegiline (L-Deprenyl)
Sembragiline
Tisolagiline
Vafidemstat

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products: Phenylalanine→Tyrosine Inhibitors: 3,4-Dihydroxystyrene α-Methylphenylalanine
THTooltip Tyrosine hydroxylase	Substrates→Products: Tyrosine→L-DOPA (levodopa) Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine α-Methyl-5-hydroxytryptophan (α-Me-5-HTP) α-Methylphenylalanine Aquayamycin Bulbocapnine Methyldopa (α-methyl-L-DOPA) Metirosine (α-methyl-p-tyrosine) Oudenone
DBHTooltip Dopamine beta-hydroxylase	Substrates→Products: Dopamine→Norepinephrine (Noradrenaline) Inhibitors: Bupicomide Disulfiram Dopastin Etamicastat Fusaric acid Nepicastat Phenopicolinic acid Tropolone Zamicastat
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors: CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products: Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nebicapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin, melatonin)

TPHTooltip Tryptophan hydroxylase

Substrates→Products: Tryptophan→5-HTP

AANATTooltip Serotonin N-acetyl transferase

Substrates→Products: Serotonin→N-Acetylserotonin

ASMTTooltip Acetylserotonin O-methyltransferase

Substrates→Products: N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase

Substrates→Products: L-Histidine→Histamine

HNMTTooltip Histamine N-methyltransferase

Substrates→Products: Histamine→N-Methylhistamine

DAOTooltip Diamine oxidase

Substrates→Products: Histamine→Imidazole acetic acid

Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins

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