Dimethoxanate: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{drugbox
			{{cs1 config\|name-list-style=vanc}}{{Drugbox
⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
		⚫	\| verifiedrevid = 443984387
⚫	\| UNII = 1E3KG5FWDB
		⚫	\| IUPAC_name = 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate
⚫	\| verifiedrevid = ~~443321035~~
		⚫	\| image = dimethoxanate.png
⚫	\| IUPAC_name = 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate
⚫	\| image = dimethoxanate.png
	\| width = 150		\| width = 150

			<!--Clinical data-->
			\| tradename = Atuss, Cothera, Cotrane, Perlatos, Pulmoll, Tussizid
			\| Drugs.com = {{drugs.com\|international\|dimethoxanate}}
		⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	\| pregnancy_category =
		⚫	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
		⚫	\| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
		⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
		⚫	\| legal_status =
		⚫	\| routes_of_administration =

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

			<!--Identifiers-->
		⚫	\| CAS_number = 477-93-0
		⚫	\| ATC_prefix = R05
		⚫	\| ATC_suffix = DB28
		⚫	\| PubChem = 10610
		⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
		⚫	\| DrugBank =
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 10165		\| ChemSpiderID = 10165
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| InChI = 1/C19H22N2O3S/c1-20(2)11-12-23-13-14-24-19(22)21-15-7-3-5-9-17(15)25-18-10-6-4-8-16(18)21/h3-10H,11-14H2,1-2H3
		⚫	\| UNII = 1E3KG5FWDB
	\| InChIKey = OOVJCSPCMCAXEX-UHFFFAOYAU
		⚫	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
		⚫	\| KEGG = D07397

			<!--Chemical data-->
		⚫	\| C=19 \| H=22 \| N=2 \| O=3 \| S=1
	\| smiles = O=C(OCCOCCN(C)C)N1c3c(Sc2c1cccc2)cccc3		\| smiles = O=C(OCCOCCN(C)C)N1c3c(Sc2c1cccc2)cccc3
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
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	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = OOVJCSPCMCAXEX-UHFFFAOYSA-N		\| StdInChIKey = OOVJCSPCMCAXEX-UHFFFAOYSA-N
⚫	\| CAS_number = 477-93-0
⚫	\| ATC_prefix = R05
⚫	\| ATC_suffix = DB28
⚫	\| PubChem = 10610
⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
⚫	\| DrugBank =
⚫	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
⚫	\| KEGG = D07397
⚫	\| C=19 \| H=22 \| N=2 \| O=3 \| S=1
	\| molecular_weight = 358.456 g/mol
⚫	\| bioavailability =
⚫	\| protein_bound =
⚫	\| metabolism =
⚫	\| elimination_half-life =
⚫	\| excretion =
⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
⚫	\| pregnancy_category=
⚫	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫	\| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫	\| legal_status =
⚫	\| routes_of_administration =
	}}		}}

			'''Dimethoxanate''' (trade names '''Cothera''', '''Cotrane''', '''Atuss''', '''Perlatoss''', '''Tossizid''')<ref>{{cite book \|author = William Andrew Publishing \|title=Pharmaceutical Manufacturing Encyclopedia \|url= https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1103 \|date=22 October 2013 \|publisher=Elsevier \|isbn=978-0-8155-1856-3 \|pages=1332–3 }}</ref> is a ] of the ] class.<ref>{{cite journal \| vauthors = Parish FA \| title = Clinical evaluation of the antitussive, dimethoxanate \| journal = Medical Times \| volume = 87 \| pages = 1488–90 \| date = November 1959 \| pmid = 14430450 }}</ref>
	'''Dimethoxanate''' is a ].

			==Side effects==
			Dimethoxanate may have ], ], and ] effects, but it may also produce nausea and vomiting.<ref>{{cite book \|isbn=9788448604271\|title=Farmacología clínica y terapéutica médica\|last1=Martín\|first1=Alfonso Velasco\|year=2004\|chapter=Tratamiento sintomático de la tos y del resfriado común\|page=260\|publisher=McGraw-Hill/Interamericana }}</ref>

			==Pharmacology==
			It binds to the ] in the brain with an ] of 41 nM.<ref>{{cite journal \| vauthors = Klein M, Musacchio JM \| title = Dextromethorphan binding sites in the guinea pig brain. \| journal = Cellular and Molecular Neurobiology \| volume = 8 \| issue = 2 \| pages = 149–156 \| date = October 10, 1988 \| doi = 10.1007/BF00711241 \| pmid = 3044591 \| s2cid = 33844132 }}</ref>

			==Society and culture==
			Dimethoxanate was introduced in Austria, Belgium, and France in 1911, and in Italy and Spain in 1963.<ref>{{cite book \|isbn=0-8103-7177-4 \|title=Drugs Available Abroad, 1st Edition \|page=67 \|date=1991 \| vauthors = Schlesser JL \|publisher=Derwent Publications Ltd.}}</ref>
			Approval for marketing in the US was withdrawn by the ] in 1975 due to lack of evidence of efficacy.<ref>{{cite report \|url=https://www.govinfo.gov/content/pkg/FR-1975-12-18/pdf/FR-1975-12-18.pdf \|docket=75N–0321 \|date=December 18, 1975 \|work=Federal Register \|volume=40 \|issue=244 \|title=Cough Preparation Containing Dimethoxanate Hydrochloride}}</ref>
			==Synthesis==
			]

			] ('''1''') is reacted with ] to give Phenothiazine-10-carbonyl chloride ('''2'''). Further reaction with 2-(2-(dimethylamino)ethoxy)ethanol ('''3''') completed the synthesis of Dimethoxanate ('''4''').

			== References ==
			{{reflist}}

	{{Cough and cold preparations}}		{{Cough and cold preparations}}
			{{Sigma receptor modulators}}

	]		]
	]		]
			]
	]		]
	]		]
	]		]
			]
			]
			]

Latest revision as of 21:47, 2 February 2024

Chemical compound Pharmaceutical compound

Dimethoxanate
Clinical data

Trade names	Atuss, Cothera, Cotrane, Perlatos, Pulmoll, Tussizid
AHFS/Drugs.com	International Drug Names
ATC code	R05DB28 (WHO)
Identifiers
IUPAC name 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate
CAS Number	477-93-0
PubChem CID	10610
ChemSpider	10165
UNII	1E3KG5FWDB
KEGG	D07397
CompTox Dashboard (EPA)	DTXSID50197257
ECHA InfoCard	100.006.838
Chemical and physical data
Formula	C₁₉H₂₂N₂O₃S
Molar mass	358.46 g·mol
3D model (JSmol)	Interactive image
SMILES O=C(OCCOCCN(C)C)N1c3c(Sc2c1cccc2)cccc3
InChI InChI=1S/C19H22N2O3S/c1-20(2)11-12-23-13-14-24-19(22)21-15-7-3-5-9-17(15)25-18-10-6-4-8-16(18)21/h3-10H,11-14H2,1-2H3 Key:OOVJCSPCMCAXEX-UHFFFAOYSA-N
(verify)

Dimethoxanate (trade names Cothera, Cotrane, Atuss, Perlatoss, Tossizid) is a cough suppressant of the phenothiazine class.

Side effects

Dimethoxanate may have analgesic, local anesthetic, and central nervous system depressant effects, but it may also produce nausea and vomiting.

Pharmacology

It binds to the sigma-1 receptor in the brain with an IC₅₀ of 41 nM.

Society and culture

Dimethoxanate was introduced in Austria, Belgium, and France in 1911, and in Italy and Spain in 1963. Approval for marketing in the US was withdrawn by the FDA in 1975 due to lack of evidence of efficacy.

Synthesis

Phenothiazine (1) is reacted with phosgene to give Phenothiazine-10-carbonyl chloride (2). Further reaction with 2-(2-(dimethylamino)ethoxy)ethanol (3) completed the synthesis of Dimethoxanate (4).

References

William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1332–3. ISBN 978-0-8155-1856-3.
Parish FA (November 1959). "Clinical evaluation of the antitussive, dimethoxanate". Medical Times. 87: 1488–90. PMID 14430450.
Martín AV (2004). "Tratamiento sintomático de la tos y del resfriado común". Farmacología clínica y terapéutica médica. McGraw-Hill/Interamericana. p. 260. ISBN 9788448604271.
Klein M, Musacchio JM (October 10, 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–156. doi:10.1007/BF00711241. PMID 3044591. S2CID 33844132.
Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 67. ISBN 0-8103-7177-4.
Cough Preparation Containing Dimethoxanate Hydrochloride (PDF). Federal Register (Report). Vol. 40. December 18, 1975. 75N–0321.
Weston, Arthur W.; DeNet, Robert W.; Michaels, R. J. (1953). "Antispasmodics. Basic Esters and Amides of Some Heterocyclic N-Carboxylic Acids". Journal of the American Chemical Society. 75 (16): 4006–4008. doi:10.1021/ja01112a038.
Seemann Carl Von, U.S. patent 2,778,824 (1957 to American Home Prod).

Cough and cold preparations (R05)

Expectorants

Mucolytics

Cough suppressants

Opium alkaloids,
opioids,
and derivatives

Other

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

v t e Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists: AC-927 BD-1008 BD-1067 CM-156 CT-1812 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also: Receptor/signaling modulators

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