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Revision as of 13:47, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CASNo').← Previous edit		Latest revision as of 11:08, 17 October 2024 edit undoKyjugn (talk | contribs)228 editsNo edit summaryTags: Visual edit Mobile edit Mobile web edit
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	{{chembox		{{chembox
			| Verifiedfields = changed
			| Watchedfields = changed
			| verifiedrevid = 457817818
		⚫	| ImageFile = Arsthinol.svg
		⚫	| ImageFile_Ref = {{Chemboximage|correct|??}}
		⚫	| ImageSize = 244
		⚫	| ImageName = Structural formula of arsthinol
		⚫	| PIN = ''N''-<nowiki/>{2-Hydroxy-5-phenyl}acetamide
		⚫	|Section1={{Chembox Identifiers
			| CASNo = 119-96-0
		⚫	| CASNo_Ref = {{Cascite|correct|CAS}}
			| ChEBI = 135465
			| ChEMBL = 1788384
		⚫	| ChemSpiderID = 8107
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| DrugBank = DB08928
		⚫	| EINECS = 204-361-7
			| KEGG_Ref = {{keggcite|correct|kegg}}
		⚫	| KEGG = D07356
		⚫	| PubChem = 8414
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = QNT09A162Y		| UNII = QNT09A162Y
		⚫	| SMILES = CC(=O)NC1=C(O)C=CC(=C1)1SCC(CO)S1
⚫	| ImageFile = Arsthinol.svg
		⚫	| SMILES1 = O=C(Nc2cc(1SCC(S1)CO)ccc2O)C
⚫	| ImageFile_Ref = {{Chemboximage|correct|??}}
		⚫	| StdInChI = 1S/C11H14AsNO3S2/c1-7(15)13-10-4-8(2-3-11(10)16)12-17-6-9(5-14)18-12/h2-4,9,14,16H,5-6H2,1H3,(H,13,15)
⚫	| ImageSize = 244
		⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫	| ImageName = Structural formula of arsthinol
		⚫	| InChI = 1/C11H14AsNO3S2/c1-7(15)13-10-4-8(2-3-11(10)16)12-17-6-9(5-14)18-12/h2-4,9,14,16H,5-6H2,1H3,(H,13,15)
⚫	| SystematicName = ''N''-{2-Hydroxy-5-phenyl}acetamide
		⚫	| StdInChIKey = MRUDSZSRLQAPOG-UHFFFAOYSA-N
⚫	| Section1 = {{Chembox Identifiers
		⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| CASNo = <!-- blanked - oldvalue: 119-96-0 -->
		⚫	| InChIKey = MRUDSZSRLQAPOG-UHFFFAOYAP}}
⚫	| CASNo_Ref = {{cascite|correct|??}}
		⚫	|Section2={{Chembox Properties
⚫	| PubChem = 8414
			| C=11 | H=14 | As=1 | N=1 | O=3 | S=2}}
	| PubChem_Ref = {{Pubchemcite|correct|PubChem}}
		⚫	|Section6={{Chembox Pharmacology
⚫	| ChemSpiderID = 8107
			| ATCCode_prefix = P01
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| ATCCode_suffix = AR01
⚫	| EINECS = 204-361-7
		⚫	| ATC_Supplemental = {{ATCvet|P51|AD01}}
⚫	| KEGG = D07356
	| ATCCode_prefix = P01		| AdminRoutes = Oral
		⚫	| Metabolism = 89 % Hepatic<ref>{{cite journal | last1 = Cristau | first1 = B | last2 = Chabas | first2 = ME | last3 = Placidi | first3 = M | year = 1975 | title = Voies et cinétiques d'excrétion de l'arsenic chez le Cobaye après injection de divers médicaments organo-arséniés | journal = ] | volume = 33 | pages = 577–89 }}</ref>}}
⚫	| ATCCode_suffix = AR01
⚫	| ATC_Supplemental = P51AD01
⚫	| SMILES = CC(=O)NC1=C(O)C=CC(=C1)1SCC(CO)S1
⚫	| SMILES1 = O=C(Nc2cc(1SCC(S1)CO)ccc2O)C
⚫	| StdInChI = 1S/C11H14AsNO3S2/c1-7(15)13-10-4-8(2-3-11(10)16)12-17-6-9(5-14)18-12/h2-4,9,14,16H,5-6H2,1H3,(H,13,15)
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫	| InChI = 1/C11H14AsNO3S2/c1-7(15)13-10-4-8(2-3-11(10)16)12-17-6-9(5-14)18-12/h2-4,9,14,16H,5-6H2,1H3,(H,13,15)
⚫	| StdInChIKey = MRUDSZSRLQAPOG-UHFFFAOYSA-N
⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫	| InChIKey = MRUDSZSRLQAPOG-UHFFFAOYAP}}
⚫	| Section2 = {{Chembox Properties
	| C = 11
	| H = 14
	| As = 1
	| N = 1
	| O = 3
	| S = 2
	| ExactMass = 346.963106116 g mol<sup>-1</sup>}}
⚫	| Section3 = {{Chembox Pharmacology
	| AdminRoutes = Oral
⚫	| Metabolism = 89 % Hepatic<ref>Cristau B, Chabas ME, Placidi M. (1975) Voies et cinétiques d'excrétion de l'arsenic chez le Cobaye après injection de divers médicaments organo-arséniés. Ann Pharm Fr 33: 577-89</ref>}}
	}}		}}
	'''Arsthinol''' (]) is an ]. It was synthesized for the first time in 1949 by Ernst A.H. Friedheim by complexation of ] with 2,3-dimercaptopropanol (])<ref>Friedheim EAH. (1949) A Five Day Peroral Treatment of Yaws with STB, a New Trivalent Arsenical. Am J Trop Med Hyg s1-29: 185		'''Arsthinol''' (]) is an ]. It was synthesized for the first time in 1949 by Ernst A.H. Friedheim by complexation of ] with 2,3-dimercaptopropanol (])<ref>{{cite journal | last1 = Friedheim | first1 = Ernst AH | year = 1949 | title = A Five Day Peroral Treatment of Yaws with STB, a New Trivalent Arsenical | journal = ] | volume = s1-29 | issue = 2 | pages = 185–188 | doi = 10.4269/ajtmh.1949.s1-29.185 | pmid = 18116845 }}</ref> and has been demonstrated to be effective against ] and ]. It was marketed a few years later by Endo Products (Balarsen, Tablets, 0.1 g).<ref>{{cite journal | last1 = Anonyme | year = 1953 | title = New and nonofficial remedies; arsthinol | journal = ] | volume = 152 | page = 531 }}</ref>
	</ref> and has been demonstrated to be effective against ] and ]. It was marketed few years latter by Endo Products (Balarsen, Tablets, 0.1 g)<ref>Anonyme. (1953) New and nonofficial remedies; arsthinol. J Am Med Assoc 152: 531</ref>.
			Among trivalent organoarsenicals, arsthinol was considered very well tolerated.<ref>{{cite journal | last1 = Brown | first1 = CH | last2 = Gebhart | first2 = WF | last3 = Reich | first3 = A | year = 1956 | title = Intestinal amebiasis: incidence, symptoms, and treatment with arsthinol (Balarsen) | journal = ] | volume = 160 | issue = 5| pages = 360–363 | doi=10.1001/jama.1956.02960400018005| pmid = 13278204 }}</ref> Recently, it was studied for its anticancer activity.<ref>{{cite journal | last1 = Gibaud | first1 = S | last2 = Alfonsi | first2 = R | last3 = Mutzenhardt | first3 = P |display-authors=et al | year = 2006 | title = (2-Phenyl- dithiarsolan-4-yl)-methanol derivatives show in vitro antileukemic activity | journal = ] | volume = 691 | issue = 5| pages = 1081–1084 | doi=10.1016/j.jorganchem.2005.11.007}}</ref><ref>{{cite journal | last1 = Becherirat | first1 = S. | last2 = Lanhers | first2 = M.-C. | last3 = Socha | first3 = M. | last4 = Yemloul | first4 = M. | last5 = Astier | first5 = A. | last6 = Loboda | first6 = C. | last7 = Aniceto | first7 = N. | last8 = Gibaud | first8 = S. | year = 2013 | title = The antitumor effects of an arsthinol-cyclodextrin complex in an heterotopic mouse model of glioma | url = https://hal.archives-ouvertes.fr/hal-01169157/file/Eur%20J%20Pharm%20Biopharm%202013%20Becherirat.pdf| journal = ] | volume = 85| issue = 3| pages = 560–568| doi = 10.1016/j.ejpb.2013.06.021 | pmid = 23831266 }}</ref>
	Among trivalent organoarsenicals, arthinol was considered as very well tolerated <ref>Brown CH, Gebhart WF, Reich A. (1956) Intestinal amebiasis: incidence, symptoms, and treatment with arsthinol (Balarsen). JAMA 160: 360-363
	</ref>. In 2006 it was studied for its antileukemic activity <ref>Gibaud S, Alfonsi R, Mutzenhardt P et al. (2006) (2-Phenyl- dithiarsolan-4-yl)-methanol derivatives show in vitro antileukemic activity. J Organomet Chem 691: 1081-1084
			==Identification==
	</ref>.
			Arsthinol has ] name of N-phenyl] ] with a ] of C11H14AsNO3S2 and is represented by the ], CC(=O)NC1=C(C=CC(=C1)2SCC(S2)CO)O.<ref>{{Cite web |last=PubChem |title=PubChem |url=https://pubchem.ncbi.nlm.nih.gov/ |access-date=2024-10-17 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
			==Properties==
			The ] of Arsthinol is 347.3 g/mol, with a ] donor count of 3 and a hydrogen bond acceptor count of 5. It has 3 rotatable bonds, an exact mass of 347.279 g/mol, and a ] of 346.963105 g/mol. The ] is 120Ų, and the compound contains 18 heavy atoms. It has no formal charge, a complexity of 308, and contains no ] atoms. There are no defined atom ], but there is 1 undefined atom stereocenter. The compound has no defined or undefined bond stereocenters, includes 1 ] unit, and is ]<ref>{{Cite web |last=PubChem |title=Arsthinol |url=https://pubchem.ncbi.nlm.nih.gov/compound/Arsthinol#section=Synonyms |access-date=2024-10-17 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref><ref>{{Cite web |title=arsthinol {{!}} C11H14AsNO3S2 |url=https://www.chemspider.com/Chemical-Structure.8107.html |access-date=2024-10-17 |website=www.chemspider.com}}</ref>
	==References==		==References==
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