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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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{{Antimicrobial-stub}} {{Antimicrobial-stub}}

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Latest revision as of 11:08, 17 October 2024

Arsthinol
Structural formula of arsthinol
Names
Preferred IUPAC name N-{2-Hydroxy-5-phenyl}acetamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.965 Edit this at Wikidata
EC Number
  • 204-361-7
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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)Key: MRUDSZSRLQAPOG-UHFFFAOYSA-N
  • 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)Key: MRUDSZSRLQAPOG-UHFFFAOYAP
SMILES
  • CC(=O)NC1=C(O)C=CC(=C1)1SCC(CO)S1
  • O=C(Nc2cc(1SCC(S1)CO)ccc2O)C
Properties
Chemical formula C11H14AsNO3S2
Molar mass 347.28 g·mol
Pharmacology
ATC code P01AR01 (WHO) QP51AD01 (WHO)
Routes of
administration 		Oral
Pharmacokinetics:
Metabolism 89 % Hepatic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Arsthinol (INN) is an antiprotozoal agent. It was synthesized for the first time in 1949 by Ernst A.H. Friedheim by complexation of acetarsol with 2,3-dimercaptopropanol (British anti-Lewisite) and has been demonstrated to be effective against amoebiasis and yaws. It was marketed a few years later by Endo Products (Balarsen, Tablets, 0.1 g).

Among trivalent organoarsenicals, arsthinol was considered very well tolerated. Recently, it was studied for its anticancer activity.

Identification

Arsthinol has IUPAC name of N-phenyl] acetamide with a molecular formula of C11H14AsNO3S2 and is represented by the SMILES notation, CC(=O)NC1=C(C=CC(=C1)2SCC(S2)CO)O.

Properties

The molecular weight of Arsthinol is 347.3 g/mol, with a hydrogen bond 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 monoisotopic mass of 346.963105 g/mol. The topological polar surface area is 120Ų, and the compound contains 18 heavy atoms. It has no formal charge, a complexity of 308, and contains no isotope atoms. There are no defined atom stereocenters, but there is 1 undefined atom stereocenter. The compound has no defined or undefined bond stereocenters, includes 1 covalently bonded unit, and is canonicalized.

References

  1. 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.
  2. Friedheim, Ernst AH (1949). "A Five Day Peroral Treatment of Yaws with STB, a New Trivalent Arsenical". Am J Trop Med Hyg. s1-29 (2): 185–188. doi:10.4269/ajtmh.1949.s1-29.185. PMID 18116845.
  3. Anonyme (1953). "New and nonofficial remedies; arsthinol". J Am Med Assoc. 152: 531.
  4. Brown, CH; Gebhart, WF; Reich, A (1956). "Intestinal amebiasis: incidence, symptoms, and treatment with arsthinol (Balarsen)". JAMA. 160 (5): 360–363. doi:10.1001/jama.1956.02960400018005. PMID 13278204.
  5. 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 (5): 1081–1084. doi:10.1016/j.jorganchem.2005.11.007.
  6. Becherirat, S.; Lanhers, M.-C.; Socha, M.; Yemloul, M.; Astier, A.; Loboda, C.; Aniceto, N.; Gibaud, S. (2013). "The antitumor effects of an arsthinol-cyclodextrin complex in an heterotopic mouse model of glioma" (PDF). Eur J Pharm Biopharm. 85 (3): 560–568. doi:10.1016/j.ejpb.2013.06.021. PMID 23831266.
  7. PubChem. "PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-10-17.
  8. PubChem. "Arsthinol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-10-17.
  9. "arsthinol | C11H14AsNO3S2". www.chemspider.com. Retrieved 2024-10-17.
Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)
Entamoeba
Tissue amebicides
Nitroimidazole derivatives
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Hydroxyquinoline derivatives
Dichloroacetamide derivatives
Aminoglycoside
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