Arsthinol: Difference between revisions

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Revision as of 13:49, 28 October 2011 editBeetstra (talk \| contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: '').← Previous edit		Revision as of 14:00, 28 October 2011 edit undoCheMoBot (talk \| contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - added verified revid - updated 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user...Next edit →
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	{{chembox		{{chembox
			\| Verifiedfields = changed
			\| verifiedrevid = 457817818
	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = QNT09A162Y		\| UNII = QNT09A162Y
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	\| Section1 = {{Chembox Identifiers		\| Section1 = {{Chembox Identifiers
	\| CASNo = 119-96-0		\| CASNo = 119-96-0
	\| CASNo_Ref = {{cascite\|~~correct~~\|??}}		\| CASNo_Ref = {{cascite\|changed\|??}}
	\| PubChem = 8414		\| PubChem = 8414
	\| PubChem_Ref = {{Pubchemcite\|correct\|PubChem}}		\| PubChem_Ref = {{Pubchemcite\|correct\|PubChem}}
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	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| EINECS = 204-361-7		\| EINECS = 204-361-7
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D07356		\| KEGG = D07356
	\| ATCCode_prefix = P01		\| ATCCode_prefix = P01
	\| ATCCode_suffix = AR01		\| ATCCode_suffix = AR01

Revision as of 14:00, 28 October 2011

{{chembox | Verifiedfields = changed | verifiedrevid = 457817818 | UNII_Ref = | UNII = QNT09A162Y | ImageFile = Arsthinol.svg | ImageFile_Ref = | ImageSize = 244 | ImageName = Structural formula of arsthinol | SystematicName = N-{2-Hydroxy-5-phenyl}acetamide | Section1 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers

CAS Number

119-96-0

3D model (JSmol)

| ChemSpider

8107

| ECHA InfoCard | 100.003.965 |- | EC Number

204-361-7

| KEGG

D07356

PubChem CID

8414

CompTox Dashboard (EPA)

DTXSID40861753

| colspan="2" |

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

| colspan="2" |

SMILES

CC(=O)NC1=C(O)C=CC(=C1)1SCC(CO)S1
O=C(Nc2cc(1SCC(S1)CO)ccc2O)C

|- | Section2 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Properties

Chemical formula

| C₁₁H₁₄AsNO₃S₂

|- | Molar mass

| 347.28 g·mol

|- | Section3 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Pharmacology

Routes of
administration

| Oral |- | colspan=2 style="text-align:left; background-color:#eaeaea;" | Pharmacokinetics: |- |-

| style="padding-left:1em;" |

Metabolism

| 89 % Hepatic

|- |- }} 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 few years latter by Endo Products (Balarsen, Tablets, 0.1 g). Among trivalent organoarsenicals, arthinol was considered as very well tolerated . In 2006 it was studied for its antileukemic activity .

References

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
Friedheim EAH. (1949) A Five Day Peroral Treatment of Yaws with STB, a New Trivalent Arsenical. Am J Trop Med Hyg s1-29: 185
Anonyme. (1953) New and nonofficial remedies; arsthinol. J Am Med Assoc 152: 531
Brown CH, Gebhart WF, Reich A. (1956) Intestinal amebiasis: incidence, symptoms, and treatment with arsthinol (Balarsen). JAMA 160: 360-363
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

Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)

Entamoeba

Tissue amebicides

Nitroimidazole derivatives	Metronidazole Tinidazole Ornidazole Nimorazole Secnidazole Azanidazole Propenidazole
Other	isoquinoline (Emetine/Dehydroemetine)

Luminal amebicides

Hydroxyquinoline derivatives

related: Chiniofon

Dichloroacetamide derivatives

Aminoglycoside

Paromomycin

Other/ungrouped

Acanthamoeba

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

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