| Revision as of 18:23, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 462988068 of page Sultiame for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 16:17, 25 September 2024 edit 2601:200:4400:6290:48f2:c399:e1ca:12db (talk)No edit summaryTags: Mobile edit Mobile web edit |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Infobox drug |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 409968742 |
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| verifiedrevid = 470474738 |
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| IUPAC_name = 4-(1,1-dioxothiazinan-2-yl)benzenesulfonamide |
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| IUPAC_name = 4-(1,1-dioxothiazinan-2-yl)benzenesulfonamide |
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| image = Sultiame.svg |
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| image = Sultiame.svg |
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| AAN = Sulthiame |
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| USAN = sulthiame |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Ospolot |
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| Drugs.com = {{drugs.com|international|sultiame}} |
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| Drugs.com = {{drugs.com|international|sultiame}} |
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| pregnancy_AU = D |
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| pregnancy_AU = D |
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| pregnancy_US = D |
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| legal_AU = S4 |
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| legal_UK = POM |
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| legal_UK = POM |
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| legal_US = Rx-only |
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| legal_US = Rx-only |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 61-56-3 --> |
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| CAS_number = 61-56-3 |
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| ATC_prefix = N03 |
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| ATC_prefix = N03 |
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| ATC_suffix = AX03 |
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| ATC_suffix = AX03 |
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| PubChem = 5356 |
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| PubChem = 5356 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB08329 |
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| DrugBank = DB08329 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5163 |
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| ChemSpiderID = 5163 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = I00Q766CZ2 |
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| UNII = I00Q766CZ2 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=10 | H=14 | N=2 | O=4 | S=2 |
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| C=10 | H=14 | N=2 | O=4 | S=2 |
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| molecular_weight = 290.0395 g/mol |
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| smiles = O=S2(=O)N(c1ccc(cc1)S(=O)(=O)N)CCCC2 |
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| smiles = O=S2(=O)N(c1ccc(cc1)S(=O)(=O)N)CCCC2 |
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| InChI = 1/C10H14N2O4S2/c11-18(15,16)10-5-3-9(4-6-10)12-7-1-2-8-17(12,13)14/h3-6H,1-2,7-8H2,(H2,11,15,16) |
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| InChIKey = HMHVCUVYZFYAJI-UHFFFAOYAA |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H14N2O4S2/c11-18(15,16)10-5-3-9(4-6-10)12-7-1-2-8-17(12,13)14/h3-6H,1-2,7-8H2,(H2,11,15,16) |
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| StdInChI = 1S/C10H14N2O4S2/c11-18(15,16)10-5-3-9(4-6-10)12-7-1-2-8-17(12,13)14/h3-6H,1-2,7-8H2,(H2,11,15,16) |
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| StdInChIKey = HMHVCUVYZFYAJI-UHFFFAOYSA-N |
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| StdInChIKey = HMHVCUVYZFYAJI-UHFFFAOYSA-N |
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}} |
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}} |
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'''Sultiame''' (or '''sulthiame''') is a ] and ] of the ] ]. It is used as an ] and in recent studies showed promise in reducing sleep disordered breathing and other symptoms of obstructive sleep apnea (OSA). |
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==History== |
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Sultiame was first synthesised in the laboratories of ] AG in the mid-1950s and eventually launched as '''Ospolot''' in ] and other markets the early 1960s. It never became a registered drug in the United States. The brand was transferred to Desitin GmbH in 1993 and is sold in several European countries, in Israel, Japan, and Australia. |
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Sultiame became established as a second-line drug for treatment of ] epilepsy in the 1960s and 1970s and was often used in combination with the established anticonvulsant ]. ] appeared particularly responsive to sultiame. Doubts subsequently arose as to whether sultiame has ] anticonvulsant properties. After discovering sultiame's ability to raise the blood levels of ],<ref name = "Hansen_1968">{{cite journal | vauthors = Hansen JM, Kristensen M, Skovsted L | title = Sulthiame (Ospolot) as inhibitor of diphenylhydatoin metabolism | journal = Epilepsia | volume = 9 | issue = 1 | pages = 17–22 | date = March 1968 | pmid = 4386877 | doi = 10.1111/j.1528-1157.1968.tb04954.x | s2cid = 20168357 }}</ref> it was assumed that sultiame would only act in combination with phenytoin. This finding, together with the equivocal results of a study in the US,<ref name = "Hansen_1968" /> resulted in a quick decline of sultiame's use. It was only in 1988, that the ] child neurologist ] discovered its specific effects in ].<ref>{{cite journal | vauthors = Doose H, Baier WK, Ernst JP, Tuxhorn I, Völzke E | title = Benign partial epilepsy--treatment with sulthiame | journal = Developmental Medicine and Child Neurology | volume = 30 | issue = 5 | pages = 683–4 | date = October 1988 | pmid = 2906619 | doi = 10.1111/j.1469-8749.1988.tb04809.x | s2cid = 37726714 }}</ref> Today, sulthiame is the drug of choice for benign focal epilepsies of childhood (such as ]) in the ]-speaking countries and Israel.<ref>{{cite journal | vauthors = Debus OM, Kurlemann G | title = Sulthiame in the primary therapy of West syndrome: a randomized double-blind placebo-controlled add-on trial on baseline pyridoxine medication | journal = Epilepsia | volume = 45 | issue = 2 | pages = 103–8 | date = February 2004 | pmid = 14738417 | doi = 10.1111/j.0013-9580.2004.19003.x | doi-access = free }}</ref><ref>{{cite journal | vauthors = Koepp MJ, Patsalos PN, Sander JW | title = Sulthiame in adults with refractory epilepsy and learning disability: an open trial | journal = Epilepsy Research | volume = 50 | issue = 3 | pages = 277–82 | date = August 2002 | pmid = 12200218 | doi = 10.1016/s0920-1211(02)00054-2 | s2cid = 13220334 }}</ref> |
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==Indications== |
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Historically, sultiame has been used to treat ] seizures. In Australia, it is currently registered for behavioural disorders associated with ]; ] behaviour; temporal lobe epilepsy; ] ]s; ] attacks; and ]s.<ref></ref> In contrast to other sulfonamide drugs, sultiame is devoid of ] activity. |
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Latest research is evaluating sultiamine for sleep apnea with early positive results.<ref></ref> |
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==Adverse effects== |
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{{unreferenced section|date=October 2015}} |
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The more common adverse effects are ], ] of face and limbs, ], ], and ]. Less common adverse effects include giddiness, rash, ], ], weight loss, ], headache, depression, drooling, increased pain, ], ]. Disturbances in ] and ] ] have been occasionally reported after long-term use. |
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== Interactions == |
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Sultiame taken together with ] may lead to severe side-effects, including psychotic reactions. The addition of sulthiame to phenytoin therapy has shown to be followed by a rise in the serum levels of phenytoin. Sultiame may also lead to a rise of ] blood levels. ] must not be consumed during treatment. |
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==Overdose== |
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], ], headache, ], ], metabolic ] with ] and ] state may occur. There is no specific ]. It is not known whether ] may help in case of overdose. |
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==Synthesis== |
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] |
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] can be reacted with ω-chlorobutylsulfonyl chloride and aqueous sodium carbonate to form the presumed intermediate (middle), which spontaneously cyclizes to give the drug. |
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== References == |
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{{reflist|1}} |
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{{Anticonvulsants}} |
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] |
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] |
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] |
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] |
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] |
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] |