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{{Short description|Chemical compound}} | |||
{{one source |date=March 2024}} | |||
{{Drugbox | {{Drugbox | ||
| verifiedrevid = |
| verifiedrevid = 443362293 | ||
| IUPAC_name |
| IUPAC_name = 2-(amino)acetic acid | ||
| image |
| image = Acediasulfone Structure.svg | ||
<!--Clinical data--> | |||
| tradename = | |||
⚫ | | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | ||
⚫ | | pregnancy_US = <!-- A / B / C / D / X --> | ||
⚫ | | pregnancy_category = | ||
⚫ | | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | ||
⚫ | | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | ||
⚫ | | legal_UK = <!-- GSL, P, POM, CD, or 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 = 80-03-5 | ||
⚫ | | ATC_prefix = none | ||
⚫ | | ATC_suffix = | ||
⚫ | | ATC_supplemental = | ||
⚫ | | PubChem = 66451 | ||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | |||
⚫ | | DrugBank = DB08926 | ||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| ChemSpiderID = 59823 | | ChemSpiderID = 59823 | ||
| KEGG = D07061 | |||
| UNII_Ref = {{fdacite|correct|FDA}} | |||
⚫ | | UNII = 30YP2YHH8W | ||
| ChEMBL_Ref = {{ebicite|correct|EBI}} | | ChEMBL_Ref = {{ebicite|correct|EBI}} | ||
| ChEMBL = 48396 | | ChEMBL = 48396 | ||
<!--Chemical data--> | |||
⚫ | | chemical_formula = | ||
⚫ | | C=14 | H=14 | N=2 | O=4 | S=1 | ||
⚫ | | smiles = C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)NCC(=O)O | ||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
| StdInChI = 1S/C14H14N2O4S/c15-10-1-5-12(6-2-10)21(19,20)13-7-3-11(4-8-13)16-9-14(17)18/h1-8,16H,9,15H2,(H,17,18) | | StdInChI = 1S/C14H14N2O4S/c15-10-1-5-12(6-2-10)21(19,20)13-7-3-11(4-8-13)16-9-14(17)18/h1-8,16H,9,15H2,(H,17,18) | ||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | ||
| StdInChIKey = FKKUMFTYSTZUJG-UHFFFAOYSA-N | | StdInChIKey = FKKUMFTYSTZUJG-UHFFFAOYSA-N | ||
| smiles1 = O=S(=O)(c1ccc(NCC(=O)O)cc1)c2ccc(N)cc2 | |||
⚫ | | CAS_number |
||
| CAS_supplemental = | |||
⚫ | | ATC_prefix |
||
⚫ | | ATC_suffix |
||
⚫ | | ATC_supplemental |
||
⚫ | | UNII = 30YP2YHH8W | ||
⚫ | | PubChem |
||
⚫ | | DrugBank |
||
⚫ | | chemical_formula |
||
⚫ | | C=14 | H=14 | N=2 | O=4 | S=1 |
||
| molecular_weight = 306.337 g/mol | |||
⚫ | | smiles |
||
⚫ | | bioavailability |
||
⚫ | | protein_bound |
||
⚫ | | metabolism |
||
⚫ | | elimination_half-life = |
||
⚫ | | excretion |
||
⚫ | | pregnancy_AU |
||
⚫ | | pregnancy_US |
||
⚫ | | pregnancy_category= |
||
⚫ | | legal_AU = |
||
⚫ | | legal_CA = |
||
⚫ | | legal_UK = |
||
⚫ | | legal_US = |
||
⚫ | | legal_status |
||
⚫ | | routes_of_administration = |
||
}} | }} | ||
'''Acediasulfone''' (]) is an ] drug, which also has ] activity. It is a long-acting ] of ], which is used for treating ]. | '''Acediasulfone''' (]) is an ] drug, which also has ] activity. It is a long-acting ] of ], which is used for treating ]. | ||
== Synthesis == | |||
Dapsone is somewhat inconvenient to administer to patients because of its rather low water solubility. | |||
] Ltd.); Rawlins, {{US patent|2589211}} (1952 to ]).]] | |||
In the search for more easily administered drugs, dapsone ('''1''') was reacted with ] to give acediasulfone ('''2''') which can be administered as a water-soluble salt. | |||
==References== | == References == | ||
<references/> | <references /> | ||
⚫ | ] | ||
⚫ | {{antimicrobial-stub}} | ||
] | |||
] | |||
⚫ | ] | ||
⚫ | {{antimicrobial-stub}} |
Latest revision as of 15:49, 8 October 2024
Chemical compoundThis article relies largely or entirely on a single source. Relevant discussion may be found on the talk page. Please help improve this article by introducing citations to additional sources. Find sources: "Acediasulfone" – news · newspapers · books · scholar · JSTOR (March 2024) |
Clinical data | |
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ATC code |
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Identifiers | |
IUPAC name
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CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.001.131 |
Chemical and physical data | |
Formula | C14H14N2O4S |
Molar mass | 306.34 g·mol |
3D model (JSmol) | |
SMILES
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InChI
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(verify) |
Acediasulfone (INN) is an antimicrobial drug, which also has antimalarial activity. It is a long-acting prodrug of dapsone, which is used for treating leprosy.
Synthesis
Dapsone is somewhat inconvenient to administer to patients because of its rather low water solubility.
In the search for more easily administered drugs, dapsone (1) was reacted with bromoacetic acid to give acediasulfone (2) which can be administered as a water-soluble salt.
References
- Jackson EL (February 1948). "Certain N-alkyl, N-carboxyalkyl and N-hydroxyalkyl derivatives of 4,4'-diaminodiphenyl sulfone". Journal of the American Chemical Society. 70 (2): 680–4. doi:10.1021/ja01182a074. PMID 18907772.
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