| Revision as of 14:24, 27 September 2010 editحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 editsm Adding category Category:Lactones (using HotCat)← Previous edit |
Latest revision as of 19:52, 29 April 2023 edit undoInnerstream (talk | contribs)Autopatrolled, Extended confirmed users4,021 editsmNo edit summary |
| (35 intermediate revisions by 25 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
| ⚫ |
| IUPAC_name = 3-oxo-1,3-dihydro-2-benzofuran-1-yl (2''S'',5''R'',6''R'')-6-{amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylate |
|
|
|
| Watchedfields = changed |
| ⚫ |
| image = Talampicillin.png |
|
|
|
| verifiedrevid = 387321143 |
| ⚫ |
| CAS_number = 47747-56-8 |
|
|
⚫ |
| IUPAC_name = 3-oxo-1,3-dihydro-2-benzofuran-1-yl (2''S'',5''R'',6''R'')-6-{amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylate |
| ⚫ |
| ATC_prefix = J01 |
|
|
⚫ |
| image = Talampicillin.svg |
| ⚫ |
| ATC_suffix = CA15 |
|
| ⚫ |
| PubChem = 5373 |
|
|
| DrugBank = |
|
| ⚫ |
| C=24|H=23|N=3|O=6|S=1 |
|
|
| molecular_weight = 481.52092 |
|
|
| bioavailability = |
|
|
| protein_bound = |
|
|
| metabolism = |
|
|
| elimination_half-life = |
|
|
| excretion = |
|
| ⚫ |
| 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 = |
|
| ⚫ |
}} |
|
|
'''Talampicillin''' is a ] ] from the ] family. |
|
|
|
|
|
|
|
<!--Clinical data--> |
| ⚫ |
{{Cell wall disruptive antibiotics}} |
|
|
|
| tradename = |
|
|
| Drugs.com = {{drugs.com|international|talampicillin}} |
|
⚫ |
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
|
⚫ |
| pregnancy_US = <!-- A / B / C / D / X --> |
|
⚫ |
| 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 --> |
|
|
|
|
|
|
<!--Identifiers--> |
|
prodgug,oral use, |
|
|
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
ampicilin + 3-oksoftalid |
|
|
⚫ |
| CAS_number = 47747-56-8 |
|
stable in acidic |
|
|
⚫ |
| ATC_prefix = J01 |
|
⚫ |
| ATC_suffix = CA15 |
|
⚫ |
| PubChem = 5373 |
|
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
|
| UNII_Ref = {{fdacite|changed|FDA}} |
|
|
| UNII = 29OJI73DPC |
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEMBL = 1322719 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 64529 |
|
|
|
|
|
|
<!--Chemical data--> |
|
⚫ |
| C=24 | H=23 | N=3 | O=6 | S=1 |
|
|
| smiles = O=C(OC2OC(=O)c1ccccc12)4N5C(=O)(NC(=O)(c3ccccc3)N)5SC4(C)C |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 1S/C24H23N3O6S/c1-24(2)17(22(31)33-23-14-11-7-6-10-13(14)21(30)32-23)27-19(29)16(20(27)34-24)26-18(28)15(25)12-8-4-3-5-9-12/h3-11,15-17,20,23H,25H2,1-2H3,(H,26,28)/t15-,16-,17+,20-,23?/m1/s1 |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = SOROUYSPFADXSN-SUWVAFIASA-N |
|
⚫ |
}} |
|
|
'''Talampicillin''' is a ] ] from the ] family. It is an acid stable prodrug that was administered orally. It is not approved by the FDA for use in the United States. It should be avoided in Liver diseases |
|
|
|
|
|
|
==Synthesis== |
|
|
] remains the penicillin of choice for many infections because of its oral activity and good potency against ]. A number of ] have been examined in attempts to improve upon the ] characteristics, and one of these is talampicillin. |
|
|
] |
|
|
One synthesis involved protecting the primary amino group of ] ('''1''') as the enamine with ] ('''2'''). THis was then esterified by reaction with 3-bromopthalide ('''3'''), and the enamine was carefully hydrolyzed with dilute HCl in acetonitrile to produce talampicillin ('''4''').{{cn|date=March 2023}} |
|
|
|
|
|
|
==References== |
|
|
{{Reflist}} |
|
⚫ |
{{Cell wall disruptive antibiotics}} |
|
|
|
|
⚫ |
] |
|
⚫ |
] |
|
|
] |
|
|
|
|
|
|
|
|
|
{{Antibiotic-stub}} |
|
{{Antibiotic-stub}} |
|
|
|
|
] |
|
|
|
|
|
] |
|
| ⚫ |
] |
|
| ⚫ |
] |
|