Talampicillin: Difference between revisions

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			{{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}}

	]

	]

Latest revision as of 19:52, 29 April 2023

Chemical compound Pharmaceutical compound

Talampicillin
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	J01CA15 (WHO)
Identifiers
IUPAC name 3-oxo-1,3-dihydro-2-benzofuran-1-yl (2S,5R,6R)-6-{amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylate
CAS Number	47747-56-8
PubChem CID	5373
ChemSpider	64529
UNII	29OJI73DPC
ChEMBL	ChEMBL1322719
CompTox Dashboard (EPA)	DTXSID1048540
ECHA InfoCard	100.051.194
Chemical and physical data
Formula	C₂₄H₂₃N₃O₆S
Molar mass	481.52 g·mol
3D model (JSmol)	Interactive image
SMILES O=C(OC2OC(=O)c1ccccc12)4N5C(=O)(NC(=O)(c3ccccc3)N)5SC4(C)C
InChI InChI=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 Key:SOROUYSPFADXSN-SUWVAFIASA-N
(what is this?) (verify)

Talampicillin is a beta lactam antibiotic from the penicillin 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

Ampicillin remains the penicillin of choice for many infections because of its oral activity and good potency against Gram-negative bacteria. A number of prodrugs have been examined in attempts to improve upon the pharmacodynamic characteristics, and one of these is talampicillin.

One synthesis involved protecting the primary amino group of ampicillin (1) as the enamine with ethyl acetoacetate (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).

References

Isaka I, Nakano K, Kashiwagi T, Koda A, Horiguchi H (January 1976). "Lactol esters of ampicillin". Chemical & Pharmaceutical Bulletin. 24 (1): 102–7. doi:10.1248/cpb.24.102. PMID 1269054.
Clayton JP, Cole M, Elson SW, Ferres H, Hanson JC, Mizen LW, Sutherland R (December 1976). "Preparation, hydrolysis, and oral absorption of lactonyl esters of penicillins". Journal of Medicinal Chemistry. 19 (12): 1385–91. doi:10.1021/jm00234a007. PMID 826629.
DE 2228012, Ferres H, Clayton MP, "Phthalide penicillin ester intermediates", issued 1972, assigned to Beecham
US 3860579, Ferres H, Clayton MP, "Phthalide Peniclillin Ester and Salts", issued 1975, assigned to Beecham
US 3951954, Murakami, "Novel oxofuryl ester derivatives of penicillin and cephalosporin", issued 1976, assigned to Yamanouchi

Antibacterials active on the cell wall and envelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) Benzathine benzylpenicillin Procaine benzylpenicillin Phenoxymethylpenicillin (V) Propicillin Pheneticillin Azidocillin Clometocillin Penamecillin
β-lactamase resistant (2nd generation)	Cloxacillin (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin Ampicillin (Pivampicillin Hetacillin Bacampicillin Lenampicillin Metampicillin Talampicillin) Epicillin
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin / Carindacillin Temocillin
Ureidopenicillins (4th generation)	Piperacillin Azlocillin Mezlocillin
Other	Mecillinam (Pivmecillinam) Sulbenicillin

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin Cefalexin Cefadroxil Cefapirin Cefazedone Cefazaflur Cefradine Cefroxadine Ceftezole Cefaloglycin Cefacetrile Cefalonium Cefaloridine Cefalotin Cefatrizine
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole Cefonicid Ceforanide Cefuzonam Cephamycin (Cefoxitin Cefotetan Cefminox Cefbuperazone Cefmetazole) Carbacephem (Loracarbef)
3rd generation	Cefixime Ceftriaxone Cefotaxime Antipseudomonal (Ceftazidime Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam Cefetamet Cefodizime Cefpimizole Cefsulodin Cefteram Ceftiolene Oxacephem (Flomoxef Latamoxef)
4th generation	Cefepime Cefozopran Cefpirome Cefquinome
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

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

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