Movatterモバイル変換

[0]ホーム

Jump to content

Talampicillin

Edit links

From Wikipedia, the free encyclopedia

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-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
CAS Number	47747-56-8^Y
PubChemCID	5373
ChemSpider	64529^N
UNII	29OJI73DPC
ChEMBL	ChEMBL1322719^N
CompTox Dashboard(EPA)	DTXSID1048540
ECHA InfoCard	100.051.194
Chemical and physical data
Formula	C₂₄H₂₃N₃O₆S
Molar mass	481.52 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(OC2OC(=O)c1ccccc12)[C@@H]4N5C(=O)[C@@H](NC(=O)[C@@H](c3ccccc3)N)[C@H]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^N Key:SOROUYSPFADXSN-SUWVAFIASA-N^N
^NY (what is this?) (verify)

Talampicillin is abeta lactam antibiotic from thepenicillin 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

[edit]

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

Talampicillin synthesis:^[1]^[2]^[3]^[4]^[5]

One synthesis involved protecting the primary amino group ofampicillin (1) as the enamine withethyl 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).^{[citation needed]}

References

[edit]

^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 thecell wall andenvelope (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

InhibitPG subunit synthesis and transport:NAM synthesis inhibition
- Fosfomycin
DADAL/AR inhibitors
- Cycloserine
- Terizidone
bactoprenol inhibitors
- Bacitracin

Other

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

This systemicantibiotic-related article is astub. You can help Wikipedia byadding missing information.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Talampicillin&oldid=1332224093"

Categories:

Hidden categories:

[8]ページ先頭