Tigemonam

Tigemonam: Tigemonam

IUPAC name

2-[[1-(2-Amino-1,3-thiazol-4-yl)- 2-[[(3S)-2,2-dimethyl-4-oxo-1- sulfooxyazetidin-3-yl]amino]-2- oxoethylidene]amino]oxyacetic acid

Identifiers

CAS number 102507-71-1

PubChem 9576769

Jmol-3D images Image 1

SMILES

CC1([C@@H](C(=O)N1OS(=O)(=O)O)NC(=O)/C(=N\OCC(=O)O)/C2=CSC(=N2)N)C

Properties

Molecular formula C₁₂H₁₅N₅O₉S₂

Molar mass 437.4056

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Tigemonam is a monobactam antibiotic.^[1]^[2]

References

^ Fuchs PC, Jones RN, Barry AL (March 1988). "In vitro antimicrobial activity of tigemonam, a new orally administered monobactam". Antimicrob. Agents Chemother. 32 (3): 346–9. PMC 172173. PMID 3259122. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=3259122.

^ Chin NX, Neu HC (January 1988). "Tigemonam, an oral monobactam". Antimicrob. Agents Chemother. 32 (1): 84–91. PMC 172104. PMID 3279906. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=3279906.

v · d · eAntibacterials: cell envelope antibiotics (J01C-J01D)

Intracellular
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)

Glycopeptide
inhibit PG chain elongation: Vancomycin^# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin

β-lactams/
(inhibit PBP
cross-links)

Penicillins/
(penams)

Extended sp.

aminopenicillins: Amoxicillin^# • Ampicillin^# (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin) • Epicillin

carboxypenicillins: Carbenicillin (Carindacillin) • Ticarcillin • Temocillin

ureidopenicillins: Azlocillin • Piperacillin • Mezlocillin
other: Mecillinam (Pivmecillinam) • Sulbenicillin

Narrow sp.

β-lactamase sensitive

Benzylpenicillin (G)^#: Clometocillin • Benzathine benzylpenicillin^# • Procaine benzylpenicillin^# • Azidocillin • Penamecillin
Phenoxymethylpenicillin (V)^#: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin

β-lactamase resistant

Cloxacillin^# (Dicloxacillin, Flucloxacillin) • Oxacillin • Meticillin • Nafcillin

Penems

Faropenem

Carbapenems

Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem

Cephalosporins/
(cephems)

1st (P Ec K)

Cefazolin^# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole

2nd (H E N)

Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)

3rd

Cefixime^# • Ceftriaxone^# • antipseudomonal (Ceftazidime^# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ^‡)

4th (antips-)

Cefepime • Cefozopran • Cefpirome • Cefquinome

5th

Ceftobiprole • Ceftaroline fosamil

Veterinary

Ceftiofur • Cefquinome • Cefovecin

Monobactams

Aztreonam • Tigemonam • Carumonam • Tabtoxin

β-lactamase inh.

penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)

Combinations

Amoxicillin/clavulanic acid^# • Imipenem/cilastatin^# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam

Other
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin

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

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)

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Tigemonam

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Tigemonam

IUPAC name 2-[[1-(2-Amino-1,3-thiazol-4-yl)- 2-[[(3S)-2,2-dimethyl-4-oxo-1- sulfooxyazetidin-3-yl]amino]-2- oxoethylidene]amino]oxyacetic acid
Identifiers
CAS number	102507-71-1
PubChem	9576769
Jmol-3D images	Image 1
SMILES CC1([C@@H](C(=O)N1OS(=O)(=O)O)NC(=O)/C(=N\OCC(=O)O)/C2=CSC(=N2)N)C
Properties
Molecular formula	C₁₂H₁₅N₅O₉S₂
Molar mass	437.4056
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Tigemonam

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