Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H15N5O9S2 |
Molecular Weight | 437.406 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)[C@H](NC(=O)C(=N/OCC(O)=O)\C2=CSC(N)=N2)C(=O)N1OS(O)(=O)=O
InChI
InChIKey=VAMSVIZLXJOLHZ-QWFSEIHXSA-N
InChI=1S/C12H15N5O9S2/c1-12(2)8(10(21)17(12)26-28(22,23)24)15-9(20)7(16-25-3-6(18)19)5-4-27-11(13)14-5/h4,8H,3H2,1-2H3,(H2,13,14)(H,15,20)(H,18,19)(H,22,23,24)/b16-7-/t8-/m1/s1
Molecular Formula | C12H15N5O9S2 |
Molecular Weight | 437.406 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Tigemonam is a dialkylazetidinone derivative patented by E. R. Squibb and Sons, Inc. as a beta-lactam agent useful for the treatment of bacterial infections. Of the orally active beta-lactams, tigemonam is one of the most potent, with a spectrum of activity similar to that of aztreonam and highly resistant to hydrolysis by the beta-lactamase enzymes. Tigemonam inhibits 90% of Escherichia coli, Klebsiella spp., Proteus spp., Salmonella spp., Haemophilus influenzae and Branhamella catarrhalis tested. In localized infections, tigemonam also demonstrated excellent in vivo activity. In acute pyelonephritis in mice caused by Escherichia coli or Proteus sp., tigemonam was very effective. In a rat lung model with Klebsiella pneumoniae, tigemonam was active with a median effective dose of 46 mg/kg compared with 160 mg/kg for cefaclor and over 200 mg/kg for amoxicillin.
Approval Year
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:23:17 GMT 2025
by
admin
on
Mon Mar 31 19:23:17 GMT 2025
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Record UNII |
82H1LDS5D0
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Record Status |
Validated (UNII)
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Record Version |
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-
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Name | Type | Language | ||
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Official Name | English | ||
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Preferred Name | English | ||
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Common Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C260
Created by
admin on Mon Mar 31 19:23:17 GMT 2025 , Edited by admin on Mon Mar 31 19:23:17 GMT 2025
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Code System | Code | Type | Description | ||
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Tigemonam
Created by
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82H1LDS5D0
Created by
admin on Mon Mar 31 19:23:17 GMT 2025 , Edited by admin on Mon Mar 31 19:23:17 GMT 2025
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6100
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102507-71-1
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SUB11046MIG
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DTXSID50883103
Created by
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100000082674
Created by
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3842
Created by
admin on Mon Mar 31 19:23:17 GMT 2025 , Edited by admin on Mon Mar 31 19:23:17 GMT 2025
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C052020
Created by
admin on Mon Mar 31 19:23:17 GMT 2025 , Edited by admin on Mon Mar 31 19:23:17 GMT 2025
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9576769
Created by
admin on Mon Mar 31 19:23:17 GMT 2025 , Edited by admin on Mon Mar 31 19:23:17 GMT 2025
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C152619
Created by
admin on Mon Mar 31 19:23:17 GMT 2025 , Edited by admin on Mon Mar 31 19:23:17 GMT 2025
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m967
Created by
admin on Mon Mar 31 19:23:17 GMT 2025 , Edited by admin on Mon Mar 31 19:23:17 GMT 2025
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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ACTIVE MOIETY |