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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
Structure of TIGEMONAM

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

HIDE SMILES / InChI
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

PubMed

PubMed

TitleDatePubMed
In vitro antimicrobial activity of tigemonam, a new orally administered monobactam.
1988 Mar
Patents
Name Type Language
TIGEMONAM
INN   MART.   MI  
INN  
Official Name English
tigemonam [INN]
Common Name English
TIGEMONAM [MI]
Common Name English
TIGEMONAM [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C260
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
Code System Code Type Description
WIKIPEDIA
Tigemonam
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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FDA UNII
82H1LDS5D0
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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INN
6100
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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CAS
102507-71-1
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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EVMPD
SUB11046MIG
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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EPA CompTox
DTXSID50883103
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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SMS_ID
100000082674
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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DRUG CENTRAL
3842
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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MESH
C052020
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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PUBCHEM
9576769
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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NCI_THESAURUS
C152619
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
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MERCK INDEX
m967
Created by admin on Fri Dec 15 18:52:03 GMT 2023 , Edited by admin on Fri Dec 15 18:52:03 GMT 2023
PRIMARY Merck Index