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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

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

PubMed

PubMed

TitleDatePubMed
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:52:03 UTC 2023
Edited
by admin
on Fri Dec 15 18:52:03 UTC 2023
Record UNII
82H1LDS5D0
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
Code System Code Type Description
WIKIPEDIA
Tigemonam
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
FDA UNII
82H1LDS5D0
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
INN
6100
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
CAS
102507-71-1
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
EVMPD
SUB11046MIG
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID50883103
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
SMS_ID
100000082674
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
DRUG CENTRAL
3842
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
MESH
C052020
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
PUBCHEM
9576769
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
NCI_THESAURUS
C152619
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY
MERCK INDEX
m967
Created by admin on Fri Dec 15 18:52:03 UTC 2023 , Edited by admin on Fri Dec 15 18:52:03 UTC 2023
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY