U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H13N5O9S2.2C5H14NO
Molecular Weight 643.731
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TIGEMONAM DICHOLINE

SMILES

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

InChI

InChIKey=FRVWKWRHJIDCFO-ZJFJOYJNSA-L
InChI=1S/C12H15N5O9S2.2C5H14NO/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;2*1-6(2,3)4-5-7/h4,8H,3H2,1-2H3,(H2,13,14)(H,15,20)(H,18,19)(H,22,23,24);2*7H,4-5H2,1-3H3/q;2*+1/p-2/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

Molecular Formula C5H13NO
Molecular Weight 103.1628
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:48:07 UTC 2023
Edited
by admin
on Fri Dec 15 17:48:07 UTC 2023
Record UNII
648358RH17
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIGEMONAM DICHOLINE
USAN  
USAN  
Official Name English
SQ-30836
Code English
TIGEMEN
Brand Name English
TIGEMONAM DICHOLINE [USAN]
Common Name English
Choline, salt with [[[(Z)-(2-amino-4-thiazolyl)[[(3S)-1-hydroxy-2,2-dimethyl-4-oxo-3-azetidinyl]carbamoyl]methylene]amino]oxy]acetic acid hydrogen sulfate (ester) (2:1)
Common Name English
SQ 30836
Code English
TIGEMONAM DICHOLINE SALT [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C260
Created by admin on Fri Dec 15 17:48:07 UTC 2023 , Edited by admin on Fri Dec 15 17:48:07 UTC 2023
Code System Code Type Description
USAN
Y-68
Created by admin on Fri Dec 15 17:48:07 UTC 2023 , Edited by admin on Fri Dec 15 17:48:07 UTC 2023
PRIMARY
MERCK INDEX
m967
Created by admin on Fri Dec 15 17:48:07 UTC 2023 , Edited by admin on Fri Dec 15 17:48:07 UTC 2023
PRIMARY Merck Index
PUBCHEM
14253084
Created by admin on Fri Dec 15 17:48:07 UTC 2023 , Edited by admin on Fri Dec 15 17:48:07 UTC 2023
PRIMARY
CAS
102916-21-2
Created by admin on Fri Dec 15 17:48:07 UTC 2023 , Edited by admin on Fri Dec 15 17:48:07 UTC 2023
PRIMARY
NCI_THESAURUS
C152620
Created by admin on Fri Dec 15 17:48:07 UTC 2023 , Edited by admin on Fri Dec 15 17:48:07 UTC 2023
PRIMARY
FDA UNII
648358RH17
Created by admin on Fri Dec 15 17:48:07 UTC 2023 , Edited by admin on Fri Dec 15 17:48:07 UTC 2023
PRIMARY
MESH
C052020
Created by admin on Fri Dec 15 17:48:07 UTC 2023 , Edited by admin on Fri Dec 15 17:48:07 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY