13-09509. Tigemonam [Archived]

Nomenclature

CAS number: 102507-71-1
[[(Z)-[1-(2-Amino-4-thiazolyl)-2-[[(3S)-2,2-dimethyl-4-oxo-1-(sulfooxy)-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]acetic acid; [[[(Z)-(2-amino-4-thiazolyl)[[(3S)-1-hydroxy-2,2-dimethyl-4-oxo-3-azetidinyl]carbamoyl]methylene]amino]oxy]acetic acid hydrogen sulfate (ester).
C12H15N5O9S2; mol wt 437.41.
C 32.95%, H 3.46%, N 16.01%, O 32.92%, S 14.66%.

Description and references

Orally active synthetic monosulfactam, structurally similar to the monobactam aztreonam. Prepn: C. Yoshida et al., J. Antibiot. 38, 1536 (1985); W. A. Slusarchyk et al., BE 904121; W. A. Slusarchyk, W. H. Koster, US 4638061 (1986, 1987 both to Squibb). Antibacterial spectrum and β-lactamase stability in vitro: S. K. Tanaka et al., Antimicrob. Agents Chemother. 31, 219 (1987); N.-X. Chin, H. C. Neu, ibid. 32, 84 (1988). Antibacterial activity and pharmacokinetics in animals: J. M. Clark et al., ibid. 31, 226 (1987).

Chemical structure

Derivative

Disodium salt.

Nomenclature

SQ-30213.
C12H13N5Na2O9S2; mol wt 481.37.
C 29.94%, H 2.72%, N 14.55%, Na 9.55%, O 29.91%, S 13.32%.

Properties

mp 140-145° (dec).

Derivative

Dicholine salt.

Nomenclature

CAS number: 102916-21-2
SQ-30836; Tigemen (BMS).
C22H41N2O11S2; mol wt 573.70.
C 46.06%, H 7.20%, N 4.88%, O 30.68%, S 11.18%.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Monobactams

Status

This monograph has been retired and is no longer subject to revision or update.