1935. Cefotiam

Nomenclature

CAS number: 61622-34-2
(6R,7R)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-[[[1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-yl]-thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7β-[2-(aminothiazol-4-yl)acetamido]-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylic acid; SCE-963.
C18H23N9O4S3; mol wt 525.63.
C 41.13%, H 4.41%, N 23.98%, O 12.18%, S 18.30%.

Description and references

Semi-synthetic cephalosporin antibiotic. Prepn: S. Terao et al., DE 2458695; M. Numata et al., US 4080498 (1975, 1978 both to Takeda); eidem, J. Antibiot. 31, 1262 (1978). Prepn of the crystalline dihydrochloride: K. Naito et al., DE 2738711; eidem, US 4146710 (1978, 1979 both to Takeda). Pharmacodynamics: K. Tsuchiya et al., ibid. 1272. Antibacterial spectrum: eidem, Antimicrob. Agents Chemother. 14, 557 (1978). Clinical trial in respiratory infections: H. M. Beumer et al., Int. J. Clin. Pharmacol. Ther. Toxicol. 23, 105 (1985).

Chemical structure

Derivative

Dihydrochloride.

Nomenclature

CAS number: 66309-69-1
Abbott 48999; CGP-14221/E; Halospor (Novartis); Pansporin (Takeda); Pansporine (Cassenne-Takeda); Spizef (Grünenthal); Sporidyn (Cyanamid).
C18H23N9O4S3.2HCl; mol wt 598.55.
C 36.12%, H 4.21%, N 21.06%, O 10.69%, S 16.07%, Cl 11.85%.

Properties

White to light yellow crystals. Sol in methanol. Slightly sol in ethanol.

Derivative

1-(Cyclohexyloxycarbonyloxy)ethyl ester dihydrochloride.

Nomenclature

CAS number: 95789-30-3
Cefotiam hexetil hydrochloride; SCE-2174; Pansporin T (Takeda); Taketiam (Takeda); Texodil (Cassenne).
C27H37N9O7S3.2HCl; mol wt 768.76.
C 42.18%, H 5.11%, N 16.40%, O 14.57%, S 12.51%, Cl 9.22%.

Description and references

Prepn: T. Nishimura et al., EP 128029; eidem, US 5120841 (1984, 1992 both to Takeda); eidem et al., J. Antibiot. 40, 81 (1987). Acute toxicity: S. Chiba et al., Oyo Yakuri 35, 179 (1988), C.A. 109, 31615c (1988). Clinical trial: H. Maier et al. Arzneim.-Forsch. 42, 980 (1992).

Properties

Colorless powder. Soly in water at pH 4.5: >1 mg/ml. LD50 in male, female mice, male, female rats (mg/kg): 1290, 1150, 1470, 1620 i.p.; >2000 s.c.; >5000 orally (Chiba).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins