Cefotiam

Title: Cefotiam
CAS Registry Number: 61622-34-2
CAS Name: (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
Additional Names: 7b-[2-(aminothiazol-4-yl)acetamido]-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylic acid
Manufacturers' Codes: SCE-963
Molecular Formula: C18H23N9O4S3
Molecular Weight: 525.63
Percent Composition: C 41.13%, H 4.41%, N 23.98%, O 12.18%, S 18.30%
Literature 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).
Derivative Type: Dihydrochloride
CAS Registry Number: 66309-69-1
Manufacturers' Codes: Abbott 48999; CGP-14221/E
Trademarks: Halospor (Novartis); Pansporin (Takeda); Pansporine (Cassenne-Takeda); Spizef (Grenthal); Sporidyn (Cyanamid)
Molecular Formula: C18H23N9O4S3.2HCl
Molecular Weight: 598.55
Percent Composition: 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 Type: 1-(Cyclohexyloxycarbonyloxy)ethyl ester dihydrochloride
CAS Registry Number: 95789-30-3
Additional Names: Cefotiam hexetil hydrochloride
Manufacturers' Codes: SCE-2174
Trademarks: Pansporin T (Takeda); Taketiam (Takeda); Texodil (Cassenne)
Molecular Formula: C27H37N9O7S3.2HCl
Molecular Weight: 768.76
Percent Composition: C 42.18%, H 5.11%, N 16.40%, O 14.57%, S 12.51%, Cl 9.22%
Literature 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).
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 1290, 1150, 1470, 1620 i.p.; >2000 s.c.; >5000 orally (Chiba)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefoxitin Cefozopran Cefpimizole Cefpiramide Cefpirome

Cefotiam
Cefotiam.jpg
Cefotiam.svg
Systematic (IUPAC) name
(6R,7R)-7-{[2-(2-amino-1,3-thiazol-4-yl)acetyl]
amino}-3-{[1-(2-dimethylaminoethyl)tetrazol-5-yl]
sulfanylmethyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]
oct-2-ene-2-carboxylic acid
Clinical data
Trade names Pansporin
AHFS/Drugs.com International Drug Names
Legal status Prescription only
Routes Intravenous, intramuscular
Pharmacokinetic data
Bioavailability 60% (intramuscular)
Protein binding 40%
Metabolism Nil
Half-life Approximately 1 hour
Excretion Renal
Identifiers
CAS number 61622-34-2 YesY
ATC code J01DC07
PubChem CID 43708
DrugBank DB00229
ChemSpider 39831 YesY
UNII 91W6Z2N718 YesY
KEGG D07648 YesY
ChEBI CHEBI:355510 YesY
ChEMBL CHEMBL1296 YesY
Chemical data
Formula C18H23N9O4S3 
Mol. mass 525.631 g/mol
 YesY (what is this?)  (verify)

Cefotiam is a parenteral second-generation cephalosporin antibiotic. It has broad spectrum activity against Gram positive and Gram negative bacteria. As a beta-lactam, its bactericidal activity results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins.

Cefotiam was launched as Pansporin in February 1981 by Takeda Pharmaceutical of Japan and has been available as a generic since February 1993.