Ceftriaxone
Title: Ceftriaxone
CAS Registry Number: 73384-59-5
CAS Name: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: (6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 72-(Z)-(O-methyloxime); cefatriaxone
Molecular Formula: C18H18N8O7S3
Molecular Weight: 554.58
Percent Composition: C 38.98%, H 3.27%, N 20.21%, O 20.19%, S 17.35%
Literature References: Parenteral third generation cephalosporin antibiotic. Prepn: M. Montavon, R. Reiner, GB 2022090; eidem, US 4327210 (1979, 1982 both to Hoffmann-La Roche); R. Reiner et al., J. Antibiot. 33, 783 (1980). In vitro and in vivo studies: P. Angehrn et al., Antimicrob. Agents Chemother. 18, 913 (1980). Pharmacokinetics: M. Seddon et al., ibid. 240. Determn in plasma, urine, bile: K. H. Trautmann, P. Haefelfinger, J. High Resolut. Chromatogr. Chromatogr. Commun. 4, 54 (1981), C.A. 94, 202437 (1981). Mechanism of action study: R. B. Wright et al., J. Antibiot. 34, 590 (1981). Kinetics in humans: K. Stoekel et al., Clin. Pharmacol. Ther. 29, 650 (1981). Toxicity data: K. Teelman et al., "Experimentelle Toxikologie von Ceftriaxon", in Ceftriaxon ein neues parenterales Cephalosporin, Proc. Hahnenklee Symp., 1981, R. Grieshalber, Ed. (Editiones Roche, Basel, 1982) pp 91-111. Review of antibacterial activity, toxicology, pharmacology and clinical studies: D. M. Richards et al., Drugs 27, 469 (1984); T. R. Beam, Pharmacotherapy 5, 237-253 (1985).
 
Derivative Type: Disodium salt hemiheptahydrate
CAS Registry Number: 104376-79-6
Manufacturers' Codes: Ro-13-9904/001
Trademarks: Rocefin (Roche); Rocephin(e) (Roche)
Molecular Formula: C18H16N8Na2O7S3.3½H2O
Molecular Weight: 661.60
Percent Composition: C 32.68%, H 3.50%, N 16.94%, Na 6.95%, O 25.39%, S 14.54%
Properties: White cryst powder, mp >155° (dec). [a]D25 -165° (c = 1 in water) (calc for water-free substance). uv max (water): 242, 272 nm (e 32300, 29530). pKa: ~3 (COOH), 3.2 (NH3+), 4.1 (enolic OH). Soly in water at 25°: ~40 g/100 ml. LD50 in male, female, mice, rats (mg/kg): 3000, 2800, 2175, 2175 i.v.; >10000 all species orally; >5000 all species s.c. (Teelman).
Melting point: mp >155° (dec)
pKa: pKa: ~3 (COOH), 3.2 (NH3+), 4.1 (enolic OH)
Optical Rotation: [a]D25 -165° (c = 1 in water) (calc for water-free substance)
Absorption maximum: uv max (water): 242, 272 nm (e 32300, 29530)
Toxicity data: LD50 in male, female, mice, rats (mg/kg): 3000, 2800, 2175, 2175 i.v.; >10000 all species orally; >5000 all species s.c. (Teelman)
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.

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