Title: Pipacycline
CAS Registry Number: 1110-80-1
CAS Name: [4S-(4a,4aa,5aa,6b,12aa)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-N-[[4-(2-hydroxyethyl)-1-piperazinyl]methyl]-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
Additional Names: N-[[4-(2-hydroxyethyl)-1-piperazinyl]methyl]tetracycline; N-[4-(b-hydroxyethyl)diethylenediamino-1-methyl]tetracycline; mepicycline; mepiciclina
Trademarks: Ambra-Vena (Lepetit); Sieromicin (Sierochimica); Valtomicina (Midy)
Molecular Formula: C29H38N4O9
Molecular Weight: 586.63
Percent Composition: C 59.37%, H 6.53%, N 9.55%, O 24.55%
Literature References: Semi-synthetic broad spectrum antibiotic related to tetracycline. Prepn: Pedrazzoli et al., Boll. Chim. Farm. 98, 516 (1959), C.A. 54, 3856a (1960); Gradnik et al., GB 888968 corresp to US 3149114 (1962 and 1964 to E.R.A.S.M.E.). Properties: eidem, Pharm. Acta Helv. 35, 529 (1960). Pharmacokinetic studies: A. Scalvini, A. Delmonte, Gazz. Med. Ital. 131, 1 (1972).
Properties: Yellow cryst powder, dec 162-163°. [a]D20 -195° (c = 0.5). [a]D20 -175° (c = 0.5 in methanol). uv max (10 g/ml 0.1N HCl): 286, 355 nm. pH of 2% aq soln, 7.2-7.4. Freely sol in water, methanol, formamide; slightly sol in ethanol, isopropanol. Practically insol in ether, benzene, chloroform. Sensitive to light, heat, and air. LD50 i.v. in white mice: 188 mg/kg (Scalvini, Delmonte).
Optical Rotation: [a]D20 -195° (c = 0.5); [a]D20 -175° (c = 0.5 in methanol)
Absorption maximum: uv max (10 g/ml 0.1N HCl): 286, 355 nm
Toxicity data: LD50 i.v. in white mice: 188 mg/kg (Scalvini, Delmonte)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Tetracyclines. |