13-07173. Penimepicycline [Archived]

Nomenclature

CAS number: 4599-60-4
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid compd with (4S,4aS,5aS,6S,12aS)-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 (1:1); N-[4-(β-hydroxyethyl)diethylenediaminomethyl]tetracycline phenoxymethylpenicillinate; mepicycline phenoxymethylpenicillinate; penicillin V compd with mepicycline; penimepiciclina; Criseocil; Geotricyn; Mepenicycline; Olimpen; Penetracyne; Peniltetra; Prestociclina.
C45H56N6O14S; mol wt 937.02.
C 57.68%, H 6.02%, N 8.97%, O 23.90%, S 3.42%.
C16H18N2O5S.C29H38N4O9.

Description and references

Semi-synthetic antibiotic. Prepn: Pedrazzoli et al., Boll. Chim. Farm. 98, 516 (1959), C.A. 54, 3856a (1960); Gradnik, Pedrazzoli, GB 897826 (1962 to E.R.A.S.M.E.), C.A. 57, 15034e (1962). Properties: Gradnik et al., Pharm. Acta Helv. 35, 529 (1960).

Properties

Yellowish-white cryst powder, dec above 143° (not corr). Sensitive to light, heat, air. Slightly bitter taste. pH of 2% aq soln, 5.5-5.7. Soly in water at 20° = 1 g/0.7 ml. [α]D20 50.5° (c = 2 in methanol).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); Tetracyclines; β-Lactams; Penicillins

Status

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