DESCRIPTIONS OF ANTIBIOTICS 



237 



gated plates; m.p. 149. 7-150. 7°C (corrected) (1) 

 or 144-147°C (3). Sublimes without deeompo.sition 

 in high vaciuun (15). Very soluble in methanol, 

 ethanol, l)utanol, jiropylene glycol (150.8 mg per 

 ml), acetone, ether, and amyl acetate (1, 3). Solu- 

 ble in cyclohexanone, methyl isolnityl ketone, 

 nitrobenzene, nitromethane, and ether. \'ery 

 sparingly soluble in water (2.5 mg per ml at 25°C), 

 acid, alkali, hot benzene, and chloroform (3). In- 

 soluble in petrolemn ether, cold benzene, cold 5 

 per cent sodium Incarbonate, and vegetable oils 

 (3, 8, 17, 18). Ultraviolet absorption spectrum 

 maximmn at 278 niju (£'1™ 298) (water or 0.1 A' 

 HCl) and 279.0 to 279.5 m/. (0.1 A' NaOH) (3). 

 [a]i^ = -25.5° (ethyl acetate) (1) or +18° (etha- 

 nol) (17). Positive KMnOj and ferrous hydroxide 

 tests (for oxidized nitrogen). Biuret test is not 

 characteristically positive; green crystals of a 

 copper salt deposit on standing (17). Negative 

 Sakaguchi, Pauly, FeCls , Molisch, Benedict 

 (boiling) (3, 8), thiosemicarbazone, boiling or cold 

 alcoholic silver nitrate, and periodic acid tests 

 (17). Stable at room temperature in ac[ueous solu- 

 tion at pH 2 to 9 for >24 hours; stable to boiling 

 for 5 hours (1). Crystallographic data given in 

 reference 40. C = 41.11%; H = 3.89%; N = 8.60%; 

 CI (nonionic) = 21.71% (1). C11H12O5N2CI, . 

 Molecular weight 323.1. Structural formula given 

 in Chapter 6. Acid or alkaline hydrolysis products 

 include dirhloroacelic acid and a basic substance, 

 C11H12N2O4 , having only ^loo the activity of 

 chloramphenicol against Shigella paradysenteriae 

 (17). Acetyl derivative of chloramphenicol : Crystal- 

 line; m.p. 141-142°C (17). A variety of derivatives 

 and analogues of chloramphenicol have been re- 

 ported (21 , 25, 29, 31 , 36, 41 , 57) . Many of these are 

 biologically active, but none is of greater in- 

 terest than the parent compovmd. Certain gen 

 eralizations concerning the relationship of biologi- 

 cal activity to structure in this group have been 

 made (42, 59). 



Biological activity: In vitro: Active on gram- 

 positive and gram-negative bacteria, rickettsiae, 

 and psittacosis group (1, 3, 4, 19). Not active on 

 filamentous fungi or yeasts (4, 19). Active on Ac- 

 tinomyces israelii and Xocardia farcinica, but not 

 other pathogenic nocardias (23). Active on certain 

 pleuropneumonia-like organisms (38). Amebista- 

 tic to Endamoeba histolytica at 125 to 250 fj.g per 

 ml, depending on conditions of the test (28). Ac- 

 tive on Tetrahymena pyrijormis (54). At bacte- 

 riostatic concentrations, inhibits intracellular 

 growth of coliphage T-1 in E. coli (50). Not active 

 on gonococci phagocytized l)y HeLa cells (62), 

 but kills Brucella phagocytized by guinea pig 



leucocytes (71). Inhil)its phagocytosis of Staph. 

 aureus by human polymorphonuclear neutrophils 

 at 15 Mg per ml (45). Prevents nitrate assimilation 

 by the fungus Scopulariopsis brevica)ilis grown in 

 static surface culture, but does not prevent as- 

 similation of other N-containing compounds or 

 nitrate when the culture is grown under submerged 

 conditions (70). Chloramphenicol inhibits synthe- 

 sis of protein and nucleic acids (67). d-Chloram- 

 phenicol is biologically inactive, but does not 

 interfere with the activity of chloramphenicol 

 (30). Chloramplienicol decomposition products 

 produced by the action of certain bacteria have 

 either a growth-stimulating effect on bacteria, or 

 interfere with the growth-inhibitory action of the 

 antibiotic (.3i)). In vivo: Active (in mice) on K. 

 pneumoniae (type A), Shigella paradysenteriae, D. 

 pneumoniae (type I), Streptococcus hemolyticus, 

 S. viridans, Borrelia novyi, Pasteurella multocida, 

 P. pestis, Sal. gallinarum, Malleomyces pseudo- 

 mallei, Clostridium tetani, and C. septicum. (4, 12, 

 14, 27, 47, 66). Slight activity on Treponema palli- 

 dum (rabbits) (19). Active at high doses on Enda- 

 moeba histolytica in rats; su])pressive but no cura- 

 tive effect in dogs (28). Active on Plasniodium 

 berghei (mice), P. gallinaceum (chicks), and P. 

 cathemerium (canary) (32). Interferes with the 

 killer action of Paramecium aurelta (37). Antitoxin 

 activity in mice against Sal. bareilly endotoxins 

 (58). Active on Rickettsia prowazekii (chick em- 

 bryo), R. orientalis (chick embryo and mice), R. 

 (ikari. R. maoscri, R. rickctt-^ii. li . tsutsugamushi , 

 R. burncti, R. conorii. and the rickettsia that 

 causes North Queensland tick tyi)hus (1, 2, 13, 

 33). Active on jisittacosis, lymphogranuloma 

 venereiun, and mouse ]>neumonitis virus (2, 9, 

 52). Inactive on St. Louis and Japanese encepha- 

 litis viruses, variola, influenza A (PR 8), A-1, and 

 B, fixed rabies, distemper, Newcastle disease, 

 vaccinia, polio (Lansing and Y-SK), Theiler's 

 intestinal, miunps, chick bronchitis, and laryngo- 

 tracheitis viruses (2, 4, 19). Active on stone-fruit 

 virus in artificially' inoculated cucumliers, and on 

 toliacco mosaic virus in tomato seedlings when 

 the chloramphenicol is introduced by vacuum (51). 

 Inhibits the virus tumor of Rumex acetosa L (11). 

 Active on crown-gall tissue of tomato (53). Pro- 

 tects wheat seedlings from Xanthonionas translu- 

 cens infections when they are grown in a solution 

 containing the antibiotic (60). Active on sarcoma 

 180 in mice when tumor cell suspension is mixed 

 with the antibiotic before inoculation and a pellet 

 of the drug is implanted sidicutaneously 1 day 

 after inoculation with such tvmior cells (64). Pro- 

 longs motility and life-span of hvunan spermatozoa 



