Clindamycin 4-palmitate

Qindamycin, 7(5)-7-chloro-7-deoxyliQcomycin [18323-44-9] (1, R = H, R = Q), also known as Cleocin, first resulted from the reaction of lincomycin and thionyl chloride (54) improved synthetic methods involve the reaction of lincomycin and triphenylphosphine dichloride or triphenylphosphine in carbon tetrachloride (55). Clindamycin is significantly more active than lincomycin against gram-positive bacteria in vitro, and is absorbed rapidly following oral adnainistration. Clindamycin 2-palmitate [36688-78-5], (6, R = R = OC(CH2) 4CH2), 2-palmitate ester of clindamycin, is... 

NB The low aqueous solubility of clindamycin-2-palmitate was recognized as a problem for accurate pX measurement, but it was rationalized that the pKa value for the parent should not be greatly altered by the remote acyl substituent. This assumption appears justified. 

Clindamycin palmitate and phosphate are rapidly hydrolyzed to the base. 

Lincos amides clindamycin hydochloride clindamycin palmitate hydrochloride clindamycin phosphate lincomycin hydrochloride monohydrate... 

L. W. Brown, High-pressure liquid chromatographic assays for clindamycin, clindamycin phosphate, and clindamycin palmitate, J. Pharm. Sci., 57 1254 (1978). 

Clidinium bromide, 473 Clinazine, 1044 Clindamycin, 473 Clindamycin hydrochloride, 473 Clindamycin palmitate hydrochloride, 473 Clindamycin phosphate, 474... 

Clindamycin Palmitate Hydrochloride Clindamycin Palmitate Hydrochloride for oral solution Glass, 0.6 M x 3 mm I.D. 1% G36/S1AB (80-100 mesh) Helium 290 FID Cholesteryl Benzoate USP (24, pp. 431 and 432)... 

THERAPEUTIC USES The oral dose of chndamycin (cleocin) for adults is 150-300 mg every 6 hours for severe infections, it is 300-600 mg every 6 hours. Children should receive 8-12 mg/kg/day of clindamycin palmitate hydrochloride (cleocin pediatric) in three or four divided doses, or for severe infections, 13-25 mg/kg/day. However, children weighing <10 kg should receive half teaspoonful of this preparation (37.5 mg) every 8 hours as a minimal dose. 

In recent years, many parent dmgs have been converted to esters to generate so-called prodmgs ia order to overcome some undesirable property such as bitter taste, poor absorption, poor solubiUty, and irritation at site of iajection. For example, antibiotics such as chloramphenicol [56-75-7] and clindamycin [18323-44-9] have been derivatized as their palmitate esters ia order to minimise their bitter taste. 

Clindamycin is absorbed rapidly from the gastrointeslini tract, even in the presence of food. It is available as ibt crystalline, water-soluble hydrochloride hydrate fhyclak. and the 2-palmitate c.stcr hydrochloride salts in oral dosigi forms and as the 2-phosphatc e.stcr in solutions for intramuv cular or intravenous injection. All forms arc chemically voi ssAwVvaw brj % aiic. 

Oral drugs with a markedly bitter taste may lead to poor patient compliance if administered as a solution or syrup. The prodrug approach has been used to improve the taste of chloramphenicol (20), clindamycin, erythromycin, and metronidazole.19 A prodrug such as chloramphenicol palmitate (21), with LogP of around 10, does not dissolve in an appreciable amount in the mouth and, therefore, does not interact with the taste receptors. 

The activities of all pancreatic enzymes are lower at birth, hence decreasing the bioavailability of drugs (e.g., ester formulation of clindamycin or chloramphenicol palmitate) requiring hydrolysis prior to absorption. 

Chndamycin palmitate, an oral prodrug, is hydrolyzed rapidly in vivo. Its absorption is similar to clindamycin. The phosphate ester of clindamycin, given parenterally, also is rapidly hydrolyzed to the active parent compound. 

Stevens-Johnson syndrome). Clindamycin has excellent activity against Propionobacterium acnes when applied topically to comedones, and because it is white, it can be cosmetically tinted to match flesh tones better than the yellow tetracyclines. A very water-insoluble palmitate hydrochloride pro-drug of clindamycin also is available (lacks bitter taste). 

Rowe EL, Anomalous solution behavior of 2-palmitate esters of lincomycin and clindamycin, /. Pharm. Sci., 68,1292-1296 (1979). 

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