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Clindamycin

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Clindamycin Basic information

Product Name:
Clindamycin
Synonyms:
  • Clindamycin (base and/or unspecified salts)
  • (2S,4R)-N-[(1S,2S)-2-Chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
  • CLDM
  • Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S)-1-methyl-4β-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside
  • Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside
  • U-21251
  • Clindamycin Base
  • 7-Chloro-7-deoxylincoMycin, 7-ChlorolincoMycin
CAS:
18323-44-9
MF:
C18H33ClN2O5S
MW:
424.98
EINECS:
242-209-1
Product Categories:
  • Inhibitors
Mol File:
18323-44-9.mol
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Clindamycin Chemical Properties

alpha 
D +214° (chloroform)
Boiling point:
134°C (rough estimate)
Density 
1.1184 (rough estimate)
refractive index 
1.6100 (estimate)
pka
7.6(at 25℃)
CAS DataBase Reference
18323-44-9(CAS DataBase Reference)
EPA Substance Registry System
L-threo-?-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio- (18323-44-9)
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Safety Information

Hazardous Substances Data
18323-44-9(Hazardous Substances Data)
Toxicity
LD50 subcutaneous in rat: 2618mg/kg
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Clindamycin Usage And Synthesis

Description

Clindamycin, a derivative of lincomycin, was fi rst isolated from Streptomyces lincolnesis in 1962 and became commercially available in 1966. It replaced lincomycin use because of its better absorption and clinical spectrum. It is active against gram-positive, gram-negative, and anaerobic organisms.

Originator

Dalacin-C,Diethelm,Switz.,1968

Uses

Clindamycin is a semi-synthetic analogue of lincomycin, prepared by chloride substitution of the exocyclic sugar hydroxy group. This affords a more hydrophobic compound with improved pharmacodynamics. Like other members of the lincosamide family, clindamycin is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans. Clindamycin acts by binding to the 23S ribosomal subunit, blocking protein synthesis. Clindamycin has been extensively studied with over 8,000 literature citations.

Definition

ChEBI: A carbohydrate-containing antibiotic that is the semisynthetic derivative of lincomycin, a natural antibiotic.

Indications

Clindamycin (Cleocin), 300 to 450 mg/day, is an extremely effective agent for acne.

Manufacturing Process

The following procedure is described in US Patent 3,475,407. A solution of 50 g of lincomycin hydrochloride, 120 g of triphenylphosphine, and 500 ml of acetonitrile in a 3 liter flask equipped with a stirrer was cooled in an ice bath and 500 ml of carbon tetrachloride was added in one portion. The reaction mixture was then stirred for 18 hours without addition of ice to the cooling
bath. The reaction was evaporated to dryness under vacuum on a 50° to 60°C water bath, yielding a clear, pale yellow viscous oil. An equal volume of water was added and the mixture shaken until all of the oil was dissolved. The resulting suspension of white solid (Ph3PO) was filtered through a sintered glass mat and discarded. The filtrate was adjusted to pH 11 by addition of 6 N aqueous sodium hydroxide. A solid precipitated.
The resulting slurry was extracted with four 300 ml portions of chloroform. The aqueous phase was discarded. The combined chloroform extract was washed once with 100 ml of saturated aqueous sodium chloride solution and the sodium chloride phase was discarded. The chloroform phase was evaporated to dryness under vacuum on a 50° to 60°C water bath and an equal volume of methanol was added to the residue and the resulting solution heated at reflux for 1 hour. The methanol solution was evaporated to dryness under vacuum on a 50° to 60°C water bath. The residue was a clear pale yellow viscous oil. An equal volume of water and 10 ml of 37% aqueous HCl was added and the resultant was shaken until the oil dissolved and a white solid (more Ph3PO) remained in suspension. The suspension was filtered through a sintered glass mat at pH 1 to 2 and the solid discarded.
The filtrate was extracted twice with 100 ml of carbon tetrachloride. The carbon tetrachloride phase was discarded. The aqueous phase was adjusted to pH 11 by addition of 6 N aqueous sodium hydroxide and extracted four times with 300 ml portions of chloroform. The combined chloroform extract was washed three times with 100 ml of saturated aqueous sodium chloride solution and the sodium chloride phase was discarded. The chloroform extract was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated to dryness under vacuum on a 50° to 60 °C water bath. The residue was a clear, colorless glass weighing 45 g analyzing about 95% 7(S)- chloro-7-deoxylincomycin. To the crude product there was added 100 ml of ethanol with warming until a clear solution was obtained. Then 150 ml ethyl acetate was added and the resultant filtered through a glass mat and the filtrate adjusted to pH 1 by the addition of saturated ethanolic HCl. Crystallization soon occurred. The resultant was allowed to stand at 0°C for 18 hours and then filtered through a sintered glass mat. The solid was dried under vacuum at 60°C for 18 hours yielding 35 g, a 67% yield of 7(S)-chloro- 7-deoxylincomycin hydrochloride as an ethanol solvate.

brand name

Cleocin (Pharmacia & Upjohn).

Therapeutic Function

Antibacterial

Biological Activity

Clindamycin is active against most anaerobes including most anaerobic grampositive cocci, nonspore forming bacilli, Clostridium (except C. diffi cile and some non-perfringens species), anaerobic gram-negative bacilli (except Fusobacterium varium ), and anaerobic gram-positive nonspore forming bacilli.
It is active against most aerobic gram-positive organisms, including viridans streptococci, most strains of pneumococci, and other strains of streptococcal organisms (except Enterococcus ). It is active against MSSA.

Contact allergens

This lincosanide antibiotic is used in topical form for acne, or systemically has been responsible for exanthematous rashes and acute generalized exanthematous pustulosis.

Mechanism of action

Clindamycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit. The use of clindamycin with macrolides is not recommended since both of them compete for binding sites to the 50S subunit.

Clinical Use

Clindamycin is effective in the treatment of most infections secondary to anaerobes and gram-positive cocci. It can be used for anaerobic pulmonary, intra-abdominal, gynecologic, pelvic, diabetic foot, and decubitus ulcer infections. Another appropriate agent should be added since the majority of these infections are polymicrobial. It can also be used as an alternative agent for patients with severe penicillin allergy. It is also used to treat Clostridium perfringens infection.
Oral preparations of clindamycin and vaginal cream are alternatives to metronidazole for the treatment of bacterial vaginosis. Topical solution is used for treatment of acne vulgaris and rosacea.
Clindamycin is extensively metabolized by the liver and the half-life is prolonged in patients with cirrhosis and hepatitis. Dose reductions are recommended in patients with acute liver disease.

Side effects

The most commonly observed adverse effect is diarrhea. The reported incidence of C. difficile colitis in patients treated with clindamycin varies from 0.1 to 10%. The syndrome may be fatal. If the patient develops C. difficile colitis, clindamycin should be discontinued and the patient should be treated for C. difficile . Other side effects include rash, nausea, vomiting, diarrhea, flatulence, abdominal distension, anorexia, and transient elevation of liver enzymes. Other less common events, such as fever, neutropenia, thrombocytopenia, and eosinophilia have been reported.

Chemical Synthesis

Clindamycin, methyl-[7-chloro-6,7,8-trideoxy-6-trans-(1-methyl-4-propylL-2-pyrrollidin-carboxamido)-1-thio-L-threo-α-D-galacto-octapyranoside] (32.5.2), which is a 7(S)-chloro-7-deoxy derivative of lincomycin, is synthesized by replacing the hydroxyl group of lincomycin (32.5.1) at C7 by treating it with triphenyl phophine in acetonitrile (Raydon reagent), in which a configuration transformation takes place in the given carbo hydrate.

Veterinary Drugs and Treatments

Topical clindamycin is an optional topical treatment for feline acne.
Clindamycin inhibits bacterial protein synthesis by binding to the 50S ribosome; primary activity is against anaerobic and grampositive aerobic bacteria. For more information on the pharmacology of clindamycin, refer to the monograph for systemic use found in the main section.

Clindamycin Preparation Products And Raw materials

Preparation Products

ClindamycinSupplier

Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Email
info@yuhaochemical.com
S.Z. PhyStandard Bio-Tech. Co., Ltd.
Tel
17727448752,0755-83725681-603
Email
rex.liu@phystandard.com;tom.liu@phystandard.com
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725;010-86181995
Email
waley188@sohu.com
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Email
contact@trustwe.com
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399-
Email
isunpharm@qq.com