Clindamycin
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Clindamycin
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CAS No:
18323-44-9
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Formula:
C18H33ClN2O5S
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Chemical Name:
Clindamycin
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Synonyms:
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-D-galacto-Octopyranoside,methyl 7-chloro-6,7,8-trideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-,trans- α-;L-threo-α-D-galacto-Octopyranoside,methyl 7-chloro-6,7,8-trideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-,(2S-trans)-;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;Clindamycin;Dalacin C;7-Chloro-7-deoxylincomycin;Clinimycin;7-Chlorolincomycin;Cleocin;7(S)-Chloro-7-deoxylincomycin;Sobelin;7-Deoxy-7(S)-chlorolincomycin;7-CDL;U 21251;Chlolincocin;Antirobe;Dalacine;Klimicin;ClindaDerm;Klindan 300;Dalacin V;Clincin;Clindam;13441-63-9;16669-21-9;24620-78-8;24696-19-3;1376624-06-4;1376758-11-0
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CAS No:
Description
Clindamycin is an oral protein synthesis inhibitory agent that has the ability to suppress the expression of virulence factors in Staphylococcus aureus at sub-inhibitory concentrations (sub-MICs). Clindamycin resistance results from enzymatic methylation of the antibiotic binding site in the 50S ribosomal subunit (23S rRNA). Clindamycin decreases the production of Panton-Valentine leucocidin (PVL), toxic-shock-staphylococcal toxin (TSST-1) or alpha-haemolysin (Hla)[1].
N-[2-chloro-1-[3,4,5-trihydroxy-6-(methylthio)-2-oxanyl]propyl]-1-methyl-4-propyl-2-pyrrolidinecarboxamide is a proline derivative.|Clindamycin is a broad spectrum antibiotic used orally, topically and parenterally for bacterial infections due to sensitive organisms. Clindamycin has been linked to rare instances of acute liver injury.|An antibacterial agent that is a semisynthetic analog of LINCOMYCIN.
Clindamycin Basic Attributes
424.98
424.98
242-209-1
DTXSID2022836
Yellow, amorphous solid
D - Dermatologicals|G - Genito urinary system and sex hormones|J - Antiinfectives for systemic use
Characteristics
127.56000
1.83
1.3±0.1 g/cm3
141 - 143ºC
628.1±55.0 °C at 760 mmHg
333.6±31.5 °C
1.574
>63.7 [ug/mL]|In water, 30.61 mg/L at 25 °C (est)
Store in tight container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.|Commercially available clindamycin phosphate vaginal cream should be stored in a tight container at 20-25 °C; freezing should be avoided. The vaginal suppositories and clindamycin phosphate vaginal cream should be stored at a controlled room temperature of 25 °C, but may be exposed to temperatures ranging from 15-30 °C; exposure to temperatures exceeding 30 °C or high humidity should be avoided. When stored as recommended, the commercially available vaginal cream is stable for 18 months following the date of manufacture. /Clindamycin phosphate/|The commercially available gel containing clindamycin phosphate (clindamycin 1%) in fixed combination with benzoyl peroxide 5% should be refrigerated at 2-8 °C until dispensed.178 Once dispensed, the gel may be stored at a room temperature up to 25 °C for up to 60 days. The gel should not be frozen. /Clindamycin phosphate/|Commercially available clindamycin phosphate 1% topical gel, lotion, and solution should be stored in tight containers at 20-25 °C; freezing should be avoided. /Clindamycin phosphate/
5.28X10-17 mm Hg at 25 °C (est)
D +214° (chloroform)
Henry's Law constant = 2.89X10-22 atm-cu m/mol at 25 °C (est)
Characteristic taste; odorless or has faint mercaptan-like odor; freely soluble in water, dimethylformamide, methanol; soluble in alcohol; practically insoluble in acetone; pKa: 7.72 in pure water /Clindamycin hydrochloride/
Mol wt: 479.47. White crystals from ethanol-ethyl acetate, mp 141-143 °C. Specific optical rotation = +144 deg at 25 °C/D (water). pKa 7.6. Soluble in water, pyridine, ethanol, DMF /Clindamycin hydrochloride monohydrate/|Mol wt: 504.97. Soluble in water /Clindamycin 2-dihydrogen phosphate/
Safety Information
STABLE IN AIR & LIGHT. /HCL/
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl clindamycin palmitate hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Clindamycin palmitate hydrochloride/|The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl clindamycin hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Clindamycin hydrochloride/|The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl clindamycin phosphate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Clindamycin phosphate/|The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Clindamycin hydrochloride is included on this list. /Clindamycin hydrochloride/|For more FDA Requirements (Complete) data for CLINDAMYCIN (7 total), please visit the HSDB record page.
|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P201, P260, P263, P264, P270, P280, P305+P351+P338, P308+P313, and P337+P313|Aggregated GHS information provided by 9 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Respiratory protection: Where respirators are deemed necessary to reduce or control occupational exposures, use NIOSH-approved respiratory protection and have an effective respirator program in place. Gloves: Chemically compatible. For handling solutions, ensure that the glove material is protective against the solvent being used. Use handling practices that minimize direct hand contact. Employees who are sensitive to natural rubber (latex) should use nitrile or other synthetic nonlatex gloves. Use of powdered latex gloves should be avoided due to the risk of latex allergy. Eye protection: Safety glasses with sideshields are recommended. Face shields or goggles may be required if splash potential exists or if corrosive materials are present. Approved eye protection (e.g., bearing the ANSI Z87 or CSA stamp) is preferred. Maintain eyewash facilities in the work area. Protective clothing: Protect exposed skin.|Airborne exposure should be controlled primarily by engineering controls such as general dilution ventilation, local exhaust ventilation, or process enclosure. Local exhaust ventilation is generally preferred to general exhaust because it can control the contaminant at its source, preventing dispersion into the work area. An industrial hygiene survey involving air monitoring may be used to determine the effectiveness of engineering controls. Effectiveness of engineering controls intended for use with highly potent materials should be assessed by use of nontoxic surrogate materials.
As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.|Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials.
Wear approved respiratory protection, chemically compatible gloves, and protective clothing. Wipe up spillage or collect spillage using a high-efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.
As a general rule, when handling USP Reference Standards, avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Clean equipment and work surfaces with suitable detergent or solvent after use. After removing gloves, wash hands and other exposed skin thoroughly.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.|As with all dry powders, it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Clindamycin concentrations in sewage water effluents of the Netherlands in 2002 ranged from approximately 60 to 240 ng/L(1). Concentrations of up to 110 ng/L were reported in an unspecified sewage treatment effluent sample(2). Clindamycin concentrations of 30 and 1000 ng/L have also been reported. It was reported present in biosolids at a concentration of 1,540 ng/kg dry weight(3).
Toxicity
Clindamycin has been linked to two forms of hepatotoxicity: transient serum aminotransferase elevations usually occurring after several days of high intravenous doses; and, an acute, idiosyncratic liver injury that arises within 1 to 3 weeks of starting therapy and is typically mild and self-limited.
Reversibility of antibiotic-induced paralysis of mouse phrenic nerve-hemidiaphragm preparation by calcium and by neostigmine.|Concurrent use of kaolin- or attapulgite-containing antidiarrheals with oral clindamycin may significantly delay the absorption of oral clindamycin; concurrent use should be avoided or patients should be advised to take adsorbent antidiarrheals not less than 2 hours before or 3 to 4 hours after oral lincomycins.|There is in vitro evidence of antagonism between erythromycin and clindamycin.|Clindamycin has been reported to antagonize the bactericidal activity of aminoglycosides in vitro, and some clinicians recommend that these drugs not be used concomitantly. However, in vivo antagonism has not been demonstrated, and clindamycin has been administered successfully in conjunction with an aminoglycoside with no apparent decrease in activity.|For more Interactions (Complete) data for CLINDAMYCIN (7 total), please visit the HSDB record page.
LD50 Rat subcutaneous 2618 mg/kg|LD50 Rat oral 2619 mg/kg /Clindamycin hydrochloride/|LD50 Mouse ip 361 mg/kg /Clindamycin hydrochloride/|LD50 Swiss Mouse ip 1145 mg/kg /Clindamycin 2-phosphate/|LD50 Swiss Mouse iv 855 mg/kg /Clindamycin 2-phosphate/
Clindamycin should be used with caution in patients with a history of GI disease, particularly colitis. Clindamycin should be used with caution in patients with severe renal and/or hepatic impairment; serum clindamycin concentrations should be monitored during high-dose therapy in these patients.|As these drugs /lincomycin and clindamycin/ may produce a lethal condition it is suggested that they should be used with appropriate discretion, especially in the elderly female who appears to be most at risk.
Clindamycin's production and use as a semi-synthetic antibiotic(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 70(SRC), determined from a structure estimation method(2), indicates that clindamycin is expected to have high mobility in soil(SRC). The pKa of clindamycin is 7.79(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of the neutral species clindamycin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-22 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Clindamycin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.3X10-17 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Utilizing the Closed Bottle Test, 3% of the Theoretical BOD was reached in 4 weeks(3) indicating that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 70(SRC), determined from a structure estimation method(2), indicates that clindamycin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-22 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A pKa of 7.79(5) indicates clindamycin will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(6), an estimated BCF of 12(SRC), from its log Kow of 2.16(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Closed Bottle Test, 3% of the Theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is not an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), clindamycin, which has an estimated vapor pressure of 5.3X10-17 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase clindamycin may be removed from the air by wet or dry deposition(SRC). Clindamycin does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
Clindamycin is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Clindamycin does not contains chromophores that absorb at wavelengths >290 nm(1) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). Clindamycin, present at 3000 ng/g biosolids which were generated in waste water treatment processes from a plant in Oregon, OH in 2007, exhibited a degradation rate constant of 0.53/day, half-life of 86 days when stored under aerobic field conditions and exposed to natural sunlight. Experiments were conducted out-of-doors starting August 13, 2007 and lasting 77 days; background concentration of clindamycin in the biosolids was 23.2 ng/g(2).
An estimated BCF of 12 was calculated in fish for clindamycin(SRC), using a log Kow of 2.16(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC),
Using a structure estimation method based on molecular connectivity indices(1), the Koc of clindamycin can be estimated to be 70(SRC). According to a classification scheme(2), this estimated Koc value suggests that clindamycin is expected to have high mobility in soil. However, the pKa of clindamycin is 7.79(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
The Henry's Law constant for clindamycin is estimated as 2.9X10-22 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that the neutral species is expected to be essentially nonvolatile from water and moist soil surfaces(2). A pKa of 7.79(3) indicates clindamycin will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. Clindamycin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.3X10-17 mm Hg(SRC), determined from a fragment constant method(4).
SURFACE WATER: Clindamycin was present at concentrations of 0.03, 0.04, 0.33, and 0.04 ug/L in samples from five sites on Wascana Creek, Saskatchewan, Canada, sampled on March 1, 2005, October 24, 2005, July 17, 2006 and May 15, 2007, respectively. Samples were collected at 0.25 m depth and were all collected downstream of sewage treatment plant outfall; method detection limit = 0.01 ug/L(1). Clindamycin concentrations in surface water of the Netherlands between 1996 and 2005 ranged from approximately 10 to 50 ng/L(2). Concentrations of up to 24 ng/L were reported in an unspecified surface water(3).
Clindamycin is distributed into milk, achieving breast milk concentrations of 0.7-3.8 ug/mL at dosages of 150 mg orally to 600 mg IV.|/EXPTL/ Clindamycin readily crosses the placenta, and cord blood concentrations of the drug have been reported to be 46% of concurrent maternal blood concentrations. Clindamycin is distributed into milk.
NIOSH (NOES Survey 1981-1983) has statistically estimated that 3168, 2870, and 10,980 workers (1697, 1274, and 8092 of these were female) were potentially exposed to clindamycin hydrochloride, clindamycin palmitate hydrochloride, and clindamycin phosphate, respectively, in the US(1). Occupational exposure to clindamycin may occur through inhalation and dermal contact with this compound at workplaces where clindamycin is produced or used. Limited monitoring data indicate that the general population may be exposed to clindamycin via dermal contact with water. Exposure to clindamycin among the general population will occur to those administered the drug, an antibiotic(SRC).
Drug Information
Clindamycin is a broad spectrum antibiotic used orally, topically and parenterally for bacterial infections due to sensitive organisms. Clindamycin has been linked to rare instances of acute liver injury.
Antiinfective Agents
Anti-Bacterial Agents|Clindamycin is used intravaginally as a vaginal cream or suppository or orally for the treatment of bacterial vaginosis (formerly called Haemophilus vaginitis, Gardnerella vaginitis, nonspecific vaginitis, Corynebacterium vaginitis, or anaerobic vaginosis). /Included in US product labeling/|Clindamycin phosphate is used topically alone or in conjunction with benzoyl peroxide in the treatment of inflammatory acne vulgaris. /Clindamycin phosphate; included in US product labeling/|Clindamycin is used parenterally in the treatment of bone and joint infections (including acute hematogenous osteomyelitis) caused by Staphylococcus aureus and as an adjunct to surgery in the treatment of chronic bone and joint infections caused by susceptible organisms. Clindamycin also is used orally or parenterally in the treatment of serious respiratory tract infections, skin and skin structure infections, or septicemia caused by susceptible strains of S. aureus, Streptococcus pneumoniae, or other streptococci (except Enterococcus faecalis). /Included in US product labeling/|For more Therapeutic Uses (Complete) data for CLINDAMYCIN (23 total), please visit the HSDB record page.
/BOXED WARNING/ Clostridium difficile associated diarrhea (CDAD) has been reported with use of nearly all antibacterial agents, including CLEOCIN HCL and may range in severity from mild diarrhea to fatal colitis. Treatment with antibacterial agents alters the normal flora of the colon leading to overgrowth of C.difficle. Because CLEOCIN HCL therapy has been associated with severe colitis which may end fatally, it should be reserved for serious infections where less toxic antimicrobial agents are inappropriate... It should not be used in patients with nonbacterial infections such as most upper respiratory tract infections. C.difficile produces toxins A and B which contribute to the development of CDAD. Hypertoxin producing strains of C. difficile cause increased morbidity and mortality, as these infections can be refractory to antimicrobial therapy and may require colectomy. CDAD must be considered in all patients who present with diarrhea following antibiotic use. Careful medical history is necessary since CDAD has been reported to occur over two months after the administration of antibacterial agents. If CDAD is suspected or confirmed, ongoing antibiotic use not directed against C. difficile may need to be discontinued. Appropriate fluid and electrolyte management, protein supplementation, antibiotic treatment of C. difficile, and surgical evaluation should be instituted as clinically indicated.|The most frequent adverse effects of topical therapy with clindamycin phosphate 1% gel, lotion, or solution are dryness of the skin and erythema. In clinical studies evaluating the clindamycin phosphate 1% topical gel, lotion, or solution, dryness was reported in 23, 18, or 19% of patients, respectively, whereas erythema was reported in 7, 14, or 16% of patients, respectively. Oiliness or oily skin was reported in 18, 10, or 1% of patients receiving the topical gel, lotion, or solution, respectively. Peeling occurred in 7 or 11% of patients receiving topical clindamycin phosphate lotion or solution, respectively. In addition, burning or pruritus were reported in 7-11% of patients receiving these topical preparations of clindamycin phosphate. /Clindamycin phosphate/|Vaginitis (including vulvovaginitis, vulvovaginal disorder, vaginal discharge, and trichomonal vaginitis) has been reported in 3.6 or 9-10.7% of nonpregnant women receiving clindamycin phosphate vaginal suppositories or cream, respectively. Vulvovaginitis has been reported in 6 or 4.4% and vulvovaginal disorder (including irritation) has been reported in 3.2 or 5.3% of nonpregnant women receiving clindamycin phosphate vaginal cream for 3 or 7 days, respectively. Vulvovaginal disorder or vaginal pain has been reported in 3.4 or 1.9%, respectively, of nonpregnant women receiving clindamycin vaginal suppositories. Trichomonas vaginalis infection reportedly occurs in 1.3% of nonpregnant women receiving clindamycin phosphate vaginal cream for 7 days. Vaginal discharge, metrorrhagia, urinary tract infection, pyelonephritis, dysuria, endometriosis, menstrual disorder, and vaginal pain each have been reported in less than 1% of patients receiving intravaginal clindamycin, and vaginal bleeding has been reported in at least one patient following use of clindamycin phosphate vaginal cream. /Clindamycin phosphate/|The most common adverse effects of therapy with clindamycin phosphate (2% clindamycin) vaginal cream or suppositories are vaginal candidiasis and vaginitis (including vulvovaginitis, vulvovaginal disorder, vaginal discharge, and trichomonal vaginitis). /Clindamycin phosphate/|For more Drug Warnings (Complete) data for CLINDAMYCIN (35 total), please visit the HSDB record page.
Staphylococcal resistance to clindamycin has been induced in vitro and has been shown to be acquired in a stepwise manner. Natural and acquired resistance to the antibiotic has been demonstrated in vitro and in vivo in strains of staphylococci, streptococci, and B. fragilis. Complete cross-resistance occurs between clindamycin and lincomycin, and there is evidence of partial cross-resistance between clindamycin and erythromycin.|Macrolide resistance due to ribosomal methylation by erm-encoded enzymes ... may produce resistance to clindamycin. However, because clindamycin is not an inducer of the methylase, there is cross-resistance only if the enzyme is produced constitutively ... Plasmid-mediated resistance to clindamycin ... has been found in Bacteroides fragilis ... it may be due to methylation of bacterial RNA found in the 50 S ribosomal subunit ...
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)
Clindamycin is nearly completely absorbed following oral admin. Peak plasma concn of 2 to 3 ug/mL are attained within 1 hr after the ingestion of 150 mg. The presence of food in stomach does not reduce absorption. The half-life of the antibiotic is about 2.9 hr, and the modest accumulation of drug is thus expected if it is given at 6-hr intervals.|Clindamycin is widely distributed in many fluids and tissues, including bone. Significant concn are not attained in cerebrospinal fluid, even when the meninges are inflamed. Concn sufficient to treat cerebral toxoplasmosis are achievable .. The drug readily crosses the placental barrier. 90% or more of clindamycin is bound to plasma proteins. Clindamycin accumulates in polymorphonuclear leukocytes, alveolar macrophages, and in abscesses.|Half-life ... is lengthened only slightly in patients with markedly impaired renal function ...|Clindamycin is distributed into many body tissues and fluids including saliva, ascites fluid, pleural fluid, synovial fluid, bone, and bile. However, even in the presence of inflamed meninges, only small amounts of the drug diffuse into CSF. The concentration of clindamycin in synovial fluid and bone is reported to be 60-80% of concurrent serum concentrations of the drug; the degree of penetration does not appear to be affected by joint inflammation. Clindamycin readily crosses the placenta, and cord blood concentrations of the drug have been reported to be 46% of concurrent maternal blood concentrations. Clindamycin is distributed into milk.|For more Absorption, Distribution and Excretion (Complete) data for CLINDAMYCIN (24 total), please visit the HSDB record page.
Clindamycin is partially metabolized to bioactive and inactive metabolites. The major bioactive metabolites are clindamycin sulfoxide and N-demethyl-clindamycin which are excreted in urine, bile, and feces. Within 24 hours, approximately 10% of an oral dose of clindamycin is excreted in urine and 3.6% is excreted in feces as active drug and metabolites; the remainder is excreted as inactive metabolites.|Only about 10% of the clindamycin admin is excreted unaltered in urine, and small quantities are found in feces ... Clindamycin is inactivated by metabolism to N-demethylclindamycin and clindamycin sulfoxide, which are excreted in the urine and bile.
The serum half-life of clindamycin is 2-3 hours in adults and children with normal renal function. The serum half-life is increased slightly in patients with markedly reduced renal or hepatic function. In neonates, the serum half-life depends on gestational and chronologic age and body weight. The serum half-life of clindamycin reportedly averages 8.7 and 3.6 hours in premature and full-term neonates, respectively, and about 3 hours in infants 4 weeks to 1 year of age; serum half-life was longer in infants weighing less than 3.5 kg than in heavier infants.|The half-life of ... /clindamycin/ is about 2.9 hr ...|Following intravaginal application of 2% clindamycin cream, the systemic half-life of the drug appears to be about 1.5-2.6 hours. Following intravaginal administration of clindamycin suppositories, the apparent elimination half-life averaged about 11 hours (range: 4-35 hours).
Clindamycin may be bacteriostatic or bactericidal in action, depending on the concentration of the drug attained at the site of infection and the susceptibility of the infecting organism. Clindamycin palmitate hydrochloride and clindamycin phosphate are inactive until hydrolyzed to free clindamycin. This hydrolysis occurs rapidly in vivo. Clindamycin appears to inhibit protein synthesis in susceptible organisms by binding to 50S ribosomal subunits; the primary effect is inhibition of peptide bond formation. The site of action appears to be the same as that of erythromycin, chloramphenicol, and lincomycin.|Clindamycin binds exclusively to the 50S subunit of bacterial ribosomes and suppresses protein synthesis.|... Clindamycin is not a substrate for macrolide efflux pumps, and strains that are resistant to macrolides by this mechanism are susceptible to clindamycin.
Emergency and supportive measures: Maintain an open airway and assist ventilation if necessary. Treat coma, seizures, hypotension, anaphylaxis, and hemolysis if they occur. Replace fluid losses resulting from gastroenteritis with intravenous crystalloids. /Antibacterial agents/|Decontamination: Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. /Antibacterial agents/|Enhanced elimination: Most antibiotics are excreted unchanged in the urine, so maintenance of adequate urine flow is important. The role of forced diuresis is unclear. Hemodialysis is not usually indicated, except perhaps in patients with renal dysfunction and a high level of a toxic agent. /Antibacterial agents/|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|For more Antidote and Emergency Treatment (Complete) data for CLINDAMYCIN (6 total), please visit the HSDB record page.
/CASE REPORTS/ Clindamycin-related anaphylactic reaction is rarely reported. We report a male patient with buccal cancer who was undergoing radical neck dissection when life-threatening anaphylactic shock developed soon after intravenous infusion of clindamycin. Immediate cardiopulmonary resuscitation was performed, and the patient recovered uneventfully. Perioperative anaphylactic shock is a serious problem due to the difficulty of judgment and potentially disastrous outcome. Immediate diagnosis and halting of drug infusion should be the first actions taken.|/CASE REPORTS/ A 73-year-old woman developed erythroderma with intense pruritus, malaise, and chills 7 days after treatment with intravenous clindamycin. Two years later she experienced a similar reaction with more rapid onset (48 hours) after treatment with aztreonam. Resolution followed withdrawal of treatment in both instances, and intradermal tests proved positive at delayed reading for both drugs.|/CASE REPORTS/ Prolongation of QT time interval may be provoked by a limited number of drugs, especially macrolide antibiotics. We describe a case of QT time interval prolongation induced by clindamycin with subsequent repeated ventricular fibrillation and resuscitation; there is no previous report in the literature of QT time prolongation caused by lincosamides.|/CASE REPORTS/ Four cases of severe pseudomembranous colitis following the use of lincomycin and clindamycin are described; 2 required emergency total colectomy and 2 died. Cases of such gravity after the use of these drugs have not been previously reported. One hundred and fifty-six orthopedic cases where clindamycin and lincomycin were used postoperatively are reviewed; 34 had diarrhea (22 per cent), and 3 of the severe cases occurred in this group. The diagnosis of pseudomembranous colitis may be difficult as the latent period from initiation of drug therapy to commencement of diarrhea may be as much as 18 days, and that from cessation of drug therapy may be as much as 11 days. The value of early sigmoidoscopy in cases of diarrhea of obscure etiology is emphasized, and the characteristic sigmoidoscopic and histological appearances of pseudomembranous colitis are described. As these drugs may produce a lethal condition it is suggested that they should be used with appropriate discretion, especially in the elderly female who appears to be most at risk.|For more Human Toxicity Excerpts (Complete) data for CLINDAMYCIN (8 total), please visit the HSDB record page.
7 Chloro 7 deoxylincomycin
Clindamycin Use and Manufacturing
Lincomycin is treated with a solution of Rydon reagent prepared from triphenylphosphine, acetonitrile, and chlorine. The base is ultimately reacted with hydrochloric acid.|First resulted from the reaction of lincomycin and thionyl chloride; improved synthetic methods involve the reaction of lincomycin and triphenylphosphine dichloride or triphenylphosphine in carbon tetrachloride.|Synthesized ... by introducing a chlorine atom at the 7 position of lincomycin.|Manufacturing Process: R.D. Birkenmeyer, Kagan, US 3475407(1969 to Upjohn).|Antibiotics are fermentation products and are isolated either as unfinished products or as intermediates, generally solid substances of limited stability. They are purified by methods normally employed in organic chemistry, which include chromatography, crystallization, and precipitation. /Antibiotics/
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.
(1972) GREATER THAN 4.54X10+5 G (FREE BASE)|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS
ESSENTIALLY 100% AS A MEDICINAL (1976)
Oral: For solution: 75 mg (of clindamycin) per 5 mL, Cleocin Pediatric (Pfizer). /Clindamycin palmitate hydrochloride/|Table: Clindamycin Hydrochloride Preparations [Table#4361]|Table: Clindamycin Phosphate in Dextrose Preparations [Table#4362]|Table: Clindamycin Phosphate Preparations [Table#4363]|For more Formulations/Preparations (Complete) data for CLINDAMYCIN (6 total), please visit the HSDB record page.
CLINDAMYCIN DIFFERS CHEMICALLY FROM LINCOMYCIN BY SUBSTITUTION OF CHLORINE ATOM FOR HYDROXYL GROUP ON PARENT COMPD. WITH THIS SLIGHT MOLECULAR MODIFICATION, CLINDAMYCIN IS...MORE POTENT THAN LINCOMYCIN.|Clindamycin is a derivative of the amino acid trans-L-4-n-propylhygrinic acid, attached to a sulfur-containing derivative of an octose. It is a congener of lincomycin ...
Analyte: Clindamycin; matrix: solutions; procedure: high performance liquid chromatography with ultraviolet detection at 214 nm|Analyte: Clindamycin; matrix: formulations; procedure: high performance liquid chromatography with ultraviolet detection at 214 nm|For more Analytic Laboratory Methods (Complete) data for CLINDAMYCIN (26 total), please visit the HSDB record page.
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Computed Properties
Molecular Weight:425.0
XLogP3:2.2
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:7
Exact Mass:424.1798710
Monoisotopic Mass:424.1798710
Topological Polar Surface Area:128
Heavy Atom Count:27
Complexity:502
Undefined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It acts on the 50S subunit of bacterial ribosomes, inhibits the synthesis of bacterial proteins by inhibiting the elongation of peptide chains, thereby eliminating the A protein and villi on the surface of bacteria, making them easy to be phagocytosed and killed. It is used to antagonize microbial infections such as Bacteroides, Gardnerella vaginalis, Mycoplasma hominis, and Streptococcus aureus associated with bacterial vaginal diseases.
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Learn More Other Chemicals
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Clindamycin palmitate hydrochloride
25507-04-4
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Clindamycin phosphate
24729-96-2
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Dehydro ClindaMycin
909032-77-5
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Clindamycin B Formula
18323-43-8
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Clindamycin B 2-Phosphate Formula
54887-31-9
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Clindamycin palmitate Formula
36688-78-5
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CLINDAMYCIN HYDROCHLORIDE Structure
58207-19-5
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Clindamycin 4-Phosphate Structure
54887-30-8
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What is Clindamycin hydrochloride
21462-39-5
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What is Oseltamivir phosphate
204255-11-8