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Clindamycin hydrochloride(CAS No. 21462-39-5)

Clindamycin hydrochloride C18H33ClN2O5S.HCl (cas 21462-39-5) Molecular Structure

21462-39-5 Structure

Identification and Related Records

【Name】
Clindamycin hydrochloride
【CAS Registry number】
21462-39-5
【Synonyms】
7(S)-Chloro-7-deoxylincomycin hyddrochloride
L-threo-a-D-galacto-Octopyranoside, methyl7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-,hydrochloride (1:1)
7-Chloro-7-deoxylincomycin hydrochloride
Antirobe vet.
【EINECS(EC#)】
244-398-6
【Molecular Formula】
C18H33ClN2O5S.HCl (Products with the same molecular formula)
【Molecular Weight】
424.98302
【Inchi】
InChI=1S/C18H33ClN2O5S/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25)/t9?,10-,11+,12?,13+,14-,15-,16-,18-/m1/s1
【InChIKey】
KDLRVYVGXIQJDK-NOWPCOIGSA-N
【Canonical SMILES】
CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl
【Isomers smiles】
CCC[C@@H]1C[C@H](N(C1)C)C(=O)NC([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)
O)O)O)C(C)Cl
【MOL File】
21462-39-5.mol

Chemical and Physical Properties

【Appearance】
white crystalline powder
【Density】
g/cm3
【Melting Point】
141℃
【Boiling Point】
628.1 °C at 760 mmHg
【Vapour】
1.79E-19mmHg at 25°C
【Flash Point】
333.6 °C
【Water】
H2O: 50 mg/mL, clear, colorless
【Solubilities】
H2O: 50 mg/mL, clear, colorless
【Color/Form】
Yellow, amorphous solid
【Storage temp】
2-8°C
【Spectral properties】
Specific optical rotation = +214 deg at 25 deg C/D (chloroform)
【Computed Properties】
Molecular Weight:424.98302 [g/mol]
Molecular Formula:C18H33ClN2O5S
XLogP3:2.2
H-Bond Donor:4
H-Bond Acceptor:7
Rotatable Bond Count:7
Tautomer Count:2
Exact Mass:424.179871
MonoIsotopic Mass:424.179871
Topological Polar Surface Area:128
Heavy Atom Count:27
Formal Charge:0
Complexity:502
Isotope Atom Count:0
Defined Atom Stereocenter Count:7
Undefined Atom Stereocenter Count:2
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:4
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:2
Effective Rotor Count:10.2
Conformer Sampling RMSD:1
CID Conformer Count:314

Safety and Handling

【Hazard Codes】
Xi: Irritant;
【Risk Statements】
R36/37/38
【Safety Statements 】
26-36-37/39
【Safety】

Hazard Codes:IrritantXi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
S36: Wear suitable protective clothing?
S37/39: Wear suitable gloves and eye/face protection
WGK Germany: 2
RTECS: GF2275000
F: 10

【Skin, Eye, and Respiratory Irritations】
Because clindamycin phosphate vaginal cream may cause ocular burning and irritation, contact with the eyes should be avoided. /Clindamycin phosphate vaginal cream/
【Formulations/Preparations】
Clindamycin palmitate /is/ an oral prepn for pediatric use ... The phosphate ester of clindamycin ... is given parenterally ... /Clindamycin palmitate, phosphate ester of clindamycin/
DOSAGE FORMS (CLINDAMYCIN EQUIV)--CAPSULES USP: 75 & 150 MG.
The oral /prepn/ of clindamycin /are/ clindamycin hydrochloride (CLEOCIN) for adults ... clindamycin palmitate hydrochloride (CLEOCIN PEDIATRIC) /for children/ ... Clindamycin phosphate (CLEOCIN PHOSPHATE) is available for im or iv use ... Clindamycin also is available as a topical soln, gel, or lotion (CLEOCIN T, others) and as a vaginal cream (CLEOCIN).
Parenteral Injection, for IV infusion: 6 mg (of clindamycin) per mL (300 mg) in 5% Dextrose Cleocin Phosphate IV (Galaxy (Baxter)), (Pfizer); 12 mg (of clindamycin) per mL (600 mg) in 5% Dextrose Cleocin Phosphate IV (Galaxy (Baxter)), (Pfizer); 18 mg (of clindamycin) per mL (900 mg) in 5% Dextrose Cleocin Phosphate IV (Galaxy (Baxter)), (Pfizer). /Clindamycin phosphate in dextrose/
Injection, for IV infusion only: 150 mg (of clindamycin) per mL (300 mg) Clindamycin Phosphate ADD-Vantage ( with benzyl alcohol 9.45 mg/mL and edetate disodium 0.5 mg/mL), (Hospira); 150 mg (of clindamycin) per mL (600 and 900 mg) Cleocin Phosphate ADD-Vantage ( with benzyl alcohol 9.45 mg/mL and edetate disodium 0.5 mg/mL), (Pfizer), Clindamycin Phosphate ADD-Vantage ( with benzyl alcohol 9.45 mg/mL and edetate disodium 0.5 mg/mL), (Hospira). /Clindamycin phosphate/
Parenteral: Injection 150 mg (of clindamycin) per mL Cleocin Phosphate ( with benzyl alcohol 9.45 mg/mL and edetate disodium 0.5 mg/mL), (Pfizer); 9 g (150 mg/mL) (of clindamycin) pharmacy bulk package Cleocin Phosphate (with benzyl alcohol 9.45 mg/mL and edetate disodium 0.5 mg/mL), (Pfizer), Clindamycin Phosphate Injection ( with benzyl alcohol 9.45 mg/mL and edetate disodium 0.5 mg/mL), (AstraZeneca), Clindamycin Phosphate Injection ( with benzyl alcohol 9.45 mg/mL and edetate disodium 0.5 mg/mL), (Hospira), Clindamycin Phosphate Injection (with benzyl alcohol 9.45 mg/mL and edetate disodium 0.5 mg/mL), (Lederle). /Clindamycin phosphate/
Oral: For solution: 75 mg (of clindamycin) per 5 mL Cleocin Pediatric (with ethylparaben), (Pfizer). /Clindamycin palmitate hydrochloride/
Oral: Capsules: 75 mg (of clindamycin) Cleocin HCl ( with tartrazine), (Pfizer), 150 mg (of clindamycin) Cleocin HCl ( with tartrazine), (Pfizer), 300 mg (of clindamycin) Cleocin HCl, (Pfizer). /Clindamycin hydrochloride/
Vaginal: Cream: 2% (of clindamycin) Cleocin ( with benzyl alcohol and propylene glycol; with 7 disposable vaginal applicators), (Pfizer). Suppositories: 100 mg (of clindamycin) Cleocin Vaginal Ovules (with vaginal applicator), (Pfizer). /Clindamycin phosphate/
Topical: Gel: 1% (of clindamycin) Cleocin T ( with allantoin, methylparaben, and propylene glycol), (Pfizer) Clindagel (with methylparaben, and propylene glycol), (Galderma) Lotion: 1% (of clindamycin) Cleocin T ( with methylparaben), (Pfizer). Pledgets (saturated with solution): 1% (of clindamycin) Cleocin T Pledgets ( with isopropyl alcohol 50% and propylene glycol), (Pfizer), Clindamycin Phosphate Pledgets, (Clay-Park), Clindamycin Phosphate Pledgets, (Glades), Clindets Pledgets ( with isopropyl alcohol 50% and propylene glycol), (Stiefel). Solution: 1% (of clindamycin) Cleocin T 1% ( with isopropyl alcohol 50% and propylene glycol), (Pfizer), Clinda-Derm ( with isopropyl alcohol 51.5% v/v and propylene glycol), (Paddock). /Clindamycin phosphate/
【Exposure Standards and Regulations】
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/
Oral dosage form new animal drug. Clindamycin capsules and tablets. ... Indications for use. For the treatment of skin infections (wounds and abscesses) due to susceptible strains of coagulase-positive staphylococci (Staphylococcus aureus or S. intermedius), deep wounds and abscesses due to susceptible strains of Bacteroides fragilis, Prevotella melaninogenicus, Fusobacterium necrophorum, and Clostridium perfringens, dental infections due to susceptible strains of S. aureus, B. fragilis, P. melaninogenicus, F. necrophorum, and C. perfringens, and osteomyelitis due to susceptible strains of S. aureus, B. fragilis, P. melaninogenicus, F. necrophorum, and C. perfringens.
Oral dosage form new animal durgs. Clindamycin solution. ... Indications for use /in dogs/. For the treatment of skin infections (wounds and abscesses) due to susceptible strains of coagulase-positive staphylococci (Staphylococcus aureus or S. intermedius), deep wounds and abscesses due to susceptible strains of Bacteroides fragilis, Prevotella melaninogenicus, Fusobacterium necrophorum, and Clostridium perfringens; dental infections due to susceptible strains of S. aureus, B. fragilis, P. melaninogenicus, F. necrophorum, and C. perfringens; and osteomyelitis due to susceptible strains of S. aureus, B. fragilis, P. melaninogenicus, F. necrophorum, and C. perfringens. ... Indications for use /in cats/. For the treatment of skin infections (wounds and abscesses) due to susceptible strains of Staphylococcus aureus, S. intermedius, Streptococcus spp.; deep wounds and abscesses due to susceptible strains of Clostridium perfringens and Bacteroides fragilis; and dental infections due to susceptible strains of S. aureus, S. intermedius, Streptococcus spp., C. perfringens, and B. fragilis.
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/
【Other Preventative Measures】
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.
【Protective Equipment and Clothing】
Because clindamycin phosphate vaginal cream may cause ocular burning and irritation, contact with the eyes should be avoided. /Clindamycin phosphate vaginal cream/
【Specification】

?Clindamycin HCl (CAS NO.21462-39-5)?is also called (2s-Trans)-methyl 7-chloro-6,7,8-trideoxy-6[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-l-threo-alpha-d-galacto-octopyranoside ; (7s)-7-Chloro-7-deoxylincomycin hydrochloride;7(s)-chloro-7-deoxylincomycin ; 7(s)-Chloro-7-deoxylincomycin HCl ; Cleocin hydrochloride .?Clindamycin HCl (CAS NO.21462-39-5) is?odorless and bitter taste. It easily soluble in water, soluble in methanol, pyridine, slightly soluble in ethanol, practically insoluble in acetone or chloroform.

【Octanol/Water Partition Coefficient】
log Kow = 2.16

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

REACTION OF LINCOMYCIN WITH RYDON REAGENT (PREPARED FROM TRIPHENYLPHOSPHINE, ACETONITRILE, AND CHLORINE) FOLLOWED BY REACTION 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.
BIRKENMEYER, KAGAN, US PATENTS 3,475,407; 3,509,127 & 3,544,551; 3,513,155 (1969; 1970 & 1970 ALL TO UPJOHN).
U.S. Exports

(1972) No Data
(1975) No Data
U.S. Imports

(1972) No Data
(1975) No Data
U.S. Production

(1972) GREATER THAN 4.54X10+5 G (FREE BASE)
(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS
Consumption Patterns

ESSENTIALLY 100% AS A MEDICINAL (1976)

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that reduce the growth or reproduction of BACTERIA.
- 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.
【Therapeutic Uses】
Antibiotics
Topical clindamycin is indicated in the treatment of acne vulgaris. It may be effective in grades II and III acne, which are characterized by inflammatory lesions such as papules and pustules. Topical antibacterials are not generally considered to be as effective as systemic antibacterials in the treatment of acne, especially more severe inflammatory acne. However, some studies have shown that clindamycin phosphate topical solution may be as effective as low-dose tetracycline for moderate cases of inflammatory acne. /Clindamycin phosphate; Included in US product labeling/
Clindamycin phosphate topical solution is used in the treatment of dermal ulcers. /Clindamycin phosphate; NOT included in US product labeling/
Topical clindamycin is used in the topical treatment of erythrasma caused by Corynebacterium minutissimum, rosacea, periorificial facial dermatitis, folliculitis, stasis, chronic lymphedema, and familial pemphigus. /NOT included in US product labeling/
Clindamycin is used in combination with pyrimethamine in the treatment of CNS toxoplasmosis in patients who are unresponsive or intolerant to standard treatment. /NOT included in US product labeling/
Clindamycin is used in the treatment of sinusitis. /NOT included in US product labeling/
Clindamycin is used in combination with primaquine in the treatment of Pneumocystis carinii pneumonia (PCP) in patients unresponsive or intolerant to standard therapy. /NOT included in US product labeling/
Clindamycin is used in the treatment of chronic suppurative otitis media. /NOT included in US product labeling/
Clindamycin is used in combination with quinine in the treatment of chloroquine-resistant malaria caused by Plasmodium falciparum in patients for whom standard therapy is contraindicated (e.g., children, pregnant women, sulfa allergy). /NOT included in US product labeling/
Clindamycin is used in the treatment of erysipelas. /NOT included in US product labeling/
Clindamycin is used concurrently with quinine in the treatment of severe babesiosis caused by Babesia microti. /NOT included in US product labeling/
Clindamycin is used in the treatment of actinomycosis. /NOT included in US product labeling/
Clindamycin is indicated in the treatment of serious skin and soft tissue infections caused by anaerobes, streptococci, and staphylococci. /Included in US product labeling/
Oral and parenteral clindamycin are indicated in the treatment of septicemia caused by anaerobes. In addition, parenteral clindamycin is indicated in the treatment of septicemia caused by streptococci and staphylococci. /Included in US product labeling/
Clindamycin is indicated in the treatment of intra-abdominal infections (such as peritonitis and abscesses) caused by anaerobes. /Included in US product labeling/
Clindamycin is indicated as a primary agent in the treatment of pneumonia, including serious respiratory tract infections (such as empyema, pneumonitis, and lung abscess) caused by anaerobes. Clindamycin is indicated as a secondary agent in the treatment of pneumonia caused by susceptible strains of pneumococci, staphylococci, and streptococci. /Included in US product labeling/
Clindamycin is indicated in the treatment of female pelvic infections, including endometritis, nongonococcal tubo-ovarian abscess, pelvic cellulitis, and postsurgical vaginal cuff infections caused by anaerobes. /Included in US product labeling/
Parenteral clindamycin is indicated in the adjunctive surgical treatment of chronic bone and joint infections, and acute hematogenous osteomyelitis caused by staphylococci. /Included in US product labeling/
Vaginal clindamycin is indicated in the local treatment of bacterial vaginosis (previously known as Haemophilus vaginitis,Gardnerella vaginitis, nonspecific vaginitis, Corynebacterium vaginitis, or anaerobic vaginosis. /Included in US product labeling/
Although a number of infections with gram-positive cocci will respond favorably to clindamycin, the high incidence of diarrhea and the occurrence of colitis require limitation of its use to infections in which it is clearly superior to other agents. Clindamycin is particularly valuable for the treatment of infections with anaerobes, especially those due to Bacteroides fragilis. It has been used successfully in combination with an aminoglycoside for infections resulting from fecal spillage (intraabdominal or pelvic abscesses and peritonitis) ... Clindamycin is not predictably useful for the treatment of bacterial brain abscesses, since penetration into the cerebrospinal fluid (CSF) is poor ...
Bacterial strains are susceptible to clindamycin at minimal inhibitory concn of < or = 0.5 ug/mL. In general, clindamycin is similar to erythromycin in its activity in vitro against susceptible strains of pneumococci, Streptococcus Pyogenes, and viridans streptococci. 90% or more of strains of streptococci, including some that are macrolide-resistant, remain susceptible to clindamycin with minimal inhibitory concentrations (MICs) less than 0.5 ug/mL ... Methicillin-susceptible strains of Staphylococcus aureus usually are susceptible to clindamycin, but methicillin-resistant strains of S. aureus and coagulase-negative staphylococci frequently are resistant. Clindamycin is more active than erythromycin or clarithromycin against anaerobic bacteria, especially Bacteroides fragilis; some strains are inhibited by < 0.1 ug/mL. Minimal inhibitory concn for other anaerobes are as follows: Bacteroides melaninogenicus, 0.1 to 1 ug/mL; Fusobacterium, < 0.5 ug/mL (although most strains of Fusobacterium varium are resistant); Peptostreptococcus, < 0.1 to 0.5 ug/mL; Peptococcus, 1 to 100 ug/mL (with 10% of strain resistant); and C. perfringens, < 0.1 to 8 ug/mL. From 10% to 20% of clostridial species other than Clostridium perfringens are resistant. Strains fo Actinomyces israelii and Nocardia asteroides are sensitive. Essentially all aerobic gram-negative bacilli are resistant. With regard to atypical organisms and parasites, mycoplasma pneumoniae is resistant. Chlamydia spp. are variably sensitive, although the clinical relevance is not established. Clindamycin shows good activity in experimental models of Pneumocystis carinii pneumonia and Toxoplasma gondii encephalitis. Clindamycin has some activity against both Plasmodium falciparum and Plasmodium vivax, but a cure rate of only 50% of patients with malaria was observed in one study ... Clindamycin has been used for treatment of babesiosis.
Clindamycin palmitate, an oral prepn for pediatric use, is an inactive prodrug, but the ester is hydrolyzed rapidly in vivo ... The phosphate ester of clindamycin, which is given parenterally, also is rapidly hydrolyzed in vivo to the active parent cmpd ... For serious infection ... iv or im admin is recommended ...
One randomized, prospective trial has shown that clindamycin ... was superior to penicillin ... for the treatment of lung abscesses ... Clindamycin has become the drug of choice instead of penicillin for treatment of lung abscess and anaerobic lung and pleural space infections.
Lincomycin and clindamycin are lincosamide antibiotics used in clinical practice. Both antibiotics are bacteriostatic and inhibit protein synthesis in sensitive bacteria. They may even be bactericidal at the higher concentrations that can be reached in vivo. Clindamycin is usually more active than lincomycin in the treatment of bacterial infections, in particular those caused by anaerobic species; and it can also be used for the treatment of important protozoal diseases, e.g. malaria, most effectively in combination with primaquine. Resistance to lincomycin and clindamycin may be caused by methylation of 23S ribosomal RNA, modification of the antibiotics by specific enzymes or active efflux from the periplasmic space. [Spizek J and Rezanka T; Appl Microbiol Biotechnol 64 (4): 455-64 (2004)]
【Biomedical Effects and Toxicity】
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 lenghtened 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.
Following IM or IV administration, clindamycin phosphate is rapidly hydrolyzed in plasma to active clindamycin. Following IM administration of clindamycin phosphate, peak serum concentrations occur within 3 hours in adults and 1 hour in children. In healthy adult males, IM doses of 300 mg of clindamycin phosphate every 8 hours result in average peak serum clindamycin concentrations of 6 ug/mL. IV doses of 600 mg of clindamycin phosphate infused over 20 minutes every 8 hours in healthy adult males result in average peak serum clindamycin concentrations of 10 ug/mL. In a study in children with infections, single IV or IM doses of 5-7 mg/kg resulted in average peak serum clindamycin concentrations of 10 or 8 ug/mL, respectively. /Clindamycin Phosphate/
Approximately 90% of an oral dose of clindamycin hydrochloride is rapidly absorbed from the GI tract. Prior to absorption, oral clindamycin palmitate hydrochloride is hydrolyzed in the GI tract to active clindamycin. Clindamycin is not inactivated by gastric acidity. Serum concentrations of clindamycin appear to be predictable, increasing linearly with increased doses. The extent of absorption and peak serum concentrations of clindamycin are not appreciably affected when either clindamycin hydrochloride capsules or clindamycin palmitate hydrochloride oral solution is administered with food, although peak serum concentrations may be delayed. Following oral administration of a single 150-mg dose of clindamycin hydrochloride to healthy fasting adults, peak serum concentrations of clindamycin average 1.9-3.9 ug/mL and are attained within 45-60 minutes; serum concentrations of clindamycin average 1.5 ug/mL at 3 hours and 0.7 ug/mL at 6 hours. Oral doses of clindamycin palmitate hydrochloride produce serum concentrations of clindamycin similar to those achieved with oral clindamycin hydrochloride. In a study in healthy children, oral administration of clindamycin palmitate hydrochloride 2, 3, or 4 mg/kg every 6 hours produced mean peak serum clindamycin concentrations of 1.24, 2.25, and 2.44 ug/mL, respectively, 1 hour after the first dose. After the fifth dose, peak serum concentrations of the drug averaged 2.46, 2.98, and 3.79 ug/mL, respectively. /Clindamycin Phosphate and Hydrochloride/
Concentration of clindamycin in bone and drainage fluid was measured in samples from 13 patients following joint replacement surgery. Mean bone concentration as 5.01 ug/mL while average drainage fluid concentration was 4.61 ug/mL following total dose of 1800 mg.
Clindamycin palmitate, an oral prepn for pediatric use, is an inactive prodrug, but the ester is hydrolyzed rapidly in vivo. Its rate and extent of absorption are similar to those of clindamycin. After several oral doses at 6-hr intervals, children attain plasma concn of 2 to 4 ug/mL with the admin of 8 to 16 mg/kg. /Clindamycin palmitate/
The phosphate ester of clindamycin, which is given parenterally, also is rapidly hydrolyzed in vivo to the active parent cmpd. After im injection, peak concn in plasma are not attained until 3 hr in adults and 1 hr in children; these values approx 6 ug/mL after a 300-mg dose and 9 ug/mL after a 600-mg dose in adults.
... 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 isexcreted as inactive metabolites.
Only about 10% of the clindamycin admin is excreted unaltered in urine, and small quantities are found in feces. However, antimicrobial activity persists in feces for 5 or more days after parenteral therapy with clindamycin is stopped; growth of clindamycin-sensitive microorganisms in colonic contents may remain suppressed for up to 2 wk. Clindamycin is inactivated by metabolism to N-demethylclindamycin and clindamycin sulfoxide, which are excreted in the urine and bile. Accumulation of clindamycin can occur in patients with severe hepatic failure, and dosage adjustments thus may be required.
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.
The distribution and elimination characteristics of clindamycin following intravaginal application of the drug have not been fully characterized. 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). Elimination of clindamycin suppositories is considered to be limited by absorption rate.
In a limited number of healthy women who received intravaginal application of a 1% vaginal cream (50 mg of clindamycin; not commercially available in the US) once daily for 7 days, average peak serum clindamycin concentrations at steady state ranged from 20-27 ng/mL; approximately 6% of the dose was absorbed systemically. In a limited number of healthy women who received intravaginal application of a 1% vaginal cream (50 mg of clindamycin) twice daily for 7 days, average peak serum clindamycin concentrations were 3-5 times higher than those in the group receiving the same dose once daily, and an average of 12-14% of the dose was absorbed systemically.
Systemic absorption of intravaginal clindamycin cream was slower and less variable in women with bacterial vaginosis than in healthy women. Following intravaginal administration of 5 g of the 2% vaginal cream (100 mg of clindamycin) daily for 7 consecutive days in a limited number of women with bacterial vaginosis, approximately 5% (range: 2-8%) of the administered dose was absorbed systemically. Peak serum clindamycin concentrations approximately 14 hours (range: 4-24 hours) after administration averaged 13 ng/mL (range: 6-34 ng/mL) and 16 ng/mL (range: 7-26 ng/mL) on days 1 and 7 of therapy, respectively. Little or no systemic accumulation of clindamycin appears to occur following repeated application of clindamycin 2% vaginal cream.
Following intravaginal administration of the suppository (100 mg of clindamycin) once daily for 3 consecutive days in a limited number of healthy women, approximately 30% (range: 6-70%) of the administered dose was absorbed systemically on day 3 of therapy as measured by the area under the concentration-time curve (AUC). Peak serum clindamycin concentrations approximately 5 hours (range: 1-10 hours) after intravaginal administration averaged 0.27 mcg/mL (range: 0.03-0.67 mcg/mL) on day 3 of therapy.
Following intravaginal administration of 5 g of the 2% vaginal cream (100 mg of clindamycin) daily for 7 consecutive days in a limited number of healthy women, approximately 5% (range: 0.6-11%) of the administered dose was absorbed systemically. Peak serum clindamycin concentrations approximately 10 hours (range: 4-24 hours) after administration averaged 18 ng/mL (range: 4-47 ng/mL) and 25 ng/mL (range: 6-61 ng/mL) on days 1 and 7 of therapy, respectively.
Clindamycin phosphate is absorbed systemically following intravaginal application of the drug as a vaginal cream or suppositories. The systemic bioavailability of intravaginally administered clindamycin 2% vaginal cream is about 5% and that of the suppositories after three 100 mg daily doses is almost 30%. Only low concentrations of the drug are achieved systemically following administration of usual intravaginal doses (e.g., 100 mg of clindamycin) relative to usual oral doses (e.g., 300 mg of clindamycin). Average serum clindamycin concentrations following IV administration of a single dose of the drug (approximately 48 mg of clindamycin) were up to 300-fold greater than those following intravaginal application of clindamycin 50 mg as the cream. In addition, the overall systemic bioavailability of clindamycin following intravaginal administration of the suppository is 2- to 20-fold lower than that with usual oral dosages and 40- to 50-fold lower than that with parenteral dosages of the drug. /Clindamycin phosphate/
Because topical application of clindamycin as the phosphate appears to result in less systemic absorption of clindamycin than does topical application of clindamycin as the hydrochloride, clindamycin phosphate is the preferred salt for topical therapy. In vivo studies indicate that clindamycin penetrates comedones following topical application. In one study, comedonal concentrations of clindamycin averaged 597 ug/g of comedonal material following twice daily application to the skin of the commercially available clindamycin phosphate topical solution. /Clindamycin phosphate/
Clindamycin phosphate is absorbed systemically following topical application of the drug. Animal studies indicate that topical application of clindamycin as the hydrochloride results in a more rapid rate of systemic absorption of clindamycin than does topical application of clindamycin as the phosphate. In humans, 0.7 ug/mL or less of clindamycin has been detected in urine following twice daily application to the skin of a 1% hydroalcoholic solution of clindamycin as the hydrochloride (not commercially available in the US). Following multiple application to the skin of a 1% hydroalcoholic solution of clindamycin as the phosphate, low concentrations of the drug (0-3 ng/mL) have been detected in serum and less than 0.2% of the dose was detected in urine unchanged. /Clindamycin phosphate/
... The maternal-fetal transfer and amniotic fluid (AF) accumulation of clindamycin (CL) at the time of delivery /was investigated/ using a highly sensitive and specific high-pressure liquid chromatographic (HPLC) method ... Patients undergoing elective cesarean delivery with normal renal and hepatic function were divided into three groups receiving a dose of 900 mg of intravenous CL at 0.25, 0.5, or 1 hr prior to procedure respectively. At the time of delivery, cord blood, AF, and maternal blood were collected simultaneously. Concentrations in plasma, cord blood, and AF of CL were quantitatively determined by HPLC. ... Maternal-fetal transfer and amniotic fluid levels of CL were evaluated in a total of 15 patients (n=4 for the 0.25 hr; n = 7 for the 0.5 hr; and n= 4 for the 1 hr groups). The preliminary results showed the mean (+/- SD) maternal plasma concentrations of CL were 6.7 +/- 2.8; 5.4 +/- 1.4; 3.6 +/- 2.3 mg/mL, at 0.25, 0.5 and 1.0 hr between the drug infusion and time of delivery. Cord blood and AF concentrations were undetectable for CL in all paired samples.
A crossover study of the bioavailability and pharmacokinetics of clindamycin was conducted in 16 healthy male subjects (mean age 27.1 yr) and in 16 male patients (mean age 36.6 yr) with acquired immunodeficiency syndrome (AIDS) after an intravenous (IV) infusion of 600 mg clindamycin phosphate (Cleocin phosphate) and an oral capsule of 600 mg clindamycin hydrochloride (Cleocin hydrochloride). Plasma clearance was 0.27 and 0.21 L/hr/kg and steady state volume of distribution (Vss) was 0.79 and 0.66 L/kg in healthy subjects and AIDS patients, respectively. Oral bioavailability was 0.75 in patients and 0.53 in healthy subjects. Peak blood levels were 7.7 mg/L in patients and 5.3 mg/L in healthy subjects. Three patients had diarrhea after oral drug and 4 had diarrhea after IV drug. No side effects were noted in healthy subjects. It was concluded that the bioavailability of clindamycin is higher and plasma clearance and Vss are lower in AIDS patients. [Gatti G et al; Antimicrob Agents Chemother 37 (May): 1137-43 (1993)] PubMed Abstract
... The serum level and urinary excretion of clindamycin on the third day and the twenty-seventh day of therapy in thirteen patients who were applying 1% clindamycin hydrochloride topically for acne /was measured/. There was no detectable antibiotic in the serum of any subject (less than 0.4 ug/mL); in contrast, clindamycin was found in the urine of ten of the thirteen patients. There was marked intersubject variation in the urinary excretion of the drug, ranging from less than 10 to 500 micrograms/day. However, there was a highly significant correlation (p less than 0.0001) for a given subject between excretion values on days 3 and 27. There was no correlation between urinary excretion of clindamycin and either racial pigmentation or severity of acne in this relatively small group of patients. After topical application of 1% clindamycin hydrochloride, an average of 4% to 5% of clindamycin appears to be absorbed systemically, but greater amounts are absorbed in some individuals. [Barza M et al; J Am Acad Dermatol 7 (2): 208-14 (1982)] PubMed Abstract
In thirteen patients, ... /clindamycin phosphate/ concentration following joint replacement was measured by the agar diffusion method. In bone, the concentration was (mean +/- s.e. mean) 5.01 ug/mL +/- 1.16, N=10; in capsule, 3.29 ug/mL +/- 0.71, N=12; measured between 1.75 and 3.75 hr after intramuscular and intravenous injections, and in drainage fluid it amounted to 4.61 ug/mL +/- 0.38, N=11 in 48 hr. [Baird P et al; Postgrad Med J 54 (628): 65-7 (1978)] PubMed Abstract
This study assessed the effect of alcoholic cirrhosis in man and of experimental liver injury in rats on the disposition and elimination of clindamycin. In 7 cirrhotics a statistically significant, although modest, prolongation of clindamycin half-life (T1/2beta) was observed as compared to values in 7 age-matched normal contrals (mean plus or minus SD: 4.46 plus or minus 0.93 hr vs 3.42 plus or minus 0.45 hr, P equals 0.02). This was primarily due to a decrease in clindamycin serum clearance in the cirrhotics, since the volume of distribution of the drug was similar in both groups (P more than 0.05). Serum protein binding of clindamycin was of the order of 79% and was comparable in both groups (P more than 0.05). There was a significant correlation between the T1/2beta of the drug and both total serum bilirubin and SGOT. The T1/2beta of clindamycin was also prolonged in rats with acute hepatic necrosis induced by administration of carbon tetrachloride and those with acute cholestasis caused by common bile duct ligation. These data suggest that liver damage, both chronic and acute, impairs the elimination of clindamycin but that this effect is small. [Avant GR et al; Am J Dig Dis 20 (3): 223-30 (1975)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 360(SRC), determined from a log Kow of 2.16(2) and a regression-derived equation(3), indicates that clindamycin is expected to have moderate mobility in soil(SRC). Volatilization of 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(4). 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(5). Clindamycin appears to slowly biodegrade in the environment as suggested by a 3% theoretical BOD in 28 days using the Closed Bottle test(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 360(SRC), determined from a log Kow of 2.16(2) and a regression-derived equation(3), indicates that clindamycin is expected to adsorb to suspended solids and sediment(SRC). Volatilization 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). According to a classification scheme(5), an estimated BCF of 9(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Clindamycin appears to slowly biodegrade in the environment as suggested by a 3% theoretical BOD in 28 days using the Closed Bottle test(7).
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 deg 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 and therefore is not expected to be susceptible to direct photolysis by sunlight(3).

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