(2S,4R)-N-{2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide

• ChemBase ID: 1061
• Molecular Formular: C18H33ClN2O5S
• Molecular Mass: 424.98302
• Monoisotopic Mass: 424.17987085
• SMILES: O1[C@@H]([C@H](O)[C@@H](O)[C@@H](O)[C@H]1C(C(C)Cl)NC(=O)[C@@H]1C[C@H](CN1C)CCC)SC
• Canonical SMILES: CCC[C@H]1CN([C@@H](C1)C(=O)NC([C@H]1O[C@H](SC)[C@@H]([C@H]([C@H]1O)O)O)C(Cl)C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-N-{2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide
• IUPAC Traditional name: 7(S)-chloro-7-deoxylincomycin
• Brand Name: Chlolincocin; Cleocin; Cleocin Hcl; Cleocin Pediatric; Cleocin Phosphate; Cleocin T; Cleocin T Gel; Cleocin T Lotion; Cleocin T Topical Solution; Clinda-Derm; Clindagel; Clindesse; Clindets; Clinimycin; Dalacin; Dalacin C; Dalacin C Flavored Granules; Dalacin C Phosphate; Dalacin T Topical Solution; Evoclin; Sobelin; Zindaclin; ResiDerm A
• Synonyms: Clindamycin Hcl; Clindamicina [INN-Spanish]; Clindamycin Hydrochloride; Clindamycin Phosphate; Clindamycine [French]; Clindamycine [INN-French]; Clindamycinum [INN-Latin]; clindamycin; Clindamycin

Database IDs

• CAS Number: 18323-44-9
• PubChem SID: 160964524; 46506073
• PubChem CID: 29029

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.163722
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.0028338
• LogD (pH = 7.4): 0.65432453
• Log P: 1.0377376
• Molar Refractivity: 105.7173 cm^3
• Polarizability: 42.705715 Å^3
• Polar Surface Area: 102.26 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.76
• LOG S: -2.14
• Solubility (Water): 3.10e+00 g/l

PROPERTIES

Physical Property

• Solubility: 30.6 mg/L
• Hydrophobicity(logP): 1.6

DETAILS

DrugBank - DB01190

• Drug Groups: approved
• Description: Clindamycin is a semisynthetic lincosamide antibiotic that has largely replaced lincomycin due to an improved side effect profile. Clindamycin inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits. It may be bacteriostatic or bactericidal depending on the organism and drug concentration.
• Indication: For the treatment of serious infections caused by susceptible anaerobic bacteria, including Bacteroides spp., Peptostreptococcus, anaerobic streptococci, Clostridium spp., and microaerophilic streptococci. May be useful in polymicrobic infections such as intra-abdominal or pelvic infections, osteomyelitis, diabetic foot ulcers, aspiration pneumonia and dental infections. May also be used to treat MSSA and respiratory infections caused by S. pneumoniae and S. pyogenes in patients who are intolerant to other indicated antibiotics or who are infected with resistant organism. May be used vaginally to treat vaginosis caused by Gardnerella vaginosa. Clindamycin reduces the toxin producing effects of S. aureus and S. pyogenes and as such, may be particularly useful for treating necrotizing fasciitis. May be used topically to treat acne.
• Pharmacology: Clindamycin is an antibiotic, similar to and a derivative of lincomycin. Clindamycin can be used in topical or systemic treatment. It is effective as an anti-anaerobic antibiotic and antiprotozoal.
• Toxicity: Adverse effects include nausea (may be dose-limiting), diarrhea, pseudomembranous colitis, allergic reactions, hepatoxicity, transient neutropenia and eosinophilia and agranulocytosis. Pseudomembranous colitis occurs in 0.01 - 10% of patients and occurs more commonly than with other antibiotics. Use of the topical formulation of clindamycin results in absorption of the antibiotic from the skin surface. Diarrhea, bloody diarrhea, and colitis (including pseudomembranous colitis) have been reported with the use of topical and systemic clindamycin.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic
• Absorption: Rapidly absorbed after oral administration with peak serum concentrations observed after about 45 minutes. Absorption of an oral dose is virtually complete (90%) and the concomitant intake of food does not appreciably modify the serum concentrations; serum levels have been uniform and predictable from person to person and dose to dose. Clindamycin does not penetrate the blood brain barrier.
• Half Life: 2.4 hours
• Protein Binding: 92-94%
• Elimination: Approximately 10% of the bioactivity is excreted in the urine and 3.6% in the feces; the remainder is excreted as bioinactive metabolites.
• References: Daum RS: Clinical practice. Skin and soft-tissue infections caused by methicillin-resistant Staphylococcus aureus. N Engl J Med. 2007 Jul 26;357(4):380-90. [Pubmed] ; Klempner MS, Styrt B: Clindamycin uptake by human neutrophils. J Infect Dis. 1981 Nov;144(5):472-9. [Pubmed] ; Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [Pubmed] ; Plaisance KI, Drusano GL, Forrest A, Townsend RJ, Standiford HC: Pharmacokinetic evaluation of two dosage regimens of clindamycin phosphate. Antimicrob Agents Chemother. 1989 May;33(5):618-20. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. Pubmed
• Plaisance KI, Drusano GL, Forrest A, Townsend RJ, Standiford HC: Pharmacokinetic evaluation of two dosage regimens of clindamycin phosphate. Antimicrob Agents Chemother. 1989 May;33(5):618-20. Pubmed
• Klempner MS, Styrt B: Clindamycin uptake by human neutrophils. J Infect Dis. 1981 Nov;144(5):472-9. Pubmed
• Daum RS: Clinical practice. Skin and soft-tissue infections caused by methicillin-resistant Staphylococcus aureus. N Engl J Med. 2007 Jul 26;357(4):380-90. Pubmed