Clindamycin

Base Information

• Chemical Name: Clindamycin
• CAS No.: 18323-44-9
• Deprecated CAS: 13441-63-9,24620-78-8,24696-19-3,16669-21-9
• Molecular Formula: C₁₈H₃₃ClN₂O₅S
• Molecular Weight: 424.989
• European Community (EC) Number: 242-209-1
• UNII: 3U02EL437C
• DSSTox Substance ID: DTXSID2022836
• Nikkaji Number: J9.300I
• Wikipedia: Clindamycin
• NCI Thesaurus Code: C377
• RXCUI: 2582
• Metabolomics Workbench ID: 144285
• ChEMBL ID: CHEMBL1753
• Mol file: 18323-44-9.mol

Synonyms:7 Chloro 7 deoxylincomycin;7-Chloro-7-deoxylincomycin;Chlolincocin;Chlorlincocin;Cleocin;Clindamycin;Clindamycin Hydrochloride;Clindamycin Monohydrochloride;Clindamycin Monohydrochloride, Monohydrate;Dalacin C;Hydrochloride, Clindamycin;Monohydrate Clindamycin Monohydrochloride;Monohydrochloride, Clindamycin;Monohydrochloride, Monohydrate Clindamycin

Chemical Property of Clindamycin

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.07E-18mmHg at 25°C
• Melting Point: 141 - 143oC
• Refractive Index: 1.6100 (estimate)
• Boiling Point: 628.077 °C at 760 mmHg
• PKA: 7.6(at 25℃)
• Flash Point: 333.649 °C
• PSA: 127.56000
• Density: 1.29 g/cm³
• LogP: 0.71830
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 424.1798710
• Heavy Atom Count: 27
• Complexity: 502

Purity/Quality:

99% ^*data from raw suppliers

Clindamycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl
• Isomeric SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl
• Recent ClinicalTrials: CAT BITE Antibiotic Prophylaxis for the Hand/Forearm (CATBITE)
• Recent EU Clinical Trials: A Multicenter, Open-Label, Evaluator-Blinded, Randomized Study to Evaluate the Safety and Tolerability of Single-Dose IV Oritavancin Versus Standard of Care for the Treatment of Pediatric Subjects with Acute Bacterial Skin And Skin Structure Infections
• Recent NIPH Clinical Trials: Study of the utility of acute-phase and remission maintenance therapy with 2.5% benzoyl peroxide gel for moderate or severe acne vulgaris
• Description: Clindamycin, a derivative of lincomycin, was first isolated from Streptomyces lincolnesis in 1962 and became commercially available in 1966. The name originates from Lincoln, Nebraska, where the organism was first isolated from a soil sample. The parent compound of clindamycin is lincomycin, which is produced by actinomycete, Streptomyces liconelnensis, which belongs to the order of Actinobacteria. It replaced lincomycin use because of its better absorption and clinical spectrum. Lincomycin belongs to the lincosamides, which is a class of antibiotics. The compounds use as antibiotic agents stems from their ability to interfere with the protein synthesis of bacteria. The chemical modification of lincomycin, clindamycin, has proven to be superior to the natural product for clinical applications. Clindamycin is better absorbed from the gastrointestinal tract and food does not interfere with its absorption. It is also eight times more active against aerobic gram-positive cocci, and it has proven activity against gram-positive and gram-negative anaerobic bacteria as well as protozoal organisms like Toxoplasma and Plasmodium species.
• 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.
• Indications: Clindamycin (Cleocin), 300 to 450 mg/day, is an extremely effective agent for acne.
• Therapeutic Function: Antibacterial
• 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.
• Drug interactions: Potentially hazardous interactions with other drugs Ciclosporin: may cause reduced ciclosporin levels. Erythromycin: antagonism demonstrated in vitro; manufacturers recommend that the two drugs should not be administered concurrently. Muscle relaxants: enhanced neuromuscular blockade.

Technology Process of Clindamycin

There total 3 articles about Clindamycin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

lincomycin hydrochloride (859-18-7) → clindamycin (16684-06-3,18323-44-9,51064-35-8)

Guidance literature:

lincomycin hydrochloride; With phosgene; In chloroform; N,N-dimethyl-formamide; at 5 - 71 ℃; for 2h; Large scale;

at 10 ℃; Temperature; Reagent/catalyst; Alkaline conditions; Large scale;

Reference yield:

→ clindamycin (16684-06-3,18323-44-9,51064-35-8)

Guidance literature:

Reference yield:

→ 7-Chlor-7-deoxylincomycin (16684-06-3,18323-44-9,51064-35-8)

Guidance literature:

Lincomycin*HCl, SOCl2;

upstream raw materials:

lincomycin hydrochloride

Downstream raw materials:

C₂₁H₃₇ClN₂O₅S

clindamycin hydrochloride

Refernces

• 1、 -. "A clindamycin phosphate ester synthesis method". Paragraph 0042-0043. . Retrieved 2017/02/28.
• 2、 -. "Method for treating inflammation". . . Retrieved 2008/06/13.