[(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-[[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carbonyl]amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate

Base Information

• Chemical Name: [(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-[[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carbonyl]amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate
• CAS No.: 24729-96-2
• Molecular Formula: C18H34ClN2O8PS
• Molecular Weight: 504.969
• Hs Code.: 29419000
• European Community (EC) Number: 246-433-0
• DSSTox Substance ID: DTXSID80860321
• Mol file: 24729-96-2.mol

Synonyms:24729-96-2;7-Epi clindamycin 2-phosphate;C18-H34-Cl-N2-O8-P-S;ST075182;DTXSID80860321;[(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-[[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carbonyl]amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate;L-threo-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-, 2-(dihydrogen phosphate), trans- .alpha.-;AKOS015960484;NCGC00389304-01;AC-11380;Methyl7-chloro-6,7,8-trideoxy-6-(1-methyl-trans-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-L-threo-alpha-D-galacto-octopyranoside2-(dihydrogenphosphate);FT-0603210;methyl 7-chloro-6,7,8-trideoxy-6-[(1-methyl-4-propylprolyl)amino]-2-O-phosphono-1-thiooctopyranoside

Chemical Property of [(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-[[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carbonyl]amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 114 °C
• Refractive Index: 122 ° (C=1, H2O)
• Boiling Point: 159°C
• PKA: pKa 0.964±0.06 (H2O t=21) (Uncertain);6.06 ±0.06 (I=0.008)(H2O t=21) (Uncertain)
• PSA: 183.90000
• Density: 1.41 g/cm³
• LogP: 0.83530
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble224mg/mL at 25°C
• Water Solubility.: Freely soluble in water
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 504.1462019
• Heavy Atom Count: 31
• Complexity: 658

Purity/Quality:

99%min ^*data from raw suppliers

Clindamycin 2-phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)OP(=O)(O)O)O)O)C(C)Cl
• Recent EU Clinical Trials: Antibiotic pharmacokinetics in women with twin pregnancy
• Description: Clindamycin phosphate is a water-soluble ester of the semisynthetic antibiotic produced by a 7 (S)-chloro-substitution of the 7 (R)-hydroxyl group of the parent antibiotic, lincomycin. It is a derivative of lincomycin(a lincosamide). It has primarily bacteriostatic action against Gram-positive aerobes and a wide range of anaerobicbacteria. It is a topical antibiotic used in the treatment of infections. These might include infections of the respiratory tract, septicaemia, peritonitis and bone infections. It is also used to treat moderate to severe acne.
• Indications: Clindamycin Phosphate Topical Solution and Clindamycin Phosphate Lotion (Clindamycin Phosphate Topical Suspension USP, 1%) contain clindamycin phosphate, USP, at a concentration equivalent to 10 mg clindamycin per milliliter. Clindamycin Phosphate Gel contains clindamycin phosphate, USP, at a concentration equivalent to 10 mg clindamycin per gram. Clindamycin Phosphate is indicated for topical application in the treatment of acne vulgaris. In view of the potential for diarrhea, bloody diarrhea and pseudomembranous colitis, the physician should consider whether other agents are more appropriate.
• Uses: Clindamycin phosphate is used topically alone or in conjunction with benzoyl peroxide in the treatment of inflammatory acne vulgaris. In weighing the potential benefits of topical clindamycin therapy, the possibility of serious adverse GI effects associated with the drug should be considered. Therapy of acne vulgaris must be individualized and frequently modified depending on the types of acne lesions which predominate and the response to therapy. Topical anti-infectives, including clindamycin, generally are effective in the treatment of mild to moderate inflammatory acne. However, use of topical anti-infectives as monotherapy may lead to bacterial resistance; this resistance is associated with decreased clinical efficacy.Topical clindamycin is particularly useful when used with benzoyl peroxide or topical retinoids. Results of clinical studies indicate that combination therapy results in a reduction in total lesion counts of 50-70%. Clindamycin 2-phosphate is a a salt of clincamycin, a semi-synthetic lincosamide. The salt is prepared by selective phosphorylation of the 2-hydroxy moiety of the sugar of clindamycin. The introduction of the phosphate affords improved solubility for injectable formulations. Like other members of the lincosamide family, clindamycin 2-phosphate is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans. Clindamycin acts by binding to the 23S ribosomal subunit, blocking protein synthesis.
• Drug interactions: Clindamycin has been shown to have neuromuscular blocking properties that may enhance the action of other neuromuscular blocking agents. Therefore it should be used with caution in patients receiving such agents.

Technology Process of [(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-[[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carbonyl]amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate

There total 8 articles about [(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-[[(2S,4R)-1-methyl-4-propylpyrrolidine-2-carbonyl]amino]propyl]-4,5-dihydroxy-2-methylsulfanyloxan-3-yl] dihydrogen phosphate 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: 96.15%

C25H40ClN8O6PS → clindamycin phosphate (24729-96-2)

Guidance literature:

With hydrogenchloride; acetic acid; In water; at 50 - 55 ℃; for 10h;

Reference yield: 92.0%

C21H36Cl3N2O7PS → clindamycin phosphate (24729-96-2)

Guidance literature:

In water; at 20 ℃; for 8h; Temperature; Acidic conditions; Green chemistry;

Reference yield: 90.0%

C9H19ClNO7PS + 1-methyl-4-propylpyrrolidine-2-carboxylic acid (13380-36-4) → clindamycin phosphate (24729-96-2)

Guidance literature:

With sodium carbonate; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; at 30 ℃; for 8h; Reagent/catalyst; Temperature;

upstream raw materials:

clindamycin hydrochloride

lincomycin hydrochloride

C₂₁H₃₇ClN₂O₅S

1-methyl-4-propylpyrrolidine-2-carboxylic acid

Refernces

• 1、 -. "Preparation method of clindamycin phosphate". Paragraph 0051; 0056-0057; 0063-0064; 0070-0071. . Retrieved 2018/03/26.
• 2、 -. "Triazole in the synthesis of clindamycin phosphate in the application of the". Paragraph 0015; 0025-0026. . Retrieved 2017/11/16.