Clindamycin Phosphate
Basic information
- CAS
24729-96-2- Standard SMILES
CCC[C@@H]1C[C@@H](C(=O)N[C@@H]([C@H]2O[C@H](SC)[C@H](OP(=O)(O)O)[C@@H](O)[C@H]2O)[C@H](C)Cl)N(C)C1- InChIKey
UFUVLHLTWXBHGZ-MGZQPHGTSA-N- Molecular formula
- C18H34ClN2O8PS
- Average molar mass
- 505 g/mol
- Monoisotopic mass
- 504.1462019
Overview
Clindamycin Phosphate is the phosphate salt form of clindamycin, a semi-synthetic, chlorinated broad spectrum antibiotic produced by chemical modification of lincomycin. Clindamycin phosphate is used in topical preparations.
Names & identifiers
- Preferred name
- Clindamycin Phosphate
- IUPAC
- [(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
- English name
- Clindamycin phosphate
- Molecular formula
- C18H34ClN2O8PS
- Molecular weight
- 504.96
Names & synonyms
Clindamycin phosphate24729-96-2Cleocin phosphateClindetsCleocin TClindagelClindesseEvoclinClinda-DermDalacin PClindamycin 2-phosphateDalacin T
Show more names
Clindamycine phosphate7(S)-CHLORO-7-DEOXYLINCOMYCINClindamycin Phosphate ImpurityMethyl 7-chloro-6,7,8-trideoxy-6-[[[(2S)-1-methyl-4β-propyl-2-pyrrolidinyl]carbonyl]amino]-2-O-phosphono-1-thio-L-threo-α-D-galacto-octopyranosideMethyl 7-chloro-6,7,8-trideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-L-threo-α-D-galacto-octopyranoside 2-(dihydrogen phosphate)Methyl7-chloro-6,7,8-trideoxy-6-(1-methyl-trans-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-L-threo-alpha-D-galacto-octopyranoside2-(dihydrogenphosphate)Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S)-1-methyl-4β-propyl-2α-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside 2-dihydrogen phosphatemethyl 7-chloro-6,7,8-trideoxy-6-(1-methyl-trans-4-propyl-l-2-pyrrolidinecarboxamido)-1-thio-l-threo-alpha-d-galacto-octopyranoside 2-(dihydrogen phosphate)
Properties
Computed structural properties
- XLogP
- -1.2
- Topological polar surface area
- 174 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 9
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 658
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 114 °C · 114 °C
- Boiling point
- 159 °C · 159°C
- Density
- 1.41 · 1.41±0.1 g/cm3(Predicted)
- refractive index
- 122 ° · 122 ° (C=1, H2O)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 224 mg/mL · DMSO: soluble224mg/mL at 25°C
- form
- solid
- pka
- 0.964 · pKa 0.964±0.06 (H2O t=21) (Uncertain);6.06 ±0.06 (I=0.008)(H2O t=21) (Uncertain)
- color
- White
- Water Solubility
- Freely soluble in water
- Merck
- 14 · 14,2356
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 214 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationClindamycin phosphate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (99.5%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Clindamycin phosphate
vLess-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- GF2625000
- hs_code
- 29419000
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
CLINDAMYCIN PHOSPHATE
Neuromuscular Blockade [PE]; Lincosamides [CS]; Lincosamide Antibacterial [EPC]; Decreased Sebaceous Gland Activity [PE]
CLINDAMYCIN PHOSPHATE GEL USP, 1%
Lincosamide Antibacterial [EPC]; Decreased Sebaceous Gland Activity [PE]; Neuromuscular Blockade [PE]; Lincosamides [CS]
CLINDAMYCIN PHOSPHATE TOPICAL SOLUTION USP, 1%
Lincosamide Antibacterial [EPC]; Decreased Sebaceous Gland Activity [PE]; Neuromuscular Blockade [PE]; Lincosamides [CS]
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionClindamycin 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.
UsesClindamycin 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%.
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Compound notes
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