Clindamycin phosphateProduct ingredient for Clindamycin

Name
Clindamycin phosphate
Drug Entry
Clindamycin

Clindamycin is a semi-synthetic lincosamide antibiotic used in the treatment of a variety of serious infections due to susceptible microorganisms14,13 as well as topically for acne vulgaris.12 It has a relatively narrow spectrum of activity that includes anaerobic bacteria as well as gram-positive cocci and bacilli and gram-negative bacilli.8 Interestingly, clindamycin appears to carry some activity against protozoans, and has been used off-label in the treatment of toxoplasmosis, malaria, and babesiosis.9

Clindamycin is derived from, and has largely replaced, lincomycin, a naturally occurring lincosamide and the eponymous member of this antibiotic class, due to its improved properties over the parent compound. The name lincomycin is derived from Lincoln, Nebraska, where it was first isolated from Streptomyces lincolnensis found in a soil sample.8

Accession Number
DBSALT000778
Structure
Thumb
Synonyms
Not Available
UNII
EH6D7113I8
CAS Number
24729-96-2
Weight
Average: 504.963
Monoisotopic: 504.146200983
Chemical Formula
C18H34ClN2O8PS
InChI Key
UFUVLHLTWXBHGZ-KUWMELJBSA-N
InChI
InChI=1S/C18H34ClN2O8PS/c1-5-6-10-7-11(21(3)8-10)17(24)20-12(9(2)19)15-13(22)14(23)16(18(28-15)31-4)29-30(25,26)27/h9-16,18,22-23H,5-8H2,1-4H3,(H,20,24)(H2,25,26,27)/t9?,10-,11+,12?,13-,14+,15-,16-,18-/m1/s1
IUPAC Name
{[(2R,3R,4S,5R,6R)-6-(2-chloro-1-{[(2S,4R)-1-methyl-4-propylpyrrolidin-2-yl]formamido}propyl)-4,5-dihydroxy-2-(methylsulfanyl)oxan-3-yl]oxy}phosphonic acid
SMILES
KEGG Drug
D01073
KEGG Compound
C11728
PubChem Compound
10346039
ChemSpider
8521497
ChEBI
3746
Wikipedia
Clindamycin
Predicted Properties
PropertyValueSource
Water Solubility3.12 mg/mLALOGPS
logP1ALOGPS
logP-0.57ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.71ChemAxon
pKa (Strongest Basic)7.56ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area148.79 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity116.59 m3·mol-1ChemAxon
Polarizability49.21 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon