Clindamycin palmitate hydrochlorideProduct ingredient for Clindamycin

Name
Clindamycin palmitate hydrochloride
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
DBSALT001215
Structure
Synonyms
Clindamycin palmitate HCl / Clindamycin palmitate hydrochloride
External IDs
U 25179E / U-25,179 E
UNII
VN9A8JM7M7
CAS Number
25507-04-4
Weight
Average: 699.85
Monoisotopic: 698.3862144
Chemical Formula
C34H64Cl2N2O6S
InChI Key
GTNDZRUWKHDICY-DJHAJVGHSA-N
InChI
InChI=1S/C34H63ClN2O6S.ClH/c1-6-8-9-10-11-12-13-14-15-16-17-18-19-21-27(38)42-32-30(40)29(39)31(43-34(32)44-5)28(24(3)35)36-33(41)26-22-25(20-7-2)23-37(26)4;/h24-26,28-32,34,39-40H,6-23H2,1-5H3,(H,36,41);1H/t24-,25+,26-,28+,29+,30-,31+,32+,34+;/m0./s1
IUPAC Name
(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-{[(2S,4R)-1-methyl-4-propylpyrrolidin-2-yl]formamido}propyl]-4,5-dihydroxy-2-(methylsulfanyl)oxan-3-yl hexadecanoate hydrochloride
SMILES
Cl.[H][C@@](NC(=O)[C@@H]1C[C@@H](CCC)CN1C)([C@H](C)Cl)[C@@]1([H])O[C@H](SC)[C@H](OC(=O)CCCCCCCCCCCCCCC)[C@@H](O)[C@H]1O
ChemSpider
10482335
ChEBI
34647
ChEMBL
CHEMBL1200632
Wikipedia
Clindamycin
Predicted Properties
PropertyValueSource
Water Solubility0.0008 mg/mLALOGPS
logP7.02ALOGPS
logP7.96Chemaxon
logS-5.9ALOGPS
pKa (Strongest Acidic)12.59Chemaxon
pKa (Strongest Basic)7.55Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area108.33 Å2Chemaxon
Rotatable Bond Count23Chemaxon
Refractivity179.31 m3·mol-1Chemaxon
Polarizability77.74 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon