Clindamycin

Names

[ Name ]:
Clindamycin

[Synonym ]:
L-threo-α-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-
7-Deoxy-7(S)-chlorolincomycin
EINECS 242-209-1
Chlorodeoxylincomycin
Methyl 7-Chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-a-D-galacto-octopyranoside
Cleocin
Clindamycin
Methyl (2S-trans)-7-Chloro-6,7,8-trideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-L-threo-a-D-galacto-octopyranoside
7-CDL
L-threo-α-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-((((2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-
MFCD00072005
(2S,4R)-N-{(1S,2S)-2-Chlor-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)tetrahydro-2H-pyran-2-yl]propyl}-1-methyl-4-propylpyrrolidin-2-carboxamid
CLDM
Methyl 7-chloro-6,7,8-trideoxy-6-{[(4R)-1-methyl-4-propyl-L-prolyl]amino}-1-thio-L-threo-α-D-galacto-octopyranoside
dalacinc
Dalacine
clinimycin
Methyl (5R)-5-[(1S,2S)-2-chloro-1-{[(4R)-1-methyl-4-propyl-L-prolyl]amino}propyl]-1-thio-β-L-arabinopyranoside
7-Chlorolincomycin
sobelin
(2S,4R)-N-{(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)tetrahydro-2H-pyran-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide
(2S,4R)-N-{(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(méthylsulfanyl)tétrahydro-2H-pyran-2-yl]propyl}-1-méthyl-4-propylpyrrolidine-2-carboxamide
chlolincocin

Biological Activity

[Description]:

Clindamycin is an oral protein synthesis inhibitory agent that has the ability to suppress the expression of virulence factors in Staphylococcus aureus at sub-inhibitory concentrations (sub-MICs). Clindamycin resistance results from enzymatic methylation of the antibiotic binding site in the 50S ribosomal subunit (23S rRNA). Clindamycin decreases the production of Panton-Valentine leucocidin (PVL), toxic-shock-staphylococcal toxin (TSST-1) or alpha-haemolysin (Hla)[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Hodille E, et al. Clindamycin suppresses virulence expression in inducible clindamycin-resistant Staphylococcus aureus strains. Ann Clin Microbiol Antimicrob. 2018 Oct 20;17(1):38.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
628.1±55.0 °C at 760 mmHg

[ Melting Point ]:
141 - 143ºC

[ Molecular Formula ]:
C₁₈H₃₃ClN₂O₅S

[ Molecular Weight ]:
424.983

[ Flash Point ]:
333.6±31.5 °C

[ Exact Mass ]:
424.179871

[ PSA ]:
127.56000

[ LogP ]:
1.83

[ Vapour Pressure ]:
0.0±4.2 mmHg at 25°C

[ Index of Refraction ]:
1.574

[ Storage condition ]:
-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RH6300000

CHEMICAL NAME :: L-threo-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-(1-methyl-4-propyl-L-2- pyrrolidinecarboxamido)-1-thio-, trans-alpha-

CAS REGISTRY NUMBER :: 18323-44-9

LAST UPDATED :: 199606

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C18-H33-Cl-N2-O5-S

MOLECULAR WEIGHT :: 425.04

WISWESSER LINE NOTATION :: T6OTJ BS1 CQ DQ EQ FYYG1&MV- BT5NTJ A1 D3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2618 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 18,185,1971

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: RMVEAG Recueil de Medecine Veterinaire. (Masson Pub. USA, Inc., Year Book Medical Pub., 35 E. Wacker Dr., Chicago IL 60601) V.1- 1824- Volume(issue)/page/year: 156,915,1980

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Gastrointestinal - other changes

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 34,794,1984 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 330 mg/kg/33D-I

TOXIC EFFECTS :: Gastrointestinal - other changes

REFERENCE :: ANTBAL Antibiotiki. (Moscow, USSR) V.1-29, 1956-84. For publisher information, see AMBIEH. Volume(issue)/page/year: 28,18,1983 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3191 No. of Facilities: 445 (estimated) No. of Industries: 1 No. of Occupations: 7 No. of Employees: 21575 (estimated) No. of Female Employees: 17442 (estimated)