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C5269

Sigma-Aldrich

Clindamycin hydrochloride

lincosamide antibiotic

Synonym(s):

(7S)-7-Chloro-7-deoxylincomycin hydrochloride, Cleocin

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About This Item

Empirical Formula (Hill Notation):
C18H33ClN2O5S · HCl
CAS Number:
21462-39-5
Molecular Weight:
461.44
Beilstein:
4070786
MDL number:
MFCD07793327
UNSPSC Code:
51101500
PubChem Substance ID:
24892772
NACRES:
NA.85

Quality Level

200

form

crystalline

impurities

≤2 mol/mol EtOH

solubility

H2O: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

Cl.CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@H](C)Cl)C2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O

InChI

1S/C18H33ClN2O5S.ClH/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4;/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25);1H/t9-,10+,11-,12+,13-,14+,15+,16+,18+;/m0./s1

InChI key

AUODDLQVRAJAJM-XJQDNNTCSA-N

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General description

Chemical structure: macrolide

Application

Clindamycin is used to study bacterial infections, such as group B streptococcal disease, bacterial resistance and plasma protein binding.
Used to study bacterial protein synthesis.

Biochem/physiol Actions

Clindamycin hydrochloride is highly effective against anaerobic species.
Clindamycin is a semi-synthetic, lincosamide antibiotic that is prepared from lincomycin. It inhibits bacterial protein synthesis by hydrogen bond interactions with the 23S rRNA component of the 50S ribosomal subunit thus inducing dissociation of the peptidyl-t-RNA complex. It has antibacterial activity against Gram-positive cocci and antiprotozoal activity against Taxoplasma.

Other Notes

Antibacterial and antiprotozoal antibiotic of the lincosamide class.
Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317 - H319 - H362

Hazard Classifications

Eye Irrit. 2 - Lact. - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sonja Löfmark et al.
The Journal of antimicrobial chemotherapy, 58(6), 1160-1167 (2006-10-19)
The aim was to study the long-term consequences of 1 week clindamycin administration regarding selection and persistence of resistance, resistance determinants and diversity of the Bacteroides spp. in the intestinal microflora. A total of 1306 Bacteroides isolates were collected from
Anouk E Muller et al.
Antimicrobial agents and chemotherapy, 54(5), 2175-2181 (2010-02-24)
The study presented here was performed to determine the pharmacokinetics of intravenously administered clindamycin in pregnant women. Seven pregnant women treated with clindamycin were recruited. Maternal blood and arterial and venous umbilical cord blood samples were obtained. Maternal clindamycin concentrations
A Burian et al.
The Journal of antimicrobial chemotherapy, 66(1), 134-137 (2010-11-04)
although plasma protein binding (PPB) is accepted to be an essential factor in reducing antimicrobial activity, little is known about the underlying mechanisms. One possibility includes impaired penetration of an antimicrobial into bacterial cells in the presence of PPB. As
Michael C Jewett et al.
Molecular systems biology, 9, 678-678 (2013-06-27)
Purely in vitro ribosome synthesis could provide a critical step towards unraveling the systems biology of ribosome biogenesis, constructing minimal cells from defined components, and engineering ribosomes with new functions. Here, as an initial step towards this goal, we report
J Spízek et al.
Applied microbiology and biotechnology, 64(4), 455-464 (2004-02-06)
Lincomycin and clindamycin are lincosamide antibiotics used in clinical practice. Both antibiotics are bacteriostatic and inhibit protein synthesis in sensitive bacteria. They may even be bactericidal at the higher concentrations that can be reached in vivo. Clindamycin is usually more
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