Clindamycin

CAT: 0804-HY-B1455-05Size: 50 mgDry Ice: NoHazardous: No

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Description

Clindamycin is an orally active and broad-spectrum bacteriostatic lincosamide antibiotic. Clindamycin can inhibit bacterial protein synthesis, possessing 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) . Clindamycin also can be used for researching malaria[1][2].

CAS Number

18323-44-9

UNSPSC

12352005

Hazard Statement

H301-H311-H331-H341

Target

Antibiotic; Bacterial; Parasite

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection; Cancer

Assay Protocol

https://www.medchemexpress.com/clindamycin.html

Purity

99.90

Solubility

DMSO : 125 mg/mL (ultrasonic) |H2O : 2 mg/mL (ultrasonic; warming; heat to 60°C)

Smiles

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

Molecular Formula

C18H33ClN2O5S

Molecular Weight

424.98

Precautions

P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361-P403+P233-P405-P501

References & Citations

[7]Yang SH, Lee MG. Dose-independent pharmacokinetics of clindamycin after intravenous and oral administration to rats: contribution of gastric first-pass effect to low bioavailability. Int J Pharm. 2007 Mar 6;332 (1-2) :17-23.|[8]Hirata N, et al. Pretreatment of mice with clindamycin improves survival of endotoxic shock by modulating the release of inflammatory cytokines. Antimicrob Agents Chemother. 2001 Sep;45 (9) :2638-42. |[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.|[2]Kremsner PG. Clindamycin in malaria treatment. J Antimicrob Chemother. 1990 Jan;25 (1) :9-14.|[3]Kishi K, et al. Clindamycin suppresses endotoxin released by ceftazidime-treated Escherichia coli O55:B5 and subsequent production of tumor necrosis factor alpha and interleukin-1 beta. Antimicrob Agents Chemother. 1999 Mar;43 (3) :616-22.|[4]Veringa EM, et al. Clindamycin at subinhibitory concentrations enhances antibody- and complement-dependent phagocytosis by human polymorphonuclear leukocytes of Staphylococcus aureus. Chemotherapy. 1987;33 (4) :243-9. |[5]Naal FD, et al. The effects of clindamycin on human osteoblasts in vitro. Arch Orthop Trauma Surg. 2008 Mar;128 (3) :317-23.|[6]Faggion PI, et al. Is the penetration of clindamycin into the masseter muscle really enough to treat odontogenic infections? Clin Oral Investig. 2021 May;25 (5) :3257-3266.

Shipping Conditions

Blue Ice

Storage Conditions

-20°C (Powder, protect from light)

Scientific Category

Reference compound1

Clinical Information

Launched

Isoform

Plasmodium

Citation 01

Chemical Information

Clindamycin

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

CAS Number	18323-44-9
PubChem CID	446598
IUPAC Name	(2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
Molecular Formula	C18H33ClN2O5S
Molecular Weight	425.0
XLogP	2.2
Topological Polar Surface Area	128
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	7
Heavy Atom Count	27
Formal Charge	0
Complexity	502

SMILES

CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl

InChI

InChI=1S/C18H33ClN2O5S/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)/t9-,10+,11-,12+,13-,14+,15+,16+,18+/m0/s1

InChIKey

KDLRVYVGXIQJDK-AWPVFWJPSA-N

Chemical Structure

2D Structure

CAS: 18323-44-9

CID: 446598

Formula: C18H33ClN2O5S

MW: 425.0

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	425.0
XLogP3	2.2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	7
Exact Mass	424.1798710
Monoisotopic Mass	424.1798710
Topological Polar Surface Area	128 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	502
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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Clindamycin

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