Clindamycin | CAS#18323-44-9 | antibacterial agent

MedKoo Cat#: 597948 | Name: Clindamycin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Clindamycin is an antibacterial agent that is a semisynthetic analog of LINCOMYCIN.

Chemical Structure

Clindamycin

CAS#18323-44-9 (free)

Theoretical Analysis

MedKoo Cat#: 597948

Name: Clindamycin

CAS#: 18323-44-9 (free)

Chemical Formula: C18H33ClN2O5S

Exact Mass: 424.1799

Molecular Weight: 424.98

Elemental Analysis: C, 50.87; H, 7.83; Cl, 8.34; N, 6.59; O, 18.82; S, 7.54

Price and Availability

Size	Price	Availability
50mg	USD 350.00	2 Weeks
100mg	USD 650.00	2 Weeks
250mg	USD 1,250.00	2 Weeks

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Related CAS #

21462-39-5 (HCl) 18323-44-9 (free) 24729-96-2 (phosphate) 58207-19-5 (HCl monohydrate) 25507-04-4 (palmitate HCl)

Synonym

Clindamycin; Dalacine; Chlolincocin; Clinimycin; U 21251; U-21251; U21251; U-21,251; U 21,251; U21,251;

IUPAC/Chemical Name

(2S,4R)-N-((1S,2S)-2-chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide

InChi Key

KDLRVYVGXIQJDK-AWPVFWJPSA-N

InChi Code

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

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

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).

In vitro activity:

Of the six S. aureus strains tested, three stains carried the lukS-PVL gene. For these three strains, the sub-MICs of clindamycin significantly decreased PVL release compared to that of the growth control (without antibiotics) (Fig. 1b). Reference: Ann Clin Microbiol Antimicrob. 2018; 17: 38. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6195712/

In vivo activity:

The present study investigated the effects of clindamycin in acute and chronic models of pain and inflammation in mice and the underlying mechanisms. Tactile hypersensitivity and paw edema induced by intraplantar (i.pl.) injection of carrageenan were attenuated by previous administration of clindamycin (200 and 400 mg/kg, i.p.). Clindamycin (100, 200 and 400 mg/kg, i.p.) also attenuated ongoing tactile hypersensitivity and paw edema induced by i.pl. injection of complete Freund's adjuvant (CFA). The antinociceptive activity of clindamycin (400 mg/kg, i.p.) in the hot plate model was attenuated by previous administration of naltrexone (5 and 10 mg/kg, i.p.), but not glibenclamide or AM251. CFA-induced production of TNF-α and CXCL-1 was reduced by clindamycin (400 mg/kg, i.p.). Concluding, clindamycin exhibits activities in acute and chronic models of pain and inflammation. Reference: Inflammopharmacology. 2020 Apr;28(2):551-561. https://pubmed.ncbi.nlm.nih.gov/31768707/

	Solvent	mg/mL	mM
Solubility
	DMSO	52.5	123.54
	DMF	30.0	70.59
	Ethanol	52.5	123.54
	PBS (pH 7.2)	0.2	0.47

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 424.98 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Rodrigues FF, Morais MI, Melo ISF, Augusto PSA, Dutra MMGB, Costa SOAM, Costa FC, Goulart FA, Braga AV, Coelho MM, Machado RR. Clindamycin inhibits nociceptive response by reducing tumor necrosis factor-α and CXCL-1 production and activating opioidergic mechanisms. Inflammopharmacology. 2020 Apr;28(2):551-561. doi: 10.1007/s10787-019-00670-w. Epub 2019 Nov 25. PMID: 31768707. 2. Hodille E, Badiou C, Bouveyron C, Bes M, Tristan A, Vandenesch F, Lina G, Dumitrescu O. Clindamycin suppresses virulence expression in inducible clindamycin-resistant Staphylococcus aureus strains. Ann Clin Microbiol Antimicrob. 2018 Oct 20;17(1):38. doi: 10.1186/s12941-018-0291-8. PMID: 30342546; PMCID: PMC6195712.

In vitro protocol:

In vivo protocol:

1: Oertel R, Schubert S, Mühlbauer V, Büttner B, Marx C, Kirch W. Determination of clindamycin and its metabolite clindamycin sulfoxide in diverse sewage samples. Environ Sci Pollut Res Int. 2014 Oct;21(20):11764-9. doi: 10.1007/s11356-013-2333-2. Epub 2013 Dec 6. PubMed PMID: 24310902. 2: Murray J, Potts A. The phototoxic and photoallergy potential of clindamycin phosphate 1.2%/ tretinoin 0.025% gel for facial acne: results of two single-center, evaluator-blinded, randomized, vehicle-controlled phase 1 studies in healthy volunteers. J Drugs Dermatol. 2014 Jan;13(1):16-22. PubMed PMID: 24385115. 3: Curis E, Pestre V, Jullien V, Eyrolle L, Archambeau D, Morand P, Gatin L, Karoubi M, Pinar N, Dumaine V, Nguyen Van JC, Babinet A, Anract P, Salmon D. Pharmacokinetic variability of clindamycin and influence of rifampicin on clindamycin concentration in patients with bone and joint infections. Infection. 2015 Aug;43(4):473-81. doi: 10.1007/s15010-015-0773-y. Epub 2015 Apr 3. PubMed PMID: 25837442. 4: Ochsendorf F. Clindamycin phosphate 1.2% / tretinoin 0.025%: a novel fixed-dose combination treatment for acne vulgaris. J Eur Acad Dermatol Venereol. 2015 Jun;29 Suppl 5:8-13. doi: 10.1111/jdv.13185. Review. PubMed PMID: 26059820. 5: Wargo KA, McCreary EK, English TM. Vancomycin Combined With Clindamycin for the Treatment of Acute Bacterial Skin and Skin-Structure Infections. Clin Infect Dis. 2015 Oct 1;61(7):1148-54. doi: 10.1093/cid/civ462. Epub 2015 Jun 16. PubMed PMID: 26082508. 6: Stein Gold L. Efficacy and Tolerability of a Fixed Combination of Clindamycin Phosphate (1.2%) and Benzoyl Peroxide (3.75%) Aqueous Gel in Moderate and Severe Acne Vulgaris Subpopulations. J Drugs Dermatol. 2015 Sep;14(9):969-74. PubMed PMID: 26355615. 7: Fernandes-Cunha GM, Gouvea DR, Fulgêncio Gde O, Rezende CM, da Silva GR, Bretas JM, Fialho SL, Lopes NP, Silva-Cunha A. Development of a method to quantify clindamycin in vitreous humor of rabbits' eyes by UPLC-MS/MS: application to a comparative pharmacokinetic study and in vivo ocular biocompatibility evaluation. J Pharm Biomed Anal. 2015 Jan;102:346-52. doi: 10.1016/j.jpba.2014.08.023. Epub 2014 Oct 2. PubMed PMID: 25459934. 8: Sun Q, Li Y, Qin L. Isolation and identification of two unknown impurities from the raw material of clindamycin hydrochloride. J Sep Sci. 2014 Oct;37(19):2682-7. doi: 10.1002/jssc.201400166. Epub 2014 Aug 20. PubMed PMID: 25044425. 9: Harper JC. The efficacy and tolerability of a fixed combination clindamycin (1.2%) and benzoyl peroxide (3.75%) aqueous gel in patients with facial acne vulgaris: gender as a clinically relevant outcome variable. J Drugs Dermatol. 2015 Apr;14(4):381-4. PubMed PMID: 25844612. 10: Join-Lambert O, Ribadeau-Dumas F, Jullien V, Kitzis MD, Jais JP, Coignard-Biehler H, Guet-Revillet H, Consigny PH, Delage M, Nassif X, Lortholary O, Nassif A. Dramatic reduction of clindamycin plasma concentration in hidradenitis suppurativa patients treated with the rifampin-clindamycin combination. Eur J Dermatol. 2014 Jan-Feb;24(1):94-5. doi: 10.1684/ejd.2013.2213. PubMed PMID: 24445967. 11: Wear CD, Towers CV, Brown MS, Weitz B, Porter S, Wolfe L. Transplacental passage of clindamycin from mother to neonate. J Perinatol. 2016 Nov;36(11):960-961. doi: 10.1038/jp.2016.122. Epub 2016 Aug 4. PubMed PMID: 27490192. 12: Kawashima M, Hashimoto H, Alió Sáenz AB, Ono M, Yamada M. Clindamycin phosphate 1·2%-benzoyl peroxide 3·0% fixed-dose combination gel has an effective and acceptable safety and tolerability profile for the treatment of acne vulgaris in Japanese patients: a phase III, multicentre, randomised, single-blinded, active-controlled, parallel-group study. Br J Dermatol. 2015 Feb;172(2):494-503. doi: 10.1111/bjd.13265. Epub 2015 Jan 7. PubMed PMID: 25040180. 13: Kilicarslan M, Gumustas M, Yildiz S, Baykara T. Preparation and characterization of chitosan-based spray-dried microparticles for the delivery of clindamycin phosphate to periodontal pockets. Curr Drug Deliv. 2014;11(1):98-111. PubMed PMID: 23947602. 14: Jarratt MT, Brundage T. Efficacy and safety of clindamycin-tretinoin gel versus clindamycin or tretinoin alone in acne vulgaris: a randomized, double-blind, vehicle-controlled study. J Drugs Dermatol. 2012 Mar;11(3):318-26. PubMed PMID: 22395582. 15: Liang X, Du L, Su F, Parekh HS, Su W. The application of quantitative NMR for the facile, rapid and reliable determination of clindamycin phosphate in a conventional tablet formulation. Magn Reson Chem. 2014 Apr;52(4):178-82. doi: 10.1002/mrc.4048. Epub 2014 Jan 27. PubMed PMID: 24464591. 16: Chang MJ, Namgung H, Choi HD, Song YR, Kim SG, Oh JM, Shin WG. Pharmacokinetics of clindamycin in the plasma and dialysate after intraperitoneal administration of clindamycin phosphoester to patients on continuous ambulatory peritoneal dialysis: an open-label, prospective, single-dose, two-institution study. Basic Clin Pharmacol Toxicol. 2012 Jun;110(6):504-9. doi: 10.1111/j.1742-7843.2011.00842.x. Epub 2012 Jan 16. PubMed PMID: 22151828. 17: Abdellatif AA, Tawfeek HM. Transfersomal Nanoparticles for Enhanced Transdermal Delivery of Clindamycin. AAPS PharmSciTech. 2016 Oct;17(5):1067-74. doi: 10.1208/s12249-015-0441-7. Epub 2015 Oct 28. Erratum in: AAPS PharmSciTech. 2016 Dec;17 (6):1507. PubMed PMID: 26511937. 18: Meti MD, Byadagi KS, Nandibewoor ST, Chimatadar SA. Multi-spectral characterization & effect of metal ions on the binding of bovine serum albumin upon interaction with a lincosamide antibiotic drug, clindamycin phosphate. J Photochem Photobiol B. 2014 Sep 5;138:324-30. doi: 10.1016/j.jphotobiol.2014.05.024. Epub 2014 Jun 28. PubMed PMID: 25033467. 19: Bulloch MN, Baccas JT, Arnold S. Clindamycin-induced hypersensitivity reaction. Infection. 2016 Jun;44(3):357-9. doi: 10.1007/s15010-015-0826-2. Epub 2015 Jul 28. PubMed PMID: 26216470. 20: Uskoković V, Desai TA. Simultaneous bactericidal and osteogenic effect of nanoparticulate calcium phosphate powders loaded with clindamycin on osteoblasts infected with Staphylococcus aureus. Mater Sci Eng C Mater Biol Appl. 2014 Apr 1;37:210-22. doi: 10.1016/j.msec.2014.01.008. Epub 2014 Jan 10. PubMed PMID: 24582242; PubMed Central PMCID: PMC3942787.