Clindamycin Hydrochloride | CAS#21462-39-5 | Ribosomal Translocation | Protein Synthesis Inhibitor

MedKoo Cat#: 540078 | Name: Clindamycin HCl

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Description:

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

Clindamycin HCl is a ribosomal translocation and protein synthesis inhibitor that displays efficacy against MRSA. It is also occasionally used to treat Plasmodium. It has the same antibacterial spectrum as lincomycin, but the antibacterial activity is four to eight times stronger than that of lincomycin.

Chemical Structure

Clindamycin HCl

CAS#21462-39-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 540078

Name: Clindamycin HCl

CAS#: 21462-39-5 (HCl)

Chemical Formula: C18H34Cl2N2O5S

Exact Mass: 0.0000

Molecular Weight: 461.44

Elemental Analysis: C, 46.85; H, 7.43; Cl, 15.36; N, 6.07; O, 17.34; S, 6.95

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
5g	USD 550.00	2 Weeks
10g	USD 850.00	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

Cleocin; Cleocin HCl; Clinsol; EC 244-398-6; EC2443986; EC-244-398-6; U 21251 F; U21251F; U-21251-F

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 hydrochloride

InChi Key

AUODDLQVRAJAJM-XJQDNNTCSA-N

InChi Code

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

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.Cl

Appearance

White to off-white 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

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Clindamycin (hydrochloride) is a semisynthetic lincosamide antibiotic, which inhibits protein synthesis by acting on the 50S ribosomal.

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	54.7	118.56
	Water	92.0	199.38

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 461.44 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: 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. 2: Cantor SL, Khan MA, Gupta A. Development and optimization of taste-masked orally disintegrating tablets (ODTs) of clindamycin hydrochloride. Drug Dev Ind Pharm. 2015;41(7):1156-64. doi: 10.3109/03639045.2014.935392. Epub 2014 Jul 7. PubMed PMID: 25000481. 3: Saridomichelakis MN, Athanasiou LV, Chatzis MK, Salame M, Katsoudas V, Pappas IS. Concentrations of clindamycin hydrochloride in homogenates of normal dog skin when administered at two oral dosage regimens. Vet Q. 2013;33(1):7-12. doi: 10.1080/01652176.2013.772315. Epub 2013 Feb 28. Erratum in: Vet Q. 2013;33(1):iii. PubMed PMID: 23445168. 4: 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. 5: 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. 6: 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. 7: Saridomichelakis MN, Athanasiou LV, Salame M, Chatzis MK, Katsoudas V, Pappas IS. Serum pharmacokinetics of clindamycin hydrochloride in normal dogs when administered at two dosage regimens. Vet Dermatol. 2011 Oct;22(5):429-35. doi: 10.1111/j.1365-3164.2011.00969.x. Epub 2011 Mar 21. PubMed PMID: 21418348. 8: Johnston TP, Mondal P, Pal D, MacGee S, Stromberg AJ, Alur H. Canine periodontal disease control using a clindamycin hydrochloride gel. J Vet Dent. 2011 Winter;28(4):224-9. PubMed PMID: 22416621. 9: 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. 10: Rauta PR, Das NM, Nayak D, Ashe S, Nayak B. Enhanced efficacy of clindamycin hydrochloride encapsulated in PLA/PLGA based nanoparticle system for oral delivery. IET Nanobiotechnol. 2016 Aug;10(4):254-61. doi: 10.1049/iet-nbt.2015.0021. PubMed PMID: 27463797. 11: 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. 12: Li H, Deng J, Yue Z, Zhang Y, Sun H, Ren X. Clindamycin hydrochloride and clindamycin phosphate: two drugs or one? A retrospective analysis of a spontaneous reporting system. Eur J Clin Pharmacol. 2017 Feb;73(2):251-253. doi: 10.1007/s00228-016-2161-7. Epub 2016 Nov 16. PubMed PMID: 27853825. 13: 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. 14: 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. 15: 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. 16: Lenarduzzi T, Langston C, Ross MK. Pharmacokinetics of clindamycin administered orally to pigeons. J Avian Med Surg. 2011 Dec;25(4):259-65. PubMed PMID: 22458181. 17: 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. 18: Barza M, Goldstein JA, Kane A, Feingold DS, Pochi PE. Systemic absorption of clindamycin hydrochloride after topical application. J Am Acad Dermatol. 1982 Aug;7(2):208-14. PubMed PMID: 6215432. 19: 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. 20: Franz TJ. On the bioavailability of topical formulations of clindamycin hydrochloride. J Am Acad Dermatol. 1983 Jul;9(1):66-73. PubMed PMID: 6886106.