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MedKoo Cat#: 540269 | Name: Lincomycin hydrochloride hydrate
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Description:

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

Lincomycin hydrochloride hydrate is a peptidyl transferase and protein translation inhibitor used to treat bacterial infections. It also inhibits growth of plasmodium.

Chemical Structure

Lincomycin hydrochloride hydrate
Lincomycin hydrochloride hydrate
CAS#7179-49-9 (HCl hydrate)

Theoretical Analysis

MedKoo Cat#: 540269

Name: Lincomycin hydrochloride hydrate

CAS#: 7179-49-9 (HCl hydrate)

Chemical Formula: C18H37ClN2O7S

Exact Mass: 460.2010

Molecular Weight: 461.01

Elemental Analysis: C, 46.90; H, 8.09; Cl, 7.69; N, 6.08; O, 24.29; S, 6.95

Price and Availability

Size Price Availability Quantity
5g USD 300.00 2 Weeks
25g USD 550.00 2 Weeks
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Related CAS #
7179-49-9 (HCl hydrate) 859-18-7 (HCl) 154-21-2
Synonym
Lincocin; Lincomix; Lincomycin HCl hydrate; NSC 70731; NSC70731; NSC- 70731;
IUPAC/Chemical Name
(2S,4R)-N-((1R,2R)-2-hydroxy-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 hydrate
InChi Key
LFZGYTBWUHCAKF-DCNJEFSFSA-N
InChi Code
InChI=1S/C18H34N2O6S.ClH.H2O/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4;;/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25);1H;1H2/t9-,10-,11+,12-,13+,14-,15-,16-,18-;;/m1../s1
SMILES Code
CCC[C@@H]1C[C@@H](C(N[C@H]([C@H](O)C)[C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O)=O)N(C)C1.Cl.O
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
>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:
Lincomycin hydrochloride monohydrate is a narrow-spectrum antibiotic, has similar effects to erythromycin, which has a good effect on gram-positive coccus, mainly used to inhibit the synthesis of bacterial cell protein.
In vitro activity:
Treatment with LM (lincomycin) or LM + DX (dexamethasone) stimulated proliferation of melanoma cells with minimal cytotoxicity, while DX did not influence cell proliferation either alone or in combination with LM. Treatment with LM alone increased tyrosinase activity slightly and reduced melanin content in a dose-dependent manner. However, LM counteracted the pronounced increase in tyrosinase elicited by DX and also abrogated the dose-dependent increase in melanin content elicited by DX. Reference: Pigment Cell Res. 1998 Jun;11(3):143-50. https://pubmed.ncbi.nlm.nih.gov/9730321/
In vivo activity:
Lincomycin (LCM), imipenem (IPM), cilastatine (CS), and ampicillin (ABPC) were used for antibiotics treatment. The survival rate of SPG/IND-treated mice was significantly increased by administering LCM or ABPC/IPM/CS, and the effect was more significant by LCM. Reference: Biol Pharm Bull. 2007 Dec;30(12):2312-6. https://pubmed.ncbi.nlm.nih.gov/18057718/
Solvent mg/mL mM comments
Solubility
DMSO 96.0 208.24
Water 50.0 108.46
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 461.01 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.

Recalculate based on batch purity %
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. Nameda S, Miura NN, Adachi Y, Ohno N. Lincomycin protects mice from septic shock in beta-glucan-indomethacin model. Biol Pharm Bull. 2007 Dec;30(12):2312-6. doi: 10.1248/bpb.30.2312. PMID: 18057718. 2. Kim DG, Kim HY, Kim MY, Lee MY, You KR. Lincomycin abrogates dexamethasone-enhanced melanogenesis in B16 melanoma cells. Pigment Cell Res. 1998 Jun;11(3):143-50. doi: 10.1111/j.1600-0749.1998.tb00724.x. PMID: 9730321.
In vitro protocol:
1. Nameda S, Miura NN, Adachi Y, Ohno N. Lincomycin protects mice from septic shock in beta-glucan-indomethacin model. Biol Pharm Bull. 2007 Dec;30(12):2312-6. doi: 10.1248/bpb.30.2312. PMID: 18057718. 2. Kim DG, Kim HY, Kim MY, Lee MY, You KR. Lincomycin abrogates dexamethasone-enhanced melanogenesis in B16 melanoma cells. Pigment Cell Res. 1998 Jun;11(3):143-50. doi: 10.1111/j.1600-0749.1998.tb00724.x. PMID: 9730321.
In vivo protocol:
1. Nameda S, Miura NN, Adachi Y, Ohno N. Lincomycin protects mice from septic shock in beta-glucan-indomethacin model. Biol Pharm Bull. 2007 Dec;30(12):2312-6. doi: 10.1248/bpb.30.2312. PMID: 18057718.
1: Czarniak P, Boddy M, Sunderland B, Hughes JD. Stability studies of lincomycin hydrochloride in aqueous solution and intravenous infusion fluids. Drug Des Devel Ther. 2016 Mar 7;10:1029-34. doi: 10.2147/DDDT.S94710. eCollection 2016. PubMed PMID: 27022242; PubMed Central PMCID: PMC4789844. 2: Kothadiya A. A multicentric, open label, randomised, postmarketing efficacy study comparing multidose of lincomycin hydrochloride capsule 500 mg with multidose cefpodoxime proxetil tablet 200 mg in patients with tonsillitis, sinusitis. J Indian Med Assoc. 2012 Aug;110(8):580-3. PubMed PMID: 23741829. 3: 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. 4: Sreeshitha Gouri S, Venkatachalam D, Dumka VK. Pharmacokinetics of lincomycin following single intravenous administration in buffalo calves. Trop Anim Health Prod. 2014 Aug;46(6):1099-102. doi: 10.1007/s11250-014-0595-4. Epub 2014 May 4. PubMed PMID: 24792222. 5: Bokhari TH, Rizvi FA, Roohi S, Hina S, Ahmad M, Khalid M, Iqbal M. Preparation, biodistribution and scintigraphic evaluation of (99m)Tc-lincomycin. Pak J Pharm Sci. 2015 Nov;28(6):1965-70. PubMed PMID: 26639473. 6: Berry SL, Read DH, Walker RL, Famula TR. Clinical, histologic, and bacteriologic findings in dairy cows with digital dermatitis (footwarts) one month after topical treatment with lincomycin hydrochloride or oxytetracycline hydrochloride. J Am Vet Med Assoc. 2010 Sep 1;237(5):555-60. doi: 10.2460/javma.237.5.555. PubMed PMID: 20807134. 7: Hu Y, Li G, Zhang Z. A flow injection chemiluminescence method for the determination of lincomycin in serum using a diperiodato-cuprate (III)-luminol system. Luminescence. 2011 Sep-Oct;26(5):313-8. doi: 10.1002/bio.1230. Epub 2010 Oct 23. PubMed PMID: 22021244. 8: Harvey RG, Noble WC, Ferguson EA. A comparison of lincomycin hydrochloride and clindamycin hydrochloride in the treatment of superficial pyoderma in dogs. Vet Rec. 1993 Apr 3;132(14):351-3. PubMed PMID: 8488640. 9: Fateeva LI, Poliak MS. [Pharmacokinetics of lincomycins in experimental staphylococcal sepsis]. Antibiotiki. 1977 Jul;22(7):624-9. Russian. PubMed PMID: 883807. 10: Albarellos GA, Montoya L, Denamiel GA, Velo MC, Landoni MF. Pharmacokinetics and bone tissue concentrations of lincomycin following intravenous and intramuscular administrations to cats. J Vet Pharmacol Ther. 2012 Dec;35(6):534-40. doi: 10.1111/j.1365-2885.2011.01355.x. Epub 2011 Dec 2. PubMed PMID: 22132730. 11: Umemura E, Wakiyama Y, Kumura K, Ueda K, Masaki S, Watanabe T, Yamamoto M, Hirai Y, Fushimi H, Yoshida T, Ajito K. Synthesis of novel lincomycin derivatives and their in vitro antibacterial activities. J Antibiot (Tokyo). 2013 Mar;66(3):195-8. doi: 10.1038/ja.2012.107. Epub 2012 Dec 12. PubMed PMID: 23232934. 12: LEWIS C, STERN KF, GRADY JE. COMPARISON IN LABORATORY ANIMALS OF THE ANTIBACTERIAL ACTIVITY AND ABSORPTION OF LINCOMYCIN HEXADECYLSULFAMATE TO LINCOMYCIN HYDROCHLORIDE. Antimicrob Agents Chemother (Bethesda). 1964;10:13-7. PubMed PMID: 14287918. 13: Cao S, Song S, Liu L, Kong N, Kuang H, Xu C. Comparison of an Enzyme-Linked Immunosorbent Assay with an Immunochromatographic Assay for Detection of Lincomycin in Milk and Honey. Immunol Invest. 2015;44(5):438-50. doi: 10.3109/08820139.2015.1021354. PubMed PMID: 26107744. 14: He G, Chen X, Yin Y, Cai W, Ke W, Kong Y, Zheng H. Preparation and antibacterial properties of O-carboxymethyl chitosan/lincomycin hydrogels. J Biomater Sci Polym Ed. 2016;27(4):370-84. doi: 10.1080/09205063.2015.1132616. Epub 2016 Jan 17. PubMed PMID: 26675323. 15: Wakiyama Y, Kumura K, Umemura E, Masaki S, Ueda K, Watanabe T, Yamamoto M, Hirai Y, Ajito K. Synthesis and structure-activity relationships of novel lincomycin derivatives. Part 2. Synthesis of 7(S)-7-deoxy-7-(4-morpholinocarbonylphenylthio)lincomycin and its 3-dimensional analysis with rRNA. J Antibiot (Tokyo). 2016 Jun;69(6):428-39. doi: 10.1038/ja.2015.125. Epub 2015 Dec 16. PubMed PMID: 26669751. 16: [New preparations: lincomycin hydrochloride; chlorophyllypt]. Farmatsiia. 1974 Mar-Apr;23(2):90-4. Russian. PubMed PMID: 4849249. 17: Chaleva E, Dzhurov A. [Toxicological and pharmacokinetic research on lincomycin hydrochloride in broiler chickens and layer hens]. Vet Med Nauki. 1987;24(8):55-63. Bulgarian. PubMed PMID: 3439027. 18: Kleinberg J, Dea FJ, Anderson JA, Leopold IH. Intraocular penetration of topically applied lincomycin hydrochloride in rabbits. Arch Ophthalmol. 1979 May;97(5):933-6. PubMed PMID: 444130. 19: Sun Q, Shi Y, Wang F, Han D, Lei H, Zhao Y, Sun Q. Study on the effects of microencapsulated Lactobacillus delbrueckii on the mouse intestinal flora. J Microencapsul. 2015;32(7):669-76. doi: 10.3109/02652048.2015.1057249. Epub 2015 Sep 7. PubMed PMID: 26471401. 20: Nakagawa K, Watanabe K, Kihara N, Koyama M, Suzuki T, Kato Y, Saito A, Nakayama I, Tomizawa M, Matsui K, Abe M, Fujimori I, Obana M, Okubo H, Okamoto Y, Ueda Y, Maehara K, Soejima R, Sawae Y, Matsumoto K. [Comparative test of the effectiveness of clindamycin phosphate and lincomycin hydrochloride on acute pneumonia (I)]. Kansenshogaku Zasshi. 1982 May;56(5):391-402. Japanese. PubMed PMID: 6811677.

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