Lincomycin | CAS#154-21-2

MedKoo Cat#: 329602 | Name: Lincomycin

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Description:

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

Lincomycin, also known as U-10149, is a lincosamide antibiotic that comes from the actinomycete Streptomyces lincolnensis. A related compound, clindamycin, is derived from lincomycin by using thionyl chloride to replace the 7-hydroxy group with a chlorine atom with inversion of chirality. Although similar in structure, antibacterial spectrum, and mechanism of action to macrolides, lincomycin is also effective against other organisms including actinomycetes and some species of Mycoplasma and Plasmodium. However, because of its adverse effects and toxicity, it is rarely used today and reserved for patients allergic to penicillin or where bacteria have developed resistance.

Chemical Structure

Lincomycin

CAS#154-21-2

Theoretical Analysis

MedKoo Cat#: 329602

Name: Lincomycin

CAS#: 154-21-2

Chemical Formula: C18H34N2O6S

Exact Mass: 406.2138

Molecular Weight: 406.54

Elemental Analysis: C, 53.18; H, 8.43; N, 6.89; O, 23.61; S, 7.89

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
25mg	USD 950.00	2 Weeks

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Related CAS #

7179-49-9 (HCl hydrate) 859-18-7 (HCl) 154-21-2

Synonym

Lincomycin; U-10149; U 10149; U10149.

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

InChi Key

OJMMVQQUTAEWLP-KIDUDLJLSA-N

InChi Code

InChI=1S/C18H34N2O6S/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)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1

SMILES Code

C[C@@H](O)[C@](NC([C@@H]1C[C@@H](CCC)CN1C)=O)([H])[C@@]2([H])O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O

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, a lincosamide antibiotic, is an antimicrobial agent used for the research of Gram-positive bacteria infections.

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/

Preparing Stock Solutions

The following data is based on the product molecular weight 406.54 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. 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. 3. 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.

In vitro protocol:

In vivo protocol:

1: Colabroy KL. Tearing down to build up: Metalloenzymes in the biosynthesis lincomycin, hormaomycin and the pyrrolo [1,4]benzodiazepines. Biochim Biophys Acta. 2016 Jun;1864(6):724-37. doi: 10.1016/j.bbapap.2016.03.001. Review. PubMed PMID: 26963649. 2: Spízek J, Rezanka T. Lincomycin, clindamycin and their applications. Appl Microbiol Biotechnol. 2004 May;64(4):455-64. Review. PubMed PMID: 14762701. 3: Spízek J, Rezanka T. Lincomycin, cultivation of producing strains and biosynthesis. Appl Microbiol Biotechnol. 2004 Feb;63(5):510-9. Review. PubMed PMID: 14593504. 4: Szajewska H, Urbańska M, Chmielewska A, Weizman Z, Shamir R. Meta-analysis: Lactobacillus reuteri strain DSM 17938 (and the original strain ATCC 55730) for treating acute gastroenteritis in children. Benef Microbes. 2014 Sep;5(3):285-93. doi: 10.3920/BM2013.0056. Review. PubMed PMID: 24463209. 5: Inoue M, Yanaihara N, Okamoto A. Salmonella ovarian abscess in a patient with rheumatoid arthritis (RA): a case report with literature review. Clin Exp Obstet Gynecol. 2014;41(4):465-7. Review. PubMed PMID: 25134301. 6: Chernomordik AB. [Antibiotic lincomycin]. Antibiotiki. 1968 Dec;13(12):1130-5. Review. Russian. PubMed PMID: 4894135. 7: Sanders E. Lincomycin: fact, fancy, and future. Med Clin North Am. 1970 Sep;54(5):1295-303. Review. PubMed PMID: 4919153. 8: Grady JE. Recent developments in lincomycin research. Int Z Klin Pharmakol Ther Toxikol. 1968;1(6):533-8. Review. PubMed PMID: 4388454. 9: Spízek J, Novotná J, Rezanka T. Lincosamides: chemical structure, biosynthesis, mechanism of action, resistance, and applications. Adv Appl Microbiol. 2004;56:121-54. Review. PubMed PMID: 15566978. 10: Kaplan K, Weinstein L. Lincomycin. Pediatr Clin North Am. 1968 Feb;15(1):131-9. Review. PubMed PMID: 4966243. 11: Spížek J, Řezanka T. Lincosamides: Chemical structure, biosynthesis, mechanism of action, resistance, and applications. Biochem Pharmacol. 2016 Dec 7. pii: S0006-2952(16)30462-2. doi: 10.1016/j.bcp.2016.12.001. [Epub ahead of print] Review. PubMed PMID: 27940264. 12: Hayashi J, Furusyo N, Kubo N, Shimono N. [Drug-induced pseudomembranous colitis]. Nihon Rinsho. 2007 Oct 28;65 Suppl 8:516-20. Review. Japanese. PubMed PMID: 18074594. 13: Kagan EZ, Sinitsyna NI, Golubev VN, Toroptseva ON. [Lincomycin and its drug forms]. Antibiot Med Biotekhnol. 1985 Oct;30(10):783-8. Review. Russian. PubMed PMID: 3911873. 14: Magerlein BJ. Modification of lincomycin. Adv Appl Microbiol. 1971;14:185-229. Review. PubMed PMID: 5003687. 15: Sanders E. Lincomycin versus erythromycin: a choice or an echo. Ann Intern Med. 1969 Mar;70(3):585-90. Review. PubMed PMID: 4886921. 16: Phillips I. Past and current use of clindamycin and lincomycin. J Antimicrob Chemother. 1981 Jun;7 Suppl A:11-8. Review. PubMed PMID: 7019190. 17: Hornish RE, Gosline RE, Nappier JM. Comparative metabolism of lincomycin in the swine, chicken, and rat. Drug Metab Rev. 1987;18(2-3):177-214. Review. PubMed PMID: 3330515. 18: Rimmer DM, Sales JE. Lincomycin and clindamycin. Antibiot Chemother (1971). 1978;25:204-16. Review. PubMed PMID: 352253. 19: Derrick CW Jr, Reilly KM. Erythromycin, lincomycin, and clindamycin. Pediatr Clin North Am. 1983 Feb;30(1):63-9. Review. PubMed PMID: 6338470. 20: Ashton H, Beveridge GW, Stevenson CJ. Lincomycin and clindamycin. Br J Dermatol. 1970 Nov;83(5):604-6. Review. PubMed PMID: 4249555.