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Alkaloids

Lincomycin

Also known as Cillimycin, Lincolnensin, Lincomicina

CAS 154-21-2Formula C18H34N2O6SMolar mass 406.55 g/molEC 205-824-6
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Lincomycin chemical structure, C18H34N2O6S, CAS 154-21-2
2D chemical structure

Key facts

What buyers check first

All properties
CAS number
154-21-2
Formula
C18H34N2O6S
Appearance
Amorphous solid
Solubility
Soluble in methanol, lower alcohols, acetone, ethyl acetate, chloroform. Slightly solubl…
HS code
294190
Category
Alkaloids
Illustrative photo, assorted laboratory chemical bottles and jars on a laboratory bench
Typical packagingIllustrative packaging image, not the actual product

What is Lincomycin?

Plain description, key identifiers and synonyms

Lincomycin is a carbohydrate-containing antibiotic produced by the actinomyces Streptomyces lincolnensis. It has a role as an antimicrobial agent and a bacterial metabolite. It is a carbohydrate-containing antibiotic, a monocarboxylic acid amide, a S-glycosyl compound, a pyrrolidinecarboxamide and a L-proline derivative.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
CAS number
154-21-2 CAS number cross-checked
EC number
205-824-6
Molecular formula
C18H34N2O6S
UNII
BOD072YW0F
MDL number
MFCD00135816
InChIKey
OJMMVQQUTAEWLP-KIDUDLJLSA-N
InChI
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
Canonical SMILES
CCCC1CC(C(=O)NC(C(C)O)C2OC(SC)C(O)C(O)C2O)N(C)C1
Isomeric 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)O

Synonyms

  • Cillimycin
  • Lincolnensin
  • Lincomicina
  • Lincomycinum
  • Jiemycin
  • Lincomycin A
  • Lincolcina
  • U 10,149A
  • (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
  • Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-alpha-D-galacto-octopyranoside
  • (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide
  • D-erythro-alpha-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-(((1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-, (2S-trans)-
  • (2S,4R)-N-((1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl)propyl)-1-methyl-4-propyl-pyrrolidine-2-carboxamide
  • (2S,4R)-N-((1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide
  • METHYL 6,8-DIDEOXY-6-((((2S,4R)-1-METHYL-4-PROPYLPYRROLIDIN-2-YL)CARBONYL)AMINO)-1-THIO-D-ERYTHRO-alpha-D-GALACTO-OCTOPYRANOSIDE
  • methyl 6,8-dideoxy-6-({[(2S,4R)-1-methyl-4-propylpyrrolidin-2-yl]carbonyl}amino)-1-thio-D-erythro-alpha-D-galacto-octopyranoside
  • LincoMed 300
  • Lincomycin Injectable 30%
  • Lincomycin Injectable, USP
  • Lincomix 20, lincomix 50
  • Hemihydrate Lincomycin Monohydrochloride
  • Lincomycin 100, lincomycin 25, lincomycin 300
  • Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-D-galacto-octopyranoside (alpha-
  • Lincocin
  • Lincomycin (USAN/INN)
Show all 34 synonyms
  • Frademicina
  • (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
  • Lincomycin (hydrochloride)
  • LCM
  • Lincomycine
  • Bactramycin
  • Lincorex
  • Lincomycin, (2S-cis)-Isomer
  • L-Mycin

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Appearance
Amorphous solidexp.
Solubility
Soluble in methanol, lower alcohols, acetone, ethyl acetate, chloroform. Slightly soluble in waterexp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
406.55 g/molcalc.
Exact mass
406.2138 Dacalc.
LogP (octanol/water)
-0.86calc.
Topological polar surface area
122.5 Ųcalc.
Hydrogen bond donors
5calc.
Hydrogen bond acceptors
8calc.
Rotatable bonds
7calc.
Heavy atoms
27calc.
Rings
2calc.
Aromatic rings
0calc.
Fraction sp3 carbons
0.94calc.
Formal charge
0calc.
Stereocentres
9calc.
Lipinski rule of five
Passes (0 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, O=C(NCC1CCCCO1)C1CCCN1

O=C(NCC1CCCCO1)C1CCCN1

2 rings, 15 atoms.

138 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS classification
Hazard pictograms

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Lincomycin suppliers

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Where suppliers are based

60 suppliers in 17 countries

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Lincomycin price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

Veterinary medication:.

Use classes: Pharmaceuticals, Animal Drugs.

Pharmacological actions

  • Anti-Bacterial Agents
  • Protein Synthesis Inhibitors

Roles

  • antimicrobial agent
  • bacterial metabolite
  • metabolite
  • prokaryotic metabolite

Pharmacology

Lincomycin is a lincosamide antibiotic derived from bacteria Streptomyces lincolnensis with activity against gram positive and anaerobic bacteria. Lincomycin binds to the 50S subunit of the bacterial ribosome resulting in the inhibition of protein synthesis and thereby produces bactericidal effects in susceptible organisms.

How it is made

Lincomycin was produced originally by the actinomycete Streptomyces lincolnensis var. lincolnensis, NRRL 2936. Subsequently, it has been produced by a variety of Streptomyces strains and by strain 1146 of Actinomyces roseolus. Extraction by standard procedures using Sarcina lutea as the assay organism on agar trays leads to a crystalline hydrochloride having molecular formula C18-H34-N2-O6-S.HCl.1/2 H2O.

Read more

A second, more dense form exists as the monohydrate, and this latter form of lincomycin hydrochloride is the Upjohn trademarked Lincocin available commercially.

Produced by streptomyces lincolnensis var lincolnensis.

Antibiotics are fermentation products and are isolated either as unfinished products or as intermediates, generally solid substances of limited stability. They are purified by methods normally employed in organic chemistry, which include chromatography, crystallization, and precipitation. (Antibiotics)

Regulatory status

Inventories, regulations and trade controls that list this substance

Health and food

  • Active ingredient in FDA approved drug labels

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Lincomycin is traded under.

HS 2941.90Indicative HS code

Antibiotics, other

World exports in 2024
$6.39B
+2.3% vs 2023, imports $6.97B
2019 to 2024
Top exporters
  1. China39.7%
  2. United States11.3%
  3. Switzerland * partner reported10.9%
Top importers
  1. Italy15.0%
  2. India * partner reported12.0%
  3. China8.7%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Lincomycin is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Lincomycin, based on the data on this page

What is Lincomycin?

Lincomycin is a carbohydrate-containing antibiotic produced by the actinomyces Streptomyces lincolnensis. It has a role as an antimicrobial agent and a bacterial metabolite.

What is the CAS number of Lincomycin?

The CAS registry number of Lincomycin is 154-21-2.

What is the molecular formula and weight of Lincomycin?

The molecular formula of Lincomycin is C18H34N2O6S and its molar mass is 406.55 g/mol.

What is Lincomycin used for?

Veterinary medication:. Use classes: Pharmaceuticals, Animal Drugs.

Is Lincomycin hazardous?

No GHS hazard classification for Lincomycin is recorded on CompoundList yet. That does not prove it is safe. Always read the supplier safety data sheet.

What is the HS code of Lincomycin?

Lincomycin is usually classified under HS code 294190 (Antibiotics, other). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Lincomycin?

CompoundList lists 60 suppliers of Lincomycin in United States, China, India, Germany and 13 more. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

Where can I buy Lincomycin in India?

6 suppliers in India list Lincomycin on CompoundList. Filter the suppliers list by country and send a request to compare prices, grades and delivery times.

What is the price of Lincomycin?

Suppliers quote Lincomycin on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

Guides for buyers

Practical guides that help when you source, ship or handle Lincomycin

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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