859-18-7

Basic information

• Product Name: Lincomycin hydrochloride
• Synonyms: METHYL 6,8-DIDEOXY-6-(1-METHYL-4-PROPYL-2-PYRROLIDINECARBOXAMIDO)-1-THIO-D-ERYTHRO-ALPHA-D-GALACTOOCTOPYRANOSIDE HYDROCHLORIDE;LINCOMYCIN HCL;LINCOMYCIN HYDROCHLORIDE;LINCOCIN HYDROCHLORIDE;ALPHA-METHYL-6,8-DIDEOXY-6-[1-METHYL-4-PROPYL-2-PYRROLIDINECARBOXAMIDO]-1-THIO-D-ERYTHRO-D-GALACTOOCTOPYRANOSIDE HYDROCHLORIDE;U-10149A;N-[2-HYDROXY-1-(3,4,5-TRIHYDROXY-6-METHYLSULFANYL-OXAN-2-YL)-PROPYL]-1-METHYL-4-PROPYL-PYRROLIDINE-2-CARBOXAMIDE;lincomycin standard solution
• CAS NO: 859-18-7
• Molecular Formula: C18H35ClN2O6S
• Molecular Weight: 443
• EINECS: 212-726-7
• Product Categories: Antibiotic Explorer;Peptide Synthesis/Antibiotics;Carbohydrates & Derivatives;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Lincocin;antibiotic;API
• Mol File: 859-18-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 156-158C
• Boiling Point: 646.8 °C at 760 mmHg
• Flash Point: 345 °C
• Appearance: white to white with yellow cast/
• Density: ==
• Vapor Pressure: 1.85E-19mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL, clear, colorless
• Water Solubility: Soluble in water.
• Stability: Hygroscopic
• BRN: 4171650
• CAS DataBase Reference: Lincomycin hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Lincomycin hydrochloride(859-18-7)
• EPA Substance Registry System: Lincomycin hydrochloride(859-18-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: RH6315000
• F: 10
• Hazardous Substances Data: 859-18-7(Hazardous Substances Data)

Usage

Antibiotic medicines

Lincomycin hydrochloride appears as a white crystalline powder at room temperature with slight odor or special smell and bitter taste. It is soluble in water and methanol. Feed often applied its hydrochloride salt form. The drug is the product during the growth of the population of the Streptomyces genus (Streptomyces lincolnensis), as a kind of lincosamides alkaline antibiotics. Through interaction with the 50S ribosomal subunit of the sensitive bacteria, it prevents the peptide chain elongation, thereby inhibiting protein synthesis of the bacterial cell with antimicrobial effect. However, at high concentrations, it also has bactericidal effect on the highly sensitive bacteria. Its antibacterial spectrum is the same as lincomycin but with a stronger antibacterial activity and can be subject to oral absorption quickly and completely (about 90%) with meal having little effect on the absorption. Lincomycin hydrochloride mainly has strong antibacterial effect against Gram-positive bacteria, and some anaerobic bacteria as well as Mycoplasma with its antibacterial spectrum narrower than erythromycin. Staphylococcus aureus, Streptococcus pneumoniae and Mycoplasma pneumonia Mycoplasma hyopneumoniae, and Mycoplasma gallisepticum are sensitive to the chemicals, but enterococci is generally resistant to the chemicals; anaerobic bacteria such as Bacteroides spp., Clostridium tetani, Clostridium difficile, Clostridium perfringens and Peptococcus are also sensitive to the chemicals. It is mainly used for the treatment of infections caused by Gram-positive bacteria in particular the various penicillin-resistant Gram-positive bacteria , the poultry chronic respiratory disease caused by Mycoplasma, swine enzootic pneumonia, anaerobic infections such as chicken necrotizing enterocolitis. It can also be used for the treatment of treponema dysentery, toxoplasmosis and actinomycosis of dogs and cats. Lincomycin hydrochloride has therapeutic effect when being used for the treatment of Sepsis, female genital tract, endometritis, non-gonococcal tubo-ovarian abscess, pelvic cellulitis; postoperative vaginal annex infections, peritonitis, abscesses, pneumonia, lung abscess, skin and soft tissue infections caused by most Gram-negative bacteria and some anaerobic bacteria. It can also be used for the surgical adjuvant treatment of Sepsis caused by streptococci and staphylococci, bone and joint infections, chronic bone and joint infections as well as the acute hematogenous osteomyelitis of Staphylococcus aureus. But this product can’t penetrate into cerebrospinal fluid and therefore not suitable for the treatment of meningitis. Topical administration can be applied for the treatment of Gram-positive bacteria purulent infection.

Clinical application

1. Oral formulations is suitable for treating respiratory infections, abdominal infection, female reproductive tract infections, pelvic infections, skin and soft tissue infections caused by sensitive Staphylococcus aureus and Streptococcus pneumoniae. 2. In addition to the treatment of the above infections, injected formulations are suitable for treatment of severe infections caused by streptococcus, pneumococcus and staphylococcus such as the surgical adjuvant therapy of septicemia, bone and joint infections, chronic bone and joint infections and Staphylococcus-induced acute hematogenous osteomyelitis. 3. Lincomycin hydrochloride may also be used for the treatment of infectious diseases in patients allergic to penicillin or not suitable for administration of penicillin-type drugs. Tablets: Each tablet 0.25g, 0.5g; Injection: each 0.2g, 0.6g. This information is edited by Xiongfeng Dai from lookchem.

Chemical Properties

Crystalline

Uses

Different sources of media describe the Uses of 859-18-7 differently. You can refer to the following data:
1. An antibiotic produced by Streptomyces lincolnensis. Lincomycin is a lincosamide antibiotic that forms cross-links within the peptidyl transferase loop region of the 23S rRNA. Inhibits bacterial protein synthesis. Antibacterial.
2. Lincomycin hydrochloride is a salt of lincomycin formed at the basic N-methylproline. The hydrochloride salt is the preferred formulation for pharmaceutical use. Lincomycin hydrochloride is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans. Lincomycin acts by binding to the 23S ribosomal subunit, blocking protein synthesis. Lincomycin has been extensively studied with over 7,000 literature citations.

Therapeutic Function

Antibacterial

Biochem/physiol Actions

Mode of action: Lincomycin inhibits bacterial protein synthesis by forming cross-links within the peptidyl transferase loop region of the 23S rRNA.? Antimicrobial spectrum: Lincomycin hydrochloride is effective against gram-positive bacteria.

Clinical Use

Lincomycin is used for the treatment of infections causedby Gram-positive organisms, notably staphylococci, β-hemolyticstreptococci, and pneumococci. It is absorbed moderatelywell orally and distributed widely in the tissues.Effective concentrations are achieved in bone for the treatmentof staphylococcal osteomyelitis but not in the cerebrospinalfluid for the treatment of meningitis. At one time,lincomycin was considered a nontoxic compound, with alow incidence of allergy (rash) and occasional GI complaints(nausea, vomiting, and diarrhea) as the only adverseeffects. Recent reports of severe diarrhea and the developmentof pseudomembranous colitis in patients treated withlincomycin (or clindamycin), however, have necessitatedreappraisal of the role of these antibiotics in therapy. In anyevent, clindamycin is superior to lincomycin for thetreatment of most infections for which these antibiotics areindicated.Lincomycin hydrochloride occurs as the monohydrate, awhite, crystalline solid that is stable in the dry state. It isreadily soluble in water and alcohol, and its aqueous solutionsare stable at room temperature. It is degraded slowlyin acid solutions but is absorbed well from the GI tract.Lincomycin diffuses well into peritoneal and pleural fluidsand into bone. It is excreted in the urine and the bile. It isavailable in capsule form for oral administration and inampules and vials for parenteral administration.

InChI:InChI=1/C18H34N2O6S.ClH/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/t9-,10-,11+,12-,13+,14+,15-,16-,18-;/m1./s1

Synthetic route

lincomycin hydrochloride (859-18-7) → (1S,2S,4R)-1-Methyl-1-oxy-4-propyl-pyrrolidine-2-carboxylic acid [(1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methanesulfonyl-tetrahydro-pyran-2-yl)-propyl]-amide

Conditions	Yield
With ammonium hydroxide; dihydrogen peroxide; acetonitrile In water at 20℃; for 0.333333h; pH=10.8;	95%

chloro-trimethyl-silane (75-77-4) + lincomycin hydrochloride (859-18-7) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → C30H66N2O6SSi4

Conditions	Yield
With pyridine at 2 - 20℃; for 8h;	89%

lincomycin hydrochloride (859-18-7) → clindamycin hydrochloride monohydrate

Conditions	Yield
In water	86%

lincomycin hydrochloride (859-18-7) → (1S,2S,4R)-1-Methyl-1-oxy-4-propyl-pyrrolidine-2-carboxylic acid [(1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methanesulfinyl-tetrahydro-pyran-2-yl)-propyl]-amide + (1S,2S,4R)-1-Methyl-1-oxy-4-propyl-pyrrolidine-2-carboxylic acid [(1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methanesulfonyl-tetrahydro-pyran-2-yl)-propyl]-amide

Conditions	Yield
With ammonium hydroxide; dihydrogen peroxide In water at 20℃; for 12h; pH=10.8;	A 66% B 30%

lincomycin hydrochloride (859-18-7) → Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside (14810-93-6)

Conditions	Yield
With hydrazine hydrate at 120℃; for 24h;	59%

lincomycin hydrochloride (859-18-7) → (1R,2S,4R)-1-Methyl-1-oxy-4-propyl-pyrrolidine-2-carboxylic acid [(1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methanesulfonyl-tetrahydro-pyran-2-yl)-propyl]-amide + (1S,2S,4R)-1-Methyl-1-oxy-4-propyl-pyrrolidine-2-carboxylic acid [(1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methanesulfonyl-tetrahydro-pyran-2-yl)-propyl]-amide

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In water at 20℃; for 12h; pH=9.75;	A 47% B 50%

D-Mannose (530-26-7) + lincomycin hydrochloride (859-18-7) → (2S,4R)-1-Methyl-4-propyl-pyrrolidine-2-carboxylic acid [(1R,2R)-2-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

Conditions	Yield
With α-mannosidase In various solvent(s) at 48℃; pH=5.0; Enzymatic reaction;	2.4%

lincomycin hydrochloride (859-18-7) → C26H50N2O6S

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / 24 h / 120 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C31H58N2O8S

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / 24 h / 120 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C9H18ClNO4S

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / 24 h / 120 °C 2: triphenylphosphine; tetrachloromethane / acetonitrile / 3 h / Reflux View Scheme

lincomycin hydrochloride (859-18-7) → C26H39ClN2O5S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrazine hydrate / 24 h / 120 °C 2.1: triphenylphosphine; tetrachloromethane / acetonitrile / 3 h / Reflux 3.1: triethylamine; isobutyl chloroformate / acetonitrile / 1 h / 10 °C 3.2: 18 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C21H31ClN2O5S

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / 24 h / 120 °C 2: triphenylphosphine; tetrachloromethane / acetonitrile / 3 h / Reflux 3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3.5 h / 20 °C 4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C26H39ClN2O7S

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / 24 h / 120 °C 2: triphenylphosphine; tetrachloromethane / acetonitrile / 3 h / Reflux 3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3.5 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C20H30ClN3O5S

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / 24 h / 120 °C 2: triphenylphosphine; tetrachloromethane / acetonitrile / 3 h / Reflux 3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C25H38ClN3O7S

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / 24 h / 120 °C 2: triphenylphosphine; tetrachloromethane / acetonitrile / 3 h / Reflux 3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C23H36N2O6S

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / 24 h / 120 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C28H44N2O8S

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / 24 h / 120 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C23H42N2O6S

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / 24 h / 120 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → C28H50N2O8S

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / 24 h / 120 °C 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C View Scheme

lincomycin hydrochloride (859-18-7) → clindamycin phosphate (24729-96-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: phosgene / chloroform; N,N-dimethyl-formamide / 2 h / 5 - 71 °C / Large scale 1.2: 10 °C / Alkaline conditions; Large scale 2.1: toluene-4-sulfonic acid / acetone / 6 h / 35 °C / Large scale 3.1: triethylamine; trichlorophosphate; 1H-imidazole / acetone / 4 h / 22 °C / Large scale 3.2: 30 °C / Large scale View Scheme

lincomycin hydrochloride (859-18-7) → clindamycin (16684-06-3, 18323-44-9, 51064-35-8)

Conditions	Yield
Stage #1: lincomycin hydrochloride With phosgene In chloroform; N,N-dimethyl-formamide at 5 - 71℃; for 2h; Large scale; Stage #2: at 10℃; Temperature; Reagent/catalyst; Alkaline conditions; Large scale;
With bis(trichloromethyl) carbonate; ester of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid and pentaerythritol In chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide at 12 - 62℃; for 13h; Temperature; Large scale;

lincomycin hydrochloride (859-18-7) → C21H37ClN2O5S

Conditions	Yield
Multi-step reaction with 2 steps 1.1: phosgene / chloroform; N,N-dimethyl-formamide / 2 h / 5 - 71 °C / Large scale 1.2: 10 °C / Alkaline conditions; Large scale 2.1: toluene-4-sulfonic acid / acetone / 6 h / 35 °C / Large scale View Scheme

lincomycin hydrochloride (859-18-7) → 7-epiclindamycin hydrochloride

Conditions	Yield
Multi-step reaction with 6 steps 1: pyridine / 8 h / 2 - 20 °C 2: acetic acid / methanol / 18 h / 30 °C 3: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 20 h / 30 °C 4: potassium carbonate / methanol / 20 h / 130 °C 5: hydrogenchloride 6: bis(trichloromethyl) carbonate / N,N-dimethyl-formamide; chloroform / 23 h / 5 - 60 °C View Scheme

lincomycin hydrochloride (859-18-7) → C18H34N2O6S*ClH

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / 8 h / 2 - 20 °C 2: acetic acid / methanol / 18 h / 30 °C 3: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 20 h / 30 °C 4: potassium carbonate / methanol / 20 h / 130 °C 5: hydrogenchloride View Scheme

lincomycin hydrochloride (859-18-7) → 2,3,4-tris-O-(trimethylsilyl)lincomycin (25420-97-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 8 h / 2 - 20 °C 2: acetic acid / methanol / 18 h / 30 °C View Scheme

lincomycin hydrochloride (859-18-7) → C34H61N3O9SSi3

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 8 h / 2 - 20 °C 2: acetic acid / methanol / 18 h / 30 °C 3: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 20 h / 30 °C View Scheme

lincomycin hydrochloride (859-18-7) → lincomycin (154-21-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 8 h / 2 - 20 °C 2: acetic acid / methanol / 18 h / 30 °C 3: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 20 h / 30 °C 4: potassium carbonate / methanol / 20 h / 130 °C View Scheme

Downstream Products

• 14810-93-6 Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside 
• 17431-55-9 clindamycin 
• 25420-97-7 2,3,4-tris-O-(trimethylsilyl)lincomycin 
• 154-21-2 lincomycin 
• 22965-79-3 methyl 6-amino-7(S)-chloro-6,7,8-trideoxy-1-thio-L-threo-α-D-galacto-octopyranoside 
• 147650-54-2 C₂₁H₃₇ClN₂O₅S 
• 16684-06-3 clindamycin 
• 24729-96-2 clindamycin phosphate 

Relevant articles and documents

Composition and method for rectal delivery of a lincosamide antibiotic drug

A suppository composition and method for rectal administration of a lincosamide antibacterial drug, such as clindamycin, lincomycin, or pirlimycin, is disclosed. The composition is a rectal suppository containing an antimicrobially effective amount of the lincosamide in particulate form dispersed in a Hard Fat suppository base, preferably a Hard Fat NF suppository base. The most preferred suppository compositions of the present invention have long term storage stability, while maintaining effectiveness against bacterial infections.