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859-18-7

Basic Information
CAS No.: 859-18-7
Name: Lincomycin hydrochloride
Article Data: 1
Molecular Structure:
Molecular Structure of 859-18-7 (Lincomycin hydrochloride)
Formula: C18H34N2O6S.HCl
Molecular Weight: 443.005
Synonyms: D-erythro-D-galacto-Octopyranoside,methyl 6,8-dideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-,monohydrochloride, trans-a- (8CI);D-erythro-a-D-galacto-Octopyranoside, methyl6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-,monohydrochloride, (2S-trans)-;D-erythro-a-D-galacto-Octopyranoside, methyl6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-,monohydrochloride (9CI);Lincomycin hydrochloride (7CI);Lincocin;Lincogap;NSC 70731;U 10149a;Lincocin Hydrochloride;
EINECS: 212-726-7
Density: ==
Melting Point: 156-158 °C
Boiling Point: 646.8 °C at 760 mmHg
Flash Point: 345 °C
Solubility: Soluble in water.
Appearance: Crystalline
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 36/37/38-20/21/22
Safety: 26-36
PSA: 147.79000
LogP: 0.27380
Synthetic route
859-18-7

lincomycin hydrochloride

(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
ConditionsYield
With ammonium hydroxide; dihydrogen peroxide; acetonitrile In water at 20℃; for 0.333333h; pH=10.8;95%
75-77-4

chloro-trimethyl-silane

859-18-7

lincomycin hydrochloride

999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

C30H66N2O6SSi4

Conditions
ConditionsYield
With pyridine at 2 - 20℃; for 8h;89%
859-18-7

lincomycin hydrochloride

clindamycin hydrochloride monohydrate

Conditions
ConditionsYield
In water86%
859-18-7

lincomycin hydrochloride

A

(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

B

(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
ConditionsYield
With ammonium hydroxide; dihydrogen peroxide In water at 20℃; for 12h; pH=10.8;A 66%
B 30%
859-18-7

lincomycin hydrochloride

14810-93-6

Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside

Conditions
ConditionsYield
With hydrazine hydrate at 120℃; for 24h;59%
859-18-7

lincomycin hydrochloride

A

(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

B

(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
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In water at 20℃; for 12h; pH=9.75;A 47%
B 50%
530-26-7

D-Mannose

859-18-7

lincomycin hydrochloride

(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
ConditionsYield
With α-mannosidase In various solvent(s) at 48℃; pH=5.0; Enzymatic reaction;2.4%
859-18-7

lincomycin hydrochloride

C26H50N2O6S

Conditions
ConditionsYield
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
859-18-7

lincomycin hydrochloride

C31H58N2O8S

Conditions
ConditionsYield
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
859-18-7

lincomycin hydrochloride

C9H18ClNO4S

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

The Lincomycin hydrochloride, with the CAS registry number 859-18-7, is also known as Lincomycin hydrochloride BP98; Lincocin; Lincorex; Lincomycin hydrochloride monohydrate. It belongs to the product categories of Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals.Its EINECS number is 212-726-7.This chemical's molecular formula is C18H34N2O6S.HCl and molecular weight is 443.00. What's more,Its systematic name is D-erythro-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-,monohydrochloride, trans-alpha-.It is a Crystalline Solid.And it is an antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.

Physical properties about Lincomycin hydrochloride are:
(1)ACD/LogP: 0.908; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.82; (4)ACD/LogD (pH 7.4): -0.20; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 5.85; (9)#H bond acceptors: 8; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 11; (12)Flash Point: 345 °C; (13)Enthalpy of Vaporization: 109.25 kJ/mol; (14)Boiling Point: 646.8 °C at 760 mmHg; (15)Vapour Pressure: 1.85E-19 mmHg at 25°C.

Safety Information of Lincomycin hydrochloride:
The Lincomycin hydrochloride is harmful by inhalation, in contact with skin and if swallowed. It ii Irritating to eyes, respiratory system and skin.When you use it ,wear suitable protective clothing.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES:Cl.O=C(N[C@@H]([C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O)[C@H](O)C)[C@H]2N(C)C[C@H](CCC)C2;
(2)Std. InChI:InChI=1S/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;
(3)Std. InChIKey:POUMFISTNHIPTI-BOMBIWCESA-N.

The toxicity data of Lincomycin hydrochloride as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 300mg/kg (300mg/kg)   Toxicology and Applied Pharmacology. Vol. 6, Pg. 476, 1964.
guinea pig LD50 intraperitoneal 732mg/kg (732mg/kg)   Bulletin of the Faculty of Pharmacy Vol. 18, Pg. 131, 1979.
monkey LD oral > 300mg/kg (300mg/kg)   Toxicology and Applied Pharmacology. Vol. 6, Pg. 476, 1964.
mouse LD50 intramuscular > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. -, Pg. 1260, 1990.
mouse LD50 intraperitoneal 750mg/kg (750mg/kg)   Bulletin of the Faculty of Pharmacy Vol. 18, Pg. 131, 1979.
mouse LD50 intravenous 214mg/kg (214mg/kg)   Toxicology and Applied Pharmacology. Vol. 6, Pg. 476, 1964.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. -, Pg. 1260, 1990.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. -, Pg. 1260, 1990.
rat LD50 intravenous 342mg/kg (342mg/kg)   Toxicology and Applied Pharmacology. Vol. 6, Pg. 476, 1964.
rat LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. -, Pg. 1260, 1990.
rat LD50 subcutaneous 9778mg/kg (9778mg/kg)   Toxicology and Applied Pharmacology. Vol. 9, Pg. 445, 1966.

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