Name: Lincomycin hydrochloride
SKU: 859-18-7

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Basic Information

Molecular Structure:
CAS No.:	859-18-7
Name:	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:	Xn, Xi
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

Conditions	Yield
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

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

...Expand

: 859-18-7
lincomycin hydrochloride

: clindamycin hydrochloride monohydrate

Conditions

Conditions	Yield
In water	86%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 859-18-7
lincomycin hydrochloride

: C26H50N2O6S

Conditions

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

: 859-18-7
lincomycin hydrochloride

: C31H58N2O8S

Conditions

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

: 859-18-7
lincomycin hydrochloride

: C9H18ClNO4S

Conditions

Conditions	Yield
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)	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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Specification