Home > Name List By other > (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- propylpyrrol...

CAS No 154-21-2 , (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

  • 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
  • Synonyms: 154-21-2;(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; STOCK1N-50613; Lincolnensin; Lincomycin (USAN/INN); Epilincomycin; AC1MHD7X; (2S-cis)-Isomer;Lincomycin; CHEMBL1447;
  • CAS Registry Number:
  • Density: 1.29 g/cm3
  • Safety Statements: Poison by intramuscular route. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits very toxic fumes of SOx and NOx.
  • Hazard Symbols: Xi :;
  • EINECS: 205-824-6
  • Molecular Weight: 406.53736
  • 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
  • Risk Statements: S26 :;
  • Molecular Formula: C18H34N2O6S
  • Molecular Structure:CAS No:154-21-2 (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,<br />5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-<br />propylpyrrolidine-2-carboxamide

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References of (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
Title: Lincomycin
CAS Registry Number: 154-21-2
CAS Name: (2S-trans)-Methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-erythro-a-D-galacto-octopyranoside
Synonyms: lincolnensin
Manufacturers' Codes: U-10149; NSC-70731
Molecular Formula: C18H34N2O6S
Molecular Weight: 406.54
Percent Composition: C 53.18%, H 8.43%, N 6.89%, O 23.61%, S 7.89%
Literature References: Antibiotic produced by Streptomyces lincolnensis var. lincolnensis. Isoln: D. J. Mason et al., Antimicrob. Agents Chemother. 1962, 555; R. R. Herr, M. E. Bergy, ibid. 560; M. E. Bergy et al., US 3086912 (1963 to Upjohn). Structure: Hoeksema et al., J. Am. Chem. Soc. 86, 4223 (1964). Synthesis: Magerlein, Tetrahedron Lett. 1970, 33. Stereoselective synthesis: S. Knapp, P. J. Kukkola, J. Org. Chem. 55, 1632 (1990). Mechanism of action: F. N. Chang in Antibiotics vol. 5(pt. 1), F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 127-134. Clinical study: F. Puleo et al., Gazz. Med. Ital. 138, 401 (1979). Toxicity data: Gray et al., Toxicol. Appl. Pharmacol. 6, 476 (1964). Comprehensive description: H. Y. Muti, F. H. Al-Hajjar, Anal. Profiles Drug Subs. Excip. 23, 269-319 (1994).
Properties: Free base, pKa￠ 7.6. More stable in salt form. Sol in methanol, lower alcohols, ethyl acetate, acetone, chloroform. Slightly sol in water (Bergy).
pKa: pKa￠ 7.6
 
Derivative Type: Hydrochloride hemihydrate
Trademarks: Lincocin (Pharmacia & Upjohn)
Molecular Formula: C18H34N2O6S.HCl.?H2O
Molecular Weight: 452.01
Percent Composition: C 47.83%, H 8.03%, N 6.20%, O 23.01%, S 7.09%, Cl 7.84%
Properties: Crystals from acetone, mp 135-140°. Also reported as mp 146-148°. [a]D25 +137° (water). No uv absorption. pKa￠ 7.60. Freely sol in water, methanol, ethanol; sparingly sol in most organic solvents other than hydrocarbons. LD50 in mice, rats (g/kg): 1 i.p.; 4 orally (Gray).
Melting point: mp 135-140°; mp 146-148°
pKa: pKa￠ 7.60
Optical Rotation: [a]D25 +137° (water)
Toxicity data: LD50 in mice, rats (g/kg): 1 i.p.; 4 orally (Gray)
 
Derivative Type: Hydrochloride monohydrate
CAS Registry Number: 7179-49-9
Trademarks: Albiotic (Pharmacia); Lincomix (Pharmacia & Upjohn)
Properties: White or almost white crystalline powder. odorless or with a slight mercaptan-like odor and a bitter taste. mp 156-158°. [a]D25 +143° (water). pH of a 1% aq. soln: 4.8.
Melting point: mp 156-158°
Optical Rotation: [a]D25 +143° (water)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Lincosamides.