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Lincomycin

Synopsis, Chemistry

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Also known as: 859-18-7, Lincomycin hcl, Frademicina, Lincomycin (hydrochloride), Mycivin, Lincomycin hydrochloride anhydrous

Molecular Formula

C₁₈H₃₅ClN₂O₆S

Molecular Weight

443.0 g/mol

InChI Key

POUMFISTNHIPTI-BOMBIWCESA-N

FDA UNII

GCW8Y9936L

An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.

1 2D Structure

Lincomycin

2 Identification

2.1 Computed Descriptors

2.1.1 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;hydrochloride

2.1.2 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

2.1.3 InChI Key

POUMFISTNHIPTI-BOMBIWCESA-N

2.1.4 Canonical SMILES

CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)O.Cl

2.1.5 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.Cl

2.2 Other Identifiers

2.2.1 UNII

GCW8Y9936L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Epilincomycin

2. Hemihydrate Lincomycin Monohydrochloride

3. Lincocin

4. Lincolnensin

5. Lincomycin

6. Lincomycin A

7. Lincomycin Monohydrochloride

8. Lincomycin Monohydrochloride, (2s-cis)-isomer

9. Lincomycin Monohydrochloride, (l-threo)-isomer

10. Lincomycin Monohydrochloride, Hemihydrate

11. Lincomycin, (2s-cis)-isomer

12. Lincomycin, (l-threo)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 859-18-7

2. Lincomycin Hcl

3. Frademicina

4. Lincomycin (hydrochloride)

5. Mycivin

6. Lincomycin Hydrochloride Anhydrous

7. Nsc 70731

8. Lincocin

9. Gcw8y9936l

10. Lincomix 20

11. Pura Ject 100

12. Ncgc00159326-02

13. Lincolnensin, Hydrochloride

14. Dsstox_cid_27780

15. Dsstox_rid_82556

16. Dsstox_gsid_47803

17. (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 Hydrochloride

18. Lincolnensin Hydrochloride

19. Antibiotic 124a, Hydrochloride

20. Lincogap

21. U 10149a

22. Lincocin Hydrochloride

23. Unii-gcw8y9936l

24. Mfcd00083647

25. Einecs 212-726-7

26. Cas-859-18-7

27. Lincomycin Hcl (lincocin)

28. Ec 212-726-7

29. Schembl192964

30. Chembl1201097

31. Dtxsid7047803

32. Hy-b0417a

33. Lincocin Hydrochloride Monohydrate

34. Tox21_111575

35. Akos024375415

36. Tox21_111575_1

37. Ccg-220302

38. Anhydrous Lincomycin Hydrochloride

39. Lincomycin Hydrochloride [who-dd]

40. Ncgc00159326-03

41. As-13720

42. Lincomycin Hydrochloride, >=90% (tlc)

43. Lincomycin Hydrochloride, >=95.0% (tlc)

44. L0166

45. Lincomycin Hydrochloride Anhdrous [mi]

46. Lincomycin Hydrochloride For System Suitability

47. 859l187

48. A841491

49. Anhydrous Lincomycin Hydrochloride [mart.]

50. Q27279041

51. Lincomycin Hydrochloride, Bioreagent, Suitable For Cell Culture

52. Lincomycin Hydrochloride, British Pharmacopoeia (bp) Reference Standard

53. (2s,4r)-n-[(1r,2r)-2-hydroxy-1-[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboximidic Acid Hydrochloride

54. (2s-trans)-methyl 6,8-dideoxy-6-(((1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-d-erythro-.alpha.-d-galacto-octopyranoside Hydrochloride

55. D-erythro-.alpha.-d-galacto-octopyranoside, Methyl 6,8-dideoxy-6-(((1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-, Monohydrochloride, (2s-trans)-

56. D-erythro-.alpha.-d-galacto-octopyranoside, Methyl 6,8-dideoxy-6-[[[(2s,4r)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-, Hydrochloride (1:1)

57. D-erythro-alpha-d-galacto-octopyranoside, Methyl 6,8-dideoxy-6-((((2s,4r)-1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-, Monohydrochloride

58. D-erythro-alpha-d-galacto-octopyranoside, Methyl 6,8-dideoxy-6-(((1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-, Monohydrochloride, (2s-trans)-

59. D-erythro-d-galacto-octopyranoside, Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-l-2-pyrrolidinecarboxamido)-1-thio-, Monohydrochloride, Trans-alpha-

60. Hydron; N-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl)propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide; Chloride;(2s,4r)-n-{(1s)-2-hydroxy-1-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(methylthio)-tetrahydro-2h-2-pyranyl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide Hydrochloride

61. Methyl (2s-trans)-6,8-dideoxy-6-(((1-methyl-4-propylpyrrolidin-2-yl)carbonyl)amino)-1-thio-d-erythro-alpha-d-galacto-octopyranoside Monohydrochloride

62. Methyl 6,8-dideoxy-6-(1-methyl-trans-4-propyl-l-2-pyrrolidinecarboxamido)-1-thio-d-erythro-.alpha.-d-galacto-octopyranoside Monohydrochloride

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₃₅ClN₂O₆S
Molecular Weight	443.0 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	442.1904357 g/mol
Monoisotopic Mass	442.1904357 g/mol
Topological Polar Surface Area	148 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	499
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Lincocin
PubMed Health	Lincomycin (Oral route, Injection route)
Drug Classes	Antibiotic, Lincosamide
Drug Label	LINCOCIN Sterile Solution contains lincomycin hydrochloride which is the monohydrated salt of lincomycin, a substance produced by the growth of a member of the lincolnensis group of Streptomyces lincolnensis (Fam. Streptomycetaceae). The chemical nam...
Active Ingredient	Lincomycin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	eq 300mg base/ml
Market Status	Prescription
Company	Pharmacia And Upjohn

2 of 2
Drug Name	Lincocin
PubMed Health	Lincomycin (Oral route, Injection route)
Drug Classes	Antibiotic, Lincosamide
Drug Label	LINCOCIN Sterile Solution contains lincomycin hydrochloride which is the monohydrated salt of lincomycin, a substance produced by the growth of a member of the lincolnensis group of Streptomyces lincolnensis (Fam. Streptomycetaceae). The chemical nam...
Active Ingredient	Lincomycin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	eq 300mg base/ml
Market Status	Prescription
Company	Pharmacia And Upjohn

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)