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2D Structure
Also known as: 982-57-0, Chloramphenicol succinate sodium, Chloramphenicol monosuccinate sodium salt, Chloramphenicol succinate sodium, 872109hx6b, Protophenicol
Molecular Formula
C15H15Cl2N2NaO8
Molecular Weight
445.2  g/mol
InChI Key
RPLOPBHEZLFENN-HTMVYDOJSA-M
FDA UNII
872109HX6B

Chloramphenicol Sodium Succinate is the sodium succinate salt form of chloramphenicol, a nitrobenzene derivate and broad-spectrum antibiotic with antibacterial activity. Chloramphenicol sodium succinate reversibly binds to the 50S subunit of bacterial ribosomes, thereby interfering with peptidyl transferase activity in the elongation process of protein synthesis. As a result, this agent prevents bacterial cell growth.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;4-[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoate
2.1.2 InChI
InChI=1S/C15H16Cl2N2O8.Na/c16-14(17)15(24)18-10(7-27-12(22)6-5-11(20)21)13(23)8-1-3-9(4-2-8)19(25)26;/h1-4,10,13-14,23H,5-7H2,(H,18,24)(H,20,21);/q;+1/p-1/t10-,13-;/m1./s1
2.1.3 InChI Key
RPLOPBHEZLFENN-HTMVYDOJSA-M
2.1.4 Canonical SMILES
C1=CC(=CC=C1C(C(COC(=O)CCC(=O)[O-])NC(=O)C(Cl)Cl)O)[N+](=O)[O-].[Na+]
2.1.5 Isomeric SMILES
C1=CC(=CC=C1[C@H]([C@@H](COC(=O)CCC(=O)[O-])NC(=O)C(Cl)Cl)O)[N+](=O)[O-].[Na+]
2.2 Other Identifiers
2.2.1 UNII
872109HX6B
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Chloramphenicol Hemisuccinate

2. Chloramphenicol Monosuccinate

3. Chloramphenicol Succinate Sodium

4. Levomycetin Succinate

2.3.2 Depositor-Supplied Synonyms

1. 982-57-0

2. Chloramphenicol Succinate Sodium

3. Chloramphenicol Monosuccinate Sodium Salt

4. Chloramphenicol Succinate Sodium

5. 872109hx6b

6. Protophenicol

7. Dsstox_cid_4747

8. Dsstox_rid_77520

9. Dsstox_gsid_24747

10. Butanedioic Acid, Mono(2-((2,2-dichloroacetyl)amino)-3-hydroxy-3-(4-nitrophenyl)propyl) Ester, Monosodium Salt, (r-(r*,r*))-

11. Sodium Chloramphenicol Succinate

12. Chloramphenicol Sodium Monosuccinate

13. Cas-982-57-0

14. Sodium 4-((2r,3r)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy)-4-oxobutanoate

15. Ccris 6204

16. Chloramphenicol-sukzinat-natrium

17. Ncgc00094619-04

18. Chloramphenicol Sodium Succinate, D-

19. Einecs 213-568-1

20. Chloramphenicol-sukzinat-natrium [german]

21. Unii-872109hx6b

22. Sodium;4-[(2r,3r)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoate

23. Chloramphenicol Sodium Succinate [usp:ban:jan]

24. Chloromycetin Succinate (tn)

25. D-threo-(-)-2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide Alpha-(sodium Succinate)

26. Schembl193134

27. Chloramphenicoli Natrii Succinas

28. Chembl1200729

29. Dtxsid2024747

30. Tox21_113484

31. Akos016340429

32. Tox21_113484_1

33. Ccg-212521

34. Ks-5158

35. Ncgc00094619-06

36. Acetamide, 2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)-, Alpha-ester With Sodium Succinate

37. Butanedioic Acid, Mono(2-((2,2-dichloroacetyl)amino)-3-hydroxy-3-(4-nitrophenyl)propyl) Ester, Monosodium Salt, (r-(r(sup *),r(sup *)))(-)

38. Chloramphenicol Sodium Succinate (jp17/usp)

39. Chloramphenicol Sodium Succinate [jan]

40. Chloramphenicol Sodium Succinate [vandf]

41. D02185

42. Chloramphenicol Sodium Succinate [mart.]

43. Chloramphenicol Sodium Succinate [who-dd]

44. Chloramphenicol Sodium Succinate [who-ip]

45. W-100087

46. Chloramphenicol Monosuccinate Sodium Salt [mi]

47. Chloramphenicol Sodium Succinate [ep Monograph]

48. Chloramphenicol Sodium Succinate [orange Book]

49. Chloramphenicoli Natrii Succinas [who-ip Latin]

50. Q27269783

51. Chloramphenicol Sodium Succinate [usp Monograph]

52. Butanedioic Acid, Mono((2r,3r)-2-((dichloroacetyl)amino)-3-hydroxy-3-(4-nitrophenyl)propyl) Ester, Monosodium Salt

53. D-threo-(-)-2,2-dichloro-n-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl)acetamide .alpha.-(sodium Succinate)

54. Sodium4-((2r,3r)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy)-4-oxobutanoate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 445.2 g/mol
Molecular Formula C15H15Cl2N2NaO8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Exact Mass444.0103151 g/mol
Monoisotopic Mass444.0103151 g/mol
Topological Polar Surface Area162 Ų
Heavy Atom Count28
Formal Charge0
Complexity541
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameChloramphenicol sodium succinate
Drug LabelIMPORTANT CONSIDERATIONS IN PRESCRIBING INJECTABLE CHLORAMPHENICOL SODIUM SUCCINATE.CHLORAMPHENICOL SODIUM SUCCINATE IS INTENDED FOR INTRAVENOUS USE ONLY. IT HAS BEENDEMONSTRATED TO BE INEFFECTIVE WHEN GIVEN INTRAMUSCULARLY.1. Chloramphenicol sodium...
Active IngredientChloramphenicol sodium succinate
Dosage FormInjectable
RouteInjection
Strengtheq 1gm base/vial
Market StatusPrescription
CompanyFresenius Kabi Usa

2 of 2  
Drug NameChloramphenicol sodium succinate
Drug LabelIMPORTANT CONSIDERATIONS IN PRESCRIBING INJECTABLE CHLORAMPHENICOL SODIUM SUCCINATE.CHLORAMPHENICOL SODIUM SUCCINATE IS INTENDED FOR INTRAVENOUS USE ONLY. IT HAS BEENDEMONSTRATED TO BE INEFFECTIVE WHEN GIVEN INTRAMUSCULARLY.1. Chloramphenicol sodium...
Active IngredientChloramphenicol sodium succinate
Dosage FormInjectable
RouteInjection
Strengtheq 1gm base/vial
Market StatusPrescription
CompanyFresenius Kabi Usa

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Amphenicols [EXT]; Amphenicol-class Antibacterial [EPC]