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Chemistry

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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

Chloramphenicol Sodium Succinate

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 Formula	C₁₅H₁₅Cl₂N₂NaO₈
Molecular Weight	445.2 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	444.0103151 g/mol
Monoisotopic Mass	444.0103151 g/mol
Topological Polar Surface Area	162 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	541
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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	Chloramphenicol sodium succinate
Drug Label	IMPORTANT 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 Ingredient	Chloramphenicol sodium succinate
Dosage Form	Injectable
Route	Injection
Strength	eq 1gm base/vial
Market Status	Prescription
Company	Fresenius Kabi Usa

2 of 2
Drug Name	Chloramphenicol sodium succinate
Drug Label	IMPORTANT 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 Ingredient	Chloramphenicol sodium succinate
Dosage Form	Injectable
Route	Injection
Strength	eq 1gm base/vial
Market Status	Prescription
Company	Fresenius 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]

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API Reference Price

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