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2D Structure
Also known as: 22199-08-2, Sulfadiazine silver, Flamazine, Sulfadiazine silver salt, Silvadene, Dermazin
Molecular Formula
C10H9AgN4O2S
Molecular Weight
357.14  g/mol
InChI Key
UEJSSZHHYBHCEL-UHFFFAOYSA-N
FDA UNII
W46JY43EJR

Antibacterial used topically in burn therapy.
Silver sulfadiazine is a Sulfonamide Antibacterial.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
silver;(4-aminophenyl)sulfonyl-pyrimidin-2-ylazanide
2.1.2 InChI
InChI=1S/C10H9N4O2S.Ag/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10;/h1-7H,11H2;/q-1;+1
2.1.3 InChI Key
UEJSSZHHYBHCEL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CN=C(N=C1)[N-]S(=O)(=O)C2=CC=C(C=C2)N.[Ag+]
2.2 Other Identifiers
2.2.1 UNII
W46JY43EJR
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Brandiazin

2. Dermazin

3. Flamazine

4. Flammazine

5. Sicazine

6. Silvadene

7. Silvederma

8. Silver Sulfafdiazine

9. Ssd

10. Ssd Af

11. Sulfadiazine, Silver

12. Sulfafdiazine, Silver

13. Sulfargen

14. Thermazene

2.3.2 Depositor-Supplied Synonyms

1. 22199-08-2

2. Sulfadiazine Silver

3. Flamazine

4. Sulfadiazine Silver Salt

5. Silvadene

6. Dermazin

7. Silver Sulphadiazine

8. Thermazene

9. Sulfadiazine, Silver

10. Dermazine

11. Geben

12. Silver Sulfadiazinate

13. Silvazine

14. Altreet-ag

15. Mfcd00072101

16. Ssd

17. W46jy43ejr

18. Chebi:9142

19. Benzenesulfonamide, 4-amino-n-2-pyrimidinyl-, Monosilver(1+) Salt

20. Silver;(4-aminophenyl)sulfonyl-pyrimidin-2-ylazanide

21. N(sup 1)-2-pyrimidinylsulfanilamide Monosilver(1+) Salt

22. Silbertone

23. Silver(i) Sulfadiazine

24. Sulfadiazin Silber

25. Dsstox_cid_28572

26. Dsstox_rid_82844

27. Dsstox_gsid_48646

28. Sulfadiazin, Silbersalz

29. Silvadene (tn)

30. Silver(1+) [(4-aminophenyl)sulfonyl](pyrimidin-2-yl)azanide

31. Sulfadiazine, Silver [usan]

32. Cas-22199-08-2

33. Nsc625324

34. Ncgc00183137-01

35. Ncgc00188438-01

36. Unii-w46jy43ejr

37. N1-2-pyrimidinylsulfanilamide Monosilver(1+) Salt

38. Sulfadiazine, Silver (usp)

39. 4-amino-n-(2-pyrimidinyl)benzenesulfonamide Silver Salt

40. Sulfadiazine, Silver [usan:usp]

41. Einecs 244-834-5

42. Sulfadiazinum Argentum

43. Nsc 625324

44. (4-amino-n-pyrimidin-2-ylbenzenesulphonamidato-nn,o1)silver

45. Silver Sulfadiazine Usp

46. Silver, (4-amino-n-(2-pyrimidinyl-.kappa.n1)benzenesulfonamidato-.kappa.o)-

47. Silver, (4-amino-n-2-pyrimidinylbenzenesulfonamidato-nn,o1)-

48. Silver (i) Sulfadiazine

49. Schembl15633

50. Sulfadiazine Silver (jp17)

51. Silver Sulfadiazine Bulk Powder

52. Chembl1382627

53. Dtxsid4048646

54. Sulfadiazine Silver [jan]

55. (4-amino-n-2-pyrimidinylbenzenesulfonamidato-nn,01)-silver

56. Sulfanilamide, N(sup 1)-2-pyrimidinyl-, Monosilver(1+) Salt

57. Silver Sulfadiazine [vandf]

58. Sulfadiazine Silver [mart.]

59. Tox21_112998

60. Tox21_113471

61. Silver Sulfadiazine [usp-rs]

62. Sulfadiazine Silver [who-dd]

63. Sulfadiazine Silver [who-ip]

64. Sulfadiazine Silver Salt [mi]

65. Akos005111099

66. Ac-3535

67. Db05245

68. Silver Sulfadiazine [green Book]

69. Silver Sulfadiazine [orange Book]

70. As-13863

71. Sy105573

72. Silver Sulfadiazine [usp Monograph]

73. Db-045839

74. Sulfadiazine, Silver [usp Impurity]

75. Ft-0630481

76. S0595

77. Sulfadiazinum Argentum [who-ip Latin]

78. D00433

79. Q420984

80. J-014582

81. Silver (4-aminophenyl)sulfonyl-pyrimidin-2-yl-azanide

82. [(4-aminophenyl)sulfonyl](pyrimidin-2-yl)azanide (ag+)

83. 4-amino-n-(2-pyrimidinyl) Benzenesulfonamide Silver Salt

84. Silver(i) ((4-aminophenyl)sulfonyl)(pyrimidin-2-yl)amide

85. Silver(1+) Ion 4-{[(pyrimidin-2-yl)azanidyl]sulfonyl}aniline

86. Benzenesulfonamide, 4-amino-n-2-pyrimidinyl-, Silver(1+) Salt (1:1)

87. 1152234-18-8

2.3.3 Other Synonyms

1. Soludiazine

2. Suthogen

3. Sulfadiazin-natrium

4. Sulfadiazine Silver

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 357.14 g/mol
Molecular Formula C10H9AgN4O2S
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Exact Mass355.94971 g/mol
Monoisotopic Mass355.94971 g/mol
Topological Polar Surface Area95.3 Ų
Heavy Atom Count18
Formal Charge0
Complexity327
Isotope Atom Count0
Defined Atom Stereocenter Count0
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 8  
Drug NameSilvadene
Active IngredientSilver sulfadiazine
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyKing Pharms

2 of 8  
Drug NameSsd
PubMed HealthSilver Sulfadiazine (On the skin)
Drug ClassesAntibacterial
Drug LabelSILVADENE Cream 1% is a soft, white, water-miscible cream containing the antimicrobial agent silver sulfadiazine in micronized form, which has the following structural formula: Each gram of SILVADENE Cream 1% contains 10 mg of micronized silver sulfa...
Active IngredientSilver sulfadiazine
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyDr Reddys La

3 of 8  
Drug NameSsd af
PubMed HealthSilver Sulfadiazine (On the skin)
Drug ClassesAntibacterial
Drug LabelSSD (1% Silver Sulfadiazine Cream) and SSD AF (1% Silver Sulfadiazine Cream), 1% are topical antibacterial preparations which have as their active antimicrobial ingredient silver sulfadiazine. The active moiety is contained within an opaque, wh...
Active IngredientSilver sulfadiazine
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyDr Reddys La

4 of 8  
Drug NameThermazene
PubMed HealthSilver Sulfadiazine (On the skin)
Drug ClassesAntibacterial
Drug LabelThermazene (silver sulfadiazine Cream, 1% is a soft, water dispersible cream containing silver sulfadiazine in micronized form for topical application. Each gram of Thermazene contains 10mg of micronized silver sulfadiazine. Thermazene contains 1...
Active IngredientSilver sulfadiazine
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyThepharmanetwork

5 of 8  
Drug NameSilvadene
Active IngredientSilver sulfadiazine
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyKing Pharms

6 of 8  
Drug NameSsd
PubMed HealthSilver Sulfadiazine (On the skin)
Drug ClassesAntibacterial
Drug LabelSILVADENE Cream 1% is a soft, white, water-miscible cream containing the antimicrobial agent silver sulfadiazine in micronized form, which has the following structural formula: Each gram of SILVADENE Cream 1% contains 10 mg of micronized silver sulfa...
Active IngredientSilver sulfadiazine
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyDr Reddys La

7 of 8  
Drug NameSsd af
PubMed HealthSilver Sulfadiazine (On the skin)
Drug ClassesAntibacterial
Drug LabelSSD (1% Silver Sulfadiazine Cream) and SSD AF (1% Silver Sulfadiazine Cream), 1% are topical antibacterial preparations which have as their active antimicrobial ingredient silver sulfadiazine. The active moiety is contained within an opaque, wh...
Active IngredientSilver sulfadiazine
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyDr Reddys La

8 of 8  
Drug NameThermazene
PubMed HealthSilver Sulfadiazine (On the skin)
Drug ClassesAntibacterial
Drug LabelThermazene (silver sulfadiazine Cream, 1% is a soft, water dispersible cream containing silver sulfadiazine in micronized form for topical application. Each gram of Thermazene contains 10mg of micronized silver sulfadiazine. Thermazene contains 1...
Active IngredientSilver sulfadiazine
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyThepharmanetwork

4.2 Drug Indication

Indicated as an adjunct for the prevention and treatment of wound sepsis in patients with second- and third-degree burns.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Silver sulfadiazine has broad antimicrobial activity. It is bactericidal for many gram- negative and gram-positive bacteria as well as being effective against yeast. Silver sulfadiazine is not a carbonic anhydrase inhibitor and may be useful in situations where such agents are contraindicated.


5.2 MeSH Pharmacological Classification

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
SILVER SULFADIAZINE
5.3.2 FDA UNII
W46JY43EJR
5.3.3 Pharmacological Classes
Sulfonamides [CS]; Sulfonamide Antibacterial [EPC]
5.4 ATC Code

D06BA01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06B - Chemotherapeutics for topical use

D06BA - Sulfonamides

D06BA01 - Silver sulfadiazine


5.5 Absorption, Distribution and Excretion

Absorption

Very limited penetration through the skin. Only when applied to very large area burns is absorption into the body generally an issue.


5.6 Mechanism of Action

Studies utilizing radioactive micronized silver sulfadiazine, electron microscopy, and biochemical techniques have revealed that the mechanism of action of silver sulfadiazine on bacteria differs from silver nitrate and sodium sulfadiazine. Silver sulfadiazine acts only on the cell membrane and cell wall to produce its bactericidal effect. A specific mechanism of action has not been determined, but silver sulfadiazine's effectiveness may possibly be from a synergistic interaction, or the action of each component. Silver is a biocide, which binds to a broad range of targets. Silver ions bind to nucleophilic amino acids, as well as sulfhydryl, amino, imidazole, phosphate, and carboxyl groups in proteins, causing protein denaturation and enzyme inhibition. Silver binds to surface membranes and proteins, causing proton leaks in the membrane, leading to cell death. Sulfadiazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.