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2D Structure
Also known as: Chlorhexidine digluconate, Hibiclens, 18472-51-0, Peridex, Dyna-hex, Bioscrub
Molecular Formula
C34H54Cl2N10O14
Molecular Weight
897.8  g/mol
InChI Key
YZIYKJHYYHPJIB-UUPCJSQJSA-N
FDA UNII
MOR84MUD8E

Chlorhexidine Gluconate is the gluconate salt form of chlorhexidine, a biguanide compound used as an antiseptic agent with topical antibacterial activity. Chlorhexidine gluconate is positively charged and reacts with the negatively charged microbial cell surface, thereby destroying the integrity of the cell membrane. Subsequently, chlorhexidine gluconate penetrates into the cell and causes leakage of intracellular components leading to cell death. Since gram positive bacteria are more negatively charged, they are more sensitive to this agent.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1E)-2-[6-[[amino-[(E)-[amino-(4-chloroanilino)methylidene]amino]methylidene]amino]hexyl]-1-[amino-(4-chloroanilino)methylidene]guanidine;(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
2.1.2 InChI
InChI=1S/C22H30Cl2N10.2C6H12O7/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18;2*7-1-2(8)3(9)4(10)5(11)6(12)13/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34);2*2-5,7-11H,1H2,(H,12,13)/t;2*2-,3-,4+,5-/m.11/s1
2.1.3 InChI Key
YZIYKJHYYHPJIB-UUPCJSQJSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1NC(=NC(=NCCCCCCN=C(N)N=C(N)NC2=CC=C(C=C2)Cl)N)N)Cl.C(C(C(C(C(C(=O)O)O)O)O)O)O.C(C(C(C(C(C(=O)O)O)O)O)O)O
2.1.5 Isomeric SMILES
C1=CC(=CC=C1N/C(=N/C(=NCCCCCCN=C(/N=C(/NC2=CC=C(C=C2)Cl)\N)N)N)/N)Cl.C(O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O.C(O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
MOR84MUD8E
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,1'-hbcb

2. Avagard

3. Chlorhexamed

4. Chlorhexidine Bigluconate

5. Chlorhexidine Digluconate

6. Corsodyl Ici

7. Curasept Ads 220

8. Dyna-hex

9. Eludril

10. Gibitan

11. Hexidine

12. Hibiclens

13. Hibident

14. Hibiscrub

15. Hibisol

16. Hibitane

17. Peridex

18. Perio Chip

2.3.2 Depositor-Supplied Synonyms

1. Chlorhexidine Digluconate

2. Hibiclens

3. 18472-51-0

4. Peridex

5. Dyna-hex

6. Bioscrub

7. Chlorhexidine D-digluconate

8. Exidine

9. Microderm

10. Periochip

11. Periogard

12. Unisept

13. Brian Care

14. Steri-stat

15. Cida-stat

16. Hibistat

17. Pharmaseal Scrub Care

18. Chg Scrub

19. Prevacare

20. Chlorhexidine Digluconate Solution

21. Chlorhexidine Di-d-gluconate

22. Mor84mud8e

23. Nsc-753971

24. Hibiscrub

25. Hibitane

26. 1,1'-hexamethylene Bis(5-(p-chlorophenyl)biguanide), Digluconate

27. 1,1'-hexamethylenebis(5-(p-chlorophenyl)biguanide) Di-d-gluconate

28. Bacticlens

29. Chlorhexamed

30. Kleersight

31. Corsodyl

32. Disteryl

33. Hibident

34. Hibidil

35. Orahexal

36. Plurexid

37. Septeal

38. Abacil

39. Fight Bac

40. Plac Out

41. Prevacare R

42. Arlacide G

43. Hibitane 5

44. 2,4,11,13-tetraazatetradecanediimidamide, N,n''-bis(4-chlorophenyl)-3,12-diimino-, Di-d-gluconate

45. Chlorhexidin Glukonatu

46. Peridex (antiseptic)

47. Bactoshield Chg 2%

48. Caswell No. 481g

49. Unii-mor84mud8e

50. Pwriochip

51. Chlorhexidin Glukonatu [czech]

52. 1,6-bis(n5-[p-chlorophenyl]-n1-biguanido)hexane

53. Phiso-med

54. Hibitane Gluconate

55. Hibiclens (tn)

56. Periogard (tn)

57. Drg-0091

58. Einecs 242-354-0

59. Peridex (tn)

60. Mfcd00083599

61. Chlohexidine Gluconate

62. Epa Pesticide Chemical Code 045504

63. Readyprep Chg

64. Chlorhexidine Gluconate [usan:usp:jan]

65. Ec 242-354-0

66. Schembl34468

67. 1,6-bis(5-(p-chlorophenyl)biguandino)hexane Digluconate

68. Chembl4297088

69. Dtxsid5034519

70. Chebi:28312

71. 1,1'-hexamethylenebis(5-(p-chlorophenyl)biguanide) Gluconate

72. 1,1'-hexamethylenebis(5-(p-chlorophenyl)biguanide)digluconate

73. Chx Plus Concentrate Premium Chlorhexidine Teat Dip Concentrate

74. Biguanide, 1,1'-hexamethylenebis(5-(p-chlorophenyl)-, Digluconate

75. Chlorhexidine Gluconate (jp17/usp)

76. Chlorhexidine Gluconate [jan]

77. Chlorhexidine Gluconate [usan]

78. Akos015896303

79. Akos025310696

80. Chlorhexidine Gluconate [mart.]

81. Chlorhexidine Gluconate [vandf]

82. Nsc 753971

83. Chlorhexidine D-digluconate [mi]

84. Chlorhexidine Digluconate [inci]

85. Chlorhexidine Gluconate [who-dd]

86. Gluconic Acid, Compd. With 1,1'-hexamethylene Bis(5-(p-chlorophenyl)biguanide) (2:1), D-

87. D-gluconic Acid, Compd. With N,n''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)

88. D-gluconic Acid, Compound With N,n''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediamidine (2:1)

89. Chlorhexidine Gluconate [orange Book]

90. Chlorhexidine Gluconate [usp Impurity]

91. Avagard Component Chlorhexidine Gluconate

92. C08038

93. D00858

94. Chlorhexidine Digluconate Solution, 20% In H2o

95. Soluprep Component Chlorhexidine Gluconate

96. Chloraprep Component Chlorhexidine Gluconate

97. Chlorhexidine Gluconate Component Of Avagard

98. Chlorhexidine Digluconate, 20% W/v Aqueous Solution

99. Chlorhexidine Gluconate Component Of Soluprep

100. J-011837

101. Chlorhexidine Gluconate Component Of Chloraprep

102. Chlorhexidine Digluconate Solution [ep Monograph]

103. 1,1'-hexamethylenebis[5-(4-chlorophenyl)biguanide] Digluconate

104. Chlorhexidine Digluconate, Pharmaceutical Secondary Standard; Certified Reference Material

105. 1,1'-hexamethylenebis[5-(p-chlorophenyl)biguanide] (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic Acid(1:2)

106. 1-(4-chlorophenyl)-3-[n-[6-[[n-[n-(4-chlorophenyl)carbamimidoyl]carbamimidoyl]amino]hexyl]carbamimidoyl]guanidine; (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic Acid

107. 2,4,11,13-tetraazatetradecanediimidamide, N,n''-bis(4-chlorophenyl)-3,12-diimino-, Digluconate

108. 2,4,11,13-tetraazatetradecanediimidamide, N,n'-bis(4-chlorophenyl)-3,12-diimino-, Di-d-gluconate

109. D-gluconic Acid, Compd With N,n''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)

110. D-gluconic Acid, Compd. With N,n''-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecane Diimidamide (2:1)

111. D-gluconic Acid, Compd. With N1,n14-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (2:1)

112. N',n'''''-hexane-1,6-diylbis[n-(4-chlorophenyl)(imidodicarbonimidic Diamide)]--d-gluconic Acid (1/2)

2.4 Create Date
2006-10-23
3 Chemical and Physical Properties
Molecular Weight 897.8 g/mol
Molecular Formula C34H54Cl2N10O14
Hydrogen Bond Donor Count18
Hydrogen Bond Acceptor Count16
Rotatable Bond Count23
Exact Mass896.3198018 g/mol
Monoisotopic Mass896.3198018 g/mol
Topological Polar Surface Area455 Ų
Heavy Atom Count60
Formal Charge0
Complexity819
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameChlorhexidine gluconate
Drug LabelChlorhexidine Gluconate is an oral rinse containing 0.12% chlorhexidine gluconate (1,11-hexamethylene bis[5-(p-chlorophenyl) biguanide] di-D-gluconate) in a base containing water, 11.6% alcohol, glycerin, PEG-40 sorbitan diisostearate, flavor, sodium...
Active IngredientChlorhexidine gluconate
Dosage FormCloth; Solution; Sponge
RouteDental; Topical
Strength0.12%; 2%; 4%
Market StatusOver the Counter; Prescription
CompanyLyne; Wockhardt; Sage Prods; Hi Tech Pharma; Teva; Xttrium; Becton Dickinson

2 of 2  
Drug NameChlorhexidine gluconate
Drug LabelChlorhexidine Gluconate is an oral rinse containing 0.12% chlorhexidine gluconate (1,11-hexamethylene bis[5-(p-chlorophenyl) biguanide] di-D-gluconate) in a base containing water, 11.6% alcohol, glycerin, PEG-40 sorbitan diisostearate, flavor, sodium...
Active IngredientChlorhexidine gluconate
Dosage FormCloth; Solution; Sponge
RouteDental; Topical
Strength0.12%; 2%; 4%
Market StatusOver the Counter; Prescription
CompanyLyne; Wockhardt; Sage Prods; Hi Tech Pharma; Teva; Xttrium; Becton Dickinson

4.2 Therapeutic Uses

Antiseptic; disinfectant. (Vet): antiseptic; disinfectant.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 371


Cleanser: As a surgical hand scrub, skin wound and general skin cleanser, health care personnel hand wash, and for preoperative skin preparation. Chlorhedine gluconate significantly reduces the number of microorganisms on the hands and forearms prior to surgery or patient care. /Chlorhexidine gluconate-topical/

Drug Facts and Comparisons 2013. Wolters Kluwer Health St. Louis, MO 2013, p. 3180


EXPL THER To determine if chlorhexidine can be used as an intervention to prolong the time to relapse of oral candidiasis. SUBJECTS AND METHODS: A double-blinded randomized clinical trial was performed in 75 HIV/AIDS subjects with oral candidiasis. Clotrimazole troche was prescribed, and the subjects were re-examined every 2 weeks until the lesions were completely eradicated. The subjects were then randomly divided into two groups; 0.12% chlorhexidine (n = 37, aged 22-52 years, mean 34 years) and 0.9% normal saline (n = 38, aged 22-55 years, mean 38 years). They were re-examined every 2 weeks until the next episode was observed. RESULTS: The time to recurrence of oral candidiasis between the chlorhexidine and the saline group was not statistically significant (P > 0.05). The following variables were significantly associated with the time of recurrence; frequency of antifungal therapy (P = 0.011), total lymphocyte (P = 0.017), alcohol consumption (P = 0.043), and candidiasis on gingiva (P = 0.048). The subjects with lower lymphocyte showed shorter oral candidiasis-free periods (P = 0.034). CONCLUSIONS: Chlorhexidine showed a small but not statistically significant effect in maintenance of oral candidiasis-free period. This lack of significance may be due to the small sample size. Further study should be performed to better assess the size of the effect, or to confirm our findings.

PMID:18627504 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3253386 Nittayananta W et al; Oral Dis. (7): 665-70 (2008)


/EXPTL Therapy:/ Rats were injected with 10 mg/kg azoxymethane sc weekly for 12 weeks to induce colorectal cancers. At 20 weeks, subtotal colectomies were performed on rats with colorectal tumors and without peritoneal implants or liver metastases. At the time of surgery, a cut portion of the tumor was placed in the abdomen for 30 minutes; the rats then randomly received peritoneal irrigation with chlorhexidine, or sterile water (control). Eight weeks postoperatively a necropsy was performed. At that time, obvious and suspected recurrences and the anastomotic area were sampled for histologic evaluation. Significant differences were seen with chlorhexidine vs. water for gross tumor (P=0.05) and microscopic tumor (P<0.05).

Stuntz M et al; Dis Colon Rectum 40 (9): 1058-8 (1997)


4.3 Drug Warning

For external use only: For external use only. Keep out of eyes, ears, and mouth. Chlorhexidine gluconate should not be used as a preoperative skin preparation of the face or head. Misuse of products containing chlorhexidine gluconate has been reported to cause serious and permanent eye injury when it has been permitted to enter and remain in the eye during surgical procedures. If chlohexidine gluconate should contact these areas, rinse out promptly and thoroughly with cold water. Avoid contact with neninges. Do not use in genital area. /Chlorhexidine gluconate-topical/

Drug Facts and Comparisons 2013. Wolters Kluwer Health St. Louis, MO 2013, p. 3180


Sensitivity: Chlorhexidine gluconate should not be used by persons who have a sensitivity to it or its components.

Drug Facts and Comparisons 2013. Wolters Kluwer Health St. Louis, MO 2013, p. 3180


Hypersensitivity reactions: Irritation, sensitization, and generalized allergic reactions have been reported with chlorhexidine-containing products, especially in the genital areas. If adverse reactions occur and last more than 72 hr, discontinue use immediately and, if severe, contact a health care provider.

Drug Facts and Comparisons 2013. Wolters Kluwer Health St. Louis, MO 2013, p. 3180


Deafness: Chlorhexidine gluconate has been reported to cause deafness when instilled in the middle ear through perforate ear drums. /Chlorhexidine gluconate-topical/

Drug Facts and Comparisons 2013. Wolters Kluwer Health St. Louis, MO 2013, p. 3180


For more Drug Warnings (Complete) data for CHLORHEXIDINE (8 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 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.)


Dermatologic Agents

Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Decreased Cell Wall Integrity [PE]
5.3 Absorption, Distribution and Excretion

34 newborn infants who had been bathed in a standard manner with Hibiscrub were studied to find out whether it was absorbed percutaneously. Low levels of chlorhexidine were found in the blood of all 10 babies sampled by heel prick, and 5 of 24 from whom venous blood was taken. /Chlorhexidine gluconate/

PMID:475414 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1545570 Cowen J et al; Arch Dis Child 54 (5): 379-83 (1979)


Percutaneous absorption of the antimicrobial agent chlorhexidine (labelled with carbon-14) was studied in rats. Less than 5% of the topically applied chlorhexidine was absorbed during a 5-day period. Excretion of absorbed radioactivity occurred mainly in the feces.

Chow CP, et al; Toxicol Lett 1(4): 213-16 (1978)


The percutaneous absorption of chlorhexidine gluconate (chlorhexidine digluconate; Hibitane) through hairless rat skin with or without stratum corneum was studied. For tests carried out on whole skin, storage in cutaneous structures after 48 hr was more important than diffusion; the reverse was observed for stripped skin. When the skin was stripped, the amount absorbed was multiplied by approximately 100, and the amount stored in skin by approximately 10. The difference in chlorhexidine diffusion observed between whole and stripped skin was related to the physicochemical characteristics of chlorhexidine. /Chlorhexidine gluconate/

Lafforque C et al; Int J Pharm 147: 243-6 (1997)


To evaluate the elimination kinetics of chlorhexidine in milk when used as an intramammary infusion to stop lactation in cows. ... The study was performed in 2 phases. Three cows were studied in each phase. All cows were treated with chlorhexidine suspension by infusion into a mastitic mammary gland quarter after 2 milkings 24 hours apart. Foremilk samples (100 mL) were collected from treated and untreated (controls) mammary gland quarters of each cow. Chlorhexidine was extracted from raw milk, and residue concentrations were quantified by use of high-performance liquid chromatography. Foremilk samples from days 2, 5, and 8 were analyzed in phase I, and samples from time 0 and days 3, 7, 14, 21, 28, 35, and 42 were analyzed in phase II. In phases I and II, there was no quantifiable transference of chlorhexidine to milk in untreated mammary gland quarters. Measurable chlorhexidine residues were found in milk from treated mammary gland quarters of 2 cows throughout the 42-day sample period in phase II. Estimated mean elimination half-life for chlorhexidine in milk was 11.5 days.

PMID:12830870 Middleton JR et al; J Am Vet Med Assoc 222 (12): 1746-9 (2003)


5.4 Biological Half-Life

To evaluate the elimination kinetics of chlorhexidine in milk when used as an intramammary infusion to stop lactation in cows. ... The study was performed in 2 phases. Three cows were studied in each phase. All cows were treated with chlorhexidine suspension by infusion into a mastitic mammary gland quarter after 2 milkings 24 hours apart. Foremilk samples (100 mL) were collected from treated and untreated (controls) mammary gland quarters of each cow. Chlorhexidine was extracted from raw milk, and residue concentrations were quantified by use of high-performance liquid chromatography. Foremilk samples from days 2, 5, and 8 were analyzed in phase I, and samples from time 0 and days 3, 7, 14, 21, 28, 35, and 42 were analyzed in phase II. In phases I and II, there was no quantifiable transference of chlorhexidine to milk in untreated mammary gland quarters. Measurable chlorhexidine residues were found in milk from treated mammary gland quarters of 2 cows throughout the 42-day sample period in phase II. Estimated mean elimination half-life for chlorhexidine in milk was 11.5 days.

PMID:12830870 Middleton JR et al; J Am Vet Med Assoc 222 (12): 1746-9 (2003)