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Chemistry

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Also known as: Thiomersal, 54-64-8, Thiomersalate, Mercurothiolate, Merthiolate, Sodium merthiolate
Molecular Formula
C9H9HgNaO2S
Molecular Weight
404.82  g/mol
InChI Key
RTKIYNMVFMVABJ-UHFFFAOYSA-L
FDA UNII
2225PI3MOV

Thimerosal
An ethylmercury-sulfidobenzoate that has been used as a preservative in VACCINES; ANTIVENINS; and OINTMENTS. It was formerly used as a topical antiseptic. It degrades to ethylmercury and thiosalicylate.
Thimerosal is a Standardized Chemical Allergen. The physiologic effect of thimerosal is by means of Increased Histamine Release, and Cell-mediated Immunity.
1 2D Structure

Thimerosal

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(2-carboxylatophenyl)sulfanyl-ethylmercury
2.1.2 InChI
InChI=1S/C7H6O2S.C2H5.Hg.Na/c8-7(9)5-3-1-2-4-6(5)10;1-2;;/h1-4,10H,(H,8,9);1H2,2H3;;/q;;2*+1/p-2
2.1.3 InChI Key
RTKIYNMVFMVABJ-UHFFFAOYSA-L
2.1.4 Canonical SMILES
CC[Hg]SC1=CC=CC=C1C(=O)[O-].[Na+]
2.2 Other Identifiers
2.2.1 UNII
2225PI3MOV
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ethylmercurithiosalicylate, Sodium

2. Mercurothiolate

3. Merthiolate

4. Sodium Ethylmercurithiosalicylate

5. Thiomersal

6. Thiomersalate

7. Vitaseptol

2.3.2 Depositor-Supplied Synonyms

1. Thiomersal

2. 54-64-8

3. Thiomersalate

4. Mercurothiolate

5. Merthiolate

6. Sodium Merthiolate

7. Sodium Ethylmercurithiosalicylate

8. Ethylmercurithiosalicylate Sodium

9. Ethylmercurithiosalicylic Acid Sodium Salt

10. Thiomersalum

11. Tiomersal

12. Ethyl(2-mercaptobenzoato-s)mercury Sodium Salt

13. O-(ethylmercurithio)benzoic Acid Sodium Salt

14. Thiomersal [inn]

15. ((o-carboxyphenyl)thio)ethylmercury Sodium Salt

16. Sodium;(2-carboxylatophenyl)sulfanyl-ethylmercury

17. [(o-carboxyphenyl)thio]ethylmercury Sodium Salt

18. 2225pi3mov

19. Chebi:9546

20. Thimerosalate

21. Thimerosalum

22. Thimerosol

23. Thimersalate

24. Thiomersalat

25. Thiomersal (inn)

26. Ncgc00094791-01

27. Elicide

28. Estivin

29. Merfamin

30. Merphol

31. Mertorgan

32. Merzonin

33. Nosemack

34. Tiomersale

35. Vitaseptol

36. Mercurothiolatum

37. Merzonin Sodium

38. Aeroaid Spray

39. Merthiolate Salt

40. Dsstox_cid_5540

41. Merthiolate Sodium

42. Vitaseptol Loesung

43. Dsstox_rid_77823

44. Dsstox_gsid_25540

45. Merseptyl (van)

46. Elcide 73

47. Elcide 75

48. Tiomersale [dcit]

49. Caswell No. 766

50. Mls001336050

51. Sodium Ethylmercuric Thiosalicylate

52. Tiomersal [inn-spanish]

53. Thiomersalum [inn-latin]

54. Sodium O-(ethylmercurithio)benzoate

55. Sodium 2-(ethylmercurithio)benzoate

56. Cas-54-64-8

57. Ethylmercurithiosalicylate Sodium Salt

58. Ethylmerkurithiosalicilan Sodny

59. Ccris 4839

60. Hsdb 7151

61. Thimerosal [usp:jan]

62. Nsc 4794

63. Smr000875330

64. Einecs 200-210-4

65. Mfcd00013062

66. Epa Pesticide Chemical Code 078901

67. Ethylmerkurithiosalicilan Sodny [czech]

68. Ethyl (sodium O-mercaptobenzoato)mercury

69. Unii-2225pi3mov

70. Thime-rosal

71. Ethylmercurithiosalicyclic Acid, Sodium Salt

72. Mercurate(1-), Ethyl(2-mercaptobenzoato(2-)-o,s)-, Sodium

73. Merthiolate (tn)

74. Mercury, Ethyl(2-mercaptobenzoate-s)-, Sodium Salt

75. Mercury, Ethyl(2-mercaptobenzoato-s)-, Sodium Salt

76. Mercury, ((o-carboxyphenyl)thio)ethyl-, Sodium Salt

77. Prestwick_1021

78. Mercurate(1-), Ethyl(o-mercaptobenzoato(2-))-, Sodium

79. Thimerosal [ii]

80. Thimerosal [mi]

81. Thimerosal (jan/usp)

82. Thimerosal [jan]

83. Mercurate(1-), Ethyl(2-mercaptobenzoate(2-)-o,s)-, Sodium Salt

84. Thimerosal [hsdb]

85. Thimerosal [inci]

86. Thimerosal [vandf]

87. Epitope Id:119682

88. Schembl3525

89. Thiomersal [mart.]

90. Ethyl(2-mercaptobenzoato-s)mercury, Sodium Salt

91. Thimerosal [usp-rs]

92. Thiomersal [who-dd]

93. Sodium (2-carboxylatophenyl)sulfanyl-ethyl-mercury

94. Ethylmercury(1+) Sodium 2-sulfidobenzoate(1:1:1)

95. Mls001336049

96. Set

97. Spectrum1500572

98. Mercury, Ethyl (2-mercaptobenzoato-s)-, Sodium Salt

99. Thimerosal, Analytical Standard

100. Dtxsid3025540

101. Thimerosal, >=97% (hplc)

102. Hms501o19

103. Mercury, Ethyl(hydrogen O-mercaptobenzoato)-, Sodium Salt

104. Thimerosal, >=95.0% (hg)

105. Thiomersal [ep Monograph]

106. Bdbm512713

107. Hms1921e07

108. Hms2092m09

109. Hms2230i04

110. Hms3371n19

111. Sodium Ethyl[2-(sulfanyl-kappas)benzoato(2-)]mercurate(1-)

112. Srct-03744

113. Thimerosal [usp Monograph]

114. Thimerosal, Bioxtra, 97-101%

115. Nsc-4794

116. Tox21_111331

117. Tox21_302176

118. Ccg-39725

119. Akos004910446

120. Akos037503710

121. Mercurate(1-), Ethyl(2-(mercapto-kappas)benzoato(2-)-kappao)-, Sodium

122. Tox21_111331_1

123. Db11590

124. Ncgc00094791-02

125. Ncgc00164425-01

126. Ncgc00178879-04

127. Ncgc00255169-01

128. Bp-30041

129. Db-052622

130. Ft-0603231

131. Thimerosal, Meets Usp Testing Specifications

132. Sodium (2-carboxylatophenylthio)(ethyl)mercury

133. D00864

134. H10793

135. Sodium [(2-carboxylatophenyl)thio]-ethylmercury

136. T-3600

137. Ethylmercurithiosalicylic Acid Na Thimerosal

138. A830286

139. Q411046

140. Sodium Ethyl[2-(mercapto-ks)benzoato(2-)]mercurate(1-)

141. Sodium Salt Of (2-carboxyphenylthio)ethylmercury

142. Sodium [(2-carboxylatophenyl)sulfanyl](ethyl)mercurate(1-)

143. Thimerosal, European Pharmacopoeia (ep) Reference Standard

144. Thimerosal, United States Pharmacopeia (usp) Reference Standard

145. Thimerosal Ready Made Solution, 100 Mg/ml In Water, 0.2 Mum Filtered

146. Thimerosal, Pharmaceutical Secondary Standard; Certified Reference Material

147. Mercurate(1-), Ethyl(2-(mercapto-kappas)benzoato(2-)-kappao)-, Sodium (1:1)

148. Sodium Ethyl(2-(mercapto-.kappa.s)benzoato(2-)-.kappa.o)mercurate(1-)

2.4 Create Date
2007-08-23
3 Chemical and Physical Properties
Molecular Weight 404.82 g/mol
Molecular Formula C9H9HgNaO2S
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass405.992739 g/mol
Monoisotopic Mass405.992739 g/mol
Topological Polar Surface Area65.4 Ų
Heavy Atom Count14
Formal Charge0
Complexity180
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 Therapeutic Uses

VET: Antibacterial, antifungal (topical)

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1661


4.2 Drug Warning

... As a precautionary public health effort to minimize exposure of mercury to infants and children, a joint statement was issued in July 1999 by the American Academy of Pediatrics and the U.S. Public Health Service recommending the removal of thimerosal from vaccines as soon as possible. Today, all routinely recommended pediatric vaccines manufactured for the U.S. market contain no thimerosal or only trace amounts. ...

National Academy of Sciences; Institute of Medicine. Available from, as of March 14, 2004: https://www.iom.edu/focuson.asp?id=4189


In June 2000, a joint statement on thimerosal in vaccines was prepared by the American Academy of Family Physicians (AAFP), the American Academy of Pediatrics (AAP), the Advisory Committee on Immunization Practices (ACIP), and the Public Health Service (PHS) in response to 1) the progress in achieving the national goal declared in July 1999 to remove thimerosal from vaccines in the recommended childhood vaccination schedule, and 2) results of recent studies that examined potential associations between exposure to mercury in thimerosal-containing vaccines and health effects. In this statement, AAFP, AAP, ACIP, and PHS recommend continuation of the current policy of moving rapidly to vaccines that are free of thimerosal as a preservative. Until adequate supplies are available, use of vaccines that contain thimerosal as a preservative is acceptable.

Morb Mortal Wkly Rep (MMWR) 49 (27): 622, 631 (2000)


4.3 Drug Indication

Used as preservative in some cosmetics, topical pharmaceuticals, and biological drug products, which includes vaccines.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Thimerosal is an organomercurial compound and derivative of thiosalicyclic acid with antibacterial and antifungal properties. Thimerosal, which consists of approximately 50% mercury by weight, has been one of the most widely used preservatives in vaccines. It is metabolized/degraded to ethylmercury and thiosalicylate. Ethylmercury is an organomercurial that must be carefully distinguished from methylmercury, a closely related substance that has been the focus of many studies. Methylmercury is the type of mercury found in various species of fish. Experimental data demonstrates that the toxicokinetics of thimerosal (ethylmercury) is vastly different from that of methyl-mercury. Thus, methyl-mercury is not a suitable reference for assessing the risk from exposure to thimerosal-derived mercury. Prior to the recent initiative to reduce or eliminate thimerosal from childhood vaccines, the maximum cumulative exposure to mercury via routine childhood vaccinations during the first 6 months of life was 187.5 micrograms. In the most recently formulated vaccines, the maximum cumulative exposure during the first 6 months of life should now be less than 3 micrograms of mercury. Currently, thimerosal may still be used in the early stages of manufacturing of certain childhood vaccines, however, only a trace remains after a chemical purification process. Note that the dose above is indicated for children 1-6 months of age is applicable only in the United States, and other countries may have varying indications.


5.2 MeSH Pharmacological Classification

Preservatives, Pharmaceutical

Substances added to pharmaceutical preparations to protect them from chemical change or microbial action. They include ANTI-BACTERIAL AGENTS and antioxidants. (See all compounds classified as Preservatives, Pharmaceutical.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
THIMEROSAL
5.3.2 FDA UNII
2225PI3MOV
5.3.3 Pharmacological Classes
Chemical Structure [CS] - Allergens
5.4 ATC Code

D - Dermatologicals

D08 - Antiseptics and disinfectants

D08A - Antiseptics and disinfectants

D08AK - Mercurial products

D08AK06 - Thiomersal


5.5 Absorption, Distribution and Excretion

Absorption

Less than 0.01% of an ingested dose is absorbed from the GI tract (rat study).


Route of Elimination

Gastrointestinal tract.


Volume of Distribution

266 L in one study


Clearance

The high concentrations of mercury identified in stool samples suggest that ethylmercury may be eliminated through the gastrointestinal tract.


Mercury concentrations were measured in the aqueous humor and excised corneal buttons of nine patients undergoing keratoplasty. A contact lens stored for several weeks in a solution containing thimerosal was applied to one eye for 4 hours. After 4 hours the lens was removed and mercury concentrations were determined in aqueous humor, corneal buttons, and the contact lens itself. Markedly elevated levels of mercury were determined in both aqueous humor and corneal buttons of subjects as compared to controls; however, there was little residual mercury on the contact lens after 4 hours.The mercury content in the corneal buttons of subjects ranged from 0.6 to 14 ng per tissue. The mercury content in samples of aqueous humor from subjects ranged from 20 to 46 ng/mL.

Goldfrank, L.R., Flomenbaum, N.E., Lewin, N.A., Weisman, R.S., Howland, M.A., Hoffman, R.S., Goldfrank's Toxicologic Emergencies 6th Ed. (1998)., McGraw-Hill, New York, N.Y., p. 918


Ten of 13 infants exposed to topical applications of a thimerosal tincture 0.1% for the treatment of exomphalos died. The total number of applications ranged from 9 to 48. Mercury concentrations were determined in various tissues from 6 of the infants. Mean tissue concentrations in fresh samples of liver, kidney, spleen, and heart ranged from 5152 to 11,330 ppb, suggesting percutaneous absorption from repeated topical applications.

Goldfrank, L.R., Flomenbaum, N.E., Lewin, N.A., Weisman, R.S., Howland, M.A., Hoffman, R.S., Goldfrank's Toxicologic Emergencies 6th Ed. (1998)., McGraw-Hill, New York, N.Y., p. 918


Urine mercury levels were studied in 26 patients with hypogammaglobulinemia who received intramuscular weekly IgG replacement therapy preserved with 0.01% thimerosal. The dosage of IgG ranged from 25 mg/kg to 50 mg/kg, containing 0.6-1.2 mg of mercury per dose. The total estimated dose of mercury administered ranged from 4 to 734 mg over a period of 6 months to 17 years. Elevated urine mercury levels were determined in 19 patients; however, no patients had clinical evidence of chronic mercury toxicity.

Goldfrank, L.R., Flomenbaum, N.E., Lewin, N.A., Weisman, R.S., Howland, M.A., Hoffman, R.S., Goldfrank's Toxicologic Emergencies 6th Ed. (1998)., McGraw-Hill, New York, N.Y., p. 918


Forty full-term infants aged 6 months and younger were given vaccines that contained thiomersal (diptheria-tetanus-acellular pertussis vaccine, hepatitis B vaccine, and in some children Haemophilus influenzae type b vaccine). 21 control infants received thiomersal-free vaccines. We obtained samples of blood, urine, and stools 3-28 days after vaccination. Total mercury (organic and inorganic) in the samples was measured by cold vapour atomic absorption. Mean mercury doses in infants exposed to thiomersal were 45.6 microg (range 37.5-62.5) for 2-month-olds and 111.3 microg (range 87.5-175.0) for 6-month-olds. Blood mercury in thiomersal-exposed 2-month-olds ranged from less than 3.75 to 20.55 nmol/L (parts per billion); in 6-month-olds all values were lower than 7.50 nmol/L. Only one of 15 blood samples from controls contained quantifiable mercury. Concentrations of mercury were low in urine after vaccination but were high in stools of thiomersal-exposed 2-month-olds (mean 82 ng/g dry weight) and in 6-month-olds (mean 58 ng/g dry weight). Estimated blood half-life of ethylmercury was 7 days (95% CI 4-10 days). Administration of vaccines containing thiomersal does not seem to raise blood concentrations of mercury above safe values in infants. Ethylmercury seems to be eliminated from blood rapidly via the stools after parenteral administration of thiomersal in vaccines.

PMID:12480426 Pichichero ME et al; Lancet 360 (9347): 1737-41(2002)


5.6 Metabolism/Metabolites

Ethylmercury (etHg) is derived from the metabolism of thimerosal (o-carboxyphenyl-thio-ethyl-sodium salt), which is the most widely used form of organic mercury.


5.7 Biological Half-Life

A study was done to study the pharmacokinetics of Thimerosal in mice. Estimated half-lives (in days) were 8.8 for blood, 10.7 for brain, 7.8 for heart, 7.7 for liver and 45.2 for kidney. The the long half-life of ethylmercury (~50 days on average in humans) results in accumulation that may be harmful to the developing fetal brain, as it is more susceptible to organomercurial compounds than the adult brain.


5.8 Mechanism of Action

Although its mechanism of action is not fully understood, thimerosal inhibits sulfhydryl-containing active site of various enzymes and binds to sulfhydryl compounds, including glutathione, cysteine, and sulfhydryl groups of proteins. In addition, thimerosal activates the InsP3 calcium channel on the endoplasmic reticular membrane, thereby triggering the release of intracellular calcium resulting in a calcium-induced calcium-influx of extracellular calcium. Therefore, thimerosal may induce or inhibit various cellular functions that are dependent on the signaling of calcium. Ethylmercury is metabolized to inorganic mercury more rapidly than methylmercury. This difference in metabolism may account for kidney pathology that can result from toxic quantities. Also, whereas the increase in oxidative stress and induction of apoptosis observed in vitro with large doses (405 g/L to 101 mg/L) of thimerosal may explain its damaging neurological effects. The effects of low-dose ethylmercury are not completely understood to date. It is known, however, that the shorter half-life of ethylmercury (the metabolite of thimerosal) allows for very limited opportunities of ethylmercury derived from thimerosal in vaccines. Ethylmercury is a lipophilic cation that is capable of crossing the blood-brain barrier. The octanol/water partition coefficients of methyl and ethylmercury are 1.4 to 1.8, at intracellular pH and [Cl], therefore, both organomercury compounds will primarily exist as intracellular lipophilic cations. It has been demonstrated that lipophilic cations accumulate inside mitochondria, in a Nernstian fashion, driven by the steady state membrane potential. As the typical mitochondrial membrane potential of astrocytes and neurons is between 140170mV, one would expect the concentration of these organomercury compounds within mitochondria to be approximately 1000 times greater than the cytosolic concentration.


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