Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H9HgO2S.Na |
Molecular Weight | 404.81 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC[Hg]SC1=C(C=CC=C1)C([O-])=O
InChI
InChIKey=RTKIYNMVFMVABJ-UHFFFAOYSA-L
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/18172138Curator's Comment: description was created based on several sources, including
https://www.fda.gov/biologicsbloodvaccines/safetyavailability/vaccinesafety/ucm096228.htm |
https://www.ncbi.nlm.nih.gov/pubmed/18049924 | https://www.ncbi.nlm.nih.gov/pubmed/10428009
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18172138
Curator's Comment: description was created based on several sources, including
https://www.fda.gov/biologicsbloodvaccines/safetyavailability/vaccinesafety/ucm096228.htm |
https://www.ncbi.nlm.nih.gov/pubmed/18049924 | https://www.ncbi.nlm.nih.gov/pubmed/10428009
Thimerosal is organomercury antiseptic and antifungal agent, used as a preservative in vaccines, immuloglobulins, nasal sprays, contact lens solutions. In USA, European Union countries thiomersal is no longer used in childhood vaccines due to public fears, although the FDA review of 1999 foud no evidence of harm from the use of thimerosal as a vaccine preservative, other than local hypersensitivity reactions. Thimerosal was used as a component of topical antiseptic solution and antiseptic ointment for treating cuts, nasal sprays, eye solutions, vaginal spermicides, diaper rash treatments, but re-evaluation of the drug in 1980-s demonstrated ineffectiveness and toxicity in topical pharmaceutical products, and topical thimerosal was withdrawn from the market. The mechanism of action of thimerosal has not been fully elucidated. It is believed that thimerosal inhibits sulfhydryl-containing active site of various enzymes and binds to sulfhydryl compounds, such as glutathione, cysteine, and SH groups of protein. In addition, thimerosal activates the InsP3 calcium channel on endoplasmic reticular membrane, thereby triggering the release of calcium from intracellular stores resulting in a calcium-induced calcium-influx of extracellular calcium. Consequently, thimerosal may induce or inhibit cellular functions dependent on calcium signaling.
CNS Activity
Sources: http://www.who.int/immunization/sage/meetings/2012/april/WHO_meeting_slides_Mitkus_040312.pdf
Curator's Comment: Mercury accumulates in the brain and is converted to inorganic mercury.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0031585 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10428009 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Inactive ingredient | AFLURIA Approved UseAFLURIA is an inactivated influenza virus vaccine indicated for active immunization of persons ages 6 months and older against influenza disease caused by influenza virus subtypes A and type B present in the vaccine. Launch Date2007 |
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Primary | MERTHIOLATE Approved UseThimerosal was used as a component of topical antiseptic solution and antiseptic ointment for treating cuts, nasal sprays, eye solutions, vaginal spermicides, diaper rash treatments |
PubMed
Title | Date | PubMed |
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Activation of methionine synthase by insulin-like growth factor-1 and dopamine: a target for neurodevelopmental toxins and thimerosal. | 2004 Apr |
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Allergic contact sensitivity in elderly patients. | 2004 Jun |
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[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004 May |
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Neurotoxic effects of postnatal thimerosal are mouse strain dependent. | 2004 Sep |
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Contact sensitivity to preservatives in Turkey. | 2005 Jun |
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Redox imbalance induced by contact sensitizers triggers the maturation of dendritic cells. | 2005 Mar |
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Alteration of the spontaneous systemic autoimmune disease in (NZB x NZW)F1 mice by treatment with thimerosal (ethyl mercury). | 2006 Jul 1 |
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Cultured lymphocytes from autistic children and non-autistic siblings up-regulate heat shock protein RNA in response to thimerosal challenge. | 2006 Sep |
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Characterization of early events involved in human dendritic cell maturation induced by sensitizers: cross talk between MAPK signalling pathways. | 2008 Aug 1 |
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Thiol-modulated mechanisms of the cytotoxicity of thimerosal and inhibition of DNA topoisomerase II alpha. | 2008 Feb |
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Mercury, vaccines, and autism: one controversy, three histories. | 2008 Feb |
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Induction of metallothionein in mouse cerebellum and cerebrum with low-dose thimerosal injection. | 2010 Apr |
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Responsiveness of human monocyte-derived dendritic cells to thimerosal and mercury derivatives. | 2010 Jul |
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Sensitization effect of thimerosal is mediated in vitro via reactive oxygen species and calcium signaling. | 2010 Jul-Aug |
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Contact sensitization in very young children. | 2011 Oct |
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Influence of environment exposures on the frequency of contact allergies in children and adolescents. | 2012 |
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Transcriptomic analyses of neurotoxic effects in mouse brain after intermittent neonatal administration of thimerosal. | 2014 Jun |
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Thimerosal induces apoptotic and fibrotic changes to kidney epithelial cells in vitro. | 2015 Dec |
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Functional and molecular effects of mercury compounds on the human OCTN1 cation transporter: C50 and C136 are the targets for potent inhibition. | 2015 Mar |
Patents
Sample Use Guides
As a component of vaccines, thimerosal is administered intramuscularly.
Route of Administration:
Intramuscular
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3373227
Antimicrobial activity of thimerosal was determined using Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus and Candida albicans. The inoculum size was 10^6 oranisms/ml in each case. Antimicrobial activity was determined employing doubling diliutions of the test agents. MIC of thimerosal was 1.5 - 0.1 ug/ml.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C28394
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NDF-RT |
N0000185508
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WHO-ATC |
D08AK06
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WHO-VATC |
QD08AK06
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EPA PESTICIDE CODE |
78901
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Code System | Code | Type | Description | ||
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5908
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THIOMERSAL
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DTXSID3025540
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SUB20886
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m10740
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PRIMARY | Merck Index | ||
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thiomersal
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2225PI3MOV
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4733
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200-210-4
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10472
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DB11590
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2225PI3MOV
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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C47751
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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SUB10980MIG
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C45678
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CONCEPT | Industrial Aid | ||
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54-64-8
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7151
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100000092521
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9546
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PRIMARY | |||
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D013849
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4794
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2548
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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1659000
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ACTIVE MOIETY
SUBSTANCE RECORD