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=CC=CC=C1C([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drug in 1980-s demonstrated ineffectiveness and toxicity in topical pharmaceutical products, and topical thimerosal was withdrawn from the market.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 |
|---|---|---|---|
Target ID: GO:0031585 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10428009 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|||
| 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 |
|---|---|---|
| Thimerosal induces apoptotic and fibrotic changes to kidney epithelial cells in vitro. | 2015-12 |
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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. | 2015-03 |
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| Transcriptomic analyses of neurotoxic effects in mouse brain after intermittent neonatal administration of thimerosal. | 2014-06 |
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| Thimerosal-induced apoptosis in mouse C2C12 myoblast cells occurs through suppression of the PI3K/Akt/survivin pathway. | 2012 |
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| Influence of environment exposures on the frequency of contact allergies in children and adolescents. | 2012 |
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| Contact sensitization in very young children. | 2011-10 |
|
| Low molecular weight thiols reduce thimerosal neurotoxicity in vitro: modulation by proteins. | 2010-10-29 |
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| Responsiveness of human monocyte-derived dendritic cells to thimerosal and mercury derivatives. | 2010-07 |
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| Induction of metallothionein in mouse cerebellum and cerebrum with low-dose thimerosal injection. | 2010-04 |
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| Sensitization effect of thimerosal is mediated in vitro via reactive oxygen species and calcium signaling. | 2010-03-17 |
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| Occludin gene expression as an early in vitro sign for mild eye irritation assessment. | 2010-02 |
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| Neonatal administration of a vaccine preservative, thimerosal, produces lasting impairment of nociception and apparent activation of opioid system in rats. | 2009-12-08 |
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| Expression of metallothionein mRNAs on mouse cerebellum microglia cells by thimerosal and its metabolites. | 2009-06-30 |
|
| Sensitizing potential of triclosan and triclosan-based skin care products in patients with chronic eczema. | 2008-10 |
|
| Characterization of early events involved in human dendritic cell maturation induced by sensitizers: cross talk between MAPK signalling pathways. | 2008-08-01 |
|
| Neurodevelopmental disorders, maternal Rh-negativity, and Rho(D) immune globulins: a multi-center assessment. | 2008-04 |
|
| Thiol-modulated mechanisms of the cytotoxicity of thimerosal and inhibition of DNA topoisomerase II alpha. | 2008-02 |
|
| Mercury, vaccines, and autism: one controversy, three histories. | 2008-02 |
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| Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis. | 2008-01-10 |
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| Thimerosal-induced apoptosis in human SCM1 gastric cancer cells: activation of p38 MAP kinase and caspase-3 pathways without involvement of [Ca2+]i elevation. | 2007-11 |
|
| Thimerosal induces TH2 responses via influencing cytokine secretion by human dendritic cells. | 2007-02 |
|
| Preservatives sensitivity in Israel: a 10-year overview (1995-2004). | 2006-10 |
|
| Cultured lymphocytes from autistic children and non-autistic siblings up-regulate heat shock protein RNA in response to thimerosal challenge. | 2006-09 |
|
| Thimerosal induces apoptosis and G2/M phase arrest in human leukemia cells. | 2006-09 |
|
| Alteration of the spontaneous systemic autoimmune disease in (NZB x NZW)F1 mice by treatment with thimerosal (ethyl mercury). | 2006-07-01 |
|
| Thimerosal induces neuronal cell apoptosis by causing cytochrome c and apoptosis-inducing factor release from mitochondria. | 2005-12 |
|
| Effects of thimerosal on NGF signal transduction and cell death in neuroblastoma cells. | 2005-07 |
|
| Contact sensitivity to preservatives in Turkey. | 2005-06 |
|
| Mitochondrial mediated thimerosal-induced apoptosis in a human neuroblastoma cell line (SK-N-SH). | 2005-06 |
|
| Immunosuppressive and autoimmune effects of thimerosal in mice. | 2005-04-15 |
|
| Neurodevelopmental disorders following thimerosal-containing childhood immunizations: a follow-up analysis. | 2005-03-15 |
|
| Redox imbalance induced by contact sensitizers triggers the maturation of dendritic cells. | 2005-03 |
|
| [Ocular tolerance of a new formulation of nonpreserved diclofenac]. | 2004-09 |
|
| Neurotoxic effects of postnatal thimerosal are mouse strain dependent. | 2004-09 |
|
| Allergic contact sensitivity in elderly patients. | 2004-06 |
|
| [Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004-05 |
|
| Activation of methionine synthase by insulin-like growth factor-1 and dopamine: a target for neurodevelopmental toxins and thimerosal. | 2004-04 |
|
| Dose-response study of thimerosal-induced murine systemic autoimmunity. | 2004-01-15 |
|
| Biochemical and molecular basis of thimerosal-induced apoptosis in T cells: a major role of mitochondrial pathway. | 2002-08 |
|
| Homozygous gene deletions of the glutathione S-transferases M1 and T1 are associated with thimerosal sensitization. | 2000-08 |
|
| Atopy and contact sensitization in psoriasis. | 2000 |
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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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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PRIMARY | |||
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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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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