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
Molecular Formula | C9H9HgO2S |
Molecular Weight | 381.82 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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drug in 1980-s demonstrated ineffectiveness and toxicity in topical pharmaceutical products, and topical thimerosal was withdrawn from the market.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 |
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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 Date1.19085125E12 |
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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 |
---|---|---|
Atopy and contact sensitization in psoriasis. | 2000 |
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Biochemical and molecular basis of thimerosal-induced apoptosis in T cells: a major role of mitochondrial pathway. | 2002 Aug |
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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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Dose-response study of thimerosal-induced murine systemic autoimmunity. | 2004 Jan 15 |
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[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004 May |
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Neurodevelopmental disorders following thimerosal-containing childhood immunizations: a follow-up analysis. | 2004 Nov-Dec |
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Neurotoxic effects of postnatal thimerosal are mouse strain dependent. | 2004 Sep |
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Thimerosal induces apoptosis and G2/M phase arrest in human leukemia cells. | 2006 Sep |
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Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis. | 2008 Jan 10 |
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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 Dec 8 |
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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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Low molecular weight thiols reduce thimerosal neurotoxicity in vitro: modulation by proteins. | 2010 Oct 29 |
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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.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 16:20:01 UTC 2023
by
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on
Fri Dec 15 16:20:01 UTC 2023
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Record UNII |
2225PI3MOV
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Record Status |
Validated (UNII)
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Record Version |
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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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PRIMARY | |||
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THIOMERSAL
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DTXSID3025540
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SUB20886
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ALTERNATIVE | |||
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m10740
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PRIMARY | Merck Index | ||
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thiomersal
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PRIMARY | |||
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2225PI3MOV
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PRIMARY | |||
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4733
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PRIMARY | |||
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200-210-4
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PRIMARY | |||
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10472
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PRIMARY | RxNorm | ||
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DB11590
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PRIMARY | |||
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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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PRIMARY | |||
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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SUB10980MIG
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PRIMARY | |||
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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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PRIMARY | |||
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9546
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PRIMARY | |||
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D013849
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PRIMARY | |||
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4794
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PRIMARY | |||
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2548
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PRIMARY | |||
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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1659000
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PRIMARY |
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |