U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of THIMEROSAL

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

HIDE SMILES / InChI

Description
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drug in 1980-s demonstrated ineffectiveness and toxicity in topical pharmaceutical products, and topical thimerosal was withdrawn from the market.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

Curator's Comment: Mercury accumulates in the brain and is converted to inorganic mercury.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
AFLURIA

Approved Use

AFLURIA 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 Date

2007
Primary
MERTHIOLATE

Approved Use

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
PubMed

PubMed

TitleDatePubMed
Thimerosal induces apoptotic and fibrotic changes to kidney epithelial cells in vitro.
2015-12
Functional and molecular effects of mercury compounds on the human OCTN1 cation transporter: C50 and C136 are the targets for potent inhibition.
2015-03
Transcriptomic analyses of neurotoxic effects in mouse brain after intermittent neonatal administration of thimerosal.
2014-06
Thimerosal-induced apoptosis in mouse C2C12 myoblast cells occurs through suppression of the PI3K/Akt/survivin pathway.
2012
Influence of environment exposures on the frequency of contact allergies in children and adolescents.
2012
Contact sensitization in very young children.
2011-10
Low molecular weight thiols reduce thimerosal neurotoxicity in vitro: modulation by proteins.
2010-10-29
Responsiveness of human monocyte-derived dendritic cells to thimerosal and mercury derivatives.
2010-07
Induction of metallothionein in mouse cerebellum and cerebrum with low-dose thimerosal injection.
2010-04
Sensitization effect of thimerosal is mediated in vitro via reactive oxygen species and calcium signaling.
2010-03-17
Occludin gene expression as an early in vitro sign for mild eye irritation assessment.
2010-02
Neonatal administration of a vaccine preservative, thimerosal, produces lasting impairment of nociception and apparent activation of opioid system in rats.
2009-12-08
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
Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis.
2008-01-10
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

Patents

Sample Use Guides

As a component of vaccines, thimerosal is administered intramuscularly.
Route of Administration: Intramuscular
In Vitro Use Guide
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.
Name Type Language
THIOMERSAL
EP   INN   MART.   WHO-DD  
INN  
Preferred Name English
THIMEROSAL
HSDB   II   INCI   JAN   MI   USP   USP-RS   VANDF  
INCI  
Official Name English
THIMEROSAL [JAN]
Common Name English
thiomersal [INN]
Common Name English
SODIUM ETHYL(2-(MERCAPTO-.KAPPA.S)BENZOATO(2-)-.KAPPA.O)MERCURATE(1-)
Common Name English
THIMEROSAL [HSDB]
Common Name English
THIMEROSAL [USP-RS]
Common Name English
THIMEROSAL [VANDF]
Common Name English
Thiomersal [WHO-DD]
Common Name English
THIMEROSAL [USP MONOGRAPH]
Common Name English
THIMEROSAL [MI]
Common Name English
MERTHIOLATE
Brand Name English
THIOMERSAL [MART.]
Common Name English
THIOMERSAL [EP MONOGRAPH]
Common Name English
NSC-4794
Code English
SODIUM SALT OF (2-CARBOXYPHENYLTHIO)ETHYLMERCURY
Common Name English
THIMEROSAL [II]
Common Name English
Ethyl (sodium O-mercaptobenzoato)mercury
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C28394
Created by admin on Mon Mar 31 18:25:10 GMT 2025 , Edited by admin on Mon Mar 31 18:25:10 GMT 2025
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
Created by admin on Mon Mar 31 18:25:10 GMT 2025 , Edited by admin on Mon Mar 31 18:25:10 GMT 2025
Code System Code Type Description
PUBCHEM
5908
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PRIMARY
WIKIPEDIA
THIOMERSAL
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PRIMARY
EPA CompTox
DTXSID3025540
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PRIMARY
EVMPD
SUB20886
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ALTERNATIVE
MERCK INDEX
m10740
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PRIMARY Merck Index
ALANWOOD
thiomersal
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PRIMARY
FDA UNII
2225PI3MOV
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PRIMARY
DRUG CENTRAL
4733
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PRIMARY
ECHA (EC/EINECS)
200-210-4
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PRIMARY
RXCUI
10472
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PRIMARY RxNorm
DRUG BANK
DB11590
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PRIMARY
DAILYMED
2225PI3MOV
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PRIMARY
NDF-RT
N0000175629
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PRIMARY Increased Histamine Release [PE]
NCI_THESAURUS
C47751
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PRIMARY
NDF-RT
N0000171131
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PRIMARY Allergens [Chemical/Ingredient]
EVMPD
SUB10980MIG
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PRIMARY
NCI_THESAURUS
C45678
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CONCEPT Industrial Aid
CAS
54-64-8
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PRIMARY
HSDB
7151
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PRIMARY
SMS_ID
100000092521
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PRIMARY
CHEBI
9546
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PRIMARY
MESH
D013849
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PRIMARY
NSC
4794
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PRIMARY
INN
2548
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PRIMARY
NDF-RT
N0000184306
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PRIMARY Cell-mediated Immunity [PE]
RS_ITEM_NUM
1659000
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PRIMARY