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=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

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drug in 1980-s demonstrated ineffectiveness and toxicity in topical pharmaceutical products, and topical thimerosal was withdrawn from the market.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
Activation of methionine synthase by insulin-like growth factor-1 and dopamine: a target for neurodevelopmental toxins and thimerosal.
2004 Apr
Allergic contact sensitivity in elderly patients.
2004 Jun
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
Neurotoxic effects of postnatal thimerosal are mouse strain dependent.
2004 Sep
Contact sensitivity to preservatives in Turkey.
2005 Jun
Redox imbalance induced by contact sensitizers triggers the maturation of dendritic cells.
2005 Mar
Alteration of the spontaneous systemic autoimmune disease in (NZB x NZW)F1 mice by treatment with thimerosal (ethyl mercury).
2006 Jul 1
Cultured lymphocytes from autistic children and non-autistic siblings up-regulate heat shock protein RNA in response to thimerosal challenge.
2006 Sep
Characterization of early events involved in human dendritic cell maturation induced by sensitizers: cross talk between MAPK signalling pathways.
2008 Aug 1
Thiol-modulated mechanisms of the cytotoxicity of thimerosal and inhibition of DNA topoisomerase II alpha.
2008 Feb
Mercury, vaccines, and autism: one controversy, three histories.
2008 Feb
Induction of metallothionein in mouse cerebellum and cerebrum with low-dose thimerosal injection.
2010 Apr
Responsiveness of human monocyte-derived dendritic cells to thimerosal and mercury derivatives.
2010 Jul
Sensitization effect of thimerosal is mediated in vitro via reactive oxygen species and calcium signaling.
2010 Jul-Aug
Contact sensitization in very young children.
2011 Oct
Influence of environment exposures on the frequency of contact allergies in children and adolescents.
2012
Transcriptomic analyses of neurotoxic effects in mouse brain after intermittent neonatal administration of thimerosal.
2014 Jun
Thimerosal induces apoptotic and fibrotic changes to kidney epithelial cells in vitro.
2015 Dec
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

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
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
THIOMERSAL
EP   INN   MART.   WHO-DD  
INN  
Official 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
THIMEROSAL [INCI]
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 Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
WHO-ATC D08AK06
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
WHO-VATC QD08AK06
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
EPA PESTICIDE CODE 78901
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
Code System Code Type Description
PUBCHEM
5908
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY
WIKIPEDIA
THIOMERSAL
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
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
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY Increased Histamine Release [PE]
NCI_THESAURUS
C47751
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
EVMPD
SUB10980MIG
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
CONCEPT Industrial Aid
CAS
54-64-8
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PRIMARY
HSDB
7151
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY
SMS_ID
100000092521
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY
CHEBI
9546
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY
MESH
D013849
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY
NSC
4794
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY
INN
2548
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
RS_ITEM_NUM
1659000
Created by admin on Fri Dec 15 16:20:01 GMT 2023 , Edited by admin on Fri Dec 15 16:20:01 GMT 2023
PRIMARY