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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

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

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in 1980-s demonstrated ineffectiveness and toxicity in topical pharmaceutical products, and topical thimerosal was withdrawn from the market.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

1.19085125E12
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
Atopy and contact sensitization in psoriasis.
2000
Biochemical and molecular basis of thimerosal-induced apoptosis in T cells: a major role of mitochondrial pathway.
2002 Aug
Activation of methionine synthase by insulin-like growth factor-1 and dopamine: a target for neurodevelopmental toxins and thimerosal.
2004 Apr
Dose-response study of thimerosal-induced murine systemic autoimmunity.
2004 Jan 15
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
Neurodevelopmental disorders following thimerosal-containing childhood immunizations: a follow-up analysis.
2004 Nov-Dec
Neurotoxic effects of postnatal thimerosal are mouse strain dependent.
2004 Sep
Thimerosal induces apoptosis and G2/M phase arrest in human leukemia cells.
2006 Sep
Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis.
2008 Jan 10
Neonatal administration of a vaccine preservative, thimerosal, produces lasting impairment of nociception and apparent activation of opioid system in rats.
2009 Dec 8
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
Low molecular weight thiols reduce thimerosal neurotoxicity in vitro: modulation by proteins.
2010 Oct 29
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:20:01 UTC 2023
Edited
by admin
on Fri Dec 15 16:20:01 UTC 2023
Record UNII
2225PI3MOV
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
WHO-ATC D08AK06
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
WHO-VATC QD08AK06
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
EPA PESTICIDE CODE 78901
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
Code System Code Type Description
PUBCHEM
5908
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
WIKIPEDIA
THIOMERSAL
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID3025540
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
EVMPD
SUB20886
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
ALTERNATIVE
MERCK INDEX
m10740
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY Merck Index
ALANWOOD
thiomersal
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
FDA UNII
2225PI3MOV
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
DRUG CENTRAL
4733
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-210-4
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
RXCUI
10472
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB11590
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
DAILYMED
2225PI3MOV
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY Increased Histamine Release [PE]
NCI_THESAURUS
C47751
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY Allergens [Chemical/Ingredient]
EVMPD
SUB10980MIG
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
CONCEPT Industrial Aid
CAS
54-64-8
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
HSDB
7151
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
SMS_ID
100000092521
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
CHEBI
9546
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
MESH
D013849
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
NSC
4794
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
INN
2548
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY Cell-mediated Immunity [PE]
RS_ITEM_NUM
1659000
Created by admin on Fri Dec 15 16:20:01 UTC 2023 , Edited by admin on Fri Dec 15 16:20:01 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY