Thimerosal

Thiomersal
Names


IUPAC name Ethyl(2-mercaptobenzoato-(2-)-O,S) mercurate(1-) sodium
Other names Mercury((o-carboxyphenyl)thio)ethyl sodium salt
Identifiers
CAS Number	54-64-8^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:9546^Y
ChEMBL	ChEMBL508338^Y
ChemSpider	10772045^Y
ECHA InfoCard	100.000.192
EC Number	200-210-4
PubChem	16684434
RTECS number	OV8400000
UNII	2225PI3MOV^Y
InChI 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^Y Key: RTKIYNMVFMVABJ-UHFFFAOYSA-L^Y InChI=1/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/rC9H10HgO2S.Na/c1-2-10-13-8-6-4-3-5-7(8)9(11)12;/h3-6H,2H2,1H3,(H,11,12);/q;+1/p-1 Key: RTKIYNMVFMVABJ-TYXNQWANAP
SMILES [Na+].[O-]C(=O)c1ccccc1S[Hg]CC
Properties
Chemical formula	C₉H₉Hg Na O₂S
Molar mass	404.81 g/mol
Appearance	White or slightly yellow powder
Density	2.508 g/cm³
Melting point	232 to 233 °C (450 to 451 °F; 505 to 506 K) (decomposition)
Solubility in water	1000 g/l (20 °C)
Pharmacology
ATC code	D08AK06 (WHO)
Hazards
Safety data sheet	External MSDS
EU classification (DSD)	Very toxic (T+) Dangerous for the environment (N) Repr. Cat. 1
R-phrases	R26/27/28 R33 R40 R50/53 R60 R61
S-phrases	S13 S28 S36 S45 S53 S60 S61
NFPA 704	1 3 1
Flash point	250 °C (482 °F; 523 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	75 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Thiomersal (INN), or thimerosal (USP), is an organomercury compound. This compound is a well established antiseptic and antifungal agent.

The pharmaceutical corporation Eli Lilly and Company gave thiomersal the trade name Merthiolate. It has been used as a preservative in vaccines, immunoglobulin preparations, skin test antigens, antivenins, ophthalmic and nasal products, and tattoo inks. Its use as a vaccine preservative was controversial, and it was phased out from routine childhood vaccines in the European Union, and a few other countries in response to popular fears. The current scientific consensus is that no convincing scientific evidence supports these fears.

In the U.S., Thiomersal has been removed from or reduced to trace amounts in all vaccines routinely recommended for children 6 years of age and younger with the exception of inactivated influenza vaccine. Vaccines with trace amounts of thiomersal contain 1 microgram or less of mercury per dose.

Morris Kharasch, a chemist at the University of Maryland, filed a patent application for thiomersal in 1927; Eli Lilly later marketed the compound under the trade name Merthiolate.In vitro tests conducted by Lilly investigators H. M. Powell and W. A. Jamieson found that it was forty to fifty times as effective as phenol against Staphylococcus aureus. It was used to kill bacteria and prevent contamination in antiseptic ointments, creams, jellies, and sprays used by consumers and in hospitals, including nasal sprays, eye drops, contact lens solutions, immunoglobulins, and vaccines. Thiomersal was used as a preservative (bactericide) so that multidose vials of vaccines could be used instead of single-dose vials, which are more expensive. By 1938, Lilly's assistant director of research listed thiomersal as one of the five most important drugs ever developed by the company.

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Wikipedia