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Details

Stereochemistry RACEMIC
Molecular Formula C13H16HgNO5.HO
Molecular Weight 483.87
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MERSALYL ACID

SMILES

[OH-].COC(C[Hg+])CNC(=O)C1=C(OCC(O)=O)C=CC=C1

InChI

InChIKey=HQRSUIDICNOLPX-UHFFFAOYSA-M
InChI=1S/C13H16NO5.Hg.H2O/c1-9(18-2)7-14-13(17)10-5-3-4-6-11(10)19-8-12(15)16;;/h3-6,9H,1,7-8H2,2H3,(H,14,17)(H,15,16);;1H2/q;+1;/p-1

HIDE SMILES / InChI

Molecular Formula C13H16HgNO5
Molecular Weight 466.86
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

MERSALYL (Mersal) is an organomercury compound, mercurial diuretics that superseded by safer diuretics such as thiazides, and is hardly used anymore. Due to the idiosyncratic nature of mercury toxicity, the risk of severe disease and sudden death are unpredictable and frequently show no warning signs. Mercurial diuretics cause diuresis by reducing the reabsorption sodium in the ascending loop of Henle, thus causing more water being delivered to the distal convoluted tubule. Unfortunately, earlier physicians misconstrued hallmark symptoms of mercury poisoning such as excessive salivation as signs of mercury's efficacy, including up until the early 1960s when the use of mercurial diuretics was halted in medicine.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Mersal

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
mersalyl 2 ml. intramuscularly, over a period of six days
Route of Administration: Intramuscular
In Vitro Use Guide
Renal cortical slices (about 5 x 5 x 0.5 mm) from New Zealand white rabbits, fed a sodium-deficient rabbit Chow for 2 to 3 weeks, were prepared. Two or three slices were incubated at 37’C for two to three periods of 1 hr each, unless otherwise indicated, in 2 ml of medium that was continuously gassed with 100% 02. The composition of the standard incubation medium was (in mM): NaC1, 145; KC1, 5.5; CaCl2, 2.0; MgCl2, 1.0; glucose, 10; N-2-hydroxyethylenepiperazine-N-2-ethanesulfonic acid, 10. The pH was adjusted to 7.0. The Na+-free and Cl--free medium was prepared by substituting Na+ with K+, and Cl- with isethionate (2-hydroxyethanesulfonate), respectively. The Na+-free modified medium did not contain 2 mM CaCl2 but contained 2 mM EGTA. In this Na+-free, high K+ medium, Ca2+ was found to exert a marked inhibitory effect on renin secretion. Therefore, Ca2+ was excluded from the medium to avoid the complication of the inhibitory effect of Ca2+ on renin secretion superimposed on the stimulatory effect of EA. The first 1-hr incubation in the standard medium served as the control. For subsequent periods, slices were incubated in media containing different ionic compositions or with MERSALYL (10mkM-3mM). In parallel, slices were incubated in the standard medium without test reagents as the time control. At the end of each incubation period, medium was collected and renin activity was determined by radioimmunoassay of angiotensin I generated following incubation of an aliquot of collected medium with plasma of 48-hr nephrectomized rabbits.
Substance Class Chemical
Record UNII
7RDI07K19U
Record Status Validated (UNII)
Record Version