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Chlormerodrin

HCID 25210
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Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
10375-56-1
Standard SMILES
COC(CNC(N)=O)[CH2][Hg][Cl]
InChIKey
BJFGVYCULWBXKF-UHFFFAOYSA-M
Molecular formula
C5H11ClHgN2O2
Average molar mass
367.2 g/mol
Monoisotopic mass
368.021549

Overview

Chlormerodrin is urea in which one of the hydrogens is substituted by a 3-chloromercury-2-methoxyprop-1-yl group. It was formerly used as a diuretic, but more potent and less toxic drugs are now available. Its radiolabelled (197Hg, 203Hg) forms were used in diagnostic aids in renal imaging and brain scans. It has a role as a diagnostic agent and a diuretic. It is an organomercury compound and a member of ureas.

Names & identifiers

Preferred name
Chlormerodrin
IUPAC
[3-(carbamoylamino)-2-methoxypropyl]-chloromercury
English name
Chloro(2-methoxy-3-ureidopropyl)(197Hg)mercury(II)
Molecular formula
C4H9ClHgO
Molecular weight
0

Names & synonyms

chlormerodrinChlormerodrineChlormeroprinMercloranNeohydrinPromeran62-37-3Chlormerodrinum3-Chloromercuri-2-methoxypropylurea1-[3-(chloromercuri)-2-methoxypropyl]ureaCHEBI:594451-(3-(Chloromercuri)-2-methoxypropyl)urea
Show more names
D03465Chlormerodrin Hg 197Chlormerodrin hg 197 (tn)Chlormerodrin hg 197 (usan)Chlormerodrin (197hg) (inn)Chloro(2-methoxy-3-ureidopropyl)(197Hg)mercury(II)3-Ureido-2-methoxypropyl(197Hg)mercury(II) chloride
(3-((Aminocarbonyl)amino)-2-methoxypropyl)chloromercury{3-[(aminocarbonyl)amino]-2-methoxypropyl}chloromercuryClormerodrinaPromeranum(3-(chloromercurio)-2-methoxypropyl)urea[3-(chloromercurio)-2-methoxypropyl]ureaRefChem:388875DTXCID601511478

Database identifiers

CAS
10375-56-1、62-37-3
PubChem CID
25210
ChEMBL

Properties

Computed structural properties

Topological polar surface area
64.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
11
Formal charge
0
Complexity
125

Experimental & physicochemical properties

LogP-0.80
Solubility2.92e+01 g/L
Melting Point152.5 °C
Physical DescriptionSolid

Physicochemical properties

FDA UNII
1 D6EFC579A · 1D6EFC579A

Chemistry & industry

Pharmacology

PharmacodynamicsChlormerodrin is a mercurial compound with toxic side effects. It is no longer used and has been replaced with new classes of diuretic drugs.
Mechanism of Action · 1 item

Chlormerodrin most likely acts by a direct renal action. Mercurial diuresis is presumed to occur through inhibition of reabsorption of water and electrolytes in the convoluted tubules, although the problem of whether the locus of action is primarily on the proximal or distal portion has not yet been settled. There is also evidence that mercurials interfere with the permeability of the membrane of tubular cells by increasing passive influx of Na<sup>+</sup> ion, Cl<sup>-</sup> ion and water into the cells, without interfering with the active extrusion of Na<sup>+</sup> ion. Lastly, there is some evidence that chlormerodrin inhibits succinic dehydrogenase, but the clinical significance of this binding is not known.

Cellular LocationsMembrane

Applications

UsesDiagnostic aid (renal function determination); radioactive agent.

Additional notes

DefinitionChEBI: Chlormerodrin containing the radioactive isotope 197Hg. It was formerly used as a diagnostic aid in determination of renal function.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
CHEMBL2110562
ChEBI
CHEBI:59445
EC Number
200-530-4