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Identification
NameChlormerodrin
Accession NumberDB00534  (APRD00864)
TypeSmall Molecule
GroupsApproved, Withdrawn
Description

Chlormerodrin is a mercurial compound with toxic side effects that was previously used as a diuretic. The radiolabeled form has been used as a diagnostic and research tool. It is no longer used and has been replaced with new classes of diuretic drugs.

Structure
Thumb
Synonyms
{3-[(aminocarbonyl)amino]-2-methoxypropyl}chloromercury
1-[3-(Chloromercuri)-2-methoxypropyl]urea
Chlormerodrina
Chlormerodrine
Chlormerodrinum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MercloranParke Davis
OrmerdanParke Davis
Brand mixturesNot Available
SaltsNot Available
Categories
UNII99T5TWO621
CAS number62-37-3
WeightAverage: 367.2
Monoisotopic: 368.021530917
Chemical FormulaC5H11ClHgN2O2
InChI KeyInChIKey=BJFGVYCULWBXKF-UHFFFAOYSA-M
InChI
InChI=1S/C5H11N2O2.ClH.Hg/c1-4(9-2)3-7-5(6)8;;/h4H,1,3H2,2H3,(H3,6,7,8);1H;/q;;+1/p-1
IUPAC Name
[3-(chloromercurio)-2-methoxypropyl]urea
SMILES
COC(CNC(N)=O)C[Hg]Cl
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as ureas. These are compounds containing two amine groups joined by a carbonyl (C=O) functional group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassUreas
Direct ParentUreas
Alternative Parents
Substituents
  • Urea
  • Organic metal salt
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Alkyl mercury compound
  • Organic transition metal salt
  • Organooxygen compound
  • Organonitrogen compound
  • Organometallic compound
  • Organomercurial-compound
  • Organic transition metal moeity
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationPreviously used as a diuretic. The radiolabeled form has been used as a diagnostic and research tool.
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 actionChlormerodrin 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+ ion, Cl- ion and water into the cells, without interfering with the active extrusion of Na+ ion. Lastly, there is some evidence that chlormerodrin inhibits succinic dehydrogenase, but the clinical significance of this binding is not known.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAs chlormerodrin has been shown to increase the levels of mercury in the kidney to toxic levels, any symptoms of overdose will most likely correspond to symptoms experienced in exposure to mercury.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9659
Caco-2 permeable-0.5979
P-glycoprotein substrateNon-substrate0.6753
P-glycoprotein inhibitor INon-inhibitor0.899
P-glycoprotein inhibitor IINon-inhibitor0.9662
Renal organic cation transporterNon-inhibitor0.8512
CYP450 2C9 substrateNon-substrate0.7687
CYP450 2D6 substrateNon-substrate0.7764
CYP450 3A4 substrateNon-substrate0.6932
CYP450 1A2 substrateNon-inhibitor0.6985
CYP450 2C9 inhibitorNon-inhibitor0.7286
CYP450 2D6 inhibitorNon-inhibitor0.9078
CYP450 2C19 inhibitorNon-inhibitor0.6618
CYP450 3A4 inhibitorNon-inhibitor0.7519
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8039
Ames testAMES toxic0.5408
CarcinogenicityNon-carcinogens0.6151
BiodegradationNot ready biodegradable0.6354
Rat acute toxicity2.4805 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9194
hERG inhibition (predictor II)Non-inhibitor0.9225
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point152.5 °CPhysProp
water solubility1.1E+004 mg/L (at 25 °C)MERCK INDEX (1996)
logP-0.80HALBACH,S (1985)
Predicted Properties
PropertyValueSource
Water Solubility29.2 mg/mLALOGPS
logP-0.5ALOGPS
logP-0.86ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)14.05ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.35 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.78 m3·mol-1ChemAxon
Polarizability18.42 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Foreman, E.L; U S . Patent 2,635,983; April 21,1953; assigned to Lakeside Laboratories, Inc.

General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Succinate-semialdehyde dehydrogenase [nad(p)+] activity
Specific Function:
Catalyzes one step in the degradation of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA).
Gene Name:
ALDH5A1
Uniprot ID:
P51649
Molecular Weight:
57214.23 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Oda Y: [Experimental study on renal succinic dehydrogenase. 2. Age differences in renal succinic dehydrogenase in rats administered diuretics]. Nihon Shonika Gakkai Zasshi. 1968 Apr 1;72(4):370-80. [PubMed:5692397 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inducer
General Function:
Sodium:potassium:chloride symporter activity
Specific Function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume.
Gene Name:
SLC12A1
Uniprot ID:
Q13621
Molecular Weight:
121449.13 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Tabern DL, Kearney J, Sohn H: The quantitative measurement of tubular chlormerodrin binding as an index of renal function: a study of 400 cases. Can Med Assoc J. 1970 Sep 26;103(6):601-7. [PubMed:5455277 ]
  4. Mannuzzu LM, Moronne MM, Macey RI: Estimate of the number of urea transport sites in erythrocyte ghosts using a hydrophobic mercurial. J Membr Biol. 1993 Apr;133(1):85-97. [PubMed:8391582 ]
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Drug created on June 13, 2005 07:24 / Updated on April 04, 2014 09:31