Chlormerodrin

Chlormerodrin is a mercurial diuretic commercially traded from 1952[1] until 1974[2] that was once used to treat patients with heart failure,[3] but is no longer in widespread use.[4] The radiolabelled form (197Hg & 203Hg) had also been used for medical imaging of the kidney and brain[5][6] and the 197Hg form was even considered a contender for 99mTc by some physicians,[7] but was ultimately discontinued by the FDA in 1989.[8]

Chlormerodrin
Names
IUPAC name
3-carbamoylamino-2-methoxypropylmercury(II) chloride
Systematic IUPAC name
3-chloro-mercura-2-methoxy propylurea
Other names
  • Chloromeridin
  • Chlormerodin
  • Chlormerodrine
  • Chlormeroprin
  • Diurone
  • Katonil
  • Mercardox
  • Mercloran
  • Mercoral
  • Merculest
  • Merilid
  • Neogidrin
  • Neohydrin
  • Oricur
  • Percapyl
  • Promeran
  • Promerane
  • 3-chloro-mercuri-2-methoxy propylurea
  • [3-(Carbamoylamino)-2-methoxypropyl](chloro)mercury
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.000.483
PubChem CID
SMILES
  • COC(CNC(N)=O)C[Hg]Cl
Properties
Chemical formula
 C5H11ClHgN2O2
Molar mass 367.20 g·mol−1
Appearance Solid
Melting point 152.5 °C (306.5 °F; 425.6 K)
Solubility in water
 11 g/l
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Renal mercury poisoning
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chlormerodrin
Clinical data
AHFS/Drugs.comMedical Encyclopedia
ATC code
  • none
Legal status
Legal status
  • US: Withdrawn
Identifiers
IUPAC name
  • 3-carbamoylamino-2-methoxypropylmercury(II) chloride
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard100.000.483
Chemical and physical data
FormulaC5H11ClHgN2O2
Molar mass367.196 g·mol−1
3D model (JSmol)
SMILES
  • COC(CNC(=O)N)C[Hg]Cl
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
  • Key:BJFGVYCULWBXKF-UHFFFAOYSA-M

References
  1. M. Sittig, Pharmaceutical Manufacturing Encyclopedia, Noyes Publications, Westwood, 1988.
  2. Crout, J. Richard (1974). "Fixed Combination Prescription Drugs: FDA Policy". The Journal of Clinical Pharmacology. 14 (5–6): 249–254. doi:10.1002/j.1552-4604.1974.tb02309.x. PMID 4829517. S2CID 5830209.
  3. Leff WA, Nussbaum HE (April 1959). "Chlormerodrin: clinical effectiveness and absence of toxicity in congestive heart failure; report of a four-year study". British Medical Journal. 1 (5126): 883–9. doi:10.1136/bmj.1.5126.883. PMC 1992943. PMID 13629153.
  4. PubChem. "Chlormerodrin". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-09-23.
  5. D. B. Sodee, B. Di Stefano, Ohio State Med. J. 1965, 61, 819–822.
  6. Yamamoto, Y. L.; Feindel, W.; Zanelli, J. (1964-09-01). "Comparative study of radioactive chlormerodrin (Neohydrin) tagged with mercury 197 and mercury 203 for brain scanning". Neurology. 14 (9): 815–820. doi:10.1212/wnl.14.9.815. ISSN 0028-3878. PMID 14215595. S2CID 43526449.
  7. D. B. Sodee, J. Nucl. Med. 1968, 9, 645.
  8. FDA, Approved Drug Products with Therapeutic Equivalence Evaluations, US Department Of Health And Human Service, 1989.


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