NAV

Melarsomine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Melarsomine
DrugBank Accession Number
DB11528
Background

Melarsomine is a trypanocidal agent marketed by Merial under the trade name Immiticide. It is the only FDA-approved treatment for adult heartworm infection in dogs, however, is is not approved for use in dogs with late-stage infection.

Type
Small Molecule
Groups
Experimental, Vet approved
Structure
Similar Structures
Weight
Average: 428.41
Monoisotopic: 428.054655
Chemical Formula
C13H21AsN8S2
Synonyms
  • Melarsomina
  • Melarsomine
  • Melarsominum
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Melarsomine dihydrochloride9CVA716Q7189141-50-4WMZUMAJTJUZEKQ-UHFFFAOYSA-N
International/Other Brands
Cymelarsan

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Aniline and substituted anilines
Direct Parent
Aniline and substituted anilines
Alternative Parents
Aminotriazines / 1,3,5-triazines / Heteroaromatic compounds / Trivalent organic arsenic compounds / Sulfenyl compounds / Secondary amines / Organoarsenic sulfides / Organic metalloid salts / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
1,3,5-triazine / Amine / Amino-1,3,5-triazine / Aminotriazine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic metalloid salt
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
374GJ0S41A
CAS number
128470-15-5
InChI Key
MGEOLZFMLHYCFZ-UHFFFAOYSA-N
InChI
InChI=1S/C13H21AsN8S2/c15-5-7-23-14(24-8-6-16)9-1-3-10(4-2-9)19-13-21-11(17)20-12(18)22-13/h1-4H,5-8,15-16H2,(H5,17,18,19,20,21,22)
IUPAC Name
N2-(4-{bis[(2-aminoethyl)sulfanyl]arsanyl}phenyl)-1,3,5-triazine-2,4,6-triamine
SMILES
NCCS[As](SCCN)C1=CC=C(NC2=NC(N)=NC(N)=N2)C=C1

References

General References
  1. Baneth G, Volansky Z, Anug Y, Favia G, Bain O, Goldstein RE, Harrus S: Dirofilaria repens infection in a dog: diagnosis and treatment with melarsomine and doramectin. Vet Parasitol. 2002 Apr 30;105(2):173-8. [Article]
  2. Moore SA, Mariani CL, Van Wettere A, Borst LB: Chronic compressive myelopathy and progressive neurologic signs associated with melarsomine dihydrochloride administration in a dog. J Am Anim Hosp Assoc. 2013 Nov-Dec;49(6):389-93. doi: 10.5326/JAAHA-MS-5911. Epub 2013 Sep 19. [Article]
  3. Tarello W: Leucocytozoon toddi in falcons from Kuwait: epidemiology, clinical signs and response to melarsomine. Parasite. 2006 Jun;13(2):179. [Article]
  4. Hettlich BF, Ryan K, Bergman RL, Marks SL, Lewis BC, Bahr A, Coates JR, Mansell J, Barton CL: Neurologic complications after melarsomine dihydrochloride treatment for Dirofilaria immitis in three dogs. J Am Vet Med Assoc. 2003 Nov 15;223(10):1456-61, 1434. [Article]
  5. Rawlings CA, Raynaud JP, Lewis RE, Duncan JR: Pulmonary thromboembolism and hypertension after thiacetarsamide vs melarsomine dihydrochloride treatment of Dirofilaria immitis infection in dogs. Am J Vet Res. 1993 Jun;54(6):920-5. [Article]
  6. Tarello W: Trypanosoma avium incidence, pathogenicity and response to melarsomine in falcons from Kuwait. Parasite. 2005 Mar;12(1):85-7. [Article]
  7. Tarello W: Serratospiculosis in falcons from Kuwait: incidence, pathogenicity and treatment with melarsomine and ivermectin. Parasite. 2006 Mar;13(1):59-63. [Article]
  8. Desquesnes M, Kamyingkird K, Vergne T, Sarataphan N, Pranee R, Jittapalapong S: An evaluation of melarsomine hydrochloride efficacy for parasitological cure in experimental infection of dairy cattle with Trypanosoma evansi in Thailand. Parasitology. 2011 Aug;138(9):1134-42. doi: 10.1017/S0031182011000771. Epub 2011 Jul 18. [Article]
  9. Raynaud JP: Thiacetarsamide (adulticide) versus melarsomine (RM 340) developed as macrofilaricide (adulticide and larvicide) to cure canine heartworm infection in dogs. Ann Rech Vet. 1992;23(1):1-25. [Article]
  10. Neiffer DL, Klein EC, Calle PP, Linn M, Terrell SP, Walker RL, Todd D, Vice CC, Marks SK: Mortality associated with melarsomine dihydrochloride administration in two North American river otters (Lontra canadensis) and a red panda (Ailurus fulgens fulgens). J Zoo Wildl Med. 2002 Sep;33(3):242-8. [Article]
KEGG Drug
D08168
ChemSpider
59365
BindingDB
50421414
RxNav
1012534
ChEMBL
CHEMBL1650564
Wikipedia
Melarsomine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.185 mg/mLALOGPS
logP1.51ALOGPS
logP0.44Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.77Chemaxon
pKa (Strongest Basic)9.98Chemaxon
Physiological Charge3Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area154.78 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity102.87 m3·mol-1Chemaxon
Polarizability40.82 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-2001900000-76aad825c881bb404b4d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kdi-0059000000-062c99abb8e0395cd1cc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-9001000000-8a2c9aaeeb45aad0c02e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-9347000000-355c7bddc7629918fe19
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9001000000-6f7e098d65d13eb93c94
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0965100000-ccbd6cb459ba9ba9393b
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at February 26, 2016 17:35 / Updated at February 21, 2021 18:53