Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H21AsN8S2.2ClH |
Molecular Weight | 501.333 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.NCCS[As](SCCN)C1=CC=C(NC2=NC(N)=NC(N)=N2)C=C1
InChI
InChIKey=WMZUMAJTJUZEKQ-UHFFFAOYSA-N
InChI=1S/C13H21AsN8S2.2ClH/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);2*1H
Melarsomine (melarsomine dihydrochloride) is an organic arsenical chemotherapeutic agent and is a trypanocidal antiparasitic drug. As of 2016 DIROBAN, a generic melarsomine dihydrochloride product, is the only FDA-approved treatment for adult heartworm (Dirofilaria immitis) infection in dogs. It is not approved for treatment in cats, or dogs in late-stage infection. It is marketed by Merial under the trade name Immiticide and is not currently available in the U.S. due to a manufacturing shortage. Sponsored by Anzac Animal Health, LLC and distributed by Zoetis, Inc., DIROBAN is a prescription animal drug supplied as a sterile powder that must be reconstituted with an accompanying sterile water diluent. The exact mode of action on D. immitis is unknown. Post-treatment mortality due to thromboembolism and/or progression of the underlying disease may occur in 10 to 20% of the Class 3 patients treated with DIROBAN.
Originator
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | DIROBAN Approved UseTreatment of stabilized, class 1, 2, and 3 heartworm disease (asymptomatic to mild, moderate, and severe, respectively) caused by immature (4 month-old, stage L5) to mature adult infections of Dirofilaria immitis in dogs. Launch Date2016 |
Sample Use Guides
DIROBAN (sterile powder for injection contains 50.0 mg melarsomine dihydrochloride and 33.75 mg glycine USP; 1 vial: when reconstituted with 2 mL of sterile water for injection (provided) contains 25 mg/mL of active ingredient) should be administered by deep intramuscular injection ONLY in the epaxial (lumbar) muscles in the third through fifth lumbar region (see graphic). DO NOT ADMINISTER AT ANY OTHER SITE. Avoid superficial injection or leakage. Use a 23 gauge 1 inch needle for dogs equal to or less than 10 kg (22 lb) in weight. Use a 22 gauge 1½ inch needle for dogs greaterthan 10 kg (22 lb). Use alternating sides with each administration. If repeated administrations are warranted avoid injecting at the same lumbar location. Record the location of the first injection(s) in the patient’s medical record for future reference.
Route of Administration:
Intravascular
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9099385
Isolated rings of pulmonary artery from heartworm-infected dogs were randomly treated with thiacetarsamide (30 ug/ml) or melarsomine dihydrochloride (30 ug/ml) for 30 minutes; untreated rings from the same dog served as control. Cumulative dose-response relations to norepinephrine, nitroglycerin, and methacholine were determined. Treatment of rings with thiacetarsamide or melarsomine depressed methacholine-induced relaxation, compared with values for untreated rings. Histologic examination of rings indicated that treatment with thiacetarsamide or melarsomine resulted in loss of endothelial cells.
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CFR |
21 CFR 522.1362
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NCI_THESAURUS |
C276
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DTXSID90237545
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89141-50-4
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m12038
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C83926
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9CVA716Q71
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1012533
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123720
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9CVA716Q71
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300000031167
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C076253
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ACTIVE MOIETY
SUBSTANCE RECORD