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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
Structure of MELARSOMINE DIHYDROCHLORIDE

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

HIDE SMILES / InChI
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
DIROBAN

Approved Use

Treatment 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 Date

2016
PubMed

PubMed

TitleDatePubMed
Heartworm and Wolbachia: therapeutic implications.
2008 Dec 10
Patents

Patents

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
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.
Name Type Language
MELARSOMINE DIHYDROCHLORIDE
GREEN BOOK  
Common Name English
MELARSOMINE DIHYDROCHLORIDE [GREEN BOOK]
Common Name English
BIS(2-AMINOETHYL) P-((4,6-DIAMINO-S-TRIAZIN-2-YL)AMINO)DITHIOBENZENEARSONITE DIHYDROCHLORIDE
Common Name English
MELARSOMINE DIHYDROCHLORIDE [MI]
Common Name English
IMMITICIDE
Brand Name English
ARSONODITHIOUS ACID, AS-(4-((4,6-DIAMINO-1,3,5-TRIAZIN-2-YL)AMINO)PHENYL)-, BIS(2-AMINOETHYL) ESTER, HYDROCHLORIDE (1:2)
Common Name English
CYMELARSAN
Common Name English
N2-(4-(BIS(2-AMINOETHYLSULFANYL)ARSANYL)PHENYL)-1,3,5-TRIAZINE-2,4,6-TRIAMINE DIHYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 522.1362
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
NCI_THESAURUS C276
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID90237545
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
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CAS
89141-50-4
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
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MERCK INDEX
m12038
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
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NCI_THESAURUS
C83926
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
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DAILYMED
9CVA716Q71
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
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RXCUI
1012533
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
PRIMARY RxNorm
PUBCHEM
123720
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
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FDA UNII
9CVA716Q71
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
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SMS_ID
300000031167
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
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MESH
C076253
Created by admin on Fri Dec 15 16:03:00 GMT 2023 , Edited by admin on Fri Dec 15 16:03:00 GMT 2023
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