MELARSOMINE DIHYDROCHLORIDE

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

Structure Search

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C13H21AsN8S2
Molecular Weight	428.411
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=8e49e345-ef33-45b9-acb1-8abb94f0060f&type=display | https://www.fda.gov/animalveterinary/safetyhealth/productsafetyinformation/ucm542087.htm | https://www.ncbi.nlm.nih.gov/pubmed/18930598

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
Heartworm disease 3 Sources: https://www.fda.gov/animalveterinary/safetyhealth/productsafetyinformation/ucm542087.htm	Curative		Approved 8583	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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/65962#section=BioAssay-Results Page: 5.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/65962#section=BioAssay-Results Page: 5.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/65962#section=BioAssay-Results Page: 5.0	no

PubMed

Title	Date	PubMed
Heartworm and Wolbachia: therapeutic implications.	2008-12-10	18930598

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:17:29 GMT 2025` Edited by `admin` on `Mon Mar 31 18:17:29 GMT 2025`
Record UNII	9CVA716Q71
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

IMMITICIDE

Preferred Name

English

MELARSOMINE DIHYDROCHLORIDE

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

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