Melarsoprol
Basic information
- CAS
494-79-1- Standard SMILES
Nc1nc(N)nc(Nc2ccc([As]3SCC(CO)S3)cc2)n1- InChIKey
JCYZMTMYPZHVBF-UHFFFAOYSA-N- Molecular formula
- C12H15AsN6OS2
- Average molar mass
- 398.3 g/mol
- Monoisotopic mass
- 397.996471
Overview
Melarsoprol is a member of triazines.
Names & identifiers
- Preferred name
- Melarsoprol
- IUPAC
- [2-[4-[(4,6-diamino-1,3,5-triazin-2-yl)amino]phenyl]-1,3,2-dithiarsolan-4-yl]methanol
- English name
- melarsoprol
- Molecular formula
- C12H15AsN6OS2
- Molecular weight
- 398.345
Names & synonyms
MELARSOPROL494-79-1Mel BMelarsoprolumRP 3854[2-[4-[(4,6-diamino-1,3,5-triazin-2-yl)amino]phenyl]-1,3,2-dithiarsolan-4-yl]methanolRP-3854DTXSID90862033ZF3786Q2E81,3,2-Dithiarsolane-4-methanol, 2-(4-((4,6-diamino-1,3,5-triazin-2-yl)amino)phenyl)-(2-(4-((4,6-diamino-1,3,5-triazin-2-yl)amino)phenyl)-1,3,2-dithiarsolan-4-yl)methanolMelarsenoxidBAL
Show more names
RP3854Melarsoprol (Mixture of DiastereoMers)2-[4-(4,6-Diamino-1,3,5-triazine-2-ylamino)phenyl]-1,3,2-dithiarsolane-4-methanol[2-[4-[(4,6-diamino-s-triazin-2-yl)amino]phenyl]-1,3,2-dithiarsolan-4-yl]methanol2-[4-[(4,6-Diamino-1,3,5-triazin-2-yl)amino]phenyl]-1,3,2-dithiarsolane-4-methanol1,3,2-Dithiarsolane-4-methanol, 2-[4-[(4,6-diamino-1,3,5-triazin-2-yl)amino]phenyl]-
Melarsenoxid BAL(2-{4-[(4,6-diamino-1,3,5-triazin-2-yl)amino]phenyl}-1,3,2-dithiarsolan-4-yl)methanolRefChem:156313DTXCID00810863P01CD01207-793-4ArsobalMelarsoprolum [INN-Latin]
Database identifiers
- CAS
494-79-1- PubChem CID
- 10311
- DTXSID
DTXSID90862033- ChEMBL
CHEMBL166- ChEBI
CHEBI:6729- UNII
- ZF3786Q2E8
- EC Number
- 207-793-4
- Nikkaji
- J9.388B
Properties
Computed structural properties
- Topological polar surface area
- 174 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 353
Experimental & physicochemical properties
Human DrugsMedicines for the treatment of 2nd stage African trypanosomiasis
Physicochemical properties
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- form
- Solid
- color
- White to Off-White
- InChI
- 1S/C12H15AsN6OS2/c14-10-17-11(15)19-12(18-10)16-8-3-1-7(2-4-8)13-21-6-9(5-20)22-13/h1-4,9,20H,5-6H2,(H5,14,15,16,17,18,19)
- InChIKey
- JCYZMTMYPZHVBF-UHFFFAOYSA-N
- SMILES
- NC1=NC(N)=NC(NC2=CC=C(C=C2)[As]3SCC(S3)CO)=N1
- REACH Annex XVII Substances List
- Melarsoprol (494-79-1)
- FDA UNII
- 3786 Q2E8 · ZF3786Q2E8
- ATC code
- 1 CD01 · P01CD01
- UNSPSC Code
- 12352107 · 12352107
- NACRES
- 77 · NA.77
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301+H331 (33.3%): Toxic if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]
P261, P264, P270, P271, P273, P301+P316, P304+P340, P316, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationRestricted substance: Melarsoprol
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Danger
- Symbol(GHS)
- GHS09,GHS06
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H331-H301-H410
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1
- Precautionary statements
- P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501-P273-P391-P501
Chemistry & industry
Pharmacology
ATC Code
P - Antiparasitic products, insecticides and repellents
QP - Antiparasitic products, insecticides and repellents
P01CD01
MeSH Pharmacological ClassificationAgents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA.
Applications
DescriptionKnowingly or unknowingly, arsenic-containing drugs have been used for treatment of parasitic conditions for thousands of years. In the late 1800s and early 1900s, Paul Ehrlich introduced the use of trivalent arsenicals. Melarsoprol, an organoarsenical, came into use in the late 1940s, and it remains the first-choice drug in the treatment of trypanosomiasis. Until 1990, it also was the only treatment for late-stage sleeping sickness.
UsesMelarsoprol is a drug used for the treatment of African trypanosomes, a sleeping sickness in humans, a disease that is typically fatal without chemotherapy.
Additional notes
DefinitionChEBI: Melarsoprol is a member of triazines.
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Compound notes
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