Chemical Property of Melarsoprol
Chemical Property:
- Vapor Pressure:6.7E-20mmHg at 25°C
- Boiling Point:688.4°C at 760 mmHg
- Flash Point:370.2°C
- PSA：173.57000
- LogP:1.55110
- Hydrogen Bond Donor Count:4
- Hydrogen Bond Acceptor Count:9
- Rotatable Bond Count:4
- Exact Mass:397.996471
- Heavy Atom Count:22
- Complexity:353
- Purity/Quality:
-
99% *data from raw suppliers
Melarsoprol(MixtureofDiastereomers) *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:
- MSDS Files:
-
SDS file from LookChem
Useful:
- Canonical SMILES:C1C(S[As](S1)C2=CC=C(C=C2)NC3=NC(=NC(=N3)N)N)CO
- Recent ClinicalTrials:Randomized Clinical Trial of Three Drug Combinations for Late-Stage Gambiense Human African Trypanosomiasis
-
Indications
Melarsoprol is only indicated for the treatment of late stage (CNS involvement) of Trypanosoma brucei gambiense and Trypanosoma brucei rhodesiense. It is a clinical experience that patients with Trypanosoma brucei rhodesiense who relapse usually respond to a second course of melarsoprol, while those with Trypanosoma brucei gambiense who relapse rarely do so [4]. Thus, patients with Trypanosoma brucei gambiense who do not respond to the first treatment course of melarsoprol should be switched to eflornithine.
-
Description
Knowingly 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.
-
Uses
Melarsoprol is a drug used for the treatment of African trypanosomes, a sleeping sickness in humans, a disease that is typically fatal without chemotherapy.
-
Clinical Use
2-p-(4,6-Diamino-s-triazin-2-yl-amino)phenyl-4-hydroxymethyl-1,3,2-dithiarsoline (Mel B, Arsobal) is prepared byreduction of a corresponding pentavalent arsanilate to thetrivalent arsenoxide followed by reaction of the latter with2,3-dimercapto-1-propanol (British anti-Lewisite [BAL]). Ithas become the drug of choice for the treatment of thelater stages of both forms of African trypanosomiasis.Melarsoprol has the advantage of excellent penetration intothe CNS and, therefore, is effective against meningoencephaliticforms of T. gambiense and T. rhodesiense.Trivalent arsenicals tend to be more toxic to the host (as wellas the parasites) than the corresponding pentavalent compounds.The bonding of arsenic with sulfur atoms tends toreduce host toxicity, increase chemical stability (to oxidation),and improve distribution of the compound to the arsenoxide.Melarsoprol shares the toxic properties of other arsenicals, however, so its use must be monitored for signsof arsenic toxicity. Late-stage sleeping sickness caused by T. brucei gambiense and T. brucei
rhodesiense It is not recommended for early-stage disease, in which alternatives
with less serious side effects are available.
