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Details

Stereochemistry RACEMIC
Molecular Formula C12H15AsN6OS2
Molecular Weight 398.339
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MELARSOPROL

SMILES

NC1=NC(NC2=CC=C(C=C2)[As]3SCC(CO)S3)=NC(N)=N1

InChI

InChIKey=JCYZMTMYPZHVBF-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C12H15AsN6OS2
Molecular Weight 398.339
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Melarsoprol is an organoarsenic compound that was used for the treatment of sleeping sickness (African trypanosomiasis) since 1949. Melarsoprol is used for the treatment of second-stage infection (involving the central nervous system). It is the only available therapy for second-stage Trypanosoma brucei rhodesiense (East African) infection. Melarsoprol is a prodrug, upon administration it is metabolized to the active form melarsen oxide, which acts by interacting with protein sulfhydryl groups and subsequently inactivating enzymes. A small but adequate amount of the drug penetrates the cerebrospinal fluid, where it is taken up and concentrated by trypanosomes. Due to the high toxicity of the drug, it is administered only in the most dangerous cases. Melarsoprol is not commercially available in the USA, but it is available as treatment IND from CDC.

Approval Year

PubMed

PubMed

TitleDatePubMed
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
[2 epidemics of arsenical encephalopathy in the treatment of trypanosomiasis, Uganda, 1992-1993].
1994
Melarsoprol refractory T. b. gambiense from Omugo, north-western Uganda.
2001 May
Genetic variants of the TbAT1 adenosine transporter from African trypanosomes in relapse infections following melarsoprol therapy.
2001 Sep 28
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:53:45 UTC 2023
Edited
by admin
on Thu Jul 06 22:53:45 UTC 2023
Record UNII
ZF3786Q2E8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MELARSOPROL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
MELARSOPROL [MI]
Common Name English
RP 3854
Code English
2-(P-(4,6-DIAMINO-S-TRIAZIN-2-YLAMINO)PHENYL)-1,3,2-DITHIARSOLANE-4-METHANOL
Common Name English
RP-3854
Code English
Melarsoprol [WHO-DD]
Common Name English
melarsoprol [INN]
Common Name English
MEL B
Brand Name English
MELARSOPROL [MART.]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 6.5.5.1
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
EU-Orphan Drug EU/3/12/1068
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
WHO-ATC P01CD01
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
WHO-VATC QP51AD04
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
FDA ORPHAN DRUG 406613
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
Code System Code Type Description
MERCK INDEX
M7153
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY Merck Index
CAS
494-79-1
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
DRUG CENTRAL
3336
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID90862033
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
SMS_ID
100000081446
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
NCI_THESAURUS
C170159
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
EVMPD
SUB08721MIG
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-793-4
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
MESH
D008549
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
FDA UNII
ZF3786Q2E8
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
WIKIPEDIA
MELARSOPROL
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
INN
457
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
DRUG BANK
DB12864
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
PUBCHEM
10311
Created by admin on Thu Jul 06 22:53:45 UTC 2023 , Edited by admin on Thu Jul 06 22:53:45 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY