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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Substance Class Chemical
Record UNII
ZF3786Q2E8
Record Status Validated (UNII)
Record Version