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Details

Stereochemistry ACHIRAL
Molecular Formula C14H12F7N5S
Molecular Weight 415.332
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DSM-265

SMILES

CC1=NC2=NC(=NN2C(NC3=CC=C(C=C3)S(F)(F)(F)(F)F)=C1)C(C)(F)F

InChI

InChIKey=OIZSVTOIBNSVOS-UHFFFAOYSA-N
InChI=1S/C14H12F7N5S/c1-8-7-11(26-13(22-8)24-12(25-26)14(2,15)16)23-9-3-5-10(6-4-9)27(17,18,19,20)21/h3-7,23H,1-2H3

HIDE SMILES / InChI

Molecular Formula C14H12F7N5S
Molecular Weight 415.332
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

DSM265 is an experimental antimalarial that selectively inhibits the parasite dihydroorotate dehydrogenase (DHODH). DSM265 is the first DHODH inhibitor to reach clinical development for treatment of malaria. DSM265 is highly selective toward DHODH of the malaria parasite Plasmodium, efficacious against both blood and liver stages of P. falciparum, and active against drug-resistant parasite isolates. The only possible DSM265-related adverse event was a moderate transient elevation in serum bilirubin.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
DSM265 for Plasmodium falciparum chemoprophylaxis: a randomised, double blinded, phase 1 trial with controlled human malaria infection.
2017 Jun
DSM265 at 400 Milligrams Clears Asexual Stage Parasites but Not Mature Gametocytes from the Blood of Healthy Subjects Experimentally Infected with Plasmodium falciparum.
2019 Apr
Identification and Mechanistic Understanding of Dihydroorotate Dehydrogenase Point Mutations in Plasmodium falciparum that Confer in Vitro Resistance to the Clinical Candidate DSM265.
2019 Jan 11
Patents

Patents

Sample Use Guides

Single dose of 400 mg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:44:49 GMT 2023
Edited
by admin
on Sat Dec 16 11:44:49 GMT 2023
Record UNII
0Q42P4YI6B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DSM-265
Common Name English
2-(1,1-DIFLUOROETHYL)-5-METHYL-N-(4-(PENTAFLUORO-.LAMBDA.6-SULFANYL)PHENYL) (1,2,4)TRIAZOLO(1,5-A)PYRIMIDIN-7-AMINE
Systematic Name English
SULFUR, (4-((2-(1,1-DIFLUOROETHYL)-5-METHYL(1,2,4)TRIAZOLO(1,5-A)PYRIMIDIN-7-YL)AMINO)PHENYL)PENTAFLUORO-, (OC-6-21)-
Systematic Name English
DSM265
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 598417
Created by admin on Sat Dec 16 11:44:49 GMT 2023 , Edited by admin on Sat Dec 16 11:44:49 GMT 2023
Code System Code Type Description
PUBCHEM
51347395
Created by admin on Sat Dec 16 11:44:49 GMT 2023 , Edited by admin on Sat Dec 16 11:44:49 GMT 2023
PRIMARY
FDA UNII
0Q42P4YI6B
Created by admin on Sat Dec 16 11:44:49 GMT 2023 , Edited by admin on Sat Dec 16 11:44:49 GMT 2023
PRIMARY
CAS
1282041-94-4
Created by admin on Sat Dec 16 11:44:49 GMT 2023 , Edited by admin on Sat Dec 16 11:44:49 GMT 2023
PRIMARY
DRUG BANK
DB12397
Created by admin on Sat Dec 16 11:44:49 GMT 2023 , Edited by admin on Sat Dec 16 11:44:49 GMT 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
DSM265 displayed maximum antimalarial effects at 3 × EC50 and above, requiring a 24- to 48-hour lag phase before parasite killing. At 1 × EC50, DSM265 parasite killing was further delayed (96-hour lag phase).
EC50
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC