CHEBI:143527 - (R)-lisofylline

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ChEBI Name (R)-lisofylline
ChEBI ID CHEBI:143527
ChEBI ASCII Name (R)-lisofylline
Definition A 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione that has (R)-configuration. A synthetic small molecule which was under development for the treatment of type 1 diabetes mellitus.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter TheOtherDave
Supplier Information eMolecules:29542986, ZINC000000119839
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Wikipedia License
Levamisole, sold under the brand name Ergamisol among others, is a medication used to treat parasitic worm infections, specifically ascariasis and hookworm infections. It is taken by mouth. Side effects may include abdominal pain, vomiting, headache, and dizziness. Use is not recommended during breastfeeding or the third trimester of pregnancy. Serious side effects may include an increased risk of infection. It belongs to the anthelmintic class of medications. Levamisole was invented in 1966 in Belgium by Janssen Pharmaceuticals. It is on the World Health Organization's List of Essential Medicines. Levamisole is also used as a dewormer for cattle.
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Formula C13H20N4O3
Net Charge 0
Average Mass 280.328
Monoisotopic Mass 280.15354
InChI InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3/t9-/m1/s1
InChIKey NSMXQKNUPPXBRG-SECBINFHSA-N
SMILES C=12N(C=NC1N(C(N(C2=O)CCCC[C@H](O)C)=O)C)C
Roles Classification
Biological Role(s): immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
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ChEBI Ontology
Outgoing (R)-lisofylline (CHEBI:143527) has role anti-inflammatory agent (CHEBI:67079)
(R)-lisofylline (CHEBI:143527) has role immunomodulator (CHEBI:50846)
(R)-lisofylline (CHEBI:143527) is a 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione (CHEBI:143565)
(R)-lisofylline (CHEBI:143527) is enantiomer of (S)-lisofylline (CHEBI:143564)
Incoming rac-lisofylline (CHEBI:143567) has part (R)-lisofylline (CHEBI:143527)
(S)-lisofylline (CHEBI:143564) is enantiomer of (R)-lisofylline (CHEBI:143527)
IUPAC Name
1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione
INNs Sources
lisofilina WHO MedNet
lisofylline WHO MedNet
lisofylline VSDB
lisofyllinum WHO MedNet
Synonyms Sources
(−)-lisofylline ChEBI
(R)-1-(5-hydroxyhexyl)-3,7-dimethylxanthine ChEBI
(R)-LSF ChEBI
1-(5R-hydroxyhexyl)-3,7-dimethylxanthine ChEBI
1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione DrugBank
1-[(R)-5-hydroxyhexyl]theobromine ChEBI
CT 1501R ChemIDplus
CT-1501R ChEBI
lisophylline ChemIDplus
Brand Name Source
ProTec KEGG DRUG
Manual Xrefs Databases
D04748 KEGG DRUG
DB12406 DrugBank
Lisofylline Wikipedia
WO2009099582 Patent
View more database links
Registry Numbers Types Sources
100324-81-0 CAS Registry Number ChemIDplus
100324-81-0 CAS Registry Number DrugBank
Citations Types Sources
10330034 PubMed citation Europe PMC
11902249 PubMed citation Europe PMC
12242464 PubMed citation Europe PMC
12717280 PubMed citation Europe PMC
15588708 PubMed citation Europe PMC
25663650 PubMed citation Europe PMC
28730281 PubMed citation Europe PMC
30300750 PubMed citation Europe PMC
7735959 PubMed citation Europe PMC
Last Modified
03 May 2019