acadesine (CHEBI:28498)

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CHEBI:28498 - acadesine

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ChEBI Name	acadesine

ChEBI ID	CHEBI:28498

Definition	A 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:2025, CHEBI:20539

Supplier Information	ChemicalBook:CB6141459, eMolecules:531173, eMolecules:29541183, Selleckchem:Alprostadil(Caverject), ZINC000003813088

Download	Molfile XML SDF

Wikipedia	License
Prostaglandin E1 (PGE1) is a naturally occurring prostaglandin with various medical uses. Alprostadil and misoprostol are synthetic forms of prostaglandin E1 used as medications. Lubiprostone, a derivative of prostaglandin E1, is also used as a medication. Prostaglandin E1 is a vasodilator. It has various effects in the body that include opening blood vessels, relaxing smooth muscle, inhibiting clotting, and causing uterine contractions. In infants with certain congenital heart defects, alprostadil is delivered by slow injection into a vein to maintain a patent ductus arteriosus until surgery can be carried out. By injection into the penis or placement in the urethra, alprostadil is used to treat erectile dysfunction. Common side effects when given to babies include decreased breathing, fever, and low blood pressure. When injected into the penis for erectile dysfunction; side effects may include penile pain, bleeding at the site of injection, and prolonged erection (priapism). Prostaglandin E1 was isolated in 1957 and approved for medical use in the United States in 1981. Misoprostol has various obstetric uses. It is used to induce abortion, to completely empty the uterus after a miscarriage, to induce labor, and to prevent and treat postpartum hemorrhage. The medication is available through many routes. It can be swallowed, dissolved in the mouth, placed in the vagina, or placed in the rectum. Misoprostol can also be used to manage duodenal ulcers and peptic ulcer disease when other medications are not effective. It is on the World Health Organization's List of Essential Medicines for its obstetric uses. Lubiprostone is a PGE1 derivative used to treat chronic constipation. It is taken orally. Common side effects include diarrhea, vomiting, and abdominal pain.
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Formula

C9H14N4O5

Net Charge

Average Mass

258.23130

Monoisotopic Mass

258.09642

InChI

InChI=1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1

InChIKey

RTRQQBHATOEIAF-UUOKFMHZSA-N

SMILES

NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N

Roles Classification
Application(s):	platelet aggregation inhibitor A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

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ChEBI Ontology
Outgoing	acadesine (CHEBI:28498) has role antineoplastic agent (CHEBI:35610) acadesine (CHEBI:28498) has role platelet aggregation inhibitor (CHEBI:50427) acadesine (CHEBI:28498) is a 1-ribosylimidazolecarboxamide (CHEBI:26556) acadesine (CHEBI:28498) is a aminoimidazole (CHEBI:22512) acadesine (CHEBI:28498) is a nucleoside analogue (CHEBI:60783)

Incoming	AICA ribonucleotide (CHEBI:18406) has functional parent acadesine (CHEBI:28498)

IUPAC Name

5-amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxamide

INNs	Sources
acadesina	WHO MedNet
acadésine	WHO MedNet
acadesine	WHO MedNet
acadesinum	WHO MedNet