Dantron

Chemical compound

A06AB03 (WHO) A06AG03 (WHO)

Identifiers

IUPAC name

1,8-dihydroxyanthracene-9,10-dione

CAS Number

117-10-2^Y

PubChem CID

2950

DrugBank

DB04816^N

ChemSpider

2845^Y

UNII

Z4XE6IBF3V

KEGG

D07107^N

ChEBI

CHEBI:3682^N

ChEMBL

ChEMBL53418^N

NIAID ChemDB

001375

CompTox Dashboard (EPA)

DTXSID9020328

ECHA InfoCard100.003.794

Chemical and physical dataFormulaC₁₄H₈O₄Molar mass240.214 g·mol⁻¹3D model (JSmol)

Interactive image

Density1.575 g/cm³ g/cm³

SMILES

O=C2c1cccc(O)c1C(=O)c3c2cccc3O

InChI

InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H^N
Key:QBPFLULOKWLNNW-UHFFFAOYSA-N^N

^NY (what is this?) (verify)

Dantron (INN), also known as chrysazin or 1,8-dihydroxyanthraquinone, is an orange-colored organic substance. Many structurally-related compounds are known.^[1] In terms of its molecular structure, it is related anthraquinone by the replacement of two hydrogen atoms by hydroxyl groups (–OH). It is used in some countries as a stimulant laxative.

It should not be confused with ondansetron, an unrelated drug that was marketed in South Africa under the trade name "Dantron".

Medical uses

In the USA, dantron is not used because it is considered to be a carcinogen.^[2]

In the UK it is considered a possible carcinogen and so its use is restricted to patients who already have a diagnosis of terminal cancer. It is mainly used in palliative care to counteract the constipating effects of opioids. Its British Approved Name was danthron, but it has now been changed to "dantron", the recommended International Nonproprietary Name.^[3]

Dantron can be administered orally, or can be administered rectally as an enema either in combination with other laxatives or alone.^[4]

Side effects

Dantron has the notable side-effect of causing red-colored urine.

References

^ Rohl AL, Moret M, Kaminsky W, Claborn K, McKinnon JJ, Kahr B (2008). "Hirshfeld Surfaces Identify Inadequacies in Computations of Intermolecular Interactions in Crystals: Pentamorphic 1,8-Dihydroxyanthraquinone". Crystal Growth & Design. 8 (12): 4517–4525. doi:10.1021/cg8005212.
^ "Danthron substance profile" (PDF). National Toxicology Program.
^ British National Formulary website (requires free registration)
^ "A06AG Enemas". WHO Collaborating Centre for Drug Statistics Methodology. World Health Organization. 13 December 2018. Retrieved 17 March 2019.