dantron
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 322159605
| IUPAC_name = 1,8-dihydroxyanthracene-9,10-dione
| image = Dantron.svg
| image2 = 1,8-Dihydroxyanthraquinone-3D-balls.png
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = Oral, rectal (enema)
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 117-10-2
| ATC_prefix = A06
| ATC_suffix = AB03
| ATC_supplemental = {{ATC|A06|AG03}}
| PubChem = 2950
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB04816
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2845
| NIAID_ChemDB = 001375
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = Z4XE6IBF3V
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D07107
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 3682
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 53418
| C=14 | H=8 | O=4
| density = 1.575 g/cm3
| smiles = O=C2c1cccc(O)c1C(=O)c3c2cccc3O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = QBPFLULOKWLNNW-UHFFFAOYSA-N
}}
Dantron (INN), also known as chrysazin or 1,8-dihydroxyanthraquinone, is an orange-colored organic substance. Many structurally-related compounds are known.{{cite journal |doi=10.1021/cg8005212 |title=Hirshfeld Surfaces Identify Inadequacies in Computations of Intermolecular Interactions in Crystals: Pentamorphic 1,8-Dihydroxyanthraquinone |date=2008 | vauthors = Rohl AL, Moret M, Kaminsky W, Claborn K, McKinnon JJ, Kahr B |journal=Crystal Growth & Design |volume=8 |issue=12 |pages=4517–4525 }} 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.{{cite web | url = https://ntp.niehs.nih.gov/ntp/roc/content/profiles/danthron.pdf | title = Danthron substance profile | work = National Toxicology Program }}
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.[http://www.bnf.org/ British National Formulary website] (requires free registration)
Dantron can be administered orally, or can be administered rectally as an enema either in combination with other laxatives or alone.{{cite web |url=https://www.whocc.no/atc_ddd_index/?code=A06AG&showdescription=yes |title=A06AG Enemas |date=13 December 2018 |work=WHO Collaborating Centre for Drug Statistics Methodology |publisher=World Health Organization |access-date=17 March 2019}}
Side effects
Dantron has the notable side-effect of causing red-colored urine.