Dantron

Dantron
Clinical data
Routes of; administration	Oral, rectal (enema)
ATC code	A06AB03 (WHO) A06AG03 (WHO);
Identifiers
	IUPAC name 1,8-dihydroxyanthracene-9,10-dione;
CAS Number	117-10-2 ;
PubChem CID	2950;
DrugBank	DB04816 ;
ChemSpider	2845 ;
UNII	Z4XE6IBF3V;
KEGG	D07107 ;
ChEBI	CHEBI:3682 ;
ChEMBL	ChEMBL53418 ;
NIAID ChemDB	001375;
Chemical and physical data
Formula	C14H8O4
Molar mass	240.214 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.575 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 ; Key:QBPFLULOKWLNNW-UHFFFAOYSA-N ;
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Short description: Chemical compound

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 United States , dantron is not used because it is considered to be a carcinogen.^[2]

In the United Kingdom 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

↑ "Hirshfeld Surfaces Identify Inadequacies in Computations of Intermolecular Interactions in Crystals: Pentamorphic 1,8-Dihydroxyanthraquinone". Crystal Growth & Design 8 (12): 4517–4525. 2008. doi:10.1021/cg8005212.
↑ "Danthron substance profile". National Toxicology Program. https://ntp.niehs.nih.gov/ntp/roc/content/profiles/danthron.pdf.
↑ British National Formulary website (requires free registration)
↑ "A06AG Enemas". WHO Collaborating Centre for Drug Statistics Methodology. World Health Organization. 13 December 2018. https://www.whocc.no/atc_ddd_index/?code=A06AG&showdescription=yes.

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[1] "Hirshfeld Surfaces Identify Inadequacies in Computations of Intermolecular Interactions in Crystals: Pentamorphic 1,8-Dihydroxyanthraquinone". Crystal Growth & Design 8 (12): 4517–4525. 2008. doi:10.1021/cg8005212.

[2] "Danthron substance profile". National Toxicology Program. https://ntp.niehs.nih.gov/ntp/roc/content/profiles/danthron.pdf.

[BNF-3] British National Formulary website (requires free registration)

[4] "A06AG Enemas". WHO Collaborating Centre for Drug Statistics Methodology. World Health Organization. 13 December 2018. https://www.whocc.no/atc_ddd_index/?code=A06AG&showdescription=yes.

v t e Drugs for constipation (laxatives and cathartics) (A06)
Stool softeners	Docusate
Stimulant laxatives	Bisacodyl Bisoxatin Cascara Castor oil Dantron Oxyphenisatine Phenolphthalein Senna glycosides Sodium picosulfate
Bulk-forming laxatives	Dietary fiber Ethulose Ispaghula Methylcellulose Polycarbophil calcium Sterculia Triticum
Lubricant laxatives	Liquid paraffin Mineral oil White petrolatum (petroleum jelly)
Osmotic laxatives	Lactitol Lactulose Laminarid Magnesium carbonate Magnesium citrate Magnesium hydroxide (milk of magnesia) Magnesium oxide Magnesium peroxide Magnesium sulfate Mannitol Pentaerythritol Polyethylene glycol (macrogol) Sodium phosphate Sodium sulfate Sodium tartrate Sorbitol
Enemas	Bisacodyl Dantron Glycerol Oil Sodium laurilsulfate Sodium lauryl sulfoacetate Sodium phosphate Sorbitol
Opioid antagonists	Naloxone (Oxycodone/naloxone) PAMORAs Alvimopan Axelopran Bevenopran Methylnaltrexone Naldemedine Naloxegol
Others	Linaclotide Lubiprostone Oxyphenisatine Prucalopride Tegaserod Ulimorelin

Dantron

Contents

Medical uses

Side effects

See also

References

Clinical data


Routes of administration	Oral, rectal (enema)
ATC code	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
Chemical and physical data
Formula	C₁₄H₈O₄
Molar mass	240.214 g·mol⁻¹
3D model (JSmol)	Interactive image
Density	1.575 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
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