CAS 117-10-2|Usaf nd-59|Altan|Laxanorm|1,8-Dihydroxyanthrachinon [Czech]|1,8-Dihydroxyanthra-9,10-quinone|1,4,5,8-Tetroxyantraquinone|Dihydroxyanthraquinone|Dorbane|Laxanthreen|1,8-Dihydroxy-9,10-an...

General Information

Structure

Molecular Formula

C₁₄H₈O₄

Molecular Mass

240.21092

Exact Mass

240.04225874

Charge

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

InChIKey

QBPFLULOKWLNNW-UHFFFAOYSA-N

Canonic Smiles

Oc1cccc2c1C(=O)c1c(C2=O)cccc1O

Isomeric Smiles

O=C1c2c(C(=O)c3c1c(O)ccc3)cccc2O

Calculated Properties

JChem

LogD (pH = 7.4)

3.48

LogD (pH = 5.5)

3.61

Log P

3.61

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.89

Polar Surface Area

74.60

Polarizability

23.19

Molar Refractivity

65.11

LOG S

-3.60

Data Source

Names and Identifiers

Brand Name

DorbanePrugolLaxanthreenDorbanexPastominDiononeDanivacLaxanormLTANAltanLaxipurRoydanChrysazineDantronIstizinDorbantylCriasazinModaneChrysazinDuolaxZwitsalaxAntrapurolNeokutin sRegulinScatron dIstinBanconLaxipurinDiaquoneIstan

Synonyms

1,8-Dihydroxy-9,10-anthracenedione1,8-Dihydroxyanthra-9,10-quinoneDantrona [inn-spanish]Dihydroxyanthraquinone1,4,5,8-Tetroxyantraquinone1,8-Dihydroxyanthrachinon [Czech]Usaf nd-591,8-Dihydroanthraquinone1,8-Dihydroxyanthrachinon1,8-DihydroxyanthraquinoneDantrone [inn-french]Danthron1,8-Dihydroxy-9,10-anthraquinoneDHAQ1,8-dihydroxyanthracene-9,10-dioneDioxyanthrachinonumDantronum [inn-latin]Dantron1,8-Dihydroxyanthra-9,10-quinone1,8-DIHYDROXYANTHRAQUINONEDanthron1,8-二羟基蒽醌丹蒽醌CHRYSAZIN PRACTICAL GRADE二羟蒽醌Chrysazine1,8-Dihydroxyanthraquinone1,8-dihydroxyanthracene-9,10-dioneDanthroneModaneDiaquoneDorbaneLaxanormIstizinLaxipurZwitsalaxLaxipurinNSC 38626LaxanthreenIstinAltanAntrapurolDantronNSC 7210ChrysazinDiononeNSC 646568DantronDanivac1,8-dihydroxy-9,10-anthraquinonechrysazin1,8-dihydroxy-9,10-anthracenedioneDioxyanthrachinonum1,8-Dihydroxyanthrachinon1,8-DihydroxyanthraquinoneDanthronChrysazin1,8-dihydroxyanthra-9,10-quinone

IUPAC Traditional name

danthron altan 1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione

IUPAC name

1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione

International Nonproprietary Name (INN)

dantrondantronumdantronedantrona

Names and Identifiers

Registration numbers

EC Number

CAS Number

MDL Number

Merck Index

Beilstein Number

ATC CODE

CHEBI ID

CHEMBL

PubChem CID

DrugBank ID

KEGG ID

Unique Ingredient Identifier

Z4XE6IBF3V

Wikipedia Title

Dantron

Chemspider ID

2845

PubChem SID

160967792465090772489334611533492

BRENDA Database

2.7.11.181.6.5.21.6.5.51.18.1.22.4.1.1811.8.1.92.4.1.1031.8.1.73.2.1.181.13.12.22

PubMed Citation Links

244341502036929219784869237709822157641322592642

MetaboLights Database

MTBLS2145MTBLS1693MTBLS2542

BRENDA Ligand Database

220864515837508271072809642878

PDBeChem Database

ACToR Database

NMRShiftDB Database

BindingDB Database

Patent number

WO2006012162US2007185145US2008262073US2005182103WO2006035021EP1582549

BKMS React Database

428782710728096220864750851583

CompTox Database

Gmelin ID

KNApSAcK Database

Protein Data Bank

Drug Central Database

KEGG DRUG Database

SureChEMBL Database

LINCS Database

Reaxys Registry

HMDB Database

SABIO-RK Database

Registration numbers

Properties

Pharmacology Properties

Oral, rectal (enema)

alters water-secretion

alters electrolyte-secretion

Direct action on intestinal mucosa

stimulates myenteric-plexus

Properties

Related Proteins

PDB Bank

3NSQ

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02157739

Crystalline
Purity: ~95%

05204925

MP Biomedicals Rare Chemical collection

Wikipedia

Dantron

DrugBank

DB04816

Drug Groups

withdrawn

Description

Withdrawn from the Canadian, US, and UK markets in 1998 due to genotoxicity.

External Links

• [Wikipedia]

Sigma Aldrich

D108103

Packaging
100, 500 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D108103.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

D450150

Used as a stimulant laxative, though due to its carcinogenic properties, is not widely prescribed.

ChEBI

CHEBI:3682

A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.

Molecule Details

References

PubChem Literature

From Data Sources

• Liu, Y., et al.: J. Med. Chem., 52, 6523 (2009)

• Grocholski, T., et al.: Biochem., 49, 934 (2009)

• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2009)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 91B, (nmr)

• Lish, P.M. et al., J. Am. Pharm. Assoc., 1958, 47, 371, (pharmacol)

• Cameron, A.W. et al., Aust. J. Chem., 1982, 35, 2095, (synth)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 87D, (ir)

• Kido, H. et al., Anal. Chim. Acta, 1960, 23, 116, (ir)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DMH400

• Aoyama, S. et al., Yakugaku Zasshi, 1932, 52, 17

• Beynon, J.H. et al., Appl. Spectrosc., 1960, 14, 156, (ms)

• Prakesh, A., Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem., 1965, 122, 272, (cryst struct)

• Ruggieri, R., Anal. Chim. Acta, 1961, 25, 145, (use)

• Berger, Y. et al., Org. Magn. Reson., 1978, 11, 375, (cmr)

• Roman Ceba, M. et al., Mikrochim. Acta, 1983, 2, 85, (detn, Mg)

• Kahr, B. et al., Angew. Chem., Int. Ed., 1992, 31, 1, (tautom)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1215

• Morley, J.O. et al., J.C.S. Perkin 2, 1973, 1626, (pmr)

• Case, M.T. et al., Drug Chem. Toxicol., 1978, 1, 89, (tox)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2970, (synonyms)

• Fairbairn, J.W. et al., J. Pharm. Pharmacol., 1970, 22, 584, (pharmacol)

• Howard, D.F. et al., Naturwissenschaften, 1982, 69, 91, (isol)

• Mueller, K. et al., Arch. Pharm. (Weinheim, Ger.), 1984, 317, 120, (synth)

• Idris, K.A. et al., Egypt. J. Chem., 1973, 67, (uv)

• Breimer, D.D. et al., Pharmacology, 1976, 14, 30, (metab)

• Gattuso, J.M. et al., Drug Saf., 1984, 10, 47, (rev)

• Khanapure, S.P. et al., J.O.C., 1987, 52, 5685, (deriv, synth, pmr, ir)

• IARC Monog., 1990, 50, 265, (rev, tox)

• Naylor, C.A. et al., J.A.C.S., 1931, 53, 4112

• Fournier, G. et al., Phytochemistry, 1975, 14, 2099, (isol)

• Grunwell, J.R. et al., J.O.C., 1991, 56, 91, (synth, pmr)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

Synonyms

IUPAC Traditional name

danthron altan 1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione

IUPAC name

1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione

International Nonproprietary Name (INN)

dantrondantronumdantronedantrona

Registration numbers

EC Number

CAS Number

MDL Number

Merck Index

Beilstein Number

ATC CODE

CHEBI ID

CHEMBL

PubChem CID

DrugBank ID

KEGG ID

Unique Ingredient Identifier

Z4XE6IBF3V

Wikipedia Title

Dantron

Chemspider ID

2845

PubChem SID

160967792465090772489334611533492

BRENDA Database

2.7.11.181.6.5.21.6.5.51.18.1.22.4.1.1811.8.1.92.4.1.1031.8.1.73.2.1.181.13.12.22

PubMed Citation Links

244341502036929219784869237709822157641322592642

MetaboLights Database

MTBLS2145MTBLS1693MTBLS2542

BRENDA Ligand Database

220864515837508271072809642878

PDBeChem Database

ACToR Database

NMRShiftDB Database

BindingDB Database

Patent number

WO2006012162US2007185145US2008262073US2005182103WO2006035021EP1582549

BKMS React Database

428782710728096220864750851583

CompTox Database

Gmelin ID

KNApSAcK Database

Protein Data Bank

Drug Central Database

KEGG DRUG Database

SureChEMBL Database

LINCS Database

Reaxys Registry

HMDB Database

SABIO-RK Database

Related Proteins

Molecule Details

Crystalline
Purity: ~95%

05204925

MP Biomedicals Rare Chemical collection

Wikipedia

Dantron

DrugBank

DB04816

Drug Groups

withdrawn

Description

Withdrawn from the Canadian, US, and UK markets in 1998 due to genotoxicity.

External Links

• [Wikipedia]

Sigma Aldrich

D108103

TRC

D450150

Used as a stimulant laxative, though due to its carcinogenic properties, is not widely prescribed.

ChEBI

CHEBI:3682

A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.

References

PubChem Literature

From Data Sources

• Liu, Y., et al.: J. Med. Chem., 52, 6523 (2009)

• Grocholski, T., et al.: Biochem., 49, 934 (2009)

• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2009)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 91B, (nmr)

• Lish, P.M. et al., J. Am. Pharm. Assoc., 1958, 47, 371, (pharmacol)

• Cameron, A.W. et al., Aust. J. Chem., 1982, 35, 2095, (synth)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 87D, (ir)

• Kido, H. et al., Anal. Chim. Acta, 1960, 23, 116, (ir)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DMH400

• Aoyama, S. et al., Yakugaku Zasshi, 1932, 52, 17

• Beynon, J.H. et al., Appl. Spectrosc., 1960, 14, 156, (ms)

• Prakesh, A., Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem., 1965, 122, 272, (cryst struct)

• Ruggieri, R., Anal. Chim. Acta, 1961, 25, 145, (use)

• Berger, Y. et al., Org. Magn. Reson., 1978, 11, 375, (cmr)

• Roman Ceba, M. et al., Mikrochim. Acta, 1983, 2, 85, (detn, Mg)

• Kahr, B. et al., Angew. Chem., Int. Ed., 1992, 31, 1, (tautom)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1215

• Morley, J.O. et al., J.C.S. Perkin 2, 1973, 1626, (pmr)

• Case, M.T. et al., Drug Chem. Toxicol., 1978, 1, 89, (tox)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2970, (synonyms)

• Fairbairn, J.W. et al., J. Pharm. Pharmacol., 1970, 22, 584, (pharmacol)

• Howard, D.F. et al., Naturwissenschaften, 1982, 69, 91, (isol)

• Mueller, K. et al., Arch. Pharm. (Weinheim, Ger.), 1984, 317, 120, (synth)

• Idris, K.A. et al., Egypt. J. Chem., 1973, 67, (uv)

• Breimer, D.D. et al., Pharmacology, 1976, 14, 30, (metab)

• Gattuso, J.M. et al., Drug Saf., 1984, 10, 47, (rev)

• Khanapure, S.P. et al., J.O.C., 1987, 52, 5685, (deriv, synth, pmr, ir)

• IARC Monog., 1990, 50, 265, (rev, tox)

• Naylor, C.A. et al., J.A.C.S., 1931, 53, 4112

• Fournier, G. et al., Phytochemistry, 1975, 14, 2099, (isol)

• Grunwell, J.R. et al., J.O.C., 1991, 56, 91, (synth, pmr)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Oral, rectal (enema)

alters water-secretion

alters electrolyte-secretion

Direct action on intestinal mucosa

stimulates myenteric-plexus

Molecule

ID:4360