Lucanthone
Also known as Lucanthonum, Lucantona, 1-((2-(Diethylamino)ethyl)amino)-4-methylthioxanthen-9-one
Key facts
What buyers check first
- CAS number
- 479-50-5
- Formula
- C20H24N2OS
- Molar mass
- 340.49 g/mol
- EC number
- 207-532-4
- HS code
- 293499
- Category
- Antibiotics and anti-infectives
What is Lucanthone?
Plain description, key identifiers and synonyms
Lucanthone is a thioxanthen-9-one compound having a methyl substituent at the 1-position and a 2-[(diethylamino)ethyl]amino substituent at the 4-position. Formerly used for the treatment of schistosomiasis. It is a prodrug, being metabolised to hycanthone. It has a role as a mutagen, an antineoplastic agent, a schistosomicide drug, a photosensitizing agent, a prodrug, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor and an adjuvant.
Identifiers
Registry numbers, names and line notations, tap to copy
- IUPAC name
- 1-[2-(diethylamino)ethylamino]-4-methylthioxanthen-9-one
- CAS number
- 479-50-5 CAS number cross-checkedOther or deprecated CAS: 548-57-2
- EC number
- 207-532-4
- Molecular formula
- C20H24N2OS
- UNII
- FC6D57000M
- InChIKey
- FBQPGGIHOFZRGH-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H24N2OS/c1-4-22(5-2)13-12-21-16-11-10-14(3)20-18(16)19(23)15-8-6-7-9-17(15)24-20/h6-11,21H,4-5,12-13H2,1-3H3
- SMILES (canonical and isomeric)
- CCN(CC)CCNC1=C2C(=C(C=C1)C)SC3=CC=CC=C3C2=O
Synonyms
- Lucanthonum
- Lucantona
- 1-((2-(Diethylamino)ethyl)amino)-4-methylthioxanthen-9-one
- 1-((2-(diethylamino)ethyl)amino)-4-methyl-9H-thioxanthen-9-one
- 1-{[2-(Diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one
- 9H-Thioxanthen-9-one, 1-((2-(diethylamino)ethyl)amino)-4-methyl-
- 1-diethylaminoethylethylamino-4-methyl-thioxanthenone
- 1-{[2-(diethylamino)ethyl]amino}-4-methylthioxanthen-9-one
- 9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-4-methyl-
- Lucanthon
- 1-[2-(diethylamino)ethylamino]-4-methylthioxanthen-9-one
- 1-((2-(Diethylamino)ethyl)amino)-4-methyl-9H-thioxanthen-9-one , Lucanthone
- 1-[[2-(Diethylamino)ethyl]amino]-4-methylthioxanthone
- Lucanthone-API
- 5-18-11-00503 (Beilstein Handbook Reference)
- 1-[2-(diethylamino)ethylamino]-4-methyl-thioxanthen-9-one
- Thioxanthen-9-one, 1-((2-(diethylamino)ethyl)amino)-4-methyl-
- 1-(2-diethylaminoethylamino)-4-methyl-thioxanthen-9-one
- 1-(2-Diethylaminoethylamino)-4-methylthiaxanthone
Physical and chemical properties
Measured values and descriptors computed from the structure
Physical and chemical properties
Measured values, check the supplier specification for your grade
No measured properties are recorded for this substance yet. Ask suppliers for a technical data sheet.
Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.
Computed descriptors
Calculated from the structure, useful for screening and formulation
| Molecular weight | 340.49 g/molcalc.Computed value |
|---|---|
| Exact mass | 340.1609 Dacalc.Computed value |
| LogP (octanol/water) | 4.48calc.Computed value |
| Topological polar surface area | 32.34 Ųcalc.Computed value |
| Hydrogen bond donors | 1calc.Computed value |
| Hydrogen bond acceptors | 4calc.Computed value |
| Rotatable bonds | 6calc.Computed value |
| Heavy atoms | 24calc.Computed value |
| Rings | 3calc.Computed value |
| Aromatic rings | 3calc.Computed value |
| Fraction sp3 carbons | 0.35calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 0calc.Computed value |
| Lipinski rule of five | Passes (0 violations)calc.Computed value |
Calculated for screening. Confirm critical figures with the supplier.
Murcko scaffold
The ring system that remains when every side chain is removed
O=c1c2ccccc2sc2ccccc12
3 rings, 15 atoms, the Thioxanthone ring system.
254 other chemicals share this scaffoldSafety and hazards
GHS classification summary, not a safety data sheet
No GHS hazard classification is recorded for this substance yet. That does not mean it is harmless.
GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.
Lucanthone suppliers
Sponsored listings first, then the documented ranking: membership, verification, replies, completeness, freshness and ratings
- China, NantongUnclaimed profileLucanthoneGrade, purity and minimum order on requestPrice on request
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Where suppliers are based
1 supplier in 1 country
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Lucanthone price
Indicative price range per kg from live supplier offers
Suppliers quote this chemical on request. Send one free request and compare quotes side by side.
Uses and applications
What the substance is used for, by industry and function
Pharmacological actions
- Schistosomicides
Roles
- adjuvant
- aetiopathogenetic role
- anthelminthic drug
- antiinfective agent
- antineoplastic agent
- antiparasitic agent
- antiplatyhelmintic drug
- enzyme inhibitor
- genotoxin
- mutagen
- pharmaceutical
- photosensitizing agent
- pro-agent
- prodrug
- schistosomicide drug
- topoisomerase inhibitor
Pharmacology
Lucanthone is an orally available thioxanthone-based DNA intercalator and inhibitor of the DNA repair enzyme apurinic-apyrimidinic endonuclease 1 (APEX1 or APE1), with anti-schistosomal and potential antineoplastic activity. Lucanthone intercalates DNA and interferes with the activity of topoisomerases I and II during replication and transcription, thereby inhibiting the synthesis of macromolecules. In addition, this agent specifically inhibits the endonuclease activity of APE1, without affecting its redox activity, resulting in un-repaired DNA strand breaks which may induce apoptosis.
Read more
Therefore, lucanthone may sensitize tumor cells to radiation and chemotherapy. Furthermore, lucanthone inhibits autophagy through the disruption of lysosomal function. The multifunctional nuclease APE1 is a key component for DNA repair, its expression is often correlated with tumor cell resistance to radio- and chemotherapy.
Regulatory status
Inventories, regulations and trade controls that list this substance
No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.
HS code and trade data
Customs classification and reported world trade statistics
Global trade
World import and export statistics for the HS code Lucanthone is traded under.
Nucleic acids and their salts, other heterocyclic compounds, not elsewhere classified in heading 2934
- United States24.5%
- Germany23.1%
- Japan4.5%
The HS code shown for Lucanthone is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.
Frequently asked questions
Quick answers about Lucanthone, based on the data on this page
What is Lucanthone?
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What is the molecular formula and weight of Lucanthone?
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Guides for buyers
Practical guides that help when you source, ship or handle Lucanthone
- Article, QualityPharma grades explained: IP vs BP vs USP vs EPWhat the Indian, British, US and European pharmacopoeias are, how their monographs differ, what multi grade claims mean and why a grade alone does not make a product fit for medicines.Read
- Article, SourcingHow to write an RFQ that gets fast and accurate quotesWhat suppliers need to quote quickly and comparably: exact product identity, quantity and packing, delivery terms, documents, samples and payment, with a ready to use template.Read
- Guide, Trade and logisticsHS codes for chemicals and why they matterHow the Harmonized System classifies chemicals, the chapters that matter, the rules for chemically defined compounds and mixtures, and practical steps to find the right code.Read
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