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Lucanthone

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Chemical compound

Pharmaceutical compound

Lucanthone
Clinical data


ATC code	none
Identifiers
IUPAC name 1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one
CAS Number	479-50-5^Y
PubChemCID	10180
DrugBank	DB04967^Y
ChemSpider	9772^N
UNII	FC6D57000M
ChEBI	CHEBI:51052^N
CompTox Dashboard(EPA)	DTXSID6023230
ECHA InfoCard	100.006.849
Chemical and physical data
Formula	C₂₀H₂₄N₂OS
Molar mass	340.49 g·mol⁻¹
^NY (what is this?) (verify)

Lucanthone is a drug used to treat parasitic diseases such asbilharziasis^[1] andschistosomiasis^[2] It is aprodrug and is converted to theactive metabolite hycanthone.^[3]

Mechanism of action

[edit]

Hycanthone binds toacetylcholine receptors in the worm^[4] and results in increased sensitivity to stimulation by5-HT causing increase inmotility, paired worms are separated and reproduction is stopped. It causes damage of theintegument andvitelline duct.

References

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^Blair DM (1958)."Lucanthone hydrochloride; a review".Bulletin of the World Health Organization.18 (5–6):989–1010.PMC 2537946.PMID 13573122.
^Standen O (1963)."Chemotherapy of Helminthic Infections". In Schnitzer RJ, Hawking F (eds.).Experimental chemotherapy. Vol. 1. New York, New York: Academic Press. p. 770.ISBN 978-1-4832-7308-2.
^Rosi D, Peruzzotti G, Dennis EW, Berberian DA, Freele H, Tullar BF, Archer S (September 1967). "Hycanthone, a new active metabolite of lucanthone".Journal of Medicinal Chemistry.10 (5):867–76.doi:10.1021/jm00317a025.PMID 4963368.
^Hillman GR, Senft AW (September 1975). "Anticholinergic properties of the antischistosomal drug hycanthone".The American Journal of Tropical Medicine and Hygiene.24 (5):827–34.doi:10.4269/ajtmh.1975.24.827.PMID 1190369.

Antiparasitics –Anthelmintics (P02) andendectocides (QP54)

Antiplatyhelmintic agents

Antitrematodals
(schistosomicides)

Bindstubulin	benzimidazole Triclabendazole^#
AChE inhibitor	phosphonic acid Metrifonate^‡
Other/unknown	quinoline Arpraziquantel Praziquantel^# (+esafoxolaner/eprinomectin) Oxamniquine^# phenol Bithionol thiazole Niridazole thioxanthone Hycanthone Lucanthone antimony compounds Stibophen Tartar emetic^‡

Anticestodals
(taeniacides)

Bindstubulin	benzimidazole Albendazole^#
Other/unknown	quinoline Praziquantel^# (+esafoxolaner/eprinomectin) salicylanilide Niclosamide^# aminoacridine Quinacrine butyrophenone Desaspidin chlorophenol Dichlorophen

Antinematodal agents
(including
macrofilaricides)

Bindstubulin	benzimidazole Mebendazole^# Albendazole^# Tiabendazole Fenbendazole Ciclobendazole Flubendazole
Glutamate-gated chloride channel,GABA receptor	avermectins Abamectin Doramectin Emamectin Eprinomectin (+esafoxolaner/praziquantel) Ivermectin^# Selamectin milbemycins Moxidectin (+fluralaner) Milbemycin oxime
NMDA	tetrahydropyrimidine Pyrantel^# pyrantel pamoate Oxantel Morantel Carbantel Febantel (akafelsantel)
Other/unknown	piperazine Piperazine Diethylcarbamazine^# thiazole Levamisole^# quinolinium Pyrvinium benzylammonium Bephenium naphthalenesulfonate Suramin^# Ascaridole^‡ Hexylresorcinol Santonin^‡ Tribendimidine Tetrachloroethylene^‡

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Intracellularchemotherapeutic agents /antineoplastic agents (L01)

SPs/MIs
(M phase)

Blockmicrotubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vindesine Vinflunine^§ Vinorelbine^#)
Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Rabacfosadine Thiopurine (Mercaptopurine^# Tioguanine^#)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine^# Carmofur Doxifluridine Floxuridine Fluorouracil^# Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine^#+daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine^#) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide^#)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Belotecan Camptothecin Cositecan^† Etirinotecan pegol^† Exatecan Gimatecan Irinotecan^# Lurtotecan^‡ Rubitecan^‡ Silatecan^§ Topotecan)
II	Podophyllum (Etoposide^# Teniposide)
II+Intercalation	Anthracyclines (Aclarubicin Amrubicin^† Daunorubicin^# (+cytarabine) Doxorubicin^# Epirubicin Idarubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Losoxantrone Mitoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril^§

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards:Bendamustine^# Chlormethine Cyclophosphamide^# (Ifosfamide^# Trofosfamide) Chlorambucil^# Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas:Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates:Busulfan (Mannosulfan Treosulfan) Aziridines:Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine^#) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine^# Mitozolomide^§ Temozolomide)
Intercalation	Streptomyces (Dactinomycin^# Bleomycin^# Mitomycins Plicamycin)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Abemaciclib Alvocidib^† Palbociclib Ribociclib Seliciclib^†) PrI Bortezomib Carfilzomib Oprozomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Fuzuloparib Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib^‡ Duvelisib Idelalisib Inavolisib Umbralisib^‡) IDH (Enasidenib Ivosidenib Olutasidenib Vorasidenib)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Celecoxib Ciltacabtagene autoleucel Demecolcine Denileukin diftitox Eflornithine Elesclomol^§ Elsamitrucin Epacadostat Eribulin Estramustine Glasdegib Idecabtagene vicleucel Imetelstat Lifileucel Lisocabtagene maraleucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Nadofaragene firadenovec Navitoclax Obecabtagene autoleucel Oblimersen^† Omacetaxine mepesuccinate Plitidepsin Tabelecleucel Retinoids (Alitretinoin Tretinoin^#) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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