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Triaziquone
Clinical data
👁 Image
Other names	2,3,5-Tris(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione Tris(aziridinyl)-p-benzoquinone
ATC code	L01AC02 (WHO)
Identifiers
IUPAC name 2,3,5-tris(aziridin-1-yl)benzo-1,4-quinone
CAS Number	68-76-8^{👁 check Y}
PubChem CID	6235
ChemSpider	5999^{👁 ☒ N}
UNII	F3D5D9P25I
KEGG	C19542^{👁 check Y}
ChEBI	CHEBI:27090^{👁 ☒ N}
CompTox Dashboard (EPA)	DTXSID1021370 👁 Edit this at Wikidata
ECHA InfoCard	100.000.629 👁 Edit this at Wikidata
Chemical and physical data
Formula	C₁₂H₁₃N₃O₂
Molar mass	231.255 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CN1C2=CC(=O)C(=C(C2=O)N3CC3)N4CC4
InChI InChI=1S/C12H13N3O2/c16-9-7-8(13-1-2-13)12(17)11(15-5-6-15)10(9)14-3-4-14/h7H,1-6H2^{👁 ☒ N} Key:PXSOHRWMIRDKMP-UHFFFAOYSA-N^{👁 ☒ N}
^{👁 ☒ N👁 check Y} (what is this?) (verify)

Triaziquone is a drug used in chemotherapy.

It is aziridinylbenzoquinone-based, and may have potential antineoplastic activity. ^[1]

It is an alkylating agent. It can react with DNA to form intrastrand crosslinks. It is a member of aziridines as well. ^[2]

References

[edit]

^ PubChem. "Triaziquone". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-10.
^ Huang CH, Kuo HS, Liu JW, Lin YL (June 2009). "Synthesis and antitumor evaluation of novel bis-triaziquone derivatives". Molecules (Basel, Switzerland). 14 (7): 2306–16. doi:10.3390/molecules14072306. PMC 6255275. PMID 19633605.

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule 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 Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine^#) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine^# Mitozolomide^§ Temozolomide)
Intercalation	Streptomyces (Dactinomycin^# Bleomycin^# (Pingyangmycin) Ixabepilone Mitomycin Plicamycin Utidelone)

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) KRAS (Adagrasib Garsorasib Sotorasib)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Cell therapy and Gene therapy	Axicabtagene ciloleucel Brexucabtagene autoleucel Ciltacabtagene autoleucel Idecabtagene vicleucel Lisocabtagene maraleucel Lifileucel Nadofaragene firadenovec Obecabtagene autoleucel Sitimagene ceradenovec Tabelecleucel Talimogene laherparepvec
Other/ungrouped	Aflibercept Arsenic trioxide^# (Realgar/Indigo naturalis^#) Asparagine depleters (Asparaginase^#/Pegaspargase) Belzutifan Bexarotene Calaspargase pegol Celecoxib Darinaparsin Demecolcine Denileukin diftitox Eflornithine Elesclomol^§ Elsamitrucin Epacadostat Eribulin Estramustine Glasdegib Idroxioleic acid Imetelstat Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Navitoclax Nirogacestat Oblimersen^† Omacetaxine mepesuccinate Para-toluenesulfonamide Pelabresib Plitidepsin Retinoids (Alitretinoin Tretinoin^#) Selinexor Tagraxofusp 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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References