Structure via PubChem · Public domain (PubChem)
pirarubicin
Sign in to saveAlso known as pinorubicin, therarubicin, THP-adriamycin
Pirarubicin (INN) is an anthracycline drug. An analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines.
Chemical data
- Formula
- C32H37NO12
- Molecular weight
- 627.6 g/mol
- IUPAC name
- (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2S)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
- SMILES
- C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O[C@H]6CCCCO6
- InChIKey
- KMSKQZKKOZQFFG-HSUXVGOQSA-N
- XLogP
- 2.7
- Polar surface area
- 204 Ų
- H-bond donors
- 5
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Research
1,262 papers- Simultaneous quantification of pirarubicin, doxorubicin, cyclophosphamide, and vincristine in human plasma of patients with non-Hodgkin's lymphoma by LC-MS/MS method.Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · 2023
- [Pirarubicin (THP-adriamycin)].Gan to kagaku ryoho. Cancer & chemotherapy · 1988
- Adenylate cyclase 1 knockdown attenuates pirarubicin-induced cardiotoxicity.Clinical and experimental pharmacology & physiology · 2024
- Pirarubicin combined with TLR3 or TLR4 agonists enhances anti-tumor efficiency.International immunopharmacology · 2024
- Astaxanthin protects against pirarubicin-induced H9c2 cardiomyocytes by adjusting microRNA-494-3p-mediated MDM4/p53 signalling pathway.The Journal of pharmacy and pharmacology · 2023
via PubMed
Wikidata facts
- Mass
- 627.2315756239999
- Has use
- medication
Show 5 more facts
- chemical formula
- C₃₂H₃₇NO₁₂
- subject has role
- antineoplastic
- isomeric SMILES
- COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O[C@H]2CCCCO2)[C@H](C)O1
- canonical SMILES
- COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)CC(O)(C(=O)CO)CC3OC1CC(N)C(OC2CCCCO2)C(C)O1
- stereoisomer of
- pirarubicin
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Pirarubicin (INN) is an anthracycline drug. An analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines.
== References ==
Excerpted from Wikipedia’s “pirarubicin” article, available under the CC BY-SA 4.0 licence.
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