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Pirarubicin

CAT: 0804-HY-13725-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-13725-01Size:5 mg
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Description
Pirarubicin is an anthracycline antibiotics, acts as a topoisomerase II inhibitor, and is a widely used for treatment of various cancers, in particular, solid tumors.
CAS Number
72496-41-4
Product Name Alternative
THP
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Antibiotic; Autophagy; Bacterial; Topoisomerase
Type
Reference compound
Related Pathways
Anti-infection; Autophagy; Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/Pirarubicin.html
Purity
99.61
Solubility
DMSO : 10 mg/mL (ultrasonic; warming; heat to 80°C)
Smiles
O=C1C2=C(C=CC=C2OC)C(C3=C(O)C4=C([C@@H](O[C@@]5([H])C[C@H](N)[C@H](O[C@@]6([H])OCCCC6)[C@H](C)O5)C[C@@](C(CO)=O)(O)C4)C(O)=C31)=O
Molecular Formula
C32H37NO12
Molecular Weight
627.64
Precautions
H302, H315, H319, H335
References & Citations
[1]Takigawa N, et al. Cytotoxic effect of topoisomerase II inhibitors against adriamycin- and etoposide-resistant small cell lung cancer sublines. Gan To Kagaku Ryoho. 1993 May;20 (7) :929-35.|[2]Nagai K, et al. Relationships between the in vitro cytotoxicity and transport characteristics of pirarubicin and doxorubicin in M5076 ovarian sarcoma cells, and comparison with those in Ehrlich ascites carcinoma cells. Cancer Chemother Pharmacol. 2002 Mar;49 (3) :244-50. Epub 2002 Jan 8.|[3]Li K, et al. Pirarubicin induces an autophagic cytoprotective response through suppression of the mammalian target of rapamycin signaling pathway in human bladder cancer cells. Biochem Biophys Res Commun. 2015 May 1;460 (2) :380-5.|[4]Wang YD, et al. Cardioprotective effects of rutin in rats exposed to pirarubicin toxicity. J Asian Nat Prod Res. 2017 Oct 27:1-13.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
Topo II
Citation 01
Biol Methods Protoc. 2025 Feb 13;10 (1) :bpaf012.|Biomolecules. 2025 Jul 6.|Cancers (Basel) . 2023 Apr 26;15 (9) :2487.|E3S Web of Conferences. 233, 02010 (2021) .|EMBO Mol Med. 2025 Nov 26.|Genomics. 2022 Jan;114 (1) :125-137.|Int J Biol Macromol. 2024 Apr 10;267 (Pt 2) :131514.|Int J Cancer. 2024 Jul 15;155 (2) :324-338.|Int J Hyperthermia. 2024 Feb 12;41 (1) :2316085.|Int J Mol Med. 2023 Jul;52 (1) :55.|Int J Mol Sci. 2025 Oct 20;26 (20) :10189.|Integr Cancer Ther. 2025 Jan-Dec:24:15347354251368410.|J Mol Med (Berl) . 2019 Aug;97 (8) :1183-1193.|Mol Med Rep. 2024 May;29 (5) :84.|Nanoscale Horiz. 2025 Jun 23;10 (7) :1465-1477.|Nanoscale. 2024 Nov 7;16 (43) :20131-20146.|Toxicol Appl Pharmacol. 2023 Mar 1:462:116411.|AAPS PharmSciTech. 2024 Sep 7;25 (7) :211.|Cancer Drug Resist. 2020 Sep 4;3 (4) :947-958.|Heliyon. 2022 Jun 8;8 (6) :e09643.|Int J Pharm. 2022 May 25;620:121761.|J Mol Liq. 2020, 114633.|J Mol Liq. 2023 Jun 12, 122324.|University of Paris. 2022 Sep 19.

Chemical Information

Pirarubicin

Pirarubicin is an anthracycline that is doxorubicin in which the hydroxy group at position 4' is replaced by a (2R)-tetrahydro-2H-pyran-2-yloxy group. It has a role as an antineoplastic agent and a cardiotoxic agent. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a member of p-quinones, a deoxy hexoside, a member of oxanes, an aminoglycoside, an anthracycline, a member of tetracenequinones and a monosaccharide derivative. It is functionally related to a doxorubicin.

CAS Number72496-41-4
PubChem CID11296583
IUPAC Name(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
Molecular FormulaC32H37NO12
Molecular Weight627.6
XLogP2.7
Topological Polar Surface Area204
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count13
Rotatable Bond Count7
Heavy Atom Count45
Formal Charge0
Complexity1120
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
InChI
InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1
InChIKey
KMSKQZKKOZQFFG-YXRRJAAWSA-N
Chemical Structure
2D Structure
2D structure of Pirarubicin
CAS: 72496-41-4
CID: 11296583
Formula: C32H37NO12
MW: 627.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight627.6
XLogP32.7
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count13
Rotatable Bond Count7
Exact Mass627.23157562
Monoisotopic Mass627.23157562
Topological Polar Surface Area204 Ų
Heavy Atom Count45
Formal Charge0
Complexity1120
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
286965-01Pirarubicin

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