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Purity: ≥98%
Pirarubicin (THP; THPADM; THPDOX; 1609RB; THP-Adriamycin; THP-Doxorubicin; Pinorubicin; Theprubicine; Therarubicin) is an analog of anthracycline with potential antitumor activity. It has been used as a topoisomerase II inhibitor to treat a number of cancers.
| Targets |
Topoisomerase II
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| ln Vitro |
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| Enzyme Assay |
Pirarubicin is widely used in intravesical chemotherapy for bladder cancer, but its efficacy is limited due to drug resistance; the mechanism has not been well studied. Emerging evidence shows that autophagy can be a novel target for cancer therapy. This study aimed to investigate the role of autophagy in pirarubicin-treated bladder cancer cells. Bladder cancer cells EJ and J82 were treated with pirarubicin, siRNA, 3-methyladenine or hydroxychloroquine. Cell proliferation and apoptosis were tested by cell survival assay and flow cytometric analysis, respectively. Autophagy was evaluated by immunoblotting before and after the treatments. The phosphorylated mammalian target of rapamycin, serine/threonine kinase p70 S6 kinase, and eukaryotic translation initiation factor 4E binding protein 1 were also investigated by immunoblotting. We found that pirarubicin could induce autophagy in bladder cancer cells. Inhibition of autophagy by 3-methyladenine, hydroxychloroquine or knockdown of autophagy related gene 3 significantly increased apoptosis in pirarubicin-treated bladder cancer cells. Pirarubicin-induced autophagy was mediated via the mTOR/p70S6K/4E-BP1 signaling pathway. In conclusion, autophagy induced by pirarubicin plays a cytoprotective role in bladder cancer cells, suggesting that inhibition of autophagy may improve efficacy over traditional pirarubicin chemotherapy in bladder cancer patients[3].
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| Cell Assay |
Cell survival analysis is done using MTS. In short, 96-well plates are used to plate cells in triplicate, with 2 × 103 cells per well, and the cells are then cultured in growth medium. Following that, cells are exposed to pirarubicin for 24 hours at three different concentrations: 2.5 μg/mL, 5 μg/mL, and 10 μg/mL. Once added, the MTS reagent (5 mg/mL) is incubated for 4 hours at 37°C. A microplate reader is used to measure the absorbance at 490 nm[3].
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| References |
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| Additional Infomation |
(7S,9S)-7-[[(2R,4S,5S,6S)-4-amino-6-methyl-5-[[(2R)-2-oxanyl]oxy]-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione is an anthracycline.
Pirarubicin is 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. (NCI04) |
| Molecular Formula |
C32H37NO12
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|---|---|
| Molecular Weight |
627.64
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| Exact Mass |
627.231
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| Elemental Analysis |
C, 61.24; H, 5.94; N, 2.23; O, 30.59
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| CAS # |
72496-41-4
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| Related CAS # |
95343-20-7
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| PubChem CID |
11296583
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| Appearance |
Pink to red solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
834.7±65.0 °C at 760 mmHg
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| Melting Point |
188-192ºC (dec.)
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| Flash Point |
458.6±34.3 °C
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| Vapour Pressure |
0.0±3.2 mmHg at 25°C
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| Index of Refraction |
1.671
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| LogP |
3.85
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
13
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
45
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| Complexity |
1120
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| Defined Atom Stereocenter Count |
7
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| 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
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| InChi Key |
KMSKQZKKOZQFFG-YXRRJAAWSA-N
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| InChi Code |
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
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| Chemical 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
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| Synonyms |
THP; THPADM; THPDOX; 1609RB; Tepirubicin; Tetrahydropyranyl-Doxorubicin; THP-Adriamycin; THP-Doxorubicin; brand names: Pinorubicin; Theprubicine; THP-ADM; Adriamycin, tetrahydropyranyl; 4'-O-Tetrahydropyranyladriamycin; DTXSID2046755; D58G680W0G; Therarubicin
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). This product is not stable in solution, please use freshly prepared working solution for optimal results. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5933 mL | 7.9664 mL | 15.9327 mL | |
| 5 mM | 0.3187 mL | 1.5933 mL | 3.1865 mL | |
| 10 mM | 0.1593 mL | 0.7966 mL | 1.5933 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05287308 | Not yet recruiting | Drug: pirarubicin Drug: epirubicin |
Breast Cancer | Chinese Academy of Medical Sciences |
March 2022 | Not Applicable |
| NCT04437160 | Recruiting | Drug: Epirubicin or Pirarubicin Drug: Cyclophosphamide |
Triple Negative Breast Cancer | Chinese Academy of Medical Sciences |
February 1, 2020 | Phase 2 |
| NCT02613026 | Completed | Drug: Pirarubicin Drug: Docetaxel |
Breast Neoplasms | 307 Hospital of PLA | July 2009 | Phase 3 |
| NCT03342300 | Withdrawn | Drug: pegylated liposomal doxorubicin Drug: pirarubicin |
Overall Survival Toxicity |
Peking University People's Hospital |
November 6, 2017 | Phase 2 Phase 3 |
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