Pirarubicin
Pirarubicin structure
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Common Name | Pirarubicin | ||
|---|---|---|---|---|
| CAS Number | 72496-41-4 | Molecular Weight | 627.636 | |
| Density | 1.5±0.1 g/cm3 | Boiling Point | 834.7±65.0 °C at 760 mmHg | |
| Molecular Formula | C32H37NO12 | Melting Point | 188-192ºC (dec.) | |
| MSDS | Chinese USA | Flash Point | 458.6±34.3 °C | |
Use of PirarubicinPirarubicin is an anthracycline antibiotics, acts as a topoisomerase II inhibitor, and is a widely used for treatment of various cancers, in particular, solid tumors. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | Pirarubicin |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| 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. |
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| Related Catalog | |
| Target |
Topoisomerase II |
| In Vitro | Pirarubicin is a topoisomerase II inhibitor[1]. Pirarubicin shows inhibitory activities against M5076 and Ehrlich cells, with IC50s of 0.366 and 0.078 μM, respectively. The cytotoxicity of Pirarubicin toward M5076 cells is lower than toward Ehrlich cells, and this is due to the much lower expression of topoisomerase II in M5076 cells than in Ehrlich cells[2]. Pirarubicin (2.5, 5, 10 μg/mL) significantly induces autophagy in a dose dependent manner in bladder cancer (T24, EJ, 5637, J82 and UM-UC-3) cells. Furthmore, Pirarubicin (5 μg/mL) induces apoptosis through inhibition of mTOR/p70S6K/4E-BP1 in bladder cancer cells, and this effect is enhanced by inhibition of autophagy[3]. |
| In Vivo | Pirarubicin (18 mg/kg, i.v.) significantly elevates serum level of BNP, CK-MB, CTnT, LDH, and MDA compared with those in the control group in acute cardiac toxicity rats. Pirarubicin also lowers heart rate, and depresses R-wave voltage, and prolongation of QT intervals in the acute cardiac toxicity model[4]. |
| Cell Assay | MTS is used to analyze cell survival. Briefly, cells are plated in 96-well plates in triplicate at 2 × 103 cells per well and cultured in growth medium. Then cells are treated with pirarubicin at different concentrations (2.5 μg/mL, 5 μg/mL, 10 μg/mL) for 24 h. MTS reagent (5 mg/mL) is added and incubated at 37°C for 4 h. The absorbance is monitored at 490 nm using a microplate reader[3]. |
| Animal Admin | An acute cardiac toxicity model is established by a single dose of 18 mg/kg pirarubicin through the caudal vein injection. Thirty-six rats are randomized equally to six groups: normal control, cardiac injury (THP) model, dexrazoxane (180 mg/kg), low-dose rutin (25 mg/kg), middle-dose rutin (50 mg/kg), and high-dose rutin (100 mg/kg). Rats in the rutin-treated group are administered different doses of rutin and CMC-Na for 7 days by gavage and a single dose of 18 mg/kg pirarubicin through caudal vein injection. Rats in the dexrazoxane-treated group receive sodium carboxymethylcellulose (CMC-Na) by gavage for six days. 40 mg/kg dexrazoxane is then administered to rats by intraperitoneal injection and 18 mg/kg pirarubicin is administered by caudal vein injection on day 7. Rats in the THP model group receive CMC-Na by gavage for seven days, followed by pirarubicin 18 mg/kg through the caudal vein injection on day 7. Rats in the normal control group receive CMC-Na by gavage for seven days, followed by saline through caudal vein injection on day 7[4]. |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Density | 1.5±0.1 g/cm3 |
|---|---|
| Boiling Point | 834.7±65.0 °C at 760 mmHg |
| Melting Point | 188-192ºC (dec.) |
| Molecular Formula | C32H37NO12 |
| Molecular Weight | 627.636 |
| Flash Point | 458.6±34.3 °C |
| Exact Mass | 627.231567 |
| PSA | 204.30000 |
| LogP | 3.85 |
| Vapour Pressure | 0.0±3.2 mmHg at 25°C |
| Index of Refraction | 1.671 |
| InChIKey | KMSKQZKKOZQFFG-CBIZWKIZSA-N |
| SMILES | COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)CC(O)(C(=O)CO)CC3OC1CC(N)C(OC2CCCCO2)C(C)O1 |
| Storage condition | 2-8°C |
This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
MUTATION DATA
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This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Hazard Codes | Xi |
|---|---|
| Risk Phrases | 36/37/38 |
| Safety Phrases | S26-S37/39 |
| RIDADR | NONH for all modes of transport |
| RTECS | QI9296000 |
This table lists relevant public references with title, journal and publication metadata for this compound.
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Synthesis and therapeutic effect of styrene-maleic acid copolymer-conjugated pirarubicin.
Cancer Sci. 106(3) , 270-8, (2015) Previously, we prepared a pirarubicin (THP)-encapsulated micellar drug using styrene-maleic acid copolymer (SMA) as the drug carrier, in which active THP was non-covalently encapsulated. We have now d... |
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Co-delivery of Pirarubicin and Paclitaxel by Human Serum Albumin Nanoparticles to Enhance Antitumor Effect and Reduce Systemic Toxicity in Breast Cancers.
Mol. Pharm. 12 , 4085-98, (2015) In our study, we aimed to develop a codelivery nanoparticulate system of pirarubicin (THP) and paclitaxel (PTX) (Co-AN) using human serum albumin to improve the therapeutic effect and reduce systemic ... |
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Porphyrin-adsorbed Allograft Bone: A Photoactive, Antibiofilm Surface.
Clin. Orthop. Relat. Res. 473 , 2865-73, (2015) Allograft bone is commonly used to augment bone stock. Unfortunately, allograft is prone to bacterial contamination and current antimicrobial therapies are inadequate. Photoactivated porphyrins combat... |
This table contains target information, in‑vitro & in‑vivo assay data for this compound.
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| [8S-[8a,10a(S*)]]-10-[[3-Amino-2,3,6-trideoxy-4-O-(tetrahydro-2H-pyran-2-yl)-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione |
| Pinorubicin |
| (1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranoside |
| Therarubicin |
| Tepirubicin |
| 4'-O-Tetrahydropyranyl Doxorubicin |
| Pirabucin |
| (8S,10S)-10-((3-Amino-2,3,6-trideoxy-4-O-(2R-tetrahydro-2H-pyran-2-yl)-α-L-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione |
| THP-Adriamycin |
| MFCD00869742 |
| (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranoside |
| 1609rb |
| (2''R)-4'-O-Tetrahydropyranyladriamycin |
| (8S,10S)-10-[[3-Amino-2,3,6-trideoxy-4-O-(tetrahydro-2H-pyran-2-yl)-a-L-lyxo-hexopyranosyl]oxy]-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,1-naphthacenedione |
| Theprubicin |
| 1609-RB |
| Therarubiein |
| THP-ADM |
| 4'-O-Tetrahydropyranyladriamycin |
| (1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranoside |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What is the LogP of Pirarubicin? |
| A: LogP of Pirarubicin is 3.85. |
| Q: What is the CAS number of Pirarubicin? |
| A: CAS number of Pirarubicin is 72496-41-4. |
| Q: What are the storage conditions for Pirarubicin? |
| A: Storage conditions for Pirarubicin: 2-8°C. |
| Q: What is the molecular formula of Pirarubicin? |
| A: Molecular formula of Pirarubicin is C32H37NO12. |
| Q: What is the melting point of Pirarubicin? |
| A: Melting point of Pirarubicin is 188-192ºC (dec.). |
| Q: What is the molecular weight of Pirarubicin? |
| A: Molecular weight of Pirarubicin is 627.636. |
| Q: What is the polar surface area (PSA) of Pirarubicin? |
| A: Polar surface area (PSA) of Pirarubicin is 204.30000. |
| Q: What is the English name of Pirarubicin? |
| A: The English name of Pirarubicin is Pirarubicin. |
| Q: What is the safety information for Pirarubicin? |
| A: Safety information for Pirarubicin: S26-S37/39. |
| Q: What is the InChIKey of Pirarubicin? |
| A: InChIKey of Pirarubicin is KMSKQZKKOZQFFG-CBIZWKIZSA-N. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| Dayang Chem (Hangzhou) Co., Ltd. |