Pirarubicin hydrochloride
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| Category | Bioactive by-products |
| Catalog number | BBF-04072 |
| CAS | 95343-20-7 |
| Molecular Weight | 664.10 |
| Molecular Formula | C32H38ClNO12 |
| Purity | >98% |
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Description
Pirarubicin Hydrochloride is an analogue of the anthracycline anti-neoplastic doxorubicin, which is an inhibitor of Topo II. It intercalates into DNA and interacts with topoisomerase II, thereby inhibiting replication and repair of DNA and RNA, and protein synthesis. It is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines.
Specification
| Related CAS | 72496-41-4 (free base) |
| Synonyms | THP Hydrochloride |
| Storage | Store at -20°C, Under Inert Atmosphere |
| 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;hydrochloride |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)OC6CCCCO6.Cl |
| InChI | InChI=1S/C32H37NO12.ClH/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;1H/t14-,17-,19-,21-,22-,31+,32-;/m0./s1 |
| InChI Key | ZPHYPKKFSHAVOE-QXTSSQDCSA-N |
Properties
| Application | Antineoplastic Agents |
| Boiling Point | 834.7°C at 760 mmHg |
| Solubility | Soluble in DMSO |
Reference Reading
1.pH-Responsive Polymer Conjugate of Pirarubicin With Styrene Maleic Acid Copolymer as a Potential Therapeutic for Ovarian Cancer.
Liu L1, Sun J2, Yin H3, Fang J4, Jin X5. J Pharm Sci. 2016 May;105(5):1595-602. doi: 10.1016/j.xphs.2016.02.025. Epub 2016 Mar 25.
Previous studies indicated the potential of styrene maleic acid copolymer (SMA)-conjugated pirarubicin (4'-O-tetrahydropyranyldoxorubicin [THP]) for targeted anticancer therapy based on the enhanced permeability and retention effect. In this study, to achieve further improved therapeutic efficacy, a pH-responsive SMA-conjugated THP-containing hydrazone bond (SMA-hyd-THP) was synthesized and evaluated in vitro and ex vivo using human ovarian cancer cells and tissues. SMA-hyd-THP showed good water solubility, forming micelles with a mean particle size of 48.0 nm, which is applicable for enhanced permeability and retention-based tumor accumulation. The THP loading in this preparation was 15% (wt/wt), and release rate of free THP from SMA-hyd-THP at physiological pH (7.4) was approximately 10% in 72 h. However, it increased rapidly at pH 6.5 (42%) and 5.5 (83%), which indicates that tumor environment of weak acidic condition (pH 6.5-6.9) is favorable for release of THP.
2.Targeting the MIR34C-5p-ATG4B-autophagy axis enhances the sensitivity of cervical cancer cells to pirarubicin.
Wu Y1, Ni Z1, Yan X1, Dai X2, Hu C3, Zheng Y4, He F1, Lian J1. Autophagy. 2016 Apr 20:0. [Epub ahead of print]
Pirarubicin (THP) is a newer generation anthracycline anticancer drug. In the clinic, THP and THP-based combination therapies have been demonstrated to be effective against various tumors without severe side effects. However, previous clinical studies have shown that most patients with cervical cancer are not sensitive to THP treatment, and the associated mechanisms are not clear. Consistent with the clinical study, we confirmed that cervical cancer cells were resistant to THP in vitro and in vivo. Our data demonstrated that THP induced a protective macroautophagy/autophagy response in cervical cancer cells, and suppression of this autophagy dramatically enhanced the cytotoxicity of THP. By scanning the mRNA level change of autophagy-related genes, we found that the upregulation of ATG4B (autophagy-related 4B cysteine peptidase) plays an important role in THP-induced autophagy. Moreover, THP increased the mRNA level of ATG4B in cervical cancer cells by promoting mRNA stability without influencing its transcription.
3.Synchronous bilateral primary breast malignant phyllodes tumor and carcinoma of the breast with Paget's disease: a case report and review of the literature.
Zhao H1, Cheng X1, Sun S1, Yang W1, Kong F1, Zeng F1. Int J Clin Exp Med. 2015 Oct 15;8(10):17839-41. eCollection 2015.
Synchronous bilateral primary breast malignant phyllodes tumor or/and carcinoma of the breast with Paget's disease is rare. In the article, we present a case of bilateral carcinoma of the breast with Paget's disease of the right breast and malignant phyllodes tumor of the left breast. A 44-years-old Chinese woman presented with a 1 month history of the right breast nipple with eczema and fester and growing and palpable mass of left breast. Molybdenum target X-ray revealed microcalcification in the right breast, which was highly suspected of malignant tumor, and round-like mass with smooth surface and homogeneous density in the left breast. Color ultrasound showed a lobulated lump which circumferential blood flows around in the left breast, and which did not show any mass in the right breast. The patient was undertaken the bilateral modified radical mastectomy. The histological diagnosis was Paget's disease associated with infiltrating ductal carcinoma in the right breast and malignant phyllodes tumor the left breast.
4.[Life-Threatening Hyponatremia by Chemotherapy in a Patient with Non-Hodgkin's Lymphoma].
Morikawa G1, Kinjo T, Hanaoka Y, Kiyono T, Okazawa K, Dan K. Gan To Kagaku Ryoho. 2015 Dec;42(13):2493-6.
Cyclophosphamide and vincristine are known to be the chemotherapeutic agents most frequently associated with hyponatremia. Here, we report the case of a 69-year-old man with non-Hodgkin's lymphoma who developed severe hyponatremia during chemotherapy. The Japanese man was diagnosed with diffuse large B-cell lymphoma, and underwent chemotherapy treatment with THP-COP (cyclophosphamide, pirarubicin, vincristine, and prednisolone). In the first course of chemotherapy, he developed hyponatremia (nadir 109 mEq/L) and his urinary N-acetyl-β-D-glucosaminidase (NAG) level had increased. After the second courses of chemotherapy with rituximab, pirarubicin, and prednisolone, without cyclophosphamide and vincristine, he had developed light hyponatremia (nadir 130 mEq/L). However, after the third and fourth courses of chemotherapy with rituximab, pirarubicin, prednisolone, and cyclophosphamide, he had developed a medium level of hyponatremia (nadir 124-125 mEq/L) and his NAG level had increased further.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
