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MedKoo Cat#: 100734 | Name: Pirarubicin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pirarubicin 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 Structure

Pirarubicin
Pirarubicin
CAS#72496-41-4 (free base)

Theoretical Analysis

MedKoo Cat#: 100734

Name: Pirarubicin

CAS#: 72496-41-4 (free base)

Chemical Formula: C32H37NO12

Exact Mass: 627.2316

Molecular Weight: 627.64

Elemental Analysis: C, 61.24; H, 5.94; N, 2.23; O, 30.59

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,250.00 2 Weeks
500mg USD 2,650.00 2 Weeks
1g USD 3,450.00 2 Weeks
2g USD 6,250.00 2 Weeks
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Related CAS #
95343-20-7 (HCl); 72496-41-4 (free base)
Synonym
Tepirubicin; Tetrahydropyranyl-Doxorubicin; THP-Adriamycin; THP-Doxorubicin. brand names: Pinorubicin; Theprubicine; Therarubicin. THPADM; THPDOX. 1609RB.
IUPAC/Chemical Name
(8S,10S)-10-(((2R,4S,5S,6S)-4-amino-6-methyl-5-(((S)-tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
InChi Key
KMSKQZKKOZQFFG-HSUXVGOQSA-N
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
SMILES Code
O=C1C2=C(O)C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@H]4C[C@H](N)[C@H](O[C@H]5CCCCO5)[C@H](C)O4)=C3C(O)=C2C(C6=C1C=CC=C6OC)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
P irarubicin 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. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).  
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pirarubicin is an anthracycline antibiotics and acts as a topoisomerase II inhibitor.
In vitro activity:
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. This study 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. Reference: Biochem Biophys Res Commun. 2015 May 1;460(2):380-5. https://pubmed.ncbi.nlm.nih.gov/25791481/
In vivo activity:
This study investigated the potential efficacy of pirarubicin (THP) in modulating rabbit conjunctival fibrosis both in vitro and in vivo and characterized the underlying mechanisms. All modeled rabbits developed conjunctival fibro-vascular lesions, which were similar to human recurrent pterygium (HRP). Both THP and MMC inhibited RCF proliferation and arrested cell cycle at the G0/G1 phase. In particular, 7.5 μmol/L THP remarkably promoted RCF autophagy by upregulating the levels of Beclin 1, Atg 5/12 conjugate, and LC3B, whereas, 15 μmol/L THP significantly triggered a cascade of mitochondrial-associated RCF apoptosis. THP induced the production of ROS and enhanced the chemoattraction of macrophages by RCF. Similar to 600 μmol/L MMC, both 7.5 μmol/L and 15 μmol/L THP attenuated postoperative conjunctival fibrosis in the models; 7.5 μmol/L THP preferentially enhanced autophagy while causing fewer side effects. THP at the dose of 7.5 μmol/L prevented postoperative conjunctival fibrosis in an animal model. Reference: Exp Eye Res. 2020 Nov;200:108215. https://pubmed.ncbi.nlm.nih.gov/32896532/
Solvent mg/mL mM
Solubility
DMF 5.0 7.97
DMSO 40.0 63.73
Ethanol 2.0 3.19
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 627.64 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Zhou X, Gan L, Liu J, Xie X, Wang T, Xiong J. Pirarubicin reduces USP22 expression by inhibiting CREB-1 phosphorylation in HeLa cells. Exp Ther Med. 2019 May;17(5):4230-4236. doi: 10.3892/etm.2019.7447. Epub 2019 Mar 27. PMID: 31007754; PMCID: PMC6468931. 2. Li K, Chen X, Liu C, Gu P, Li Z, Wu S, Xu K, Lin T, Huang J. 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. doi: 10.1016/j.bbrc.2015.03.042. Epub 2015 Mar 17. PMID: 25791481. 3. Duan L, Tang H, Lan Y, Shi H, Pu P, He Q. Ring finger protein 10 improves pirarubicin-induced cardiac inflammation by regulating the AP-1/Meox2 signaling pathway. Toxicol Appl Pharmacol. 2023 Mar 1;462:116411. doi: 10.1016/j.taap.2023.116411. Epub 2023 Feb 3. PMID: 36740146. 4. Xu LJ, Rong SS, Xu YS, Zheng LB, Qiu WY, Zhang X, Jiang LJ, Duan RP, Tian T, Yao YF. Anti-fibrosis potential of pirarubicin via inducing apoptotic and autophagic cell death in rabbit conjunctiva. Exp Eye Res. 2020 Nov;200:108215. doi: 10.1016/j.exer.2020.108215. Epub 2020 Sep 5. PMID: 32896532.
In vitro protocol:
1. Zhou X, Gan L, Liu J, Xie X, Wang T, Xiong J. Pirarubicin reduces USP22 expression by inhibiting CREB-1 phosphorylation in HeLa cells. Exp Ther Med. 2019 May;17(5):4230-4236. doi: 10.3892/etm.2019.7447. Epub 2019 Mar 27. PMID: 31007754; PMCID: PMC6468931. 2. Li K, Chen X, Liu C, Gu P, Li Z, Wu S, Xu K, Lin T, Huang J. 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. doi: 10.1016/j.bbrc.2015.03.042. Epub 2015 Mar 17. PMID: 25791481.
In vivo protocol:
1. Duan L, Tang H, Lan Y, Shi H, Pu P, He Q. Ring finger protein 10 improves pirarubicin-induced cardiac inflammation by regulating the AP-1/Meox2 signaling pathway. Toxicol Appl Pharmacol. 2023 Mar 1;462:116411. doi: 10.1016/j.taap.2023.116411. Epub 2023 Feb 3. PMID: 36740146. 2. Xu LJ, Rong SS, Xu YS, Zheng LB, Qiu WY, Zhang X, Jiang LJ, Duan RP, Tian T, Yao YF. Anti-fibrosis potential of pirarubicin via inducing apoptotic and autophagic cell death in rabbit conjunctiva. Exp Eye Res. 2020 Nov;200:108215. doi: 10.1016/j.exer.2020.108215. Epub 2020 Sep 5. PMID: 32896532.
1: Pan C, Jiang D, Huang J, Xu Z, Yang D, Xue F, Huang Z, Xiao L, Zhou S, Yu Z. A sarcomatoid malignancy originating in the right cervical lymph nodes with atypical pathological characteristics: a case report of an incidental finding. AME Case Rep. 2024 Jun 5;8:71. doi: 10.21037/acr-23-147. PMID: 39091555; PMCID: PMC11292068. 2: Liu X, Li X, Ma J, Zhang J, Zhu Y. [Patient-derived renal pelvic carcinoma organoids: establishment and sensitivity to chemotherapeutic drugs]. Sheng Wu Gong Cheng Xue Bao. 2024 Jul 25;40(7):2211-2222. Chinese. doi: 10.13345/j.cjb.230796. PMID: 39044585. 3: Xie S, Sun Y, Zhao X, Xiao Y, Zhou F, Lin L, Wang W, Lin B, Wang Z, Fang Z, Wang L, Zhang Y. An update of the molecular mechanisms underlying anthracycline induced cardiotoxicity. Front Pharmacol. 2024 Jun 26;15:1406247. doi: 10.3389/fphar.2024.1406247. PMID: 38989148; PMCID: PMC11234178. 4: Li Y, Zhang L, Zheng G, Li J, Ma Z, Jia X, Chen Y. Myxoinflammatory fibroblastic sarcoma of the liver: Case report and literature review. Medicine (Baltimore). 2024 Jul 5;103(27):e38796. doi: 10.1097/MD.0000000000038796. PMID: 38968455; PMCID: PMC11224870. 5: He H, He M, Wang Y, Xiong H, Xiong Y, Shan M, Liu D, Guo Z, Kou Y, Zhang Y, Yang M, Lian J, Sun L, He F. Berberine increases the killing effect of pirarubicin on HCC cells by inhibiting ATG4B-autophagy pathway. Exp Cell Res. 2024 Jun 1;439(1):114094. doi: 10.1016/j.yexcr.2024.114094. Epub 2024 May 13. PMID: 38750718. 6: Zhang F, Wei D, Xie S, Ren L, Qiao S, Li L, Ji J, Fan Z. Erratum: CircZCCHC2 decreases pirarubicin sensitivity and promotes triple-negative breast cancer development via the miR-1200/TPR axis. iScience. 2024 Apr 25;27(5):109786. doi: 10.1016/j.isci.2024.109786. Erratum for: iScience. 2024 Jan 26;27(3):109057. doi: 10.1016/j.isci.2024.109057. PMID: 38706852; PMCID: PMC11068616. 7: Lin HL, Zheng QQ, Huang RL, Hu R, Liu XD, Wang JY. Exploration of treatment in childhood Langerhans cell histiocytosis based on inflammatory and malignant symptoms: a pilot study. Orphanet J Rare Dis. 2024 Apr 23;19(1):174. doi: 10.1186/s13023-024-03151-8. PMID: 38654381; PMCID: PMC11040991. 8: He X, Liang D, Zhou J, Li K, Xie B, Liang C, Liu C, Chen Z, Chen X, Long A, Zhuo S, Su X, Luo Y, Chen W, Zhao F, Jiang X. Nucleus-targeting DNase I self- assembly delivery system guided by pirarubicin for programmed multi-drugs release and combined anticancer therapy. Int J Biol Macromol. 2024 May;267(Pt 2):131514. doi: 10.1016/j.ijbiomac.2024.131514. Epub 2024 Apr 10. PMID: 38608986. 9: Yoneda A, Shichino H, Hishiki T, Matsumoto K, Ohira M, Kamijo T, Kuroda T, Soejima T, Nakazawa A, Takimoto T, Yokota I, Teramukai S, Takahashi H, Fukushima T, Hara J, Kaneko M, Ikeda H, Tajiri T, Mugishima H, Nakagawara A. A nationwide phase II study of delayed local treatment for children with high-risk neuroblastoma: The Japan Children's Cancer Group Neuroblastoma Committee Trial JN-H-11. Pediatr Blood Cancer. 2024 Jun;71(6):e30976. doi: 10.1002/pbc.30976. Epub 2024 Apr 5. PMID: 38577760. 10: Wang L, Ma J, Chen C, Lin B, Xie S, Yang W, Qian J, Zhang Y. Isoquercitrin alleviates pirarubicin-induced cardiotoxicity in vivo and in vitro by inhibiting apoptosis through Phlpp1/AKT/Bcl-2 signaling pathway. Front Pharmacol. 2024 Mar 18;15:1315001. doi: 10.3389/fphar.2024.1315001. PMID: 38562460; PMCID: PMC10982373. 11: Hirakata M, Tomikawa E, Sakai C, Uchida M, Okano T, Shimozono R, Kawai M, Itaba S, Munakata L, Suzuki R, Oshida K. TXB-001, a newly-developed polymer- conjugated anthracycline: Significantly lower adverse effects in animal models of alopecia and hand-foot syndrome. Toxicol Appl Pharmacol. 2024 Apr;485:116912. doi: 10.1016/j.taap.2024.116912. Epub 2024 Mar 22. PMID: 38521368. 12: Lan Y, Tian F, Tang H, Pu P, He Q, Duan L. Food therapy of scutellarein ameliorates pirarubicin‑induced cardiotoxicity in rats by inhibiting apoptosis and ferroptosis through regulation of NOX2‑induced oxidative stress. Mol Med Rep. 2024 May;29(5):84. doi: 10.3892/mmr.2024.13208. Epub 2024 Mar 22. PMID: 38516760; PMCID: PMC10979251. 13: Nakashima S, Ohara S, Imai Y, Nakano H, Uchida T, Inoue M, Hagihara M. [Diffuse large B-cell lymphoma concurrent with Kaposi's sarcoma in the same lymph node in a human immunodeficiency virus-negative patient]. Rinsho Ketsueki. 2024;65(2):74-77. Japanese. doi: 10.11406/rinketsu.65.74. PMID: 38448001. 14: Shi G, Wang L, Peng G, An X, Lu X, Wu H, Li Y. Misdiagnosis of eosinophilic cystitis: A case report and literature review. Medicine (Baltimore). 2024 Feb 16;103(7):e36668. doi: 10.1097/MD.0000000000036668. PMID: 38363913; PMCID: PMC10869055. 15: Zhang F, Wei D, Xie S, Ren L, Qiao S, Li L, Ji J, Fan Z. CircZCCHC2 decreases pirarubicin sensitivity and promotes triple-negative breast cancer development via the miR-1200/TPR axis. iScience. 2024 Jan 26;27(3):109057. doi: 10.1016/j.isci.2024.109057. Erratum in: iScience. 2024 Apr 25;27(5):109786. doi: 10.1016/j.isci.2024.109786. PMID: 38361605; PMCID: PMC10867422. 16: Wu M, Zhang W, Zhou X, Wang Z, Li S, Guo C, Yang Y, Zhang R, Zhang Z, Sun X, Gong T. An in situ forming gel co-loaded with pirarubicin and celecoxib inhibits postoperative recurrence and metastasis of breast cancer. Int J Pharm. 2024 Mar 25;653:123897. doi: 10.1016/j.ijpharm.2024.123897. Epub 2024 Feb 14. PMID: 38360289. 17: Xu Y, Sun G, Yang T, Li H, Hu P, Luo W, Zhang T, Liu H, Chen G, Ye Z, Wu Y, Yu J, Chen W, Zhao K, Liu C, Zhang H. Validation of hyperthermia as an enhancer of chemotherapeutic efficacy: insights from a bladder cancer organoid model. Int J Hyperthermia. 2024;41(1):2316085. doi: 10.1080/02656736.2024.2316085. Epub 2024 Feb 12. PMID: 38346911. 18: Hasegawa T, Tsukigawa K, Commey K, Sakuragi M, Imoto S, Taguchi K, Nishi K, Otagiri M, Yamasaki K. Preparation and in Vitro Characterization of Fatty-Acid Modified Pirarubicin Nanosuspensions Stabilized by Albumin. Chem Pharm Bull (Tokyo). 2024;72(1):21-27. doi: 10.1248/cpb.c23-00701. PMID: 38171901. 19: Refugia J, Tsivian M. Single instillation intravesical chemotherapy after radical nephroureterectomy for upper tract urothelial carcinoma: current evidence and future directions. Transl Androl Urol. 2023 Nov 30;12(11):1753-1760. doi: 10.21037/tau-23-236. Epub 2023 Nov 9. PMID: 38106679; PMCID: PMC10719762. 20: Guo C, Wu M, Guo Z, Zhang R, Wang Z, Peng X, Dong J, Sun X, Zhang Z, Xiao P, Gong T. Hypoxia-Responsive Golgi-Targeted Prodrug Assembled with Anthracycline for Improved Antitumor and Antimetastasis Efficacy. ACS Nano. 2023 Dec 26;17(24):24972-24987. doi: 10.1021/acsnano.3c07183. Epub 2023 Dec 13. PMID: 38093174.

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