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MedKoo Cat#: 200135 | Name: Apatinib mesylate
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Description:

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

Rivoceranib, also known as Apatinib and YN-968D1, is an orally bioavailable, small-molecule receptor tyrosine kinase inhibitor with potential antiangiogenic and antineoplastic activities. The free-base form is also known as Rivoceranib. Apatinib selectively binds to and inhibits vascular endothelial growth factor receptor 2, which may inhibit VEGF-stimulated endothelial cell migration and proliferation and decrease tumor microvessel density. In addition, this agent mildly inhibits c-Kit and c-SRC tyrosine kinases.

Chemical Structure

Apatinib mesylate
Apatinib mesylate
CAS#1218779-75-9 (mesylate)

Theoretical Analysis

MedKoo Cat#: 200135

Name: Apatinib mesylate

CAS#: 1218779-75-9 (mesylate)

Chemical Formula: C25H27N5O4S

Exact Mass: 0.0000

Molecular Weight: 493.58

Elemental Analysis: C, 60.83; H, 5.51; N, 14.19; O, 12.97; S, 6.50

Price and Availability

Size Price Availability Quantity
5mg USD 90.00 Ready to ship
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,250.00 Ready to ship
500mg USD 2,650.00 Ready to Ship
1g USD 3,650.00 Ready to Ship
2g USD 6,450.00 Ready to ship
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Related CAS #
1218779-89-5 (HCl) 1218779-75-9 (mesylate) 811803-05-1 (free base)
Synonym
YN-968D1; YN 968D1; YN968D1; Rivoceranib; Apatinib; Apatinib mesylate.
IUPAC/Chemical Name
N-(4-(1-cyanocyclopentyl)phenyl)-2-((pyridin-4-ylmethyl)amino)nicotinamide methanesulfonate
InChi Key
FYJROXRIVQPKRY-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H23N5O.CH4O3S/c25-17-24(11-1-2-12-24)19-5-7-20(8-6-19)29-23(30)21-4-3-13-27-22(21)28-16-18-9-14-26-15-10-18;1-5(2,3)4/h3-10,13-15H,1-2,11-12,16H2,(H,27,28)(H,29,30);1H3,(H,2,3,4)
SMILES Code
O=C(C1=CC=CN=C1NCC2=CC=NC=C2)NC3=CC=C(C4(C#N)CCCC4)C=C3.CS(=O)(O)=O
Appearance
white 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
Related: 1218779-75-9 (Apatinib mesylate salt) 811803-05-1 (Apatinib free base). Apatinib, also known as YN968D1, is a tyrosine kinase inhibitor that selectively inhibits the vascular endothelial growth factor receptor-2 (VEGFR2, also known as KDR). It is an orally bioavailable, small molecule agent which is thought to inhibit angiogenesis in cancer cells; specifically apatinib inhibits VEGF-mediated endothelial cell migration and proliferation thus blocking new blood vessel formation in tumor tissue. This agent also mildly inhibits c-Kit and c-SRC tyrosine kinases.    History of Apatinib: Apatinib was first synthesized by Advenchen Laboratories in California, USA and is being developed by Jiangsu Hengrui Medicine (China), LSK BioPartners (US) and Bukwang Pharmaceutical Company (Korea). It is an investigational cancer drug currently undergoing clinical trials as a potential targeted treatment for metastatic gastric carcinoma, metastatic breast cancer and advanced hepatocellular carcinoma. (source: http://en.wikipedia.org/wiki/Apatinib).   Development status of Apatinib: There is a Phase II/III study recruiting patients in China to determine whether apatinib can improve progression free survival compared with placebo in patients with metastatic gastric carcinoma who have failed two lines of chemotherapy (September, 2009). As of November, 2010, two additional Phase 2 clinical studies have been initiated for apatinib in metastatic triple-negative breast cancer patients and advanced hepatocellular carcinoma. On March 7, 2011, Bukwang announced that it filed an IND to the Korean FDA to begin Human clinical studies of Apatinib in Phase 2.  (source: http://en.wikipedia.org/wiki/Apatinib).    
Biological target:
Apatinib mesylate (YN968D1, Rivoceranib) is a potent inhibitor of the VEGF signaling pathway with IC50 values of 1 nM, 13 nM, 429 nM and 530 nM for VEGFR-2, Ret (c-Ret), c-Kit and c-Src, respectively.
In vitro activity:
To evaluate the role of Apatinib in osteosarcoma cells, flow cytometry was used to analyze the cells after Annexin V-FITC and propidium iodide (PI) staining. Apatinib-induced apoptosis significantly when compared with the control group (Figure 3a). As a key indicator of apoptosis, the level of cleaved-PARP increased after treatment with Apatinib for 48 h, or with 10 μM Apatinib for different time points (Figure 3d). To determine whether Apatinib inhibited cell proliferation by inducing cell-cycle arrest, the distribution of cell cycle in osteosarcoma cells treated with Apatinib was evaluated. As shown in Figure 3b, accumulation of cells by Apatinib resulted in the G0/G1 phase, whereas a corresponding reduction in both KHOS and MG63 cells in the G2/M and S phases. The expression of cyclin D1 decreased after treatment with Apatinib, as analyzed by western blot (Figure 3d). Terminal deoxynucleotidyl transferase-mediated nick-end labeling staining (TUNEL staining) were used to confirm apoptosis. Treatment with Apatinib increased TUNEL-positive cells when compared with the control (Figure 3c). All the data suggest that Apatinib induces apoptosis and G0/G1-phase arrest. Reference: Cell Death Dis. 2017 Aug 24;8(8):e3015. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5596600/
In vivo activity:
Apatinib was valid in tumor growth inhibition in vivo. The tumor volume decreased when compared with the control group (Figures 7a and b). In accordance with the in vitro experiment, Figure 7c shows that Apatinib treatment increased the level of LC3-II and Bax, whereas the level of BCL-2 and VEGFR2 decreased in vivo. Immunohistochemistry showed that Apatinib decreased the expression of VEGFR2, p-STAT3 and BCL-2 in tumors formed by KHOS cells (Figure 7d). All the results revealed that Apatinib inhibited the growth of osteosarcoma in vivo. Reference: Cell Death Dis. 2017 Aug 24;8(8):e3015. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5596600/
Solvent mg/mL mM
Solubility
DMSO 50.0 101.30
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 493.58 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. Liu K, Ren T, Huang Y, Sun K, Bao X, Wang S, Zheng B, Guo W. Apatinib promotes autophagy and apoptosis through VEGFR2/STAT3/BCL-2 signaling in osteosarcoma. Cell Death Dis. 2017 Aug 24;8(8):e3015. doi: 10.1038/cddis.2017.422. PMID: 28837148; PMCID: PMC5596600. 2. Yang C, Qin S. Apatinib targets both tumor and endothelial cells in hepatocellular carcinoma. Cancer Med. 2018 Sep;7(9):4570-4583. doi: 10.1002/cam4.1664. Epub 2018 Aug 14. PMID: 30109780; PMCID: PMC6144148.
In vitro protocol:
1. Liu K, Ren T, Huang Y, Sun K, Bao X, Wang S, Zheng B, Guo W. Apatinib promotes autophagy and apoptosis through VEGFR2/STAT3/BCL-2 signaling in osteosarcoma. Cell Death Dis. 2017 Aug 24;8(8):e3015. doi: 10.1038/cddis.2017.422. PMID: 28837148; PMCID: PMC5596600. 2. Yang C, Qin S. Apatinib targets both tumor and endothelial cells in hepatocellular carcinoma. Cancer Med. 2018 Sep;7(9):4570-4583. doi: 10.1002/cam4.1664. Epub 2018 Aug 14. PMID: 30109780; PMCID: PMC6144148.
In vivo protocol:
1. Liu K, Ren T, Huang Y, Sun K, Bao X, Wang S, Zheng B, Guo W. Apatinib promotes autophagy and apoptosis through VEGFR2/STAT3/BCL-2 signaling in osteosarcoma. Cell Death Dis. 2017 Aug 24;8(8):e3015. doi: 10.1038/cddis.2017.422. PMID: 28837148; PMCID: PMC5596600. 2. Yang C, Qin S. Apatinib targets both tumor and endothelial cells in hepatocellular carcinoma. Cancer Med. 2018 Sep;7(9):4570-4583. doi: 10.1002/cam4.1664. Epub 2018 Aug 14. PMID: 30109780; PMCID: PMC6144148.
1: Pan Z, Luo Z, He H, Chen Y, Zhao B, Yang Z, Li L. Observation of the therapeutic effect of apatinib in advanced platinum-resistant recurrent epithelial ovarian cancer. J Ovarian Res. 2023 Feb 23;16(1):44. doi: 10.1186/s13048-022-01055-4. PMID: 36823642; PMCID: PMC9948331. 2: Ren Y, Wang T, Cheng X, Ke G, Huang Y, Yang H, Huang X, Tian W, Wang H. Efficacy and safety of apatinib in patients with recurrent uterine malignancy: a prospective, single-center, single-arm, phase 2 study. Ann Transl Med. 2023 Jan 31;11(2):106. doi: 10.21037/atm-22-6463. PMID: 36819505; PMCID: PMC9929780. 3: Gumbleton M, Allan S, Conway H, Boucher K, Marvin J, Hawks J, Burnett W, Van Brocklin M, Whisenant J, Gilcrease G, Gupta S. A phase I open-label study of the safety and efficacy of apatinib (rivoceranib) administered to patients with advanced malignancies to improve sensitivity to pembrolizumab in the second- or later-line setting (APPEASE). BMC Res Notes. 2023 Feb 16;16(1):16. doi: 10.1186/s13104-023-06283-5. PMID: 36797744; PMCID: PMC9936706. 4: Wu Y, Ou S, Liao X, Han C, Yang C, Qin W, Tan Y, Lao Q, Peng T, Ye X. Massive Hepatocellular Carcinoma with Situs Inversus Totalis Achieved a Complete Response Following Camrelizumab Plus Apatinib and Combined with Two-Stage Hepatectomy: A Case Report. Pharmgenomics Pers Med. 2023 Feb 7;16:111-120. doi: 10.2147/PGPM.S376596. PMID: 36785780; PMCID: PMC9921441. 5: Chen J, Zhai J, Li M, Liu S, Gong X, Yu H, Wei H, Chen W. In vitro and in vivo analyses on anti-NSCLC activity of apatinib: rediscovery of a new drug target V600E mutation. Cancer Cell Int. 2023 Feb 9;23(1):21. doi: 10.1186/s12935-022-02723-7. PMID: 36759818; PMCID: PMC9909954. 6: Wang X, Wu X, Yang Y, Xu W, Tian H, Lian B, Chi Z, Si L, Sheng X, Kong Y, Zhou L, Mao L, Li S, Tang B, Yan X, Bai X, Guo J, Cui C. Apatinib combined with camrelizumab in advanced acral melanoma patients: An open-label, single-arm phase 2 trial. Eur J Cancer. 2023 Mar;182:57-65. doi: 10.1016/j.ejca.2022.12.027. Epub 2023 Jan 12. PMID: 36753834. 7: Ding X, Zhang WJ, You R, Zou X, Wang ZQ, Ouyang YF, Peng L, Liu YP, Duan CY, Yang Q, Lin C, Xie YL, Chen SY, Liu YL, Gu CM, Xie RQ, Huang PY, Hong MH, Hua YJ, Chen MY. Camrelizumab Plus Apatinib in Patients With Recurrent or Metastatic Nasopharyngeal Carcinoma: An Open-Label, Single-Arm, Phase II Study. J Clin Oncol. 2023 Feb 3:JCO2201450. doi: 10.1200/JCO.22.01450. Epub ahead of print. PMID: 36735896. 8: Ye L, Zhang L, Li R, Pan X, Li J, Dou S, Jiang W, Wang C, Chen W, Zhu G. Combined all-trans retinoic acid with low-dose apatinib in treatment of recurrent/metastatic head and neck adenoid cystic carcinoma: A single-center, secondary analysis of a phase II study. Cancer Med. 2023 Feb 3. doi: 10.1002/cam4.5653. Epub ahead of print. PMID: 36734294. 9: Yang D, Xu F, Lai X, Li Y, Hou T, Wu L, Ma D, Li Z. Identifying predictive biomarkers of apatinib in third-line treatment of advanced colorectal cancer through comprehensive genomic profiling. Anticancer Drugs. 2023 Mar 1;34(3):431-438. doi: 10.1097/CAD.0000000000001451. Epub 2022 Nov 18. PMID: 36730496. 10: Correction: αPD-1-mesoCAR-T cells partially inhibit the growth of advanced/refractory ovarian cancer in a patient along with daily apatinib. J Immunother Cancer. 2023 Jan;11(1):e001162corr1. doi: 10.1136/jitc-2020-001162corr1. Erratum for: J Immunother Cancer. 2021 Feb;9(2): PMID: 36707091; PMCID: PMC9884919. 11: Lv H, He Y, Nie C, Du F, Chen X. Adding of apatinib and camrelizumab to overcome de novo trastuzumab resistance of HER2-positive gastric cancer: A case report and literature review. Front Pharmacol. 2023 Jan 9;13:1067557. doi: 10.3389/fphar.2022.1067557. PMID: 36699065; PMCID: PMC9868577. 12: Fan W, Ding J, Zhong W. Efficacy and Safety of Third-Line Apatinib plus Chemotherapy in Metastatic Triple-Negative Breast Cancer Patients: A Multicenter, Retrospective, Cohort Study. Tohoku J Exp Med. 2023 Jan 26. doi: 10.1620/tjem.2023.J006. Epub ahead of print. PMID: 36696982. 13: Yang XM, Ye PP, Liu XL, Guo ZX, Kan M, Li Q, Song LL, Liu HY, Chen KG, Shi JY, Zhang YH, Li Y, Zhao FR, van den Anker J, Li Y, Zhao W. Population pharmacokinetics and pharmacogenetics of apatinib in adult cancer patients. Br J Clin Pharmacol. 2023 Jan 20. doi: 10.1111/bcp.15665. Epub ahead of print. PMID: 36662574. 14: Ma Y, Zhao W, Sun P, Deng W, Deng J, Zong H, Wang J, Guo Y, Liu H, Cang S, Shang K, Chen X, Wang J, He D, Wu G, Zhang Z, Zhang L, Xu F, Tian C, Qiao C, Chen G, Zhang G, Ma T, Gao L, Zhang G, Liu J, Eslick GD, Almhanna K, Lino-Silva LS, Aprile G, Li N, Luo S. Apatinib in the treatment of gastric cancer in Henan Province: a multicenter prospective real-world observational study (Ahead- HAP01). Ann Transl Med. 2022 Dec;10(24):1372. doi: 10.21037/atm-22-5995. PMID: 36660622; PMCID: PMC9843423. 15: Huang J, Chen X, Guo J, Song L, Mu Y, Zhao H, Du C. Apatinib combined with trastuzumab and albumin-bound paclitaxel for treatment of HER2+ breast cancer with brain metastases resistant to anti-HER2 TKIs: A case report. Oncol Lett. 2022 Dec 20;25(2):56. doi: 10.3892/ol.2022.13642. PMID: 36644147; PMCID: PMC9827463. 16: Pan L, Tian Y, Wang K, Tang J, Liu J, Zhang J, Wang M, Liu J, Xu H, Chen X. Low-dose apatinib combined with camrelizumab and the SOX regimen in the neoadjuvant treatment of locally advanced gastric/gastroesophageal junction adenocarcinoma (SPACE-neo): a protocol for an open-label, single-arm, clinical trial. J Gastrointest Oncol. 2022 Dec;13(6):3300-3313. doi: 10.21037/jgo-22-1158. PMID: 36636043; PMCID: PMC9830353. 17: Zhao M, Ma H, Cheng P, Yang H, Zhao Y, Han Q. Apatinib combined with temozolomide treatment for pseudoprogression in glioblastoma: A case report. Medicine (Baltimore). 2022 Dec 9;101(49):e32156. doi: 10.1097/MD.0000000000032156. PMID: 36626518; PMCID: PMC9750629. 18: Healthcare Engineering JO. Retracted: Effect of Apatinib Combined with Seggio on the Expression of Serum AFP and CA724 and Long-Term Survival Rate in Patients with Advanced Gastric Cancer Undergoing Comfortable Nursing Intervention. J Healthc Eng. 2022 Dec 8;2022:9756408. doi: 10.1155/2022/9756408. PMID: 36530787; PMCID: PMC9754829. 19: He L, Shen X, Liu Y, Gao L, Wu J, Yu C, Li G, Wang X, Shao X. The reversal of anti-HER2 resistance in advanced HER2-positive breast cancer using apatinib: two cases reports and literature review. Transl Cancer Res. 2022 Nov;11(11):4206-4217. doi: 10.21037/tcr-22-2483. PMID: 36523304; PMCID: PMC9745359. 20: Wang J, Huang D, Yang W, Song Q, Jia Y, Chen P, Cheng Y. The efficacy and safety of Apatinib in the treatment of advanced non-small cell lung cancer: A retrospective trial. Front Oncol. 2022 Nov 23;12:1030798. doi: 10.3389/fonc.2022.1030798. PMID: 36505785; PMCID: PMC9727187.