Withaferin A
featured

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

MedKoo CAT#: 530668

CAS#: 5119-48-2

Description: Withaferin A is a steroidal lactone, derived from Acnistus arborescens,Withania somnifera (Indian Winter cherry or Ashwagandha in Sanskrit) and other members of Solanaceae family. It has been traditionally used in ayurvedic medicine. It is the first member of the withanolide class of ergostane type product to be discovered. This natural product has wide range of pharmacological activities including cardioprotective, anti-inflammatory, immuno-modulatory, anti-angiogenesis, anti-metastasis and anti-carcinogenic properties.


Price and Availability

Size
Price

5mg
USD 450
Size
Price

Size
Price

Withaferin A, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 530668
Name: Withaferin A
CAS#: 5119-48-2
Chemical Formula: C28H38O6
Exact Mass: 470.2668
Molecular Weight: 470.606
Elemental Analysis: C, 71.46; H, 8.14; O, 20.40


Synonym: Withaferin A; NSC 101088; NSC-101088; NSC101088; NSC 273757; NSC-273757; NSC273757.

IUPAC/Chemical Name: (4S,4aR,5aR)-4-hydroxy-9-((2R,3R)-3-hydroxy-4-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)butan-2-yl)-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-one

InChi Key: CQUCHTRQSNYVGJ-YBVJNLSVSA-N

InChi Code: InChI=1S/C28H38O6/c1-14-16(13-33-25(14)32)11-21(29)15(2)18-5-6-19-17-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(17)9-10-26(18,19)3/h7-8,15,17-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,17?,18?,19?,20?,21-,23+,24-,26?,27?,28-/m1/s1

SMILES Code: CC12C(CCC2[C@@H](C)[C@H](O)CC(CO3)=C(C)C3=O)C4C[C@@H]5[C@](C6(C)C4CC1)(O5)[C@@H](O)C=CC6=O


Technical Data

Appearance:
White to off-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

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).

Harmonized System Code:
293490


References

1: Chang E, Pohling C, Beygui N, Patel CB, Rosenberg J, Ha DH, Gambhir SS. Synergistic inhibition of glioma cell proliferation by Withaferin A and tumor treating fields. J Neurooncol. 2017 Jul 5. doi: 10.1007/s11060-017-2534-5. [Epub ahead of print] PubMed PMID: 28681243.

2: Chung SS, Wu Y, Okobi Q, Adekoya D, Atefi M, Clarke O, Dutta P, Vadgama JV. Proinflammatory Cytokines IL-6 and TNF-α Increased Telomerase Activity through NF-κB/STAT1/STAT3 Activation, and Withaferin A Inhibited the Signaling in Colorectal Cancer Cells. Mediators Inflamm. 2017;2017:5958429. doi: 10.1155/2017/5958429. Epub 2017 Jun 6. PubMed PMID: 28676732; PubMed Central PMCID: PMC5476880.

3: Hou WC, Miao XH, Ma LJ, Bai XX, Liu Q, Song L. WITHAFERIN A INDUCES APOPTOSIS IN RAT C6 GLIOMA CELLS THROUGH REGULATING NF-KB NUCLEAR TRANSLOCATION AND ACTIVATION OF CASPASE CASCADE. Afr J Tradit Complement Altern Med. 2017 Jan 13;14(2):319-324. doi: 10.21010/ajtcam.v14i2.33. eCollection 2017. PubMed PMID: 28573248; PubMed Central PMCID: PMC5446457.

4: Royston KJ, Udayakumar N, Lewis K, Tollefsbol TO. A Novel Combination of Withaferin A and Sulforaphane Inhibits Epigenetic Machinery, Cellular Viability and Induces Apoptosis of Breast Cancer Cells. Int J Mol Sci. 2017 May 19;18(5). pii: E1092. doi: 10.3390/ijms18051092. PubMed PMID: 28534825; PubMed Central PMCID: PMC5455001.

5: Moselhy J, Suman S, Alghamdi M, Chandarasekharan B, Das TP, Houda A, Ankem M, Damodaran C. Withaferin A Inhibits Prostate Carcinogenesis in a PTEN-deficient Mouse Model of Prostate Cancer. Neoplasia. 2017 Jun;19(6):451-459. doi: 10.1016/j.neo.2017.04.005. Epub 2017 May 7. PubMed PMID: 28494348.

6: Falkenberg KD, Jakobs A, Matern JC, Dörner W, Uttarkar S, Trentmann A, Steinmann S, Coulibaly A, Schomburg C, Mootz HD, Schmidt TJ, Klempnauer KH. Withaferin A, a natural compound with anti-tumor activity, is a potent inhibitor of transcription factor C/EBPβ. Biochim Biophys Acta. 2017 Jul;1864(7):1349-1358. doi: 10.1016/j.bbamcr.2017.05.003. Epub 2017 May 2. PubMed PMID: 28476645.

7: Szarc Vel Szic K, Declerck K, Crans RAJ, Diddens J, Scherf DB, Gerhäuser C, Vanden Berghe W. Epigenetic silencing of triple negative breast cancer hallmarks by Withaferin A. Oncotarget. 2017 Jun 20;8(25):40434-40453. doi: 10.18632/oncotarget.17107. PubMed PMID: 28467815.

8: Sultana F, Neog MK, Rasool M. Withaferin-A, a steroidal lactone encapsulated mannose decorated liposomes ameliorates rheumatoid arthritis by intriguing the macrophage repolarization in adjuvant-induced arthritic rats. Colloids Surf B Biointerfaces. 2017 Jul 1;155:349-365. doi: 10.1016/j.colsurfb.2017.04.046. Epub 2017 Apr 23. PubMed PMID: 28454064.

9: Kunimasa K, Nagano T, Shimono Y, Dokuni R, Kiriu T, Tokunaga S, Tamura D, Yamamoto M, Tachihara M, Kobayashi K, Satouchi M, Nishimura Y. Glucose metabolism-targeted therapy and withaferin A are effective for epidermal growth factor receptor tyrosine kinase inhibitor-induced drug-tolerant persisters. Cancer Sci. 2017 Jul;108(7):1368-1377. doi: 10.1111/cas.13266. Epub 2017 Jun 19. PubMed PMID: 28445002.

10: Yu Y, Katiyar SP, Sundar D, Kaul Z, Miyako E, Zhang Z, Kaul SC, Reddel RR, Wadhwa R. Withaferin-A kills cancer cells with and without telomerase: chemical, computational and experimental evidences. Cell Death Dis. 2017 Apr 20;8(4):e2755. doi: 10.1038/cddis.2017.33. PubMed PMID: 28425984.

11: Santhekadur PK. Is Withaferin A, a magic bullet for metabolic syndrome? Biomed Pharmacother. 2017 Aug;92:1135-1137. doi: 10.1016/j.biopha.2017.04.002. Epub 2017 Apr 14. PubMed PMID: 28413154.

12: Li AX, Sun M, Li X. Withaferin-A induces apoptosis in osteosarcoma U2OS cell line via generation of ROS and disruption of mitochondrial membrane potential. Eur Rev Med Pharmacol Sci. 2017 Mar;21(6):1368-1374. PubMed PMID: 28387888.

13: Liu X, Chen L, Liang T, Tian XD, Liu Y, Zhang T. Withaferin A induces mitochondrial-dependent apoptosis in non-small cell lung cancer cells via generation of reactive oxygen species. J BUON. 2017 Jan-Feb;22(1):244-250. PubMed PMID: 28365961.

14: Tahara T, Streit U, Pelish HE, Shair MD. STAT3 Inhibitory Activity of Structurally Simplified Withaferin A Analogues. Org Lett. 2017 Apr 7;19(7):1538-1541. doi: 10.1021/acs.orglett.7b00332. Epub 2017 Mar 28. PubMed PMID: 28350459.

15: Zhang QZ, Guo YD, Li HM, Wang RZ, Guo SG, Du YF. Protection against cerebral infarction by Withaferin A involves inhibition of neuronal apoptosis, activation of PI3K/Akt signaling pathway, and reduced intimal hyperplasia via inhibition of VSMC migration and matrix metalloproteinases. Adv Med Sci. 2017 Mar;62(1):186-192. doi: 10.1016/j.advms.2016.09.003. Epub 2017 Mar 7. PubMed PMID: 28282606.

16: Basha SH, Thakur A, Samad FA. Insights from the predicted structural analysis of carborane substituted withaferin A with Indoleamine - 2,3-dioxygenase as a potent inhibitor. Bioinformation. 2016 Nov 30;12(9):374-380. doi: 10.6026/97320630012374. eCollection 2016. PubMed PMID: 28250615; PubMed Central PMCID: PMC5314838.

17: Yan X, Huang G, Liu Q, Zheng J, Chen H, Huang Q, Chen J, Huang H. Withaferin A protects against spinal cord injury by inhibiting apoptosis and inflammation in mice. Pharm Biol. 2017 Dec;55(1):1171-1176. doi: 10.1080/13880209.2017.1288262. PubMed PMID: 28228044.

18: Chirumamilla CS, Pérez-Novo C, Van Ostade X, Vanden Berghe W. Molecular insights into cancer therapeutic effects of the dietary medicinal phytochemical withaferin A. Proc Nutr Soc. 2017 May;76(2):96-105. doi: 10.1017/S0029665116002937. Epub 2017 Feb 6. PubMed PMID: 28162105.

19: Samanta SK, Sehrawat A, Kim SH, Hahm ER, Shuai Y, Roy R, Pore SK, Singh KB, Christner SM, Beumer JH, Davidson NE, Singh SV. Disease Subtype-Independent Biomarkers of Breast Cancer Chemoprevention by the Ayurvedic Medicine Phytochemical Withaferin A. J Natl Cancer Inst. 2016 Dec 31;109(6). pii: djw293. doi: 10.1093/jnci/djw293. Print 2017 Jun. PubMed PMID: 28040797.

20: Ghosh K, De S, Das S, Mukherjee S, Sengupta Bandyopadhyay S. Withaferin A Induces ROS-Mediated Paraptosis in Human Breast Cancer Cell-Lines MCF-7 and MDA-MB-231. PLoS One. 2016 Dec 29;11(12):e0168488. doi: 10.1371/journal.pone.0168488. eCollection 2016. PubMed PMID: 28033383; PubMed Central PMCID: PMC5199013.