Bufogenin
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MedKoo CAT#: 529902

CAS#: 465-39-4

Description: Bufogenin, also known as Bufotenine or Resibufogenin, a drug potentially for the treatment of pancreatic cancer.


Chemical Structure

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Bufogenin
CAS# 465-39-4

Theoretical Analysis

MedKoo Cat#: 529902
Name: Bufogenin
CAS#: 465-39-4
Chemical Formula: C24H32O4
Exact Mass: 384.23
Molecular Weight: 384.520
Elemental Analysis: C, 74.97; H, 8.39; O, 16.64

Price and Availability

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10mg USD 800 2 Weeks
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Synonym: RBG; Bufotenine; Resibufogenin

IUPAC/Chemical Name: 14,15beta-Epoxy-3beta-hydroxy-5beta-bufa-20,22-dienolide

InChi Key: ATLJNLYIJOCWJE-CWMZOUAVSA-N

InChi Code: InChI=1S/C24H32O4/c1-22-9-7-16(25)11-15(22)4-5-18-17(22)8-10-23(2)19(12-20-24(18,23)28-20)14-3-6-21(26)27-13-14/h3,6,13,15-20,25H,4-5,7-12H2,1-2H3/t15-,16+,17+,18-,19-,20-,22+,23-,24-/m1/s1

SMILES Code: O=C(C=C1)OC=C1[C@H]2C[C@@H]3[C@]4(O3)[C@]5([H])CC[C@]6([H])C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]24C

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

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 384.52 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:
In vitro protocol:
In vivo protocol:

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1: Zheng C, Zheng B, Yao T. [Study on quality standards for Lingmaoxiang Jiedu pills]. Zhongguo Zhong Yao Za Zhi. 2010 Feb;35(3):305-7. Chinese. PubMed PMID: 20422994.

2: Shimada K, Ro JS, Kanno C, Nambara T. Occurrence of bufogenin conjugates in the skin of Korean toad. Chem Pharm Bull (Tokyo). 1987 Dec;35(12):4996-9. PubMed PMID: 2837336.

3: Wang ZY, Wang HL, Zhou J, Ma HY, Gong Y, Yan WL, Qian DW. [Comparison of chemical composition between fresh and processed Bufonis Venenum by UPLC-TQ-MS]. Zhongguo Zhong Yao Za Zhi. 2015 Oct;40(20):3967-73. Chinese. PubMed PMID: 27062811.

4: Chu Q, Xu H, Gao M, Guan X, Liu H, Deng S, Huo X, Liu K, Tian Y, Ma X. Liver-targeting Resibufogenin-loaded poly(lactic-co-glycolic acid)-D-α-tocopheryl polyethylene glycol 1000 succinate nanoparticles for liver cancer therapy. Int J Nanomedicine. 2016 Jan 27;11:449-63. doi: 10.2147/IJN.S93541. PubMed PMID: 26869788; PubMed Central PMCID: PMC4734807.

5: Ichikawa M, Sowa Y, Iizumi Y, Aono Y, Sakai T. Resibufogenin Induces G1-Phase Arrest through the Proteasomal Degradation of Cyclin D1 in Human Malignant Tumor Cells. PLoS One. 2015 Jun 29;10(6):e0129851. doi: 10.1371/journal.pone.0129851. PubMed PMID: 26121043; PubMed Central PMCID: PMC4488249.

6: Ning J, Yu ZL, Hu LH, Wang C, Huo XK, Deng S, Hou J, Wu JJ, Ge GB, Ma XC, Yang L. Characterization of phase I metabolism of resibufogenin and evaluation of the metabolic effects on its antitumor activity and toxicity. Drug Metab Dispos. 2015 Mar;43(3):299-308. doi: 10.1124/dmd.114.060996. PubMed PMID: 25504504.

7: Wang ZJ, Sun L, Heinbockel T. Resibufogenin and cinobufagin activate central neurons through an ouabain-like action. PLoS One. 2014 Nov 24;9(11):e113272. doi: 10.1371/journal.pone.0113272. PubMed PMID: 25420080; PubMed Central PMCID: PMC4242513.

8: Liu JQ, Si N, Yang J, Zhao HY, Bian BL, Wang HJ. [Identification of bufadienolides profiling in cinobufacino by HPLC-DAD-FT-ICR-MS method]. Yao Xue Xue Bao. 2014 Feb;49(2):244-8. Chinese. PubMed PMID: 24761616.

9: Mou LY, Xin XL, Chen L, Dong PP, Lan R, Su DH, Huang J, Wang JH, Zhan LB. Biotransformation of resibufogenin by Actinomucor elegans. J Asian Nat Prod Res. 2014;16(6):623-8. doi: 10.1080/10286020.2014.921911. PubMed PMID: 24911667.

10: Xin XL, Sun JH, Wang XB, Xi RG, Wang G, Lan R, Su DH, Li H, Huo XK, Wang C. Microbial transformation of resibufogenin by Curvularia lunata AS 3.4381. J Asian Nat Prod Res. 2014;16(3):290-5. doi: 10.1080/10286020.2013.878332. PubMed PMID: 24456251.

11: Wang W, Liu MD, Yan YY, Ye Y, Zhao JH, Xiong H, Xiao M, Liao LC. [Determination of cinobufagin and resibufogenin in liver tissue by HPLC-MS/MS]. Fa Yi Xue Za Zhi. 2013 Aug;29(4):268-72. Chinese. PubMed PMID: 24350542.

12: Zhu ZT, Deng S, Liu D, Zhang BJ, Sun HZ, Tian Y, Wang CY, Wang L, Ma XC. Isolation and identification of phase I metabolites of resibufogenin in rats. Xenobiotica. 2013 May;43(5):479-85. doi: 10.3109/00498254.2012.728728. PubMed PMID: 23153055.

13: Puschett JB. Marinobufagenin predicts and resibufogenin prevents preeclampsia: a review of the evidence. Am J Perinatol. 2012 Nov;29(10):777-85. doi: 10.1055/s-0032-1316447. Review. PubMed PMID: 22814872.

14: Cao W, Chen Y, Yuan L, He JJ. [Determination of protein binding rates of cinobufagin and resibufogenin with different plasmas by HPLC]. Yao Xue Xue Bao. 2012 Sep;47(9):1200-4. Chinese. PubMed PMID: 23227551.

15: Xie RF, Li ZC, Gao B, Shi ZN, Zhou X. Bufothionine, a possible effective component in cinobufocini injection for hepatocellular carcinoma. J Ethnopharmacol. 2012 Jun 1;141(2):692-700. doi: 10.1016/j.jep.2011.12.018. PubMed PMID: 22210051.

16: Xing J, Chen L, Song J, Guo C, Yang G, Zeng A. Separation and determination of resibufogenin and cinobufagin in Chansu using reversed-phase liquid chromatography with γ-cyclodextrin as mobile-phase modifier. J Sep Sci. 2012 Aug;35(15):1884-92. doi: 10.1002/jssc.201200058. PubMed PMID: 22623502.

17: Boos TL, Cheng K, Greiner E, Deschamps JR, Jacobson AE, Rice KC. Configurational reassignment and improved preparation of the competitive IL-6 receptor antagonist 20R,21R-epoxyresibufogenin-3-formate. J Nat Prod. 2012 Apr 27;75(4):661-8. doi: 10.1021/np2008957. PubMed PMID: 22360661; PubMed Central PMCID: PMC3351795.

18: Uddin MN, Agunanne EE, Horvat D, Puschett JB. Resibufogenin administration prevents oxidative stress in a rat model of human preeclampsia. Hypertens Pregnancy. 2012;31(1):70-8. doi: 10.3109/10641955.2010.525275. PubMed PMID: 21174582.

19: Zheng J, Su DH, Zhang DS, Xin XL, Liu JY, Tian Y, Wei Q, Cui X. Novel microbial transformation of resibufogenin by Absidia coerules. Nat Prod Commun. 2011 Nov;6(11):1581-4. PubMed PMID: 22224264.

20: Hao S, Bao YM, An LJ, Cheng W, Zhao RG, Bi J, Wang HS, Sun CS, Liu JW, Jiang B. Effects of Resibufogenin and Cinobufagin on voltage-gated potassium channels in primary cultures of rat hippocampal neurons. Toxicol In Vitro. 2011 Dec;25(8):1644-53. doi: 10.1016/j.tiv.2011.07.001. PubMed PMID: 21798339.