Triptolide
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MedKoo CAT#: 406463

CAS#: 38748-32-2

Description: Triptolide, also known as PG490, is a diterpenoid epoxide found in the Thunder God Vine, Tripterygium wilfordii, which has been used in traditional Chinese medicine for more than two thousand years to treat immune-related disorders. Triptolide is a promising immunosuppressive and anti-inflammatory agent. Triptolide is a also a potent anti-cancer agent against many cancer cell lines.

Chemical Structure

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Triptolide
CAS# 38748-32-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406463
Name: Triptolide
CAS#: 38748-32-2
Chemical Formula: C20H24O6
Exact Mass: 360.16
Molecular Weight: 360.400
Elemental Analysis: C, 66.65; H, 6.71; O, 26.64

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1050 Ready to ship
500mg USD 2250 2 weeks
1g USD 3450 2 weeks
2g USD 6450 2 weeks
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Synonym: PG490; PG-490; PG 490; NSC163062; NSC-163062; NSC 163062; Tripterygium wilfordii; Triptolide.

IUPAC/Chemical Name: (6aS,7aS,8R,8aR,9aS,9bS,10aS,10bS)-8-hydroxy-8a-isopropyl-10b-methyl-1,5,5b,6,6a,8,8a,9a,9b,10b-decahydrotris(oxireno)[2',3':4b,5;2'',3'':6,7;2''',3''':8a,9]phenanthro[1,2-c]furan-3(2H)-one.

InChi Key: DFBIRQPKNDILPW-KTGKZQHOSA-N

InChi Code: InChI=1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11?,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1

SMILES Code: O=C(OC1)C2=C1[C@@](C[C@H]3[C@]4(O3)[C@@]5(O6)[C@@H]6[C@H](O7)[C@@]7(C(C)C)[C@H]4O)([H])[C@]5(C)CC2

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:         

Biological target: Triptolide is a NF-κB activation inhibitor.
In vitro activity: To investigate if triptolide has an effect on lung cancer cell migration, triptolide treated NSCLC (non-small cell lung cancer) cells were plated on Transwell filters coated with the solid substrate chemoattractant fibronectin. Triptolide treatment significantly decreased the migration of all three lung cancer cell lines compared to the DMSO control cells (Figure 2). Cellular adhesion to fibronectin was similar between the control and treatment groups in all three cell lines indicating that triptolide does not affect cell attachment to the extracellular matrix. Reference: Ann Thorac Surg. 2015 Nov;100(5):1817-24. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4630145/
In vivo activity: The effect of triptolide in lung cancer cell metastasis was investigated in vivo. Tail vein injections of H358 cells were performed in NOD SCID gamma (NSG) mice as an experimental model to assess metastatic colonization. Mice treated with triptolide had significantly less metastatic colonization of the lungs compared to the vehicle control mice (Figure 4). This data suggests that triptolide could be a potential therapeutic for targeting lung cancer progression. Reference: Ann Thorac Surg. 2015 Nov;100(5):1817-24. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4630145/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 37.4 103.77
DMF 12.0 33.30
DMF:PBS (pH 7.2) (1:1) 0.5 1.39

Preparing Stock Solutions

The following data is based on the product molecular weight 360.40 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. Reno TA, Kim JY, Raz DJ. Triptolide Inhibits Lung Cancer Cell Migration, Invasion, and Metastasis. Ann Thorac Surg. 2015 Nov;100(5):1817-24; discussion 1824-5. doi: 10.1016/j.athoracsur.2015.05.074. Epub 2015 Aug 20. PMID: 26298168; PMCID: PMC4630145.
In vitro protocol: 1. Reno TA, Kim JY, Raz DJ. Triptolide Inhibits Lung Cancer Cell Migration, Invasion, and Metastasis. Ann Thorac Surg. 2015 Nov;100(5):1817-24; discussion 1824-5. doi: 10.1016/j.athoracsur.2015.05.074. Epub 2015 Aug 20. PMID: 26298168; PMCID: PMC4630145.
In vivo protocol: 1. Reno TA, Kim JY, Raz DJ. Triptolide Inhibits Lung Cancer Cell Migration, Invasion, and Metastasis. Ann Thorac Surg. 2015 Nov;100(5):1817-24; discussion 1824-5. doi: 10.1016/j.athoracsur.2015.05.074. Epub 2015 Aug 20. PMID: 26298168; PMCID: PMC4630145.

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1: Zheng Y, Zhang WJ, Wang XM. Triptolide with potential medicinal value for diseases of the central nervous system. CNS Neurosci Ther. 2013 Feb;19(2):76-82. doi: 10.1111/cns.12039. Epub 2012 Dec 18. Review. PubMed PMID: 23253124.

2: Tang W, Zuo JP. Immunosuppressant discovery from Tripterygium wilfordii Hook f: the novel triptolide analog (5R)-5-hydroxytriptolide (LLDT-8). Acta Pharmacol Sin. 2012 Sep;33(9):1112-8. doi: 10.1038/aps.2012.108. Epub 2012 Aug 27. Review. PubMed PMID: 22922344.

3: Han R, Rostami-Yazdi M, Gerdes S, Mrowietz U. Triptolide in the treatment of psoriasis and other immune-mediated inflammatory diseases. Br J Clin Pharmacol. 2012 Sep;74(3):424-36. doi: 10.1111/j.1365-2125.2012.04221.x. Review. PubMed PMID: 22348323; PubMed Central PMCID: PMC3477344.

4: Zhou ZL, Yang YX, Ding J, Li YC, Miao ZH. Triptolide: structural modifications, structure-activity relationships, bioactivities, clinical development and mechanisms. Nat Prod Rep. 2012 Apr;29(4):457-75. doi: 10.1039/c2np00088a. Epub 2012 Jan 23. Review. PubMed PMID: 22270059.

5: Liu Q. Triptolide and its expanding multiple pharmacological functions. Int Immunopharmacol. 2011 Mar;11(3):377-83. doi: 10.1016/j.intimp.2011.01.012. Epub 2011 Jan 19. Review. PubMed PMID: 21255694.

6: Pan J. RNA polymerase - an important molecular target of triptolide in cancer cells. Cancer Lett. 2010 Jun 28;292(2):149-52. doi: 10.1016/j.canlet.2009.11.018. Epub 2010 Jan 4. Review. PubMed PMID: 20045594.

7: Qiu D, Kao PN. Immunosuppressive and anti-inflammatory mechanisms of triptolide, the principal active diterpenoid from the Chinese medicinal herb Tripterygium wilfordii Hook. f. Drugs R D. 2003;4(1):1-18. Review. PubMed PMID: 12568630.

8: Chen BJ. Triptolide, a novel immunosuppressive and anti-inflammatory agent purified from a Chinese herb Tripterygium wilfordii Hook F. Leuk Lymphoma. 2001 Jul;42(3):253-65. Review. PubMed PMID: 11699390.

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