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

MedKoo CAT#: 206077

CAS#: 199796-52-6

Description: DHA-paclitaxel, also know as Taxoprexin, is prodrug comprised of the naturally occurring omega-3 fatty acid docosahexaenoic acid (DHA) covalently conjugated to the anti-microtubule agent paclitaxel. Because tumor cells take up DHA, DHA-paclitaxel is delivered directly to tumor tissue, where the paclitaxel moiety binds to tubulin and inhibits the disassembly of microtubules, thereby resulting in the inhibition of cell division. Paclitaxel also induces apoptosis by binding to and blocking the function of the apoptosis inhibitor protein Bcl-2 (B-cell Leukemia 2). DHA-paclitaxel exhibits improved pharmacokinetic and toxicity profiles when compared to conventional paclitaxel and has demonstrated antineoplastic activity in animal models of cancer.

Chemical Structure

CAS# 199796-52-6

Theoretical Analysis

MedKoo Cat#: 206077
Name: DHA-paclitaxel
CAS#: 199796-52-6
Chemical Formula: C69H81NO15
Exact Mass: 1,163.56
Molecular Weight: 1,164.380
Elemental Analysis: C, 71.17; H, 7.01; N, 1.20; O, 20.61

Price and Availability

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Note: Price will be listed if it is available in the future.

Synonym: DHA-paclitaxel; DHA-Taxol; DHA-Tax; Docosahexaenoic Acid-Paclitaxel conjugate; US brand name: Taxoprexin.

IUPAC/Chemical Name: (2aR,4S,4aS,6R,9S,11S,12S,12bS)-9-(((2R,3S)-3-benzamido-2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy)-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diyl diacetate.


InChi Code: InChI=1S/C69H81NO15/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-35-42-55(74)83-59(57(49-36-29-26-30-37-49)70-63(76)50-38-31-27-32-39-50)65(78)82-52-44-69(79)62(84-64(77)51-40-33-28-34-41-51)60-67(7,53(73)43-54-68(60,45-80-54)85-48(4)72)61(75)58(81-47(3)71)56(46(52)2)66(69,5)6/h9-10,12-13,15-16,18-19,21-22,24-34,36-41,52-54,57-60,62,73,79H,8,11,14,17,20,23,35,42-45H2,1-7H3,(H,70,76)/b10-9-,13-12-,16-15-,19-18-,22-21-,25-24-/t52-,53-,54+,57-,58+,59+,60-,62-,67+,68-,69+/m0/s1

SMILES Code: O=C1[C@H](OC(C)=O)C(C2(C)C)=C(C)[C@@H](OC([C@@H]([C@H](C3=CC=CC=C3)NC(C4=CC=CC=C4)=O)OC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)=O)C[C@@]2(O)[C@@H](OC(C5=CC=CC=C5)=O)[C@@]6([H])[C@@]1(C)[C@@H](O)C[C@@H]7[C@@]6(OC(C)=O)CO7

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: >5 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

Product Data:

Preparing Stock Solutions

The following data is based on the product molecular weight 1164.380000000000000000000000000000 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.

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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

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1: Homsi J, Bedikian AY, Papadopoulos NE, Kim KB, Hwu WJ, Mahoney SL, Hwu P. Phase 2 open-label study of weekly docosahexaenoic acid-paclitaxel in patients with metastatic uveal melanoma. Melanoma Res. 2010 Dec;20(6):507-10. doi: 10.1097/CMR.0b013e3283403ce9. PubMed PMID: 20881508. 2: Bedikian AY, DeConti RC, Conry R, Agarwala S, Papadopoulos N, Kim KB, Ernstoff M. Phase 3 study of docosahexaenoic acid-paclitaxel versus dacarbazine in patients with metastatic malignant melanoma. Ann Oncol. 2011 Apr;22(4):787-93. doi: 10.1093/annonc/mdq438. Epub 2010 Sep 20. PubMed PMID: 20855467. 3: Homsi J, Bedikian AY, Kim KB, Papadopoulos NE, Hwu WJ, Mahoney SL, Hwu P. Phase 2 open-label study of weekly docosahexaenoic acid-paclitaxel in cutaneous and mucosal metastatic melanoma patients. Melanoma Res. 2009 Aug;19(4):238-42. doi: 10.1097/CMR.0b013e32832a1e2f. PubMed PMID: 19521262. 4: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 May;30(4):313-31. PubMed PMID: 18773127. 5: Fracasso PM, Picus J, Wildi JD, Goodner SA, Creekmore AN, Gao F, Govindan R, Ellis MJ, Tan BR, Linette GP, Fu CJ, Pentikis HS, Zumbrun SC, Egorin MJ, Bellet RE. Phase 1 and pharmacokinetic study of weekly docosahexaenoic acid-paclitaxel, Taxoprexin, in resistant solid tumor malignancies. Cancer Chemother Pharmacol. 2009 Feb;63(3):451-8. doi: 10.1007/s00280-008-0756-0. Epub 2008 Apr 15. PubMed PMID: 18414864. 6: Jones RJ, Hawkins RE, Eatock MM, Ferry DR, Eskens FA, Wilke H, Evans TR. A phase II open-label study of DHA-paclitaxel (Taxoprexin) by 2-h intravenous infusion in previously untreated patients with locally advanced or metastatic gastric or oesophageal adenocarcinoma. Cancer Chemother Pharmacol. 2008 Mar;61(3):435-41. Epub 2007 Apr 18. PubMed PMID: 17440725. 7: Payne M, Ellis P, Dunlop D, Ranson M, Danson S, Schacter L, Talbot D. DHA-paclitaxel (Taxoprexin) as first-line treatment in patients with stage IIIB or IV non-small cell lung cancer: report of a phase II open-label multicenter trial. J Thorac Oncol. 2006 Nov;1(9):984-90. PubMed PMID: 17409983. 8: Harries M, O'Donnell A, Scurr M, Reade S, Cole C, Judson I, Greystoke A, Twelves C, Kaye S. Phase I/II study of DHA-paclitaxel in combination with carboplatin in patients with advanced malignant solid tumours. Br J Cancer. 2004 Nov 1;91(9):1651-5. PubMed PMID: 15494716; PubMed Central PMCID: PMC2410023. 9: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Apr;26(3):211-44. PubMed PMID: 15148527. 10: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Mar;26(2):129-61. PubMed PMID: 15071612.