:DHA-paclitaxel

{{short description|Investigational drug}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 376090820

| ImageFile = Taxoprexin.png

| ImageSize = 200px

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| IUPACName = 1,7β-Dihydroxy-9-oxo-5β,20-epoxytax-11-ene-2α,4α,10β,13α-tetrayl 4,10-diacetate 13-[(2R,3S)-3-benzamido-2-{[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxy}-3-phenylpropanoate] 2-benzoate

| SystematicName = (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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-methano[1]benzoxeto[3,4-a][10]annulene-6,9,12,12b-tetrayl 6,12b-diacetate 9-[(2R,3S)-3-benzamido-2-{[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxy}-3-phenylpropanoate] 12-benzoate

| OtherNames = Docosahexaenoyl-paclitaxel; Taxoprexin

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 199796-52-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = OJE5810C4F

| PubChem = 6918473

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 5293670

| SMILES = O=C(c1ccccc1)N[C@@H](c2ccccc2)[C@@H](OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)C(=O)O[C@@H]5C(=C4/[C@@H](OC(=O)C)C(=O)[C@]7([C@H]([C@H](OC(=O)c3ccccc3)[C@@](O)(C4(C)C)C5)[C@@]6(OC(=O)C)[C@H](OC6)C[C@@H]7O)C)/C

| InChI = 1/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

| InChIKey = LRCZQSDQZJBHAF-PUBGEWHCBO

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = LRCZQSDQZJBHAF-PUBGEWHCSA-N}}

|Section2={{Chembox Properties

| C=69 | H=81 | N=1 | O=15

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|Section3={{Chembox Hazards

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|Section5={{Chembox Pharmacology

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DHA-paclitaxel (or Taxoprexin) is an investigational drug (from Protarga Inc) made by linking paclitaxel to docosahexaenoic acid (DHA), a fatty acid that is easily taken up by tumor cells; the DHA-paclitaxel “appears not to be cytotoxic until the bond with DHA is cleaved within the cell.”{{Cite journal | author = Whelan, Jo | journal = Drug Discovery Today | volume = 7 | issue =2 | year = 2002 | pages = 90–92 | doi = 10.1016/S1359-6446(01)02149-3 | pmid = 11790612 | title = Targeted taxane therapy for cancer}} The advantage of DHA-paclitaxel over paclitaxel is DHA-paclitaxel's ability to carry much higher concentrations of paclitaxel to the cells, which are maintained for longer periods in the tumor cells, thus increasing their action. With increased activity, DHA-paclitaxel, also known as Taxoprexin, may have a more successful response in cancer patients than Taxol, and it may be able to treat more types of cancer than Taxol has been able to treat.