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Drug

D0899 | docetaxel

Molecular Formula C43H53NO14
Molecular Weight 807.9
Structure
State solid
Clearance * 21 L/h/m2 [Total body clearance, cancer patients after IV administration of 20–115 mg/m2]
Volume of distribution The initial rapid decline represents distribution to the peripheral compartments and the late (terminal) phase is due, in part, to a relatively slow efflux of docetaxel from the peripheral compartment. * 113 L
Route of elimination Docetaxel was eliminated in both the urine and feces following oxidative metabolism of the tert-butyl ester group, but fecal excretion was the main elimination route. Within 7 days, urinary and fecal excretion accounted for approximately 6% and 75% of the administered radioactivity, respectively.
Protein binding In vitro studies show that 94% protein bound, mainly to a1-acid glycoprotein, albumin, and lipoproteins. When measured in cancer patients, docetaxel is 97% bound to plasma protein. Dexamethasone does not affect the protein binding of docetaxel.
Half life Dose-dependent. Doses of 70 mg per square meter of body surface area (mg/m 2 ) or higher produce a triphasic elimination profile. With lower doses, assay limitations precluded detection of the terminal elimination phase. The half-life of the alpha, beta, and gamma phase are 4 minutes, 36 minutes, and 11.1 hours, respectively.
Absorption The pharmacokinetic profile is consistent with a three-compartment model. The area under the curve (AUC) was dose proportional following doses of 70 mg/m2 to 115 mg/m2 with infusion times of 1 to 2 hours.
Trade names Taxol
Description Anti-cancer

L

L01CD02 Docetaxel


[L01CD] Taxanes


[L01C] PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS


[L01] ANTINEOPLASTIC AGENTS


[L] Antineoplastic and immunomodulating agents

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 14.96±29.77 human qHTS-HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL human HepG2 MMP assay Negative IC50 163
MEMBRANE POTENTIAL 12.07±4.78 rat hepatocytes MMP assay decrease IC50 163
FUSION 185

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 10 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H319 (70%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H341 (80%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]


H351 (20%): Suspected of causing cancer [Warning Carcinogenicity]


H360 (40%): May damage fertility or the unborn child [Danger Reproductive toxicity]


H361 (50%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H362 (20%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]


H372 (40%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P260, P263, P264, P270, P280, P281, P305+P351+P338, P308+P313, P314, P337+P313, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)


  • (1R,2aR,4S,4aS,6R,9S,11S,12S,12aR)-1-Acetoxy-9-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-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]oxet-12-yl benzoate (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl (aR,bS)-b-[[(1,1-dimethylethoxy)carbonyl]amino]-a-hydroxybenzenepropanoate
    (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10 (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-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]oxet-12-yl benzoate (2alpha,5beta,7beta,10beta,13alpha)-4-(acetyloxy)-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
    (2beta,5beta,7alpha,8alpha,10alpha,13alpha)-4-(acetyloxy)-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate 114977-28-5 114977-28-5, Docetaxel
    4-(acetyloxy)-13alpha-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7beta,10beta-trihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate 5?,20-Epoxy-1,7?,10?-trihydroxy-9-oxotax-11-ene-2?,4,13?-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-3-phenylpropanoate] 699121PHCA
    AB0072965 AB01273941-01 AB01273941-02
    AC-383 AK-72918 AKOS015960718
    AKOS024457953 ANX-514 Anhydrous Docetaxel, European Pharmacopoeia (EP) Reference Standard
    BDBM36351 BRD-K30577245-001-04-3 BRD-K30577245-341-01-9
    Benzenepropanoic acid, beta-(((1,1-dimethylethoxy)carbonyl)amino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (alphaR,betaS)- Benzenepropanoic acid, beta-(((1,1-dimethylethoxy)carbonyl)amino)-alpha-hydroxy-, 12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester Benzenepropanoic acid,1-dimethylethoxy)carbonyl]amino]-.alpha.-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (.alpha.R,.beta.S);
    C11231 CAS-114977-28-5 CD-195
    CD0182 CHEBI:4672 CHEMBL92
    CID148124 CS-1144 D07866
    D4102 DB01248 DSSTox_CID_20464
    DSSTox_GSID_40464 DSSTox_RID_79497 DTXSID0040464
    Docecad Docefrez Docetaxel (JAN/INN)
    Docetaxel (TN) Docetaxel - Taxotere Docetaxel Winthrop
    Docetaxel [INN] Docetaxel anhydrous Docetaxel intermediate
    Docetaxel(Taxotere) Docetaxel, 98% Docetaxel, Trihydrate
    Docetaxel, purum, >=97.0% (HPLC) Docetaxol Docetaxolum
    Docetaxolum [INN-Latin] EX-A1206 EmDOC
    GTPL6809 HMS2089K08 HSDB 6965
    HY-B0011 InChI=1/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,5 KS-1452
    MCULE-1930158681 MFCD00800737 N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetylpaclitaxel
    N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol N-debenzoyl-N-Boc-10-deacetyl taxol N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyltaxol
    NCGC00181306-01 NCGC00181306-02 NCGC00181306-04
    NCGC00242509-01 NSC 628503 NSC-628503
    NSC628503 Q-100074 Q420436
    RP 56976 RP-56976 RP56976
    SC-16998 SCHEMBL4419 SDP-014
    SID 530 SR-01000003023 SR-01000003023-5
    SYP-0704A TXL Taxoel
    Taxotere Taxotere (Aventis) Taxotere (TN)
    Taxotere(R) Tox21_112781 Tox21_112781_1
    Tox21_113088 UNII-699121PHCA W-1428
    W-60384 XRP-6976L Z1551429742
    ZDZOTLJHXYCWBA-VCVYQWHSSA- ZDZOTLJHXYCWBA-VCVYQWHSSA-N ZINC85537053
    [2aR-[2a?,4?,4a?,6?,9?(?R*,?S*),11?,12?,12a?,12b?]]-?-[[(1,1-Dimethylethoxy)carbonyl]amino]-?-hydroxy-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester benzenepropanoic acid [acetoxy-[(2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenyl-propanoyl]oxy-trihydroxy-tetramethyl-oxo-[?]yl] benzoate bind-014
    docetaxel docetaxel 114977-28-5

    DrugBank Name docetaxel
    DrugBank DB01248
    CAS Number 114915-14-9, 114915-20-7, 114977-28-5, 125354-16-7, 148408-66-6
    PubChem Compound 148124
    KEGG Compound ID C11231
    KEGG Drug D02165
    ChEBI 59809
    PharmGKB PA449383