Docetaxel (CED0000933)

Record Information

Version

1.0

Creation Date

2009-07-30 17:58:51 UTC

Update Date

2026-05-14 16:59:07 UTC

Accession Number

CHEM002514

Identification

Common Name

Docetaxel

Class

Small Molecule

Description

Docetaxel belongs to the diterpenoids, a subclass of prenol lipids within the organic compounds. With an average molecular weight of 807.88 g/mol, Docetaxel is a heavy molecule. This exogenous solid, with the formula C43H53NO14, is used as an antineoplastic agent, a photosensitizing agent, and an antimalarial. It is recorded as being found in household cleaning and consumer products such as soap dispensers, electrical and electronic equipment such as antennas, and healthcare, pharmaceuticals and veterinary products. The compound is administered intravenously and has been detected in the liver and kidney. Docetaxel is used to treat various cancers, including breast cancer (PMC10155940), prostate cancer (PMC10313599, PMC1697755), ovarian cancer (PMC10091760, PMC7676468, PMC8072532), lung cancer (PMC3383615), pancreatic cancer (PMC10003701), angiosarcoma (PMC12591960, PMC5102718), and squamous cell carcinoma (PMC10314637), as well as cancer generally (PMC3480876, PMC6102750). It has a therapeutic effect on breast cancer (PMC11173842), thyroid cancer (PMC10003701), and necrosis (PMC3834492). However, it is associated with bradycardia (decrease) (PMC6180974) and pneumonitis (PMC12273849). The compound targets nine proteins, including the apoptosis regulator Bcl-2 (BCL2), Microtubule-associated protein 2 (MAP2), Microtubule-associated protein 4 (MAP4), Microtubule-associated protein tau (MAPT), and Nuclear receptor subfamily 1 group I member 2 (NR1I2). Docetaxel specifically binds to the beta-subunit of the tubulin beta-1 chain (TUBB1), locking these building blocks and hyper-stabilizing the structure of microtubules. This action interferes with normal microtubule growth and destroys the cell's ability to use its cytoskeleton flexibly, which is the opposite effect of drugs like colchicine that cause depolymerization.

Contaminant Type

Amine
Antimalarial
Antineoplastic Agent
Antineoplastic Agent, Phytogenic
Drug
Ester
Ether
Human Neurotoxin
Metabolite
Organic Compound
Radiation-Sensitizing Agent
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Debenzoyl-N-(tert-butoxycarbonyl)-10-deacetylpaclitaxel	ChEBI
N-Debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol	ChEBI
TXL	ChEBI
Taxotere	Kegg
Docetaxel anhydrous	HMDB
Docetaxel, trihydrate	HMDB
Docetaxel trihydrate	HMDB
Docetaxol	HMDB
N-Debenzoyl-N-tert-butoxycarbonyl-10-deacetyltaxol	HMDB
Taxoltere metro	HMDB
Docetaxel hydrate	HMDB
N Debenzoyl N tert butoxycarbonyl 10 deacetyltaxol	HMDB

Chemical Formula

C₄₃H₅₃NO₁₄

Average Molecular Mass

807.879 g/mol

Monoisotopic Mass

807.347 g/mol

CAS Registry Number

114977-28-5

IUPAC Name

(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

Traditional Name

(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-[(tert-butoxycarbonyl)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

SMILES

[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)C5=CC=CC=C5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1

InChI Identifier

InChI=1S/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,44,52)/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1

InChI Key

ZDZOTLJHXYCWBA-VCVYQWHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Taxanes and derivatives

Alternative Parents

Substituents

Taxane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Benzenoid
Cyclic alcohol
Carbamic acid ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Carbonic acid derivative
Oxetane
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Polyol
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetracyclic diterpenoid (CHEBI:4672 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Kidney
Liver

Applications

Biological Roles

antimalarial

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	232°C
Boiling Point	Not Available
Solubility	Insoluble

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.59	ALOGPS
logP	2.92	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	224.45 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	203.9 m³·mol⁻¹	ChemAxon
Polarizability	82.15 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-056r-0597250110-87ceab2cb1907efad869	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0kmi-0069066000-3564c38332034a6ece44	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ke9-2110021900-f5d0bc483676fe5dc3e1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-056r-6520040900-5dc2943e6be89bc86b0c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a6r-6900660000-2867151287c5a0346e02	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05iu-4410040920-b828ec76844ebea2d7a8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05i3-9210270300-f8577941b1621d9b82e5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-9300140000-7ac14648b028058fac74	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-003r-0390210310-072c630f13bc0f81269a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-1590201200-973eb03969da7056a8a6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0abc-3910101210-42478cd96d93fb415eeb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-3390000110-65c0d7adc2d422e11f9c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pdi-5940101000-da55ca527881bac1ac24	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0059-9601000000-3666f54ffa6e69c8958a	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Docetaxel interferes with the normal function of microtubule growth. Whereas drugs like colchicine cause the depolymerization of microtubules in vivo, docetaxel arrests their function by having the opposite effect; it hyper-stabilizes their structure. This destroys the cell's ability to use its cytoskeleton in a flexible manner. Specifically, docetaxel binds to the β-subunit of tubulin. Tubulin is the 'building block' of mictotubules, and the binding of docetaxel locks these building blocks in place. The resulting microtubule/docetaxel complex does not have the ability to disassemble. This adversely affects cell function because the shortening and lengthening of microtubules (termed dynamic instability) is necessary for their function as a transportation highway for the cell. Chromosomes, for example, rely upon this property of microtubules during mitosis. Further research has indicated that docetaxel induces programmed cell death (apoptosis) in cancer cells by binding to an apoptosis stopping protein called Bcl-2 (B-cell leukemia 2) and thus arresting its function. Oral LD₅₀ in rat is >2000 mg/kg.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Anticipated complications of overdosage include: bone marrow suppression, peripheral neurotoxicity, and mucositis. In two reports of overdose, one patient received 150 mg/m² and the other received 200 mg/m² as 1-hour infusions. Both patients experienced severe neutropenia, mild asthenia, cutaneous reactions, and mild paresthesia, and recovered without incident.

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
3387.0	Log mg/kg	[1900:6000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference
lung cancer	is_treatment_for	Not Available	PMC3383615
cancer	is_treatment_for	Not Available	PMC3480876 , PMC6102750
breast cancer	is_treatment_for	Not Available	PMC10155940
breast cancer	has_therapeutic_effect_on	Not Available	PMC11173842
Prostate cancer	is_treatment_for	Not Available	PMC10313599 , PMC1697755
necrosis	has_therapeutic_effect_on	Not Available	PMC3834492
angiosarcoma	is_treatment_for	Not Available	PMC12591960 , PMC5102718
thyroid cancer	has_therapeutic_effect_on	Not Available	PMC10003701
ovarian cancer	is_treatment_for	Not Available	PMC10091760 , PMC7676468 , PMC8072532
pancreatic cancer	is_treatment_for	Not Available	PMC10003701
pneumonitis	associated_with	Not Available	PMC12273849
bradycardia	associated_with	decrease	PMC6180974
squamous cell carcinoma	is_treatment_for	Not Available	PMC10314637
cardiac arrest	associated_with	decrease	PMC6180974

Exposure Sources

Source ID	Source	Sector	Reference
358	Antineoplastic agents	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
564	Soap Dispensers	Household cleaning & consumer products	Not Available
630	Toys	Recreation & sports surfaces	Not Available

Pathways

4 pathways

Docetaxel Pathway

Docetaxel Action Pathway

Docetaxel Action Pathway (New)

Docetaxel Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Growth hormone-releasing hormone receptor	Q02643	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	144.488
Click to view 3D structure	Substance-K receptor	P21452	Humans	Predicted (SEA)	9.9647
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	490.762
Click to view 3D structure	NS3	A3EZJ3	Hepatitis C virus	Predicted (SEA)	24.2111
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	508.2
Click to view 3D structure	Solute carrier organic anion transporter family member 1B1	Q9Y6L6	Humans	Predicted (SEA)	26.0016
Click to view 3D structure	Solute carrier organic anion transporter family member 1B3	Q9NPD5	Humans	Predicted (SEA)	18.9174
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Predicted (SEA)	214.163
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase Src	P12931	Humans	Predicted (SEA)	1326.63
Click to view 3D structure	Fibroblast growth factor receptor 1	P11362	Humans	Predicted (SEA)	1297.82
Click to view 3D structure	Tyrosine-protein kinase Mer	Q12866	Humans	Predicted (SEA)	352.501
Click to view 3D structure	Tyrosine-protein kinase ABL1	P00519	Humans	Predicted (SEA)	1287.08
Click to view 3D structure	Cholecystokinin receptor type A	P32238	Humans	Predicted (SEA)	168.232
Click to view 3D structure	Nucleotide-binding oligomerization domain-containing protein 2	Q9HC29	Humans	Predicted (SEA)	82.7537
Click to view 3D structure	Lysine-specific histone demethylase 1A	O60341	Humans	Predicted (SEA)	176.484
Click to view 3D structure	Botulinum neurotoxin type A	P0DPI0	Clostridium botulinum	Predicted (SEA)	5.76084
Click to view 3D structure	Beta tubulin	Q25270	Leishmania donovani	Predicted (SEA)	0.233548
Click to view 3D structure	Tubulin beta-3 chain	Q13509	Humans	Predicted (SEA)	2.41333
Click to view 3D structure	Cathepsin S	P25774	Humans	Predicted (SEA)	2204.22
Click to view 3D structure	Procathepsin L	P25975	Bos taurus	Predicted (SEA)	441.094
Click to view 3D structure	Cathepsin K	P43235	Humans	Predicted (SEA)	1963.12
Click to view 3D structure	Sterol O-acyltransferase 2	O88908	Mus musculus	Predicted (SEA)	8.17417
Click to view 3D structure	Platelet-activating factor receptor	Q62035	Mus musculus	Predicted (SEA)	4.35956
Click to view 3D structure	Procathepsin L	P07711	Humans	Predicted (SEA)	2960.92
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	O75469	Humans	Known	Not Available
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Known	Not Available
Click to view 3D structure	Growth hormone-releasing hormone receptor	Q02643	Humans	Known	Not Available
Click to view 3D structure	Kinesin-like protein KIF11	P52732	Humans	Known	Not Available
Click to view 3D structure	Microtubule-associated protein 2	P11137	Humans	Known	Not Available
Click to view 3D structure	Microtubule-associated protein 4	P27816	Humans	Known	Not Available
Click to view 3D structure	Microtubule-associated protein tau	P10636	Humans	Known	Not Available
Click to view 3D structure	Apoptosis regulator Bcl-2	P10415	Humans	Known	Docetaxel interferes with the normal function of microtubule growth. Whereas drugs like colchicine cause the depolymerization of microtubules in vivo, docetaxel arrests their function by having the opposite effect; it hyper-stabilizes their structure. This destroys the cell's ability to use its cytoskeleton in a flexible manner. Specifically, docetaxel binds to the β-subunit of tubulin. Tubulin is the "building block" of mictotubules, and the binding of docetaxel locks these building blocks in place. The resulting microtubule/docetaxel complex does not have the ability to disassemble. This adversely affects cell function because the shortening and lengthening of microtubules (termed dynamic instability) is necessary for their function as a transportation highway for the cell. Chromosomes, for example, rely upon this property of microtubules during mitosis. Further research has indicated that docetaxel induces programmed cell death (apoptosis) in cancer cells by binding to an apoptosis stopping protein called Bcl-2 (B-cell leukemia 2) and thus arresting its function.
Click to view 3D structure	Tubulin beta-1 chain	Q9H4B7	Humans	Known	Docetaxel interferes with the normal function of microtubule growth. Whereas drugs like colchicine cause the depolymerization of microtubules in vivo, docetaxel arrests their function by having the opposite effect; it hyper-stabilizes their structure. This destroys the cell's ability to use its cytoskeleton in a flexible manner. Specifically, docetaxel binds to the β-subunit of tubulin. Tubulin is the "building block" of mictotubules, and the binding of docetaxel locks these building blocks in place. The resulting microtubule/docetaxel complex does not have the ability to disassemble. This adversely affects cell function because the shortening and lengthening of microtubules (termed dynamic instability) is necessary for their function as a transportation highway for the cell. Chromosomes, for example, rely upon this property of microtubules during mitosis. Further research has indicated that docetaxel induces programmed cell death (apoptosis) in cancer cells by binding to an apoptosis stopping protein called Bcl-2 (B-cell leukemia 2) and thus arresting its function.