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Identification
- Summary
Docetaxel is a taxoid antineoplastic agent used in the treatment of various cancers, such as locally advanced or metastatic breast cancer, metastatic prostate cancer, gastric adenocarcinoma, and head and neck cancer.
- Brand Names
- Docivyx, Taxotere
- Generic Name
- Docetaxel
- DrugBank Accession Number
- DB01248
- Background
Docetaxel is a clinically well established anti-mitotic chemotherapy medication used for the treatment of different types of cancer, including breast, ovarian, and non-small cell lung cancer. Docetaxel is a complex diterpenoid molecule and a semisynthetic analogue of paclitaxel.6,7 Docetaxel reversibly binds to microtubulin with high affinity in a 1:1 stoichiometric ratio, allowing it to prevent cell division and promote to cell death.6 Compared to paclitaxel, docetaxel is two times more potent as an inhibitor of microtubule depolymerization. Docetaxel binds to microtubules but does not interact with dimeric tubulin.5
The use of docetaxel may lead to udesired outcomes such as hepatic impairment, hematologic effects, enterocolitis and neutropenic colitis, hypersensitivity reactions, fluid retention, second primary malignancies, embryo-fetal toxicity, and tumor lysis syndrome.7 Docetaxel was approved by the FDA in 1996 and is available in solution for injection for intravenous or parenteral administration.6
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Docetaxel (DB01248)
- Weight
- Average: 807.8792
Monoisotopic: 807.346605409 - Chemical Formula
- C43H53NO14
- Synonyms
- Docetaxel
- Docetaxel anhydrous
- N-Debenzoyl-N-(tert-butoxycarbonyl)-10-deacetylpaclitaxel
- N-Debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol
- TXL
- External IDs
- CKD-810
- RP-6976
Pharmacology
- Indication
Docetaxel is indicated as a single agent for the treatment of locally advanced or metastatic breast cancer after chemotherapy failure; and with doxorubicin and cyclophosphamide as adjuvant treatment of operable node-positive BC. It is also indicated as a single agent for locally advanced or metastatic non-small cell lung cancer (NSCLC) after platinum therapy failure; and with cisplatin for unresectable, locally advanced or metastatic untreated NSCLC. For the treatment of metastatic castration-resistant prostate cancer, docetaxel is indicated with prednisone. Docetaxel is also indicated with cisplatin and fluorouracil for untreated, advanced gastric adenocarcinoma, including the gastroesophageal junction, and with cisplatin and fluorouracil for induction treatment of locally advanced squamous cell carcinoma of the head and neck (SCCHN).7
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Esophageal cancer ••• ••••• Treatment of Locally advanced breast cancer •••••••••••• Treatment of Metastatic bladder cancer ••• ••••• Treatment of Metastatic breast cancer •••••••••••• Used in combination to treat Metastatic hormone refractory prostate cancer Regimen in combination with: Prednisone (DB00635) •••••••••••• - Contraindications & Blackbox Warnings
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Docetaxel is a taxoid antineoplastic agent. It promotes the assembly of microtubules from tubulin dimers and stabilizes microtubules by preventing depolymerization. This stability results in the inhibition of the normal dynamic reorganization of the microtubule network which is essential for vital interphase and mitotic cellular functions. In addition, docetaxel induces abnormal arrays or "bundles" of microtubules throughout the cell cycle and multiple asters of microtubules during mitosis.4,5
The use of docetaxel may lead to treatment-related deaths in breast cancer and non-small cell lung cancer patients, hepatic impairment, hematologic effects, enterocolitis and neutropenic colitis, hypersensitivity reactions, fluid retention, second primary malignancies, cutaneous reactions, neurologic reactions, eye disorders, asthenia, embryo-fetal toxicity, and tumor lysis syndrome.7
- Mechanism of action
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 microtubules, 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), thus arresting its function.4,5,7
Target Actions Organism ATubulin beta-1 chain Not Available Humans AMicrotubule-associated protein 2 Not Available Humans AMicrotubule-associated protein 4 Not Available Humans AMicrotubule-associated protein tau Not Available Humans UApoptosis regulator Bcl-2 Not Available Humans UNuclear receptor subfamily 1 group I member 2 binderHumans - Absorption
The pharmacokinetic profile of docetaxel is consistent with a three-compartment model. The initial rapid decline represents the distribution to the peripheral compartments, and the late (terminal) phase is partly due to a relatively slow efflux of docetaxel from the peripheral compartment. The area under the curve (AUC) was dose proportional at doses between 70 mg/m2 and 115 mg/m2 with infusion times of 1 to 2 hours.7,9 In a group of patients with solid tumors given 100 mg/m2 of docetaxel intravenously, the Cmax and AUC were 2.41 μg/mL and 5.93 μg⋅h/mL, respectively.1,3
- Volume of distribution
Docetaxel has a steady-state volume of distribution of 113 L. Its pharmacokinetic profile is consistent with a three-compartment pharmacokinetic model.7,9
- Protein binding
In vitro studies show that 94% of docetaxel is bound to proteins, mainly alpha-1-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.7,9
- Metabolism
Docetaxel undergoes hepatic metabolism. In vitro drug interaction studies revealed that docetaxel is metabolized by the CYP3A4 isoenzyme.7,9 CYP3A5 also plays a role in the metabolism of this drug.1 In humans, docetaxel is metabolized by CYP3A4/5 into four metabolites: M1, M2, M3 and M4. Docetaxel undergoes hydroxylation of the synthetic isobutoxy side chain, forming metabolite M2. The oxidation of M2 forms an unstable aldehyde that is immediately cyclised into the stereoisomers M1 and M3. M4 is then formed by the oxidation of M1/M3.2
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- Route of elimination
Docetaxel was eliminated in 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. In the first 48 hours, approximately 80% of the radioactivity recovered was excreted in feces. One major and three minor metabolites were excreted at this point, with less than 8% as the unchanged drug.7,9
- Half-life
With plasma sampling up to 8 to 22 days after docetaxel infusion, the terminal elimination half-life was 116 hours.7 Doses between 70 and 115 mg/m2 with infusion times of 1 to 2 hours produce a triphasic elimination profile. The half-life of the alpha, beta, and gamma phases are 4 minutes, 36 minutes, and 11.1 hours, respectively.9
- Clearance
After the administration of 20–115 mg/m2 of intravenous docetaxel to cancer patients, the total body clearance was 21 L/h/m2.9 In patients aged 1 to 20 years with solid tumors that received 55 mg/m2 to 235 mg/m2 of docetaxel in a 1-hour intravenous infusion every 3 weeks, clearance was 17.3 L/h/m2.7
- Adverse Effects
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There is no known antidote for an overdose of docetaxel injection. In case of overdose, patients should be closely monitored in specialized units. Some of the anticipated complications of overdosage include: bone marrow suppression, peripheral neurotoxicity, and mucositis. After an overdose is discovered, patients should receive granulocyte colony-stimulating factor (G-CSF) as soon as possible. Other appropriate symptomatic measures should be taken as needed.7
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.7 In rats, the oral LD50 of docetaxel is >2000 mg/kg. The intravenous LD50 in mice is 138 mg/kg.8
- Pathways
Pathway Category Docetaxel Action Pathway Drug action - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Canalicular multispecific organic anion transporter 1 --- (G;G) / (C;G) G Allele ADR Directly Studied Patients with this polymorphism in ABCC2 are at a higher risk of experiencing drug-induced leukopenia and drug-induced neutropenia when treated with docetaxel. Details
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Docetaxel can be increased when it is combined with Abametapir. Abatacept The metabolism of Docetaxel can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Docetaxel. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Docetaxel. Acalabrutinib The metabolism of Docetaxel can be decreased when combined with Acalabrutinib. - Food Interactions
- Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum levels of docetaxel.
- Exercise caution with St. John's Wort. This herb induces CYP3A4 metabolism, which may reduce the serum concentration of docetaxel.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Docetaxel trihydrate 15H5577CQD 148408-66-6 XCDIRYDKECHIPE-QHEQPUDQSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Docetaxel 40 mg/ml Solution 80 mg / 2 mL Intravenous Actavis Pharma Company Not applicable Not applicable Canada 
Act Docetaxel 40 mg/ml Solution 20 mg / 0.5 mL Intravenous Actavis Pharma Company Not applicable Not applicable Canada Docefrez Kit 20 mg/0.8mL Intravenous Sun Pharma Global FZE 2011-05-03 2016-12-31 US 
Docefrez Kit 80 mg/4mL Intravenous Sun Pharma Global FZE 2011-05-03 2011-08-10 US Docetaxel Injection, solution 20 mg/1mL Intravenous Mc Kesson Packaging Services A Buisness Unit Of Mc Kesson Corporation 2012-07-01 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Docetaxel Injection, solution, concentrate 80 mg/4mL Intravenous Teva Parenteral Medicines, Inc. 2015-12-31 2018-11-30 US Docetaxel Injection, solution 20 mg/1mL Intravenous Dr. Reddy's Laboratories Limited 2017-08-22 Not applicable US Docetaxel Injection, solution, concentrate 160 mg/8mL Intravenous Winthrop U.S, a business of sanofi-aventis U.S. LLC 2016-10-23 Not applicable US Docetaxel Injection 10 mg/1mL Intravenous Xiromed, Llc 2021-10-25 Not applicable US Docetaxel Injection, solution 20 mg/1mL Intravenous Dr. Reddy's Laboratories Limited 2014-11-10 Not applicable US
Categories
- ATC Codes
- L01CD02 — Docetaxel
- Drug Categories
- Agents Causing Muscle Toxicity
- Antimitotic Agents
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- BCRP/ABCG2 Substrates
- Cardiotoxic antineoplastic agents
- Cyclodecanes
- Cycloparaffins
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Diterpenes
- Hepatotoxic Agents
- Immunosuppressive Agents
- Microtubule Inhibition
- Microtubule Inhibitors
- Mitosis Modulators
- Myelosuppressive Agents
- Narrow Therapeutic Index Drugs
- OATP1B3 substrates
- P-glycoprotein substrates
- P-glycoprotein substrates with a Narrow Therapeutic Index
- Taxane Derivatives
- Taxoids
- Terpenes
- Tubulin Modulators
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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
- Benzoic acid esters / Tricarboxylic acids and derivatives / Benzoyl derivatives / Fatty acid esters / Monosaccharides / Tertiary alcohols / Carbamate esters / Secondary alcohols / Oxetanes / Carboxylic acid esters show 10 more
- Substituents
- Alcohol / Aromatic heteropolycyclic compound / Benzenoid / Benzoate ester / Benzoic acid or derivatives / Benzoyl / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tetracyclic diterpenoid (CHEBI:4672)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 699121PHCA
- CAS number
- 114977-28-5
- InChI Key
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N
- InChI
- 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
- 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
- SMILES
- [H][C@@]1(C[C@@]2(O)[C@@H](OC(=O)C3=CC=CC=C3)[C@]3([H])[C@@]4(CO[C@@H]4C[C@H](O)[C@@]3(C)C(=O)[C@H](O)C(=C1C)C2(C)C)OC(C)=O)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1
References
- Synthesis Reference
Nicholas J. Sisti, Charles S. Swindell, "Method for docetaxel synthesis." U.S. Patent US5688977, issued September, 1991.
US5688977- General References
- Kenmotsu H, Tanigawara Y: Pharmacokinetics, dynamics and toxicity of docetaxel: Why the Japanese dose differs from the Western dose. Cancer Sci. 2015 May;106(5):497-504. doi: 10.1111/cas.12647. Epub 2015 Mar 25. [Article]
- Hendrikx JJ, Dubbelman AC, Rosing H, Schinkel AH, Schellens JH, Beijnen JH: Quantification of docetaxel and its metabolites in human plasma by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2013 Sep 15;27(17):1925-34. doi: 10.1002/rcm.6654. [Article]
- Extra JM, Rousseau F, Bruno R, Clavel M, Le Bail N, Marty M: Phase I and pharmacokinetic study of Taxotere (RP 56976; NSC 628503) given as a short intravenous infusion. Cancer Res. 1993 Mar 1;53(5):1037-42. [Article]
- Pienta KJ: Preclinical mechanisms of action of docetaxel and docetaxel combinations in prostate cancer. Semin Oncol. 2001 Aug;28(4 Suppl 15):3-7. doi: 10.1016/s0093-7754(01)90148-4. [Article]
- Bissery MC, Nohynek G, Sanderink GJ, Lavelle F: Docetaxel (Taxotere): a review of preclinical and clinical experience. Part I: Preclinical experience. Anticancer Drugs. 1995 Jun;6(3):339-55, 363-8. doi: 10.1097/00001813-199506000-00001. [Article]
- Authors unspecified: Docetaxel. . [Article]
- FDA Approved Drug Products: DOCETAXEL injection for intravenous use (May 2023) [Link]
- Pfizer: Docetaxel Injection SDS [Link]
- FDA Approved Drug Products: TAXOTERE (docetaxel) for injection concentrate (December 1999) [Link]
- External Links
- Human Metabolome Database
- HMDB0015378
- KEGG Drug
- D02165
- KEGG Compound
- C11231
- PubChem Compound
- 148124
- PubChem Substance
- 46506766
- ChemSpider
- 130581
- BindingDB
- 36351
- 1299922
- ChEBI
- 4672
- ChEMBL
- CHEMBL92
- ZINC
- ZINC000085537053
- Therapeutic Targets Database
- DAP000590
- PharmGKB
- PA449383
- PDBe Ligand
- TXL
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Docetaxel
- PDB Entries
- 1ia0 / 1tub
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Breast Cancer / Stages II-III Breast Cancer 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Malnutrition / Nasopharyngeal Carcinoma (NPC) 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Neoplasms of the Prostate 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Prostate Cancer 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Non-Muscle-invasive Bladder Cancer (NMIBC) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Sanofi-Aventis Inc.
- Dosage Forms
Form Route Strength Injection Parenteral 20 mg Solution Intramuscular 21.338 mg Solution Intravenous 20.00 mg Injection 10 mg/mL Injection 20 mg/2ml Solution / drops Ophthalmic 2 MG/ML Injection, solution, concentrate Intravenous 40 mg/ml Solution Intravenous 20.000 mg Solution 20 mg/1ml Injection, solution, concentrate Intravenous 20.0 mg/ml Injection Intravenous 40 mg/ml Kit Intravenous 20 mg/0.8mL Kit Intravenous 80 mg/4mL Powder Intravenous Injection, solution, concentrate Intravenous 80 mg/2ml Injection Parenteral 10 mg/mL Injection, solution, concentrate Intravenous 21.34 mg/0.5ml Injection Intravenous 20 mg/ml Injection Intravenous 80 mg/ml Injection Intravenous 10 mg/1mL Injection Intravenous 160 mg/8mL Injection Intravenous 20 mg/2ml Injection Intravenous 80 mg/4mL Injection, solution Intravenous 10 mg/1mL Injection, solution Intravenous 160 mg/8mL Injection, solution Intravenous 20 mg/1mL Injection, solution Intravenous 80 mg/4mL Injection, solution, concentrate Intravenous 160 mg/8mL Injection, solution, concentrate Intravenous 20 mg/2mL Injection, solution, concentrate Intravenous 20 mg/1mL Injection, solution, concentrate Intravenous 200 mg/20mL Injection, solution, concentrate Intravenous 80 mg/8mL Injection; injection, solution, concentrate Intravenous 40 mg/mL Kit Intravenous 40 mg/1mL Solution Intravenous 20 mg/1mL Solution Intravenous 21.340 mg Solution, concentrate Intravenous 120 mg Solution, concentrate Intravenous 160 mg Injection, powder, lyophilized, for solution Intravenous 20 mg Solution, concentrate Intravenous 20 mg Solution, concentrate Intravenous 80 mg Solution Parenteral 80 mg Solution, concentrate Intravenous 8000000 mg Injection, solution, concentrate Intravenous; Parenteral 160 MG/8ML Injection, solution, concentrate Intravenous; Parenteral 20 MG/1ML Injection, solution, concentrate Intravenous; Parenteral 80 MG/4ML Injection, solution, concentrate 40 MG/ML Solution Intravenous 20 mg/ml Injection, solution, concentrate Intravenous Injection, solution Intravenous 160 mg/16mL Injection, solution Intravenous 20 mg/2mL Injection, solution Intravenous 80 mg/8mL Injection Solution Intravenous 10 mg / mL Solution Intravenous 20 mg / 0.72 mL Solution Intravenous 20 mg / mL Solution Intravenous 80 mg / 2.88 mL Injection, solution, concentrate Intravenous 180 MG/9ML Injection Parenteral 20 mg/ml Injection, solution, concentrate Intravenous 200 mg/10ml Injection Intravenous 20 mg/1mL Injection, solution, concentrate Intravenous; Parenteral 10 MG/ML Injection, powder, lyophilized, for solution Parenteral 80 mg Injection, solution, concentrate Intravenous 10 mg/ml Injection, powder, lyophilized, for solution Parenteral 20 mg Injection, solution, concentrate Intravenous 20 mg/ml Injection, solution, concentrate Intravenous 20 mg/0.72ml Injection, solution, concentrate Intravenous 80 mg/2.88ml Injection, solution, concentrate Intravenous 21.34 mg/ml Solution Intravenous 160 mg Solution Intravenous 40 mg Injection, solution, concentrate 160 mg/8ml Injection, powder, lyophilized, for solution Intravenous 80 mg Solution Intravenous 20 mg/0.5ml Solution Intravenous 80 mg/2ml Injection Intravenous 20 mg/0.5ml Injection Intravenous 80 mg/2ml Injection, solution, concentrate Intravenous 160 mg Injection, solution, concentrate Intravenous 20 mg Injection, solution, concentrate Intravenous 40 mg Injection, solution, concentrate Intravenous 40 mg/2ml Injection, solution Intravenous 20 mg/0.5ml Injection, solution Intravenous 80 mg/2.0ml Injection, solution Intravenous 20 mg/ml Solution Intravenous 160 mg/16ml Solution Intravenous 20 mg/2ml Solution Intravenous 80 mg/8mL Injection, solution, concentrate Intravenous 10 mg/1ml Injection Intravenous 10 mg/ml Solution Intravenous 20.00 mg Solution Intravenous 80.0000 mg Injection, powder, for solution Intravenous 20 mg Solution 40 mg/1ml Solution Intravenous 80 mg Solution, concentrate Intravenous 40.0 mg/ml Solution Intravenous 20 mg Kit; solution Intravenous 20 mg / 0.5 mL Kit; solution Intravenous 80 mg / 2 mL Injection, solution, concentrate Intravenous 160 mg/16ml Solution Intravenous 160 mg / 8 mL Solution Intravenous 80 mg / 4 mL Solution Intravenous 20.000 mg/ml Injection, solution, concentrate Intravenous; Parenteral 20 MG/ML Injection, solution, concentrate Intravenous 120 MG/6ML Injection, solution, concentrate Intravenous 140 MG/7ML Solution Intravenous 10 mg Injection, solution, concentrate Intravenous 20 mg/0.5ml Injection, solution, concentrate Intravenous 40 mg/1mL Injection, solution, concentrate Intravenous 80 MG Injection, solution, concentrate Intravenous 80 mg/4mL Injection, solution, concentrate Intravenous; Parenteral 20 MG Solution Intravenous 20 mg / 0.5 mL Solution Intravenous 80 mg / 2 mL Injection Intravenous 20 mg Injection, solution Intravenous Injection Intravenous 80 mg Solution Intravenous 80 mg/4ml Solution Parenteral 20.000 mg Injection Intravenous Injection, solution Intravenous 40 mg/1ml - Prices
Unit description Cost Unit Taxotere 20 mg/0.5 ml vial 477.37USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5438072 No 1995-08-01 2014-05-22 US US4814470 No 1989-03-21 2010-05-14 US CA2150576 No 2005-06-21 2013-11-26 Canada CA2149055 No 2003-01-07 2013-11-08 Canada US8940786 No 2015-01-27 2033-09-30 US US9308195 No 2016-04-12 2033-09-30 US US9763880 No 2017-09-19 2033-09-30 US US10842770 No 2020-11-24 2031-08-04 US US10398785 No 2019-09-03 2036-03-14 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 232 °C PhysProp water solubility Insoluble FDA label logP 2.4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0127 mg/mL ALOGPS logP 2.59 ALOGPS logP 2.92 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 11.9 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 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9743 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.8252 P-glycoprotein substrate Substrate 0.8259 P-glycoprotein inhibitor I Inhibitor 0.644 P-glycoprotein inhibitor II Non-inhibitor 0.5139 Renal organic cation transporter Non-inhibitor 0.9393 CYP450 2C9 substrate Non-substrate 0.816 CYP450 2D6 substrate Non-substrate 0.8828 CYP450 3A4 substrate Substrate 0.7119 CYP450 1A2 substrate Non-inhibitor 0.8299 CYP450 2C9 inhibitor Non-inhibitor 0.8737 CYP450 2D6 inhibitor Non-inhibitor 0.8972 CYP450 2C19 inhibitor Non-inhibitor 0.8421 CYP450 3A4 inhibitor Non-inhibitor 0.7324 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8776 Ames test Non AMES toxic 0.8382 Carcinogenicity Non-carcinogens 0.9133 Biodegradation Not ready biodegradable 0.9934 Rat acute toxicity 2.5741 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9907 hERG inhibition (predictor II) Non-inhibitor 0.7905
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 272.1359646 predictedDarkChem Lite v0.1.0 [M-H]- 284.5782646 predictedDarkChem Lite v0.1.0 [M-H]- 259.6681 predictedDeepCCS 1.0 (2019) [M-H]- 272.1359646 predictedDarkChem Lite v0.1.0 [M-H]- 284.5782646 predictedDarkChem Lite v0.1.0 [M-H]- 259.6681 predictedDeepCCS 1.0 (2019) [M+H]+ 268.2214646 predictedDarkChem Lite v0.1.0 [M+H]+ 284.5180646 predictedDarkChem Lite v0.1.0 [M+H]+ 261.53506 predictedDeepCCS 1.0 (2019) [M+H]+ 268.2214646 predictedDarkChem Lite v0.1.0 [M+H]+ 284.5180646 predictedDarkChem Lite v0.1.0 [M+H]+ 261.53506 predictedDeepCCS 1.0 (2019) [M+Na]+ 268.5515646 predictedDarkChem Lite v0.1.0 [M+Na]+ 282.6669646 predictedDarkChem Lite v0.1.0 [M+Na]+ 267.50125 predictedDeepCCS 1.0 (2019) [M+Na]+ 268.5515646 predictedDarkChem Lite v0.1.0 [M+Na]+ 282.6669646 predictedDarkChem Lite v0.1.0 [M+Na]+ 267.50125 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Tubulin is the major constituent of microtubules, a cylinder consisting of laterally associated linear protofilaments composed of alpha- and beta-tubulin heterodimers. Microtubules grow by the addition of GTP-tubulin dimers to the microtubule end, where a stabilizing cap forms. Below the cap, tubulin dimers are in GDP-bound state, owing to GTPase activity of alpha-tubulin
- Specific Function
- GTP binding
- Gene Name
- TUBB1
- Uniprot ID
- Q9H4B7
- Uniprot Name
- Tubulin beta-1 chain
- Molecular Weight
- 50326.56 Da
References
- Gligorov J, Lotz JP: Preclinical pharmacology of the taxanes: implications of the differences. Oncologist. 2004;9 Suppl 2:3-8. [Article]
- Matesanz R, Barasoain I, Yang CG, Wang L, Li X, de Ines C, Coderch C, Gago F, Barbero JJ, Andreu JM, Fang WS, Diaz JF: Optimization of taxane binding to microtubules: binding affinity dissection and incremental construction of a high-affinity analog of paclitaxel. Chem Biol. 2008 Jun;15(6):573-85. doi: 10.1016/j.chembiol.2008.05.008. [Article]
- Snyder JP, Nettles JH, Cornett B, Downing KH, Nogales E: The binding conformation of Taxol in beta-tubulin: a model based on electron crystallographic density. Proc Natl Acad Sci U S A. 2001 Apr 24;98(9):5312-6. Epub 2001 Apr 17. [Article]
- Belani CP, Eckardt J: Development of docetaxel in advanced non-small-cell lung cancer. Lung Cancer. 2004 Dec;46 Suppl 2:S3-11. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- The exact function of MAP2 is unknown but MAPs may stabilize the microtubules against depolymerization. They also seem to have a stiffening effect on microtubules
- Specific Function
- calmodulin binding
- Gene Name
- MAP2
- Uniprot ID
- P11137
- Uniprot Name
- Microtubule-associated protein 2
- Molecular Weight
- 199524.51 Da
References
- McGrogan BT, Gilmartin B, Carney DN, McCann A: Taxanes, microtubules and chemoresistant breast cancer. Biochim Biophys Acta. 2008 Apr;1785(2):96-132. Epub 2007 Nov 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Non-neuronal microtubule-associated protein. Promotes microtubule assembly
- Specific Function
- microtubule binding
- Gene Name
- MAP4
- Uniprot ID
- P27816
- Uniprot Name
- Microtubule-associated protein 4
- Molecular Weight
- 121003.805 Da
References
- McGrogan BT, Gilmartin B, Carney DN, McCann A: Taxanes, microtubules and chemoresistant breast cancer. Biochim Biophys Acta. 2008 Apr;1785(2):96-132. Epub 2007 Nov 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Promotes microtubule assembly and stability, and might be involved in the establishment and maintenance of neuronal polarity (PubMed:21985311). The C-terminus binds axonal microtubules while the N-terminus binds neural plasma membrane components, suggesting that tau functions as a linker protein between both (PubMed:21985311, PubMed:32961270). Axonal polarity is predetermined by TAU/MAPT localization (in the neuronal cell) in the domain of the cell body defined by the centrosome. The short isoforms allow plasticity of the cytoskeleton whereas the longer isoforms may preferentially play a role in its stabilization
- Specific Function
- actin binding
- Gene Name
- MAPT
- Uniprot ID
- P10636
- Uniprot Name
- Microtubule-associated protein tau
- Molecular Weight
- 78927.025 Da
References
- McGrogan BT, Gilmartin B, Carney DN, McCann A: Taxanes, microtubules and chemoresistant breast cancer. Biochim Biophys Acta. 2008 Apr;1785(2):96-132. Epub 2007 Nov 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells (PubMed:1508712, PubMed:8183370). Regulates cell death by controlling the mitochondrial membrane permeability (PubMed:11368354). Appears to function in a feedback loop system with caspases (PubMed:11368354). Inhibits caspase activity either by preventing the release of cytochrome c from the mitochondria and/or by binding to the apoptosis-activating factor (APAF-1) (PubMed:11368354). Also acts as an inhibitor of autophagy: interacts with BECN1 and AMBRA1 during non-starvation conditions and inhibits their autophagy function (PubMed:18570871, PubMed:20889974, PubMed:21358617). May attenuate inflammation by impairing NLRP1-inflammasome activation, hence CASP1 activation and IL1B release (PubMed:17418785)
- Specific Function
- BH domain binding
- Gene Name
- BCL2
- Uniprot ID
- P10415
- Uniprot Name
- Apoptosis regulator Bcl-2
- Molecular Weight
- 26265.66 Da
References
- Gligorov J, Lotz JP: Preclinical pharmacology of the taxanes: implications of the differences. Oncologist. 2004;9 Suppl 2:3-8. [Article]
- Marshall J, Chen H, Yang D, Figueira M, Bouker KB, Ling Y, Lippman M, Frankel SR, Hayes DF: A phase I trial of a Bcl-2 antisense (G3139) and weekly docetaxel in patients with advanced breast cancer and other solid tumors. Ann Oncol. 2004 Aug;15(8):1274-83. [Article]
- Inoue Y, Gika M, Abiko T, Oyama T, Saitoh Y, Yamazaki H, Nakamura M, Abe Y, Kawamura M, Kobayashi K: Bcl-2 overexpression enhances in vitro sensitivity against docetaxel in non-small cell lung cancer. Oncol Rep. 2005 Feb;13(2):259-64. [Article]
- Petrylak DP: Chemotherapy for androgen-independent prostate cancer. World J Urol. 2005 Feb;23(1):10-3. Epub 2005 Feb 1. [Article]
- Miyoshi Y, Uemura H, Kubota Y: [Treatment of androgen-independent hormone refractory prostate cancer using docetaxel]. Nihon Rinsho. 2005 Feb;63(2):298-302. [Article]
- Magi-Galluzzi C, Zhou M, Reuther AM, Dreicer R, Klein EA: Neoadjuvant docetaxel treatment for locally advanced prostate cancer: a clinicopathologic study. Cancer. 2007 Sep 15;110(6):1248-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
- Specific Function
- DNA-binding transcription activator activity, RNA polymerase II-specific
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Ikezoe T, Hisatake Y, Takeuchi T, Ohtsuki Y, Yang Y, Said JW, Taguchi H, Koeffler HP: HIV-1 protease inhibitor, ritonavir: a potent inhibitor of CYP3A4, enhanced the anticancer effects of docetaxel in androgen-independent prostate cancer cells in vitro and in vivo. Cancer Res. 2004 Oct 15;64(20):7426-31. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Baumhakel M, Kasel D, Rao-Schymanski RA, Bocker R, Beckurts KT, Zaigler M, Barthold D, Fuhr U: Screening for inhibitory effects of antineoplastic agents on CYP3A4 in human liver microsomes. Int J Clin Pharmacol Ther. 2001 Dec;39(12):517-28. [Article]
- Clarke SJ, Rivory LP: Clinical pharmacokinetics of docetaxel. Clin Pharmacokinet. 1999 Feb;36(2):99-114. doi: 10.2165/00003088-199936020-00002. [Article]
- Hirth J, Watkins PB, Strawderman M, Schott A, Bruno R, Baker LH: The effect of an individual's cytochrome CYP3A4 activity on docetaxel clearance. Clin Cancer Res. 2000 Apr;6(4):1255-8. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
- Specific Function
- all-trans retinoic acid 18-hydroxylase activity
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57469.95 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity)
- Specific Function
- aromatase activity
- Gene Name
- CYP1B1
- Uniprot ID
- Q16678
- Uniprot Name
- Cytochrome P450 1B1
- Molecular Weight
- 60845.33 Da
References
- Bournique B, Lemarie A: Docetaxel (Taxotere) is not metabolized by recombinant human CYP1B1 in vitro, but acts as an effector of this isozyme. Drug Metab Dispos. 2002 Nov;30(11):1149-52. doi: 10.1124/dmd.30.11.1149. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- Wils P, Phung-Ba V, Warnery A, Lechardeur D, Raeissi S, Hidalgo IJ, Scherman D: Polarized transport of docetaxel and vinblastine mediated by P-glycoprotein in human intestinal epithelial cell monolayers. Biochem Pharmacol. 1994 Oct 7;48(7):1528-30. [Article]
- Shirakawa K, Takara K, Tanigawara Y, Aoyama N, Kasuga M, Komada F, Sakaeda T, Okumura K: Interaction of docetaxel ("Taxotere") with human P-glycoprotein. Jpn J Cancer Res. 1999 Dec;90(12):1380-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds, and xenobiotics from cells. Lipophilic anion transporter that mediates ATP-dependent transport of glucuronide conjugates such as estradiol-17-beta-o-glucuronide and GSH conjugates such as leukotriene C4 (LTC4) (PubMed:12527806, PubMed:15256465). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Mediates multidrug resistance (MDR) in cancer cells by preventing the intracellular accumulation of certain antitumor drugs, such as, docetaxel and paclitaxel (PubMed:15256465, PubMed:23087055). Does not transport glycocholic acid, taurocholic acid, MTX, folic acid, cAMP, or cGMP (PubMed:12527806)
- Specific Function
- ABC-type glutathione S-conjugate transporter activity
- Gene Name
- ABCC10
- Uniprot ID
- Q5T3U5
- Uniprot Name
- ATP-binding cassette sub-family C member 10
- Molecular Weight
- 161627.375 Da
References
- Hopper-Borge E, Xu X, Shen T, Shi Z, Chen ZS, Kruh GD: Human multidrug resistance protein 7 (ABCC10) is a resistance factor for nucleoside analogues and epothilone B. Cancer Res. 2009 Jan 1;69(1):178-84. doi: 10.1158/0008-5472.CAN-08-1420. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10779507, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (17-beta-glucuronosyl estradiol, dehydroepiandrosterone sulfate (DHEAS), and estrone 3-sulfate), as well as eicosanoid leukotriene C4, prostaglandin E2 and L-thyroxine (T4) (PubMed:10779507, PubMed:11159893, PubMed:12568656, PubMed:15159445, PubMed:17412826, PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). Shows a pH-sensitive substrate specificity towards sulfated steroids, taurocholate and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Involved in the clearance of bile acids and organic anions from the liver (PubMed:22232210). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins) such as pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:15159445). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Baker SD, Verweij J, Cusatis GA, van Schaik RH, Marsh S, Orwick SJ, Franke RM, Hu S, Schuetz EG, Lamba V, Messersmith WA, Wolff AC, Carducci MA, Sparreboom A: Pharmacogenetic pathway analysis of docetaxel elimination. Clin Pharmacol Ther. 2009 Feb;85(2):155-63. doi: 10.1038/clpt.2008.95. Epub 2008 May 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Functions as a Na(+)-independent bidirectional multispecific transporter (PubMed:11327718, PubMed:18216183, PubMed:21446918, PubMed:28945155). Contributes to the renal and hepatic elimination of endogenous organic compounds from the systemic circulation into the urine and bile, respectively (PubMed:11327718, PubMed:25904762). Capable of transporting a wide range of purine and pyrimidine nucleobases, nucleosides and nucleotides, with cGMP, 2'deoxyguanosine and GMP being the preferred substrates (PubMed:11327718, PubMed:18216183, PubMed:26377792, PubMed:28945155). Functions as a pH- and chloride-independent cGMP bidirectional facilitative transporter that can regulate both intracellular and extracellular levels of cGMP and may be involved in cGMP signaling pathways (PubMed:18216183, PubMed:26377792). Mediates orotate/glutamate bidirectional exchange and most likely display a physiological role in hepatic release of glutamate into the blood (PubMed:21446918). Involved in renal secretion and possible reabsorption of creatinine (PubMed:25904762, PubMed:28945155). Able to uptake prostaglandin E2 (PGE2) and may contribute to PGE2 renal excretion (Probable). Also transports alpha-ketoglutarate and urate (PubMed:11327718, PubMed:26377792). Apart from the orotate/glutamate exchange, the counterions for the uptake of other SLC22A7/OAT2 substrates remain to be identified (PubMed:26377792)
- Specific Function
- alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- Kobayashi Y, Ohshiro N, Sakai R, Ohbayashi M, Kohyama N, Yamamoto T: Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). J Pharm Pharmacol. 2005 May;57(5):573-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- Molecular Weight
- 72313.47 Da
References
- Fellner S, Bauer B, Miller DS, Schaffrik M, Fankhanel M, Spruss T, Bernhardt G, Graeff C, Farber L, Gschaidmeier H, Buschauer A, Fricker G: Transport of paclitaxel (Taxol) across the blood-brain barrier in vitro and in vivo. J Clin Invest. 2002 Nov;110(9):1309-18. [Article]
- Nakanishi T, Ross DD: Breast cancer resistance protein (BCRP/ABCG2): its role in multidrug resistance and regulation of its gene expression. Chin J Cancer. 2012 Feb;31(2):73-99. doi: 10.5732/cjc.011.10320. Epub 2011 Nov 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that binds and hydrolyzes ATP to enable active transport of various substrates including many drugs, toxicants and endogenous compound across cell membranes. Transports a wide variety of conjugated organic anions such as sulfate-, glucuronide- and glutathione (GSH)-conjugates of endo- and xenobiotics substrates (PubMed:10220572, PubMed:10421658, PubMed:11500505, PubMed:16332456). Mediates hepatobiliary excretion of mono- and bis-glucuronidated bilirubin molecules and therefore play an important role in bilirubin detoxification (PubMed:10421658). Mediates also hepatobiliary excretion of others glucuronide conjugates such as 17beta-estradiol 17-glucosiduronic acid and leukotriene C4 (PubMed:11500505). Transports sulfated bile salt such as taurolithocholate sulfate (PubMed:16332456). Transports various anticancer drugs, such as anthracycline, vinca alkaloid and methotrexate and HIV-drugs such as protease inhibitors (PubMed:10220572, PubMed:11500505, PubMed:12441801). Confers resistance to several anti-cancer drugs including cisplatin, doxorubicin, epirubicin, methotrexate, etoposide and vincristine (PubMed:10220572, PubMed:11500505)
- Specific Function
- ABC-type glutathione S-conjugate transporter activity
- Gene Name
- ABCC2
- Uniprot ID
- Q92887
- Uniprot Name
- ATP-binding cassette sub-family C member 2
- Molecular Weight
- 174205.64 Da
References
- Fellner S, Bauer B, Miller DS, Schaffrik M, Fankhanel M, Spruss T, Bernhardt G, Graeff C, Farber L, Gschaidmeier H, Buschauer A, Fricker G: Transport of paclitaxel (Taxol) across the blood-brain barrier in vitro and in vivo. J Clin Invest. 2002 Nov;110(9):1309-18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Mediates export of organic anions and drugs from the cytoplasm (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Confers resistance to anticancer drugs by decreasing accumulation of drug in cells, and by mediating ATP- and GSH-dependent drug export (PubMed:9281595). Hydrolyzes ATP with low efficiency (PubMed:16230346). Catalyzes the export of sphingosine 1-phosphate from mast cells independently of their degranulation (PubMed:17050692). Participates in inflammatory response by allowing export of leukotriene C4 from leukotriene C4-synthezing cells (By similarity). Mediates ATP-dependent, GSH-independent cyclic GMP-AMP (cGAMP) export (PubMed:36070769). Thus, by limiting intracellular cGAMP concentrations negatively regulates the cGAS-STING pathway (PubMed:36070769)
- Specific Function
- ABC-type glutathione S-conjugate transporter activity
- Gene Name
- ABCC1
- Uniprot ID
- P33527
- Uniprot Name
- Multidrug resistance-associated protein 1
- Molecular Weight
- 171589.5 Da
References
- Fellner S, Bauer B, Miller DS, Schaffrik M, Fankhanel M, Spruss T, Bernhardt G, Graeff C, Farber L, Gschaidmeier H, Buschauer A, Fricker G: Transport of paclitaxel (Taxol) across the blood-brain barrier in vitro and in vivo. J Clin Invest. 2002 Nov;110(9):1309-18. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 29, 2024 14:47