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Identification
- Summary
Paclitaxel is a taxoid chemotherapeutic agent used as first-line and subsequent therapy for the treatment of advanced carcinoma of the ovary, and other various cancers including breast and lung cancer.
- Brand Names
- Abraxane, Taxol
- Generic Name
- Paclitaxel
- DrugBank Accession Number
- DB01229
- Background
Paclitaxel is a chemotherapeutic agent marketed under the brand name Taxol among others. Used as a treatment for various cancers, paclitaxel is a mitotic inhibitor that was first isolated in 1971 from the bark of the Pacific yew tree which contains endophytic fungi that synthesize paclitaxel. It is available as an intravenous solution for injection and the newer formulation contains albumin-bound paclitaxel marketed under the brand name Abraxane.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Paclitaxel (DB01229)
- Weight
- Average: 853.9061
Monoisotopic: 853.330955345 - Chemical Formula
- C47H51NO14
- Synonyms
- 5beta,20-Epoxy-1,2-alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine
- ABI-007 COMPONENT PACLITAXEL
- BENZENEPROPANOIC ACID, .BETA.-(BENZOYLAMINO)-.ALPHA.-HYDROXY-, (2AR,4S,4AS,6R,9S,11S,12S,12AR,12BS)-6,12B-BIS(ACETYLOXY)-12-(BENZOYLOXY)-2A,3,4,4A,5,6,9,10,11,12,12A,12B-DODECAHYDRO-4,11-DIHYDROXY-4A,8,13,13-TETRAMETHYL-5-OXO-7,11-METHANO-1H-CYCLODECA(3,
- liposomal encapsulated paclitaxel
- NAB-PACLITAXEL COMPONENT PACLITAXEL
- Nanoparticulate paclitaxel
- Paclitaxel
- paclitaxel protein-bound particles
- Paclitaxel protein-bound particles for injection suspension
- Taxol A
- External IDs
- ABI-007
- BMS 181339-01
- BMS-181339-01
- DHP 107
- MBT 0206
- MBT-0206
- NK 105
- NK-105
- NK105
- NSC 125973
- NSC-125973
- QW-8184
- S-8184
Pharmacology
- Indication
Used in the treatment of Kaposi's sarcoma and cancer of the lung, ovarian, and breast. Abraxane® is specfically indicated for the treatment of metastatic breast cancer and locally advanced or metastatic non-small cell lung cancer.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Advanced cervical cancer ••• ••••• ••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• ••••••••••• Used in combination to treat Advanced head and neck cancer ••• ••••• ••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• ••••••••••• Used in combination to treat Advanced ovarian cancer Regimen in combination with: Cisplatin (DB00515) •••••••••••• ••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• ••••••••••• Treatment of Advanced soft tissue sarcoma ••• ••••• ••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• ••••••••••• Treatment of Esophageal cancer ••• ••••• ••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• ••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Paclitaxel is a taxoid antineoplastic agent indicated as first-line and subsequent therapy for the treatment of advanced carcinoma of the ovary, and other various cancers including breast cancer. Paclitaxel is a novel antimicrotubule agent that 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 that is essential for vital interphase and mitotic cellular functions. In addition, paclitaxel induces abnormal arrays or "bundles" of microtubules throughout the cell cycle and multiple asters of microtubules during mitosis.
- Mechanism of action
Paclitaxel interferes with the normal function of microtubule growth. Whereas drugs like colchicine cause the depolymerization of microtubules in vivo, paclitaxel 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, paclitaxel binds to the β subunit of tubulin. Tubulin is the "building block" of mictotubules, and the binding of paclitaxel locks these building blocks in place. The resulting microtubule/paclitaxel 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 paclitaxel 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.
Target Actions Organism ATubulin beta-1 chain inhibitorHumans AApoptosis regulator Bcl-2 inhibitorHumans AMicrotubule-associated protein 4 Not Available Humans AMicrotubule-associated protein 2 Not Available Humans AMicrotubule-associated protein tau Not Available Humans UNuclear receptor subfamily 1 group I member 2 inducerHumans - Absorption
When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the maximum plasma concentration (Cmax) is 195 ng/mL, while the AUC is 6300 ng•h/mL.
- Volume of distribution
- 227 to 688 L/m^2 [apparent volume of distribution at steady-state, 24 hour infusion]
- Protein binding
89%-98% bound to plasma protein. The presence of cimetidine, ranitidine, dexamethasone, or diphenhydramine did not affect protein binding of paclitaxel.
- Metabolism
Hepatic. In vitro studies with human liver microsomes and tissue slices showed that paclitaxel was metabolized primarily to 6a-hydrox-ypaclitaxel by the cytochrome P450 isozyme CYP2C8; and to two minor metabolites, 3’-p-hydroxypaclitaxel and 6a, 3’-p-dihydroxypaclitaxel, by CYP3A4.
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- Route of elimination
In 5 patients administered a 225 or 250 mg/m2 dose of radiolabeled paclitaxel as a 3-hour infusion, a mean of 71% of the radioactivity was excreted in the feces in 120 hours, and 14% was recovered in the urine.
- Half-life
When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the elimination half=life is 52.7 hours.
- Clearance
- 21.7 L/h/m2 [Dose 135 mg/m2, infusion duration 24 h]
- 23.8 L/h/m2 [Dose 175 mg/m2, infusion duration 24 h]
- 7 L/h/m2 [Dose 135 mg/m2, infusion duration 3 h]
- 12.2 L/h/m2 [Dose 175 mg/m2, infusion duration 3 h]
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Rat (ipr) LD50=32530 µg/kg. Symptoms of overdose include bone marrow suppression, peripheral neurotoxicity, and mucositis. Overdoses in pediatric patients may be associated with acute ethanol toxicity.
- Pathways
Pathway Category Paclitaxel Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
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 softwareAbaloparatide The risk or severity of adverse effects can be increased when Paclitaxel is combined with Abaloparatide. Abametapir The serum concentration of Paclitaxel can be increased when it is combined with Abametapir. Abatacept The metabolism of Paclitaxel can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Paclitaxel. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Paclitaxel. - Food Interactions
- Avoid echinacea. Co-administration may decrease the effectiveness of immunosuppressants, and echinacea may induce CYP3A4 increasing paclitaxel metabolism.
- Exercise caution with grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of paclitaxel.
- Exercise caution with St. John's Wort. This herb induces the CYP3A4 metabolism of paclitaxel and may reduce its serum concentration.
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.- International/Other Brands
- NanoPac / Paxceed
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Abraxane Injection, powder, lyophilized, for suspension 100 mg/20mL Intravenous Abraxis BioScience, LLC 2005-02-10 Not applicable US 
Abraxane Injection, powder, for suspension 5 mg/ml Intravenous Bristol Myers Squibb Pharma Eeig 2016-09-07 Not applicable EU 
Abraxane Injection, powder, for suspension 5 mg/ml Intravenous Bristol Myers Squibb Pharma Eeig 2016-09-07 Not applicable EU Abraxane for Injectable Suspension Powder, for suspension 100 mg / vial Intravenous Bristol Myers Squibb 2006-08-31 Not applicable Canada 
Apealea Injection, powder, for solution 60 mg Intravenous Inceptua Ab 2020-12-16 2024-02-09 EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aj-paclitaxel Solution 6 mg / mL Intravenous Agila Jamp Canada Inc Not applicable Not applicable Canada Apo-paclitaxel Injectable Solution 6 mg / mL Intravenous Apotex Corporation 2005-02-07 Not applicable Canada Onxol Injection, solution, concentrate 6 mg/1mL Intravenous IVAX Pharmaceuticals Inc 2002-01-25 2010-07-31 US Paclitaxel Injection, solution 6 mg/1mL Intravenous Novadoz Pharmaceuticals Llc 2020-08-26 Not applicable US Paclitaxel Injection, solution 30 mg/5mL Intravenous Breckenridge Pharmaceutical, Inc. 2016-09-30 2019-05-31 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ANZATAX 150MG/25ML ENJ. SOL. ICEREN FLAKON, 1 ADET Paclitaxel (150 mg/25ml) Injection, solution Intravenous ORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ. 2020-03-17 Not applicable Turkey 
ANZATAX 300 MG/50 ML IV ENJ. SOL. ICEREN FLAKON, 1 ADET Paclitaxel (300 mg/50ml) Injection, solution Intravenous ORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ. 2019-04-30 Not applicable Turkey ANZATAX 30MG/5ML ENJ. SOL. ICEREN FLAKON, 1 ADET Paclitaxel (30 mg/5ml) Injection, solution Intravenous ORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ. 2017-05-02 Not applicable Turkey TAXOL 100 MG/17 ML FLAKON, 1 ADET Paclitaxel (100 mg/17ml) Injection Intravenous BRISTOL-MYERS SQUIBB İLAÇLARI INC. İSTANBUL ŞUBESİ 2018-08-20 2018-08-20 Turkey TAXOL 30 MG/5 ML FLAKON, 1 ADET Paclitaxel (30 mg/5ml) Injection Intravenous BRISTOL-MYERS SQUIBB İLAÇLARI INC. İSTANBUL ŞUBESİ 2018-08-20 2018-08-20 Turkey
Categories
- ATC Codes
- L01CD01 — Paclitaxel
- L01CD — Taxanes
- L01C — PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS
- L01 — ANTINEOPLASTIC AGENTS
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- Drug Categories
- Agents Causing Muscle Toxicity
- Albumins
- Amino Acids, Peptides, and Proteins
- Antimitotic Agents
- Antineoplastic Agents
- Antineoplastic Agents, Phytogenic
- Antineoplastic and Immunomodulating Agents
- BSEP/ABCB11 Inhibitors
- BSEP/ABCB11 Substrates
- BSEP/ABCB11 Substrates with a Narrow Therapeutic Index
- Cardiotoxic antineoplastic agents
- Cyclodecanes
- Cycloparaffins
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (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 Inducers
- Cytochrome P-450 Substrates
- Diterpenes
- Hypotensive Agents
- Immunosuppressive Agents
- Microtubule Inhibition
- Microtubule Inhibitors
- Mitosis Modulators
- Myelosuppressive Agents
- Narrow Therapeutic Index Drugs
- Neurotoxic agents
- OATP1B3 substrates
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- P-glycoprotein substrates with a Narrow Therapeutic Index
- Proteins
- 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
- Tetracarboxylic acids and derivatives / Benzoic acid esters / Benzoyl derivatives / Alpha-acyloxy ketones / Fatty acid esters / Tertiary alcohols / Secondary alcohols / Oxetanes / Carboxylic acid esters / Cyclic alcohols and derivatives show 9 more
- Substituents
- Alcohol / Alpha-acyloxy ketone / Aromatic heteropolycyclic compound / Benzenoid / Benzoate ester / Benzoic acid or derivatives / Benzoyl / Carbonyl group / Carboximidic acid / Carboximidic acid derivative show 25 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- taxane diterpenoid, tetracyclic diterpenoid (CHEBI:45863)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- P88XT4IS4D
- CAS number
- 33069-62-4
- InChI Key
- RCINICONZNJXQF-MZXODVADSA-N
- InChI
- InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
- IUPAC Name
- (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-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@]12[C@H](OC(=O)C3=CC=CC=C3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)C4=CC=CC=C4)C4=CC=CC=C4)C(C)=C([C@@H](OC(C)=O)C(=O)[C@]1(C)[C@@H](O)C[C@H]1OC[C@@]21OC(C)=O)C3(C)C
References
- Synthesis Reference
Hendricus B. A. de Bont, Ruben G. G. Leenders, Johan W. Scheeren, Hidde J. Haisma, Dick de Vos, "Paclitaxel prodrugs, method for preparation as well as their use in selective chemotherapy." U.S. Patent US5760072, issued September, 1989.
US5760072- General References
- Wall ME, Wani MC: Camptothecin and taxol: discovery to clinic--thirteenth Bruce F. Cain Memorial Award Lecture. Cancer Res. 1995 Feb 15;55(4):753-60. [Article]
- Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT: Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc. 1971 May 5;93(9):2325-7. [Article]
- Fuchs DA, Johnson RK: Cytologic evidence that taxol, an antineoplastic agent from Taxus brevifolia, acts as a mitotic spindle poison. Cancer Treat Rep. 1978 Aug;62(8):1219-22. [Article]
- Saville MW, Lietzau J, Pluda JM, Feuerstein I, Odom J, Wilson WH, Humphrey RW, Feigal E, Steinberg SM, Broder S, et al.: Treatment of HIV-associated Kaposi's sarcoma with paclitaxel. Lancet. 1995 Jul 1;346(8966):26-8. [Article]
- Authors unspecified: ABI 007. Drugs R D. 2004;5(3):155-9. [Article]
- Gaitanis A, Staal S: Liposomal doxorubicin and nab-paclitaxel: nanoparticle cancer chemotherapy in current clinical use. Methods Mol Biol. 2010;624:385-92. doi: 10.1007/978-1-60761-609-2_26. [Article]
- External Links
- Human Metabolome Database
- HMDB0015360
- KEGG Drug
- D00491
- KEGG Compound
- C07394
- PubChem Compound
- 36314
- PubChem Substance
- 46506910
- ChemSpider
- 10368587
- BindingDB
- 50001839
- 56946
- ChEBI
- 45863
- ChEMBL
- CHEMBL428647
- ZINC
- ZINC000096006020
- Therapeutic Targets Database
- DNC001411
- PharmGKB
- PA450761
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- TA1
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Paclitaxel
- PDB Entries
- 1jff / 2hxf / 2hxh / 2p4n / 2wbe / 3dco / 3edl / 3iz0 / 3j6g / 3j6p … show 97 more
- FDA label
- Download (220 KB)
- MSDS
- Download (74 KB)
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 Borderline Resectable Pancreatic Adenocarcinoma / Chemotherapy Effects / Pancreatic Adenocarcinoma Locally Advanced / Post-pancreatectomy 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Breast Cancer 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Adenocarcinoma of the Lung / Adenosquamous Lung Carcinoma / Lung Cancer, Nonsmall Cell, Stage IIIA / Lung Large Cell Carcinoma / Recurrent Non-small Cell Lung Cancer / Squamous Cell Lung Cancer / Stage IIA Non-small Cell Lung Cancer / Stage IIB Non-small Cell Lung Cancer / Stage IIIB Non-Small Cell Lung Cancer 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Advanced Pancreatic Ductal Adenocarcinoma / Pancreatic Cancer 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Breast Cancer 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Abraxis BioScience Inc.
- Accord Healthcare
- APP Pharmaceuticals
- Barr Pharmaceuticals
- Bedford Labs
- Ben Venue Laboratories Inc.
- Bristol-Myers Squibb Co.
- Ebewe Pharma
- Ethex Corp.
- Fresenius Kabi AB
- Hospira Inc.
- Intas Pharmaceuticals Ltd.
- Ivax Pharmaceuticals
- Mead Johnson and Co.
- Pharmachemie BV
- Pliva Inc.
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- Dosage Forms
Form Route Strength Injection, powder, for suspension Intravenous 5 mg/ml Injection, powder, lyophilized, for solution Intravenous 100 mg Injection, powder, lyophilized, for suspension Intravenous 100 mg/20mL Powder Intravenous 100 mg Powder Intravenous; Parenteral 5 MG/ML Powder, for suspension Intravenous 100 mg / vial Powder 100 mg/1vial Injection, powder, for suspension Intravenous drip 100 mg Suspension Intravenous 100.000 mg Solution Intravenous 6.00 mg Solution Parenteral 100 mg Injection 6 mg/ml Solution Intravenous Injection, solution Intravenous 150 mg/25ml Injection, powder, for solution Intravenous 60 mg Powder, for solution Intravenous 60 MG Solution Intravenous 300.00 mg Injection, solution, concentrate Intravenous 100 mg/16.7ml Injection, solution, concentrate Intravenous 300 mg/50ml Injection, solution, concentrate Intravenous 6 mg/ mL Injection Parenteral 6 mg/ml Solution Intravenous 300.000 mg Injection Parenteral 100 mg Injection Parenteral 30 mg Injection Intravenous Injection, solution, concentrate Intravenous 100 mg/16.6ml Injection, solution, concentrate Intravenous 150 mg/25ml Injection, solution, concentrate Intravenous Injection, solution, concentrate Intravenous 600 mg/100ml Solution Intravenous 150 mg/25ml Solution Intravenous 30 mg/5ml Solution Intravenous 6 mg/ml Injection Intravenous 6 mg/ml Injection Intravenous 100 MG/17ML Injection, solution, concentrate Intravenous 6.0 mg/ml Injection Intravenous 6 mg/5ml Powder Intravenous 5 mg/ml Solution Intravenous 6.000 mg Solution Parenteral 30.000 mg Solution 6 mg/1ml Injection, solution, concentrate Intravenous 6 mg/1mL Injection 6 mg/5ml Injection Intravenous 100 mg/16.7mL Injection Intravenous 30 mg/5mL Injection Intravenous 300 mg/50mL Injection Intravenous 6 mg/1mL Injection, solution Intravenous 100 mg/16.7mL Injection, solution Intravenous 30 mg/5mL Injection, solution Intravenous 300 mg/50mL Solution Intravenous 10000000 mg Solution, concentrate Intravenous 100 mg Injection Intravenous 100 mg Solution, concentrate Intravenous 150 mg Solution Intravenous 3000000 mg Solution Parenteral 300 mg Injection, solution, concentrate Intravenous; Parenteral 6 MG/ML Liquid Intravenous 6 mg / mL Solution Intravenous 6 mg / mL Injection, solution, concentrate 100 mg/16.7ml Injection, solution, concentrate 150 mg/25ml Injection, solution, concentrate 300 mg/50ml Powder Not applicable 1 g/1g Aerosol 6 mg/1ml Solution Intravenous 30 mg Solution Intravenous 300 mg Solution Intravenous; Parenteral 30 mg Solution Parenteral 600 mg Solution Intravenous 100 mg Injection, solution, concentrate Intravenous 30 mg/5ml Solution Intravenous 150 mg Injection, solution, concentrate Intravenous 6 mg/ml Powder 30 mg/1vial Injection, powder, for solution Parenteral 100 mg Injection, powder, for solution Parenteral 30 mg Solution, concentrate Intravenous 300 mg Solution Intravenous 30.000 mg Injection, solution Intravenous 6 mg/ mL Injection, solution Intravenous 6 mg/ml Solution Intravenous 6 mg Injection, solution Intravenous 6 mg/1mL Solution, concentrate Intravenous 100 MG/16.7ML Solution, concentrate Intravenous 30 mg Solution, concentrate Intravenous 6 mg Injection, solution Intravenous 100 mg/16.67mL Solution Parenteral 6.000 mg - Prices
Unit description Cost Unit Abraxane 100 mg vial 1119.6USD vial Taxol 30 mg/5 ml vial 35.06USD ml Onxol 30 mg/5 ml vial 34.54USD ml Onxol 300 mg/50 ml vial 34.54USD ml Paclitaxel 300 mg/50 ml vial 5.31USD ml Paclitaxel 100 mg/16.7 ml vial 4.45USD ml Paclitaxel 30 mg/5 ml vial 3.54USD ml Paclitaxel 150 mg/25 ml vial 3.36USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5498421 No 1996-03-12 2013-03-12 US US5439686 No 1995-08-08 2013-02-22 US CA2155947 No 2007-08-21 2014-02-22 Canada CA2086874 No 1998-09-01 2013-01-07 Canada US7923536 Yes 2011-04-12 2024-06-09 US US8034375 Yes 2011-10-11 2027-02-13 US US8138229 Yes 2012-03-20 2024-06-09 US US8268348 Yes 2012-09-18 2026-08-21 US US8314156 Yes 2012-11-20 2024-06-09 US USRE41884 No 2010-10-26 2016-08-14 US US7758891 Yes 2010-07-20 2026-08-21 US US9101543 Yes 2015-08-11 2026-08-21 US US7820788 Yes 2010-10-26 2025-04-27 US US8853260 Yes 2014-10-07 2021-04-10 US US9597409 Yes 2017-03-21 2032-09-04 US US9393318 Yes 2016-07-19 2032-09-04 US US9511046 Yes 2016-12-06 2034-07-12 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 216-217 °C FDA label water solubility Insoluble FDA label logP 3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00556 mg/mL ALOGPS logP 3.2 ALOGPS logP 3.54 Chemaxon logS -5.2 ALOGPS pKa (Strongest Acidic) 11.9 Chemaxon pKa (Strongest Basic) -1.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 221.29 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 218.29 m3·mol-1 Chemaxon Polarizability 87.15 Å3 Chemaxon Number of Rings 7 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 + 0.914 Blood Brain Barrier - 0.9748 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.8345 P-glycoprotein inhibitor I Inhibitor 0.5509 P-glycoprotein inhibitor II Non-inhibitor 0.7309 Renal organic cation transporter Non-inhibitor 0.9349 CYP450 2C9 substrate Non-substrate 0.837 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.7278 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8937 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9158 Biodegradation Not ready biodegradable 0.9491 Rat acute toxicity 2.4391 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9978 hERG inhibition (predictor II) Non-inhibitor 0.7982
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 300.8367263 predictedDarkChem Lite v0.1.0 [M-H]- 274.3408263 predictedDarkChem Lite v0.1.0 [M-H]- 274.4514 predictedDeepCCS 1.0 (2019) [M+H]+ 298.0097263 predictedDarkChem Lite v0.1.0 [M+H]+ 273.7180263 predictedDarkChem Lite v0.1.0 [M+H]+ 276.17508 predictedDeepCCS 1.0 (2019) [M+Na]+ 301.0209263 predictedDarkChem Lite v0.1.0 [M+Na]+ 282.50406 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Cheung CH, Chen HH, Kuo CC, Chang CY, Coumar MS, Hsieh HP, Chang JY: Survivin counteracts the therapeutic effect of microtubule de-stabilizers by stabilizing tubulin polymers. Mol Cancer. 2009 Jul 3;8:43. doi: 10.1186/1476-4598-8-43. [Article]
- Horwitz SB: Mechanism of action of taxol. Trends Pharmacol Sci. 1992 Apr;13(4):134-6. [Article]
- Kovacs P, Csaba G, Pallinger E, Czaker R: Effects of taxol treatment on the microtubular system and mitochondria of Tetrahymena. Cell Biol Int. 2007 Jul;31(7):724-32. Epub 2007 Jan 14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Gan Y, Wientjes MG, Au JL: Expression of basic fibroblast growth factor correlates with resistance to paclitaxel in human patient tumors. Pharm Res. 2006 Jun;23(6):1324-31. Epub 2006 Jun 8. [Article]
- Thomadaki H, Talieri M, Scorilas A: Treatment of MCF-7 cells with taxol and etoposide induces distinct alterations in the expression of apoptosis-related genes BCL2, BCL2L12, BAX, CASPASE-9 and FAS. Biol Chem. 2006 Aug;387(8):1081-6. [Article]
- Yoshino T, Shiina H, Urakami S, Kikuno N, Yoneda T, Shigeno K, Igawa M: Bcl-2 expression as a predictive marker of hormone-refractory prostate cancer treated with taxane-based chemotherapy. Clin Cancer Res. 2006 Oct 15;12(20 Pt 1):6116-24. [Article]
- Matsuyoshi S, Shimada K, Nakamura M, Ishida E, Konishi N: Bcl-2 phosphorylation has pathological significance in human breast cancer. Pathobiology. 2006;73(4):205-12. [Article]
- Zhang X, Wang Q, Ling MT, Wong YC, Leung SC, Wang X: Anti-apoptotic role of TWIST and its association with Akt pathway in mediating taxol resistance in nasopharyngeal carcinoma cells. Int J Cancer. 2007 May 1;120(9):1891-8. [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
- 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
- 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
- Actions
- Inducer
- 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
- Harmsen S, Meijerman I, Beijnen JH, Schellens JH: Nuclear receptor mediated induction of cytochrome P450 3A4 by anticancer drugs: a key role for the pregnane X receptor. Cancer Chemother Pharmacol. 2009 Jun;64(1):35-43. doi: 10.1007/s00280-008-0842-3. Epub 2008 Oct 7. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- 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
- Fischer V, Rodriguez-Gascon A, Heitz F, Tynes R, Hauck C, Cohen D, Vickers AE: The multidrug resistance modulator valspodar (PSC 833) is metabolized by human cytochrome P450 3A. Implications for drug-drug interactions and pharmacological activity of the main metabolite. Drug Metab Dispos. 1998 Aug;26(8):802-11. [Article]
- Sonnichsen DS, Liu Q, Schuetz EG, Schuetz JD, Pappo A, Relling MV: Variability in human cytochrome P450 paclitaxel metabolism. J Pharmacol Exp Ther. 1995 Nov;275(2):566-75. [Article]
- Wang Y, Wang M, Qi H, Pan P, Hou T, Li J, He G, Zhang H: Pathway-dependent inhibition of paclitaxel hydroxylation by kinase inhibitors and assessment of drug-drug interaction potentials. Drug Metab Dispos. 2014 Apr;42(4):782-95. doi: 10.1124/dmd.113.053793. Epub 2014 Jan 29. [Article]
- Desai PB, Duan JZ, Zhu YW, Kouzi S: Human liver microsomal metabolism of paclitaxel and drug interactions. Eur J Drug Metab Pharmacokinet. 1998 Jul-Sep;23(3):417-24. [Article]
- Nallani SC, Goodwin B, Buckley AR, Buckley DJ, Desai PB: Differences in the induction of cytochrome P450 3A4 by taxane anticancer drugs, docetaxel and paclitaxel, assessed employing primary human hepatocytes. Cancer Chemother Pharmacol. 2004 Sep;54(3):219-29. doi: 10.1007/s00280-004-0799-9. Epub 2004 Jun 3. [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
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). 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 (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874)
- Specific Function
- aromatase activity
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Purohit A, Singh A, Ghilchik MW, Reed MJ: Inhibition of tumor necrosis factor alpha-stimulated aromatase activity by microtubule-stabilizing agents, paclitaxel and 2-methoxyestradiol. Biochem Biophys Res Commun. 1999 Jul 22;261(1):214-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Rochat B, Morsman JM, Murray GI, Figg WD, McLeod HL: Human CYP1B1 and anticancer agent metabolism: mechanism for tumor-specific drug inactivation? J Pharmacol Exp Ther. 2001 Feb;296(2):537-41. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). 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:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Yu L, Shi D, Ma L, Zhou Q, Zeng S: Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87. doi: 10.1002/bdd.1842. Epub 2013 Jun 3. [Article]
- Dai D, Zeldin DC, Blaisdell JA, Chanas B, Coulter SJ, Ghanayem BI, Goldstein JA: Polymorphisms in human CYP2C8 decrease metabolism of the anticancer drug paclitaxel and arachidonic acid. Pharmacogenetics. 2001 Oct;11(7):597-607. [Article]
- Sonnichsen DS, Liu Q, Schuetz EG, Schuetz JD, Pappo A, Relling MV: Variability in human cytochrome P450 paclitaxel metabolism. J Pharmacol Exp Ther. 1995 Nov;275(2):566-75. [Article]
- Desai PB, Duan JZ, Zhu YW, Kouzi S: Human liver microsomal metabolism of paclitaxel and drug interactions. Eur J Drug Metab Pharmacokinet. 1998 Jul-Sep;23(3):417-24. [Article]
- Flockhart Table of Drug Interactions [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Catalyzes the transport of the major hydrophobic bile salts, such as taurine and glycine-conjugated cholic acid across the canalicular membrane of hepatocytes in an ATP-dependent manner, therefore participates in hepatic bile acid homeostasis and consequently to lipid homeostasis through regulation of biliary lipid secretion in a bile salts dependent manner (PubMed:15791618, PubMed:16332456, PubMed:18985798, PubMed:19228692, PubMed:20010382, PubMed:20398791, PubMed:22262466, PubMed:24711118, PubMed:29507376, PubMed:32203132). Transports taurine-conjugated bile salts more rapidly than glycine-conjugated bile salts (PubMed:16332456). Also transports non-bile acid compounds, such as pravastatin and fexofenadine in an ATP-dependent manner and may be involved in their biliary excretion (PubMed:15901796, PubMed:18245269)
- Specific Function
- ABC-type bile acid transporter activity
- Gene Name
- ABCB11
- Uniprot ID
- O95342
- Uniprot Name
- Bile salt export pump
- Molecular Weight
- 146405.83 Da
References
- Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [Article]
- Lecureur V, Sun D, Hargrove P, Schuetz EG, Kim RB, Lan LB, Schuetz JD: Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35. [Article]
- Wilson A. (2016). New horizons in predictive drug metabolism and pharmacokinetics. The Royal Society of Chemistry. [ISBN:978-1-84973-828-6]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- P-glycoprotein was associated with drug resistance in tumour cells and reduced therapeutic effectiveness of paclitaxel.
- 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
- Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [Article]
- Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [Article]
- Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [Article]
- Jang SH, Wientjes MG, Au JL: Kinetics of P-glycoprotein-mediated efflux of paclitaxel. J Pharmacol Exp Ther. 2001 Sep;298(3):1236-42. [Article]
- Li D, Jang SH, Kim J, Wientjes MG, Au JL: Enhanced drug-induced apoptosis associated with P-glycoprotein overexpression is specific to antimicrotubule agents. Pharm Res. 2003 Jan;20(1):45-50. [Article]
- Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [Article]
- Kim S, Kim SS, Bang YJ, Kim SJ, Lee BJ: In vitro activities of native and designed peptide antibiotics against drug sensitive and resistant tumor cell lines. Peptides. 2003 Jul;24(7):945-53. [Article]
- Walle UK, Walle T: Taxol transport by human intestinal epithelial Caco-2 cells. Drug Metab Dispos. 1998 Apr;26(4):343-6. [Article]
- Lecureur V, Sun D, Hargrove P, Schuetz EG, Kim RB, Lan LB, Schuetz JD: Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35. [Article]
- Collett A, Tanianis-Hughes J, Hallifax D, Warhurst G: Predicting P-glycoprotein effects on oral absorption: correlation of transport in Caco-2 with drug pharmacokinetics in wild-type and mdr1a(-/-) mice in vivo. Pharm Res. 2004 May;21(5):819-26. [Article]
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Heijn M, Hooijberg JH, Scheffer GL, Szabo G, Westerhoff HV, Lankelma J: Anthracyclines modulate multidrug resistance protein (MRP) mediated organic anion transport. Biochim Biophys Acta. 1997 May 22;1326(1):12-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Chen ZS, Hopper-Borge E, Belinsky MG, Shchaveleva I, Kotova E, Kruh GD: Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10). Mol Pharmacol. 2003 Feb;63(2):351-8. [Article]
- Zhou Y, Hopper-Borge E, Shen T, Huang XC, Shi Z, Kuang YH, Furukawa T, Akiyama S, Peng XX, Ashby CR Jr, Chen X, Kruh GD, Chen ZS: Cepharanthine is a potent reversal agent for MRP7(ABCC10)-mediated multidrug resistance. Biochem Pharmacol. 2009 Mar 15;77(6):993-1001. doi: 10.1016/j.bcp.2008.12.005. Epub 2008 Dec 25. [Article]
- 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
- Smith NF, Acharya MR, Desai N, Figg WD, Sparreboom A: Identification of OATP1B3 as a high-affinity hepatocellular transporter of paclitaxel. Cancer Biol Ther. 2005 Aug;4(8):815-8. [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]
Drug created at June 13, 2005 13:24 / Updated at October 08, 2024 09:29