Paclitaxel

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAdvanced cervical cancer••• •••••••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• •••••••••••
Used in combination to treatAdvanced head and neck cancer••• •••••••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• •••••••••••
Used in combination to treatAdvanced ovarian cancerRegimen in combination with: Cisplatin (DB00515)••••••••••••••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• •••••••••••
Treatment ofAdvanced soft tissue sarcoma••• •••••••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• •••••••••••
Treatment ofEsophageal cancer••• •••••••••••• ••••••••• •••••••••• •••••••••• ••••••••• •••••••••• ••••••••• •••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ATubulin beta-1 chain
inhibitor
Humans
AApoptosis regulator Bcl-2
inhibitor
Humans
AMicrotubule-associated protein 4Not AvailableHumans
AMicrotubule-associated protein 2Not AvailableHumans
AMicrotubule-associated protein tauNot AvailableHumans
UNuclear receptor subfamily 1 group I member 2
inducer
Humans
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
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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
PathwayCategory
Paclitaxel Action PathwayDrug 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.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Abaloparatide.
AbametapirThe serum concentration of Paclitaxel can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Paclitaxel can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Paclitaxel.
AbemaciclibThe 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

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International/Other Brands
NanoPac / Paxceed
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AbraxaneInjection, powder, for suspension5 mg/mlIntravenousBristol Myers Squibb Pharma Eeig2016-09-07Not applicableEU flag
AbraxaneInjection, powder, lyophilized, for suspension100 mg/20mLIntravenousAbraxis BioScience, LLC2005-02-10Not applicableUS flag
AbraxaneInjection, powder, for suspension5 mg/mlIntravenousBristol Myers Squibb Pharma Eeig2016-09-07Not applicableEU flag
Abraxane for Injectable SuspensionPowder, for suspension100 mg / vialIntravenousCelgene2006-08-31Not applicableCanada flag
ApealeaInjection, powder, for solution60 mgIntravenousInceptua Ab2020-12-16Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Aj-paclitaxelSolution6 mg / mLIntravenousAgila Jamp Canada IncNot applicableNot applicableCanada flag
Apo-paclitaxel InjectableSolution6 mg / mLIntravenousApotex Corporation2005-02-07Not applicableCanada flag
OnxolInjection, solution, concentrate6 mg/1mLIntravenousIVAX Pharmaceuticals Inc2002-01-252010-07-31US flag
PaclitaxelInjection, solution6 mg/1mLIntravenousSagent Pharmaceuticals2024-02-01Not applicableUS flag
PaclitaxelInjection, solution30 mg/5mLIntravenousAlvogen Inc.2017-12-272020-08-01US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ANZATAX 150MG/25ML ENJ. SOL. ICEREN FLAKON, 1 ADETPaclitaxel (150 mg/25ml)Injection, solutionIntravenousORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ.2020-03-17Not applicableTurkey flag
ANZATAX 300 MG/50 ML IV ENJ. SOL. ICEREN FLAKON, 1 ADETPaclitaxel (300 mg/50ml)Injection, solutionIntravenousORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ.2019-04-30Not applicableTurkey flag
ANZATAX 30MG/5ML ENJ. SOL. ICEREN FLAKON, 1 ADETPaclitaxel (30 mg/5ml)Injection, solutionIntravenousORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ.2017-05-02Not applicableTurkey flag
TAXOL 100 MG/17 ML FLAKON, 1 ADETPaclitaxel (100 mg/17ml)InjectionIntravenousBRISTOL-MYERS SQUIBB İLAÇLARI INC. İSTANBUL ŞUBESİ2018-08-202018-08-20Turkey flag
TAXOL 30 MG/5 ML FLAKON, 1 ADETPaclitaxel (30 mg/5ml)InjectionIntravenousBRISTOL-MYERS SQUIBB İLAÇLARI INC. İSTANBUL ŞUBESİ2018-08-202018-08-20Turkey flag

Categories

ATC Codes
L01CD01 — PaclitaxelL01CD51 — Paclitaxel and encequidar
Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Authors unspecified: ABI 007. Drugs R D. 2004;5(3):155-9. [Article]
  6. 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]
Human Metabolome Database
HMDB0015360
KEGG Drug
D00491
KEGG Compound
C07394
PubChem Compound
36314
PubChem Substance
46506910
ChemSpider
10368587
BindingDB
50001839
RxNav
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 85 more
FDA label
Download (220 KB)
MSDS
Download (74 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentEsophageal Squamous Cell Carcinoma (ESCC)1
4Active Not RecruitingTreatmentOvarian Cancer1
4Active Not RecruitingTreatmentSafety and Efficacy1
4Active Not RecruitingTreatmentSquamous Cell Carcinoma of the Head and Neck (SCCHN)1
4CompletedNot AvailableCancer1

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
FormRouteStrength
Injection, powder, for suspensionIntravenous5 mg/ml
Injection, powder, lyophilized, for solutionIntravenous100 mg
Injection, powder, lyophilized, for suspensionIntravenous100 mg/20mL
PowderIntravenous100 mg
PowderIntravenous; Parenteral5 MG/ML
Powder, for suspensionIntravenous100 mg / vial
Powder100 mg/1vial
Injection, powder, for suspensionIntravenous drip100 mg
SuspensionIntravenous100.000 mg
SolutionIntravenous6.00 mg
SolutionParenteral100 mg
Injection
SolutionIntravenous
Injection, solutionIntravenous150 mg/25ml
Injection, powder, for solutionIntravenous60 mg
Powder, for solutionIntravenous60 MG
SolutionIntravenous300.00 mg
Injection, solution, concentrateIntravenous100 mg/16.7ml
Injection, solution, concentrateIntravenous300 mg/50ml
InjectionParenteral6 mg/ml
SolutionIntravenous300.000 mg
InjectionParenteral100 mg
InjectionParenteral30 mg
Injection, solution, concentrateIntravenous100 mg/16.6ml
Injection, solution, concentrateIntravenous150 mg/25ml
Injection, solution, concentrateIntravenous
Injection, solution, concentrateIntravenous600 mg/100ml
SolutionIntravenous150 mg/25ml
SolutionIntravenous30 mg/5ml
SolutionIntravenous6 mg/ml
InjectionIntravenous100 MG/17ML
Injection, solution, concentrateIntravenous6.0 mg/ml
InjectionIntravenous6 mg/5ml
SolutionIntravenous6.000 mg
SolutionParenteral30.000 mg
Solution6 mg/1ml
Injection, solution, concentrateIntravenous6 mg/1mL
InjectionIntravenous6 MG
InjectionIntravenous
InjectionIntravenous100 mg/16.7mL
InjectionIntravenous30 mg/5mL
InjectionIntravenous300 mg/50mL
InjectionIntravenous6 mg/1mL
Injection, solutionIntravenous100 mg/16.7mL
Injection, solutionIntravenous30 mg/5mL
Injection, solutionIntravenous300 mg/50mL
SolutionIntravenous10000000 mg
Solution, concentrateIntravenous100 mg
InjectionIntravenous100 mg
Solution, concentrateIntravenous150 mg
SolutionIntravenous3000000 mg
SolutionParenteral300 mg
Injection, solution, concentrateIntravenous; Parenteral6 MG/ML
LiquidIntravenous6 mg / mL
SolutionIntravenous6 mg / mL
Injection, solution, concentrate100 mg/16.7ml
Injection, solution, concentrate150 mg/25ml
Injection, solution, concentrate300 mg/50ml
PowderNot applicable1 g/1g
Aerosol6 mg/1ml
SolutionIntravenous30 mg
SolutionIntravenous300 mg
SolutionIntravenous; Parenteral30 mg
SolutionParenteral600 mg
SolutionIntravenous100 mg
Injection, solution, concentrateIntravenous30 mg/5ml
SolutionIntravenous150 mg
Injection, solution, concentrateIntravenous6 mg/ml
Injection6 mg/ml
Powder30 mg/1vial
Injection, powder, for solutionParenteral100 mg
Injection, powder, for solutionParenteral30 mg
Solution, concentrateIntravenous300 mg
InjectionIntravenous6 MG/ML
SolutionIntravenous30.000 mg
Injection, solutionIntravenous
Injection, solutionIntravenous6 mg/ml
SolutionIntravenous6 mg
Injection, solutionIntravenous6 mg/1mL
Solution, concentrateIntravenous100 MG/16.7ML
Solution, concentrateIntravenous30 mg
Solution, concentrateIntravenous6 mg
SolutionParenteral6.000 mg
Prices
Unit descriptionCostUnit
Abraxane 100 mg vial1119.6USD vial
Taxol 30 mg/5 ml vial35.06USD ml
Onxol 30 mg/5 ml vial34.54USD ml
Onxol 300 mg/50 ml vial34.54USD ml
Paclitaxel 300 mg/50 ml vial5.31USD ml
Paclitaxel 100 mg/16.7 ml vial4.45USD ml
Paclitaxel 30 mg/5 ml vial3.54USD ml
Paclitaxel 150 mg/25 ml vial3.36USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5498421No1996-03-122013-03-12US flag
US5439686No1995-08-082013-02-22US flag
CA2155947No2007-08-212014-02-22Canada flag
CA2086874No1998-09-012013-01-07Canada flag
US7923536Yes2011-04-122024-06-09US flag
US8034375Yes2011-10-112027-02-13US flag
US8138229Yes2012-03-202024-06-09US flag
US8268348Yes2012-09-182026-08-21US flag
US8314156Yes2012-11-202024-06-09US flag
USRE41884No2010-10-262016-08-14US flag
US7758891Yes2010-07-202026-08-21US flag
US9101543Yes2015-08-112026-08-21US flag
US7820788Yes2010-10-262025-04-27US flag
US8853260Yes2014-10-072021-04-10US flag
US9597409Yes2017-03-212032-09-04US flag
US9393318Yes2016-07-192032-09-04US flag
US9511046Yes2016-12-062034-07-12US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)216-217 °CFDA label
water solubilityInsolubleFDA label
logP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00556 mg/mLALOGPS
logP3.2ALOGPS
logP3.54Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)11.9Chemaxon
pKa (Strongest Basic)-1.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area221.29 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity218.29 m3·mol-1Chemaxon
Polarizability87.15 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.914
Blood Brain Barrier-0.9748
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8345
P-glycoprotein inhibitor IInhibitor0.5509
P-glycoprotein inhibitor IINon-inhibitor0.7309
Renal organic cation transporterNon-inhibitor0.9349
CYP450 2C9 substrateNon-substrate0.837
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7278
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8937
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9158
BiodegradationNot ready biodegradable0.9491
Rat acute toxicity2.4391 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9978
hERG inhibition (predictor II)Non-inhibitor0.7982
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-3971000000-2a76bfe38de6d5790a39
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kjc-0140053940-bd5867173a272ae3b8d4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-3300090220-7551f7ed0bc51849f318
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0rkc-0190062740-e529b7dd9b0358d37620
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0umr-5930054650-650fb2bce0e5f73e5d3d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-1903001250-ed34aa0c79447940ea2d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9310000320-4cb693262ad6c8e8c9db
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-300.8367263
predicted
DarkChem Lite v0.1.0
[M-H]-274.3408263
predicted
DarkChem Lite v0.1.0
[M-H]-274.4514
predicted
DeepCCS 1.0 (2019)
[M+H]+298.0097263
predicted
DarkChem Lite v0.1.0
[M+H]+273.7180263
predicted
DarkChem Lite v0.1.0
[M+H]+276.17508
predicted
DeepCCS 1.0 (2019)
[M+Na]+301.0209263
predicted
DarkChem Lite v0.1.0
[M+Na]+282.50406
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Structural constituent of cytoskeleton
Specific Function
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain (By similarity).
Gene Name
TUBB1
Uniprot ID
Q9H4B7
Uniprot Name
Tubulin beta-1 chain
Molecular Weight
50326.56 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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]
  4. Horwitz SB: Mechanism of action of taxol. Trends Pharmacol Sci. 1992 Apr;13(4):134-6. [Article]
  5. 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
Ubiquitin protein ligase binding
Specific Function
Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial membrane permeability. Appea...
Gene Name
BCL2
Uniprot ID
P10415
Uniprot Name
Apoptosis regulator Bcl-2
Molecular Weight
26265.66 Da
References
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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
Structural molecule activity
Specific Function
Non-neuronal microtubule-associated protein. Promotes microtubule assembly.
Gene Name
MAP4
Uniprot ID
P27816
Uniprot Name
Microtubule-associated protein 4
Molecular Weight
121003.805 Da
References
  1. 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
Structural molecule activity
Specific 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.
Gene Name
MAP2
Uniprot ID
P11137
Uniprot Name
Microtubule-associated protein 2
Molecular Weight
199524.51 Da
References
  1. 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
Structural constituent of cytoskeleton
Specific Function
Promotes microtubule assembly and stability, and might be involved in the establishment and maintenance of neuronal polarity. The C-terminus binds axonal microtubules while the N-terminus binds neu...
Gene Name
MAPT
Uniprot ID
P10636
Uniprot Name
Microtubule-associated protein tau
Molecular Weight
78927.025 Da
References
  1. 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
Zinc ion binding
Specific 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 an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. 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
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. 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
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. 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
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Flockhart Table of Drug Interactions [Link]

Transporters

Details
1. Bile salt export pump
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. 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]
  2. 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]
  3. Wilson A. (2016). New horizons in predictive drug metabolism and pharmacokinetics. The Royal Society of Chemistry. [ISBN:978-1-84973-828-6]
Details
2. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
P-glycoprotein was associated with drug resistance in tumour cells and reduced therapeutic effectiveness of paclitaxel.
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. 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]
  8. Walle UK, Walle T: Taxol transport by human intestinal epithelial Caco-2 cells. Drug Metab Dispos. 1998 Apr;26(4):343-6. [Article]
  9. 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]
  10. 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]
  11. Kuo CC, Hsieh HP, Pan WY, Chen CP, Liou JP, Lee SJ, Chang YL, Chen LT, Chen CT, Chang JY: BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo. Cancer Res. 2004 Jul 1;64(13):4621-8. [Article]
  12. Li YC, Fung KP, Kwok TT, Lee CY, Suen YK, Kong SK: Mitochondria-targeting drug oligomycin blocked P-glycoprotein activity and triggered apoptosis in doxorubicin-resistant HepG2 cells. Chemotherapy. 2004 Jun;50(2):55-62. [Article]
  13. Kwak JO, Lee SH, Lee GS, Kim MS, Ahn YG, Lee JH, Kim SW, Kim KH, Lee MG: Selective inhibition of MDR1 (ABCB1) by HM30181 increases oral bioavailability and therapeutic efficacy of paclitaxel. Eur J Pharmacol. 2010 Feb 10;627(1-3):92-8. doi: 10.1016/j.ejphar.2009.11.008. Epub 2009 Nov 10. [Article]
  14. Woodahl EL, Crouthamel MH, Bui T, Shen DD, Ho RJ: MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8. doi: 10.1007/s00280-008-0906-4. Epub 2009 Jan 4. [Article]
  15. Tiwari AK, Sodani K, Wang SR, Kuang YH, Ashby CR Jr, Chen X, Chen ZS: Nilotinib (AMN107, Tasigna) reverses multidrug resistance by inhibiting the activity of the ABCB1/Pgp and ABCG2/BCRP/MXR transporters. Biochem Pharmacol. 2009 Jul 15;78(2):153-61. doi: 10.1016/j.bcp.2009.04.002. Epub 2009 Apr 11. [Article]
  16. Noguchi K, Kawahara H, Kaji A, Katayama K, Mitsuhashi J, Sugimoto Y: Substrate-dependent bidirectional modulation of P-glycoprotein-mediated drug resistance by erlotinib. Cancer Sci. 2009 Sep;100(9):1701-7. doi: 10.1111/j.1349-7006.2009.01213.x. Epub 2009 May 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. 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
Substrate
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion.
Gene Name
ABCC10
Uniprot ID
Q5T3U5
Uniprot Name
Multidrug resistance-associated protein 7
Molecular Weight
161627.375 Da
References
  1. 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]
  2. 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]
  3. 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
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. 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
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. 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 March 18, 2024 16:48