Trabectedin

Identification

Summary

Trabectedin is an alkylating agent approved for the treatment of unresectable or metastatic soft tissue sarcoma (liposarcoma or leiomyosarcoma).

Brand Names
Yondelis
Generic Name
Trabectedin
DrugBank Accession Number
DB05109
Background

Trabectedin, also referred as ET-743 during its development, is a marine-derived antitumor agent discovered in the Carribean tunicate Ecteinascidia turbinata and now produced synthetically. Trabectedin has a unique mechanism of action. It binds to the minor groove of DNA interfering with cell division and genetic transcription processes and DNA repair machinery. It is approved for use in Europe, Russia and South Korea for the treatment of advanced soft tissue sarcoma. It is currently under evaluation for the treatment of breast cancer, prostate cancer, in addition to pediatric sarcomas. Both the European Commission and the U.S. Food and Drug Administration (FDA) have approved trabectedin as an orphan drug in soft tissue sarcomas and ovarian cancer. On October 23, 2015, the FDA approved trabectedin, (as Yondelis), for the treatment of specific soft tissue sarcomas.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 761.837
Monoisotopic: 761.261829923
Chemical Formula
C39H43N3O11S
Synonyms
  • Ecteinascidin 743
  • Trabectedin
  • Trabectedina
External IDs
  • ET-743
  • NSC 684766
  • NSC-648766

Pharmacology

Indication

Indicated for treatment of advanced soft tissue sarcoma in patients refractory to or unsuitable to receive anthracycline or ifosfamide chemotherapy in Europe, Russia and South Korea. Approved for orphan drug status by the U.S. FDA for treatment of soft tissue sarcomas and ovarian cancer. Investigated for use/treatment in cancer/tumors (unspecified), gastric cancer, ovarian cancer, pediatric indications, sarcoma, and solid tumors.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofMetastatic leiomyosarcoma••••••••••••
Treatment ofMetastatic liposarcoma••••••••••••
Used in combination to treatRelapsed platinum-sensitive ovarian cancerRegimen in combination with: Doxorubicin (DB00997)••••••••••••
Treatment ofUnresectable leiomyosarcoma••••••••••••
Treatment ofUnresectable liposarcoma••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Two of the rings in the drug's structure allows it to covalently bind to the minor groove of DNA. The third ring protrudes from the DNA which lets it interact with nearby nuclear proteins. This has the additive effect of blocking cell division at the G2 phase.

Mechanism of action

Trabectedin interacts with the minor groove of DNA and alkylates guanine at the N2 position, which bends towards the major groove. In this manner, it is thought that the drug affects various transcription factors involved in cell proliferation, particularly via the transcription-coupled nucleotide excision repair system. Trabectedin blocks the cell cycle at the G2 phase, while cells at the G1 phase are most sensitive to the drug. It also inhibits overexpression of the multidrug resistance-1 gene (MDR-1) coding for the P-glycoprotein that is a major factor responsible for cells developing resistance to cancer drugs. The agent is also thought to interfere with the nucleotide excision repair pathways of cancer cells, suggesting that it could be effective in the treatment of many cancer types including melanoma and sarcoma, as well as lung, breast, ovarian, endometrial and prostate cancers; clinical evaluations are underway in these indications.

TargetActionsOrganism
ADNA
binder
Humans
Absorption

Administered intravenously.

Volume of distribution

Not Available

Protein binding

94 to 98%

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

33-50 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
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
AbametapirThe serum concentration of Trabectedin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Trabectedin can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Trabectedin.
AbirateroneThe metabolism of Trabectedin can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Trabectedin.
Food Interactions
  • Avoid alcohol. There may be an additive hepatotoxic effect if alcohol and trabectedin are coadministered.
  • Avoid St. John's Wort. This herb induces CYP3A4 metabolism, which may reduce the serum concentration of trabectedin.
  • Exercise caution with grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of trabectedin.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
YondelisInjection, powder, for solution1 mgIntravenousPharma Mar2020-12-16Not applicableEU flag
YondelisInjection, powder, lyophilized, for solution0.05 mg/1mLIntravenousJanssen Products, LP2015-10-23Not applicableUS flag
YondelisInjection, powder, for solution0.25 mgIntravenousPharma Mar2020-12-16Not applicableEU flag
YondelisPowder, for solution1 mg / vialIntravenousValeo Pharma Corp.2010-08-05Not applicableCanada flag

Categories

ATC Codes
L01CX01 — Trabectedin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzazocines. These are organic compounds containing the benzazocine ring system, which consists of a benzene ring bound to an azocine ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzazocines
Direct Parent
Benzazocines
Alternative Parents
Tetrahydroisoquinolines / Alpha amino acids and derivatives / Benzodioxoles / Anisoles / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Alkyl aryl ethers / N-methylpiperazines / Aralkylamines / Dicarboxylic acids and derivatives
show 14 more
Substituents
1,4-diazinane / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Acetal / Alkanolamine / Alkyl aryl ether / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Anisole
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, acetate ester, polyphenol, organic sulfide, bridged compound, isoquinoline alkaloid, hemiaminal, lactone, azaspiro compound, organic heteropolycyclic compound, oxaspiro compound (CHEBI:84050)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
ID0YZQ2TCP
CAS number
114899-77-3
InChI Key
PKVRCIRHQMSYJX-AIFWHQITSA-N
InChI
InChI=1S/C39H43N3O11S/c1-16-9-20-10-22-37(46)42-23-13-50-38(47)39(21-12-25(48-5)24(44)11-19(21)7-8-40-39)14-54-36(30(42)29(41(22)4)26(20)31(45)32(16)49-6)28-27(23)35-34(51-15-52-35)17(2)33(28)53-18(3)43/h9,11-12,22-23,29-30,36-37,40,44-46H,7-8,10,13-15H2,1-6H3/t22-,23-,29+,30+,36+,37-,39+/m0/s1
IUPAC Name
(1R,2R,3R,11S,12S,14R,26R)-5,6',12-trihydroxy-6,7'-dimethoxy-7,21,30-trimethyl-27-oxo-3',4'-dihydro-2'H-17,19,28-trioxa-24-thia-13,30-diazaspiro[heptacyclo[12.9.6.1^{3,11}.0^{2,13}.0^{4,9}.0^{15,23}.0^{16,20}]triacontane-26,1'-isoquinoline]-4,6,8,15,20,22-hexaen-22-yl acetate
SMILES
[H][C@@]12[C@@H]3SC[C@]4(NCCC5=C4C=C(OC)C(O)=C5)C(=O)OC[C@H](N1[C@@H](O)[C@@H]1CC4=CC(C)=C(OC)C(O)=C4[C@H]2N1C)C1=C2OCOC2=C(C)C(OC(C)=O)=C31

References

Synthesis Reference

Elias J. Corey, David Gin, "Process for producing ecteinascidin compounds." U.S. Patent US5721362, issued December, 1995.

US5721362
General References
  1. Tavecchio M, Natoli C, Ubezio P, Erba E, D'Incalci M: Dynamics of cell cycle phase perturbations by trabectedin (ET-743) in nucleotide excision repair (NER)-deficient and NER-proficient cells, unravelled by a novel mathematical simulation approach. Cell Prolif. 2007 Dec;40(6):885-904. [Article]
  2. Krasner CN, McMeekin DS, Chan S, Braly PS, Renshaw FG, Kaye S, Provencher DM, Campos S, Gore ME: A Phase II study of trabectedin single agent in patients with recurrent ovarian cancer previously treated with platinum-based regimens. Br J Cancer. 2007 Dec 17;97(12):1618-24. Epub 2007 Nov 13. [Article]
  3. Carter NJ, Keam SJ: Trabectedin : a review of its use in the management of soft tissue sarcoma and ovarian cancer. Drugs. 2007;67(15):2257-76. [Article]
  4. Authors unspecified: Trabectedin: Ecteinascidin 743, Ecteinascidin-743, ET 743, ET-743, NSC 684766. Drugs R D. 2006;7(5):317-28. [Article]
  5. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Human Metabolome Database
HMDB0015609
PubChem Compound
108150
PubChem Substance
99443229
ChemSpider
97236
RxNav
1716278
ChEBI
84050
ChEMBL
CHEMBL450449
ZINC
ZINC000150338708
PharmGKB
PA165958349
PDBe Ligand
ECT
Wikipedia
Trabectedin
FDA label
Download (824 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, for solutionParenteral0.25 mg
Injection, powder, for solutionParenteral1 mg
Injection, powder, for solution0.25 MG
Injection, powder, for solution1 MG
Injection, powder, for solutionIntravenous0.25 MG
Injection, powder, for solutionIntravenous1 MG
Injection, powder, lyophilized, for solutionIntravenous0.05 mg/1mL
Powder, for solutionIntravenous1 mg / vial
SolutionIntravenous1.000 mg
Injection, solution, concentrateIntravenous1 mg
Injection, powder, lyophilized, for solutionIntravenous
Injection, powder, for solutionIntravenous1.0 mg
Injection, powder, lyophilized, for solutionIntravenous1 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2428160No2009-10-132021-11-06Canada flag
CA2373794No2005-10-112020-05-15Canada flag
US8895557Yes2014-11-252028-07-07US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.328 mg/mLALOGPS
logP2.04ALOGPS
logP4.19Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.26Chemaxon
pKa (Strongest Basic)7.2Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area168.72 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity196.92 m3·mol-1Chemaxon
Polarizability77.98 Å3Chemaxon
Number of Rings9Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5216
Blood Brain Barrier-0.9238
Caco-2 permeable-0.6788
P-glycoprotein substrateSubstrate0.8988
P-glycoprotein inhibitor INon-inhibitor0.6957
P-glycoprotein inhibitor IINon-inhibitor0.74
Renal organic cation transporterNon-inhibitor0.8321
CYP450 2C9 substrateNon-substrate0.8211
CYP450 2D6 substrateNon-substrate0.7689
CYP450 3A4 substrateSubstrate0.6512
CYP450 1A2 substrateNon-inhibitor0.804
CYP450 2C9 inhibitorNon-inhibitor0.5287
CYP450 2D6 inhibitorNon-inhibitor0.6514
CYP450 2C19 inhibitorNon-inhibitor0.5436
CYP450 3A4 inhibitorInhibitor0.8832
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6677
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.8734
BiodegradationNot ready biodegradable0.9782
Rat acute toxicity2.6136 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9942
hERG inhibition (predictor II)Inhibitor0.5329
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0zgr-0090000100-1fbe6c879e491f9c397c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0000000900-5b2557629548ffe064dd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0000000900-da83309cb19fa34e4fb2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ka-0000000900-5c6f7bb0a80570ad73e9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0000000900-b0e624eb8a12e14ccfaa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-07cu-0110003900-305718947456583aa595
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uy3-0000003900-cddb477770a266e7ceee
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-268.9202408
predicted
DarkChem Lite v0.1.0
[M-H]-263.4573408
predicted
DarkChem Lite v0.1.0
[M-H]-246.56053
predicted
DeepCCS 1.0 (2019)
[M+H]+269.2515408
predicted
DarkChem Lite v0.1.0
[M+H]+261.7799408
predicted
DarkChem Lite v0.1.0
[M+H]+248.38542
predicted
DeepCCS 1.0 (2019)
[M+Na]+269.3608408
predicted
DarkChem Lite v0.1.0
[M+Na]+261.9268408
predicted
DarkChem Lite v0.1.0
[M+Na]+254.158
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Binder
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. D'Incalci M, Galmarini CM: A review of trabectedin (ET-743): a unique mechanism of action. Mol Cancer Ther. 2010 Aug;9(8):2157-63. doi: 10.1158/1535-7163.MCT-10-0263. Epub 2010 Jul 20. [Article]
  3. Marco E, David-Cordonnier MH, Bailly C, Cuevas C, Gago F: Further insight into the DNA recognition mechanism of trabectedin from the differential affinity of its demethylated analogue ecteinascidin ET729 for the triplet DNA binding site CGA. J Med Chem. 2006 Nov 16;49(23):6925-9. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Vermeir M, Hemeryck A, Cuyckens F, Francesch A, Bockx M, Van Houdt J, Steemans K, Mannens G, Aviles P, De Coster R: In vitro studies on the metabolism of trabectedin (YONDELIS) in monkey and man, including human CYP reaction phenotyping. Biochem Pharmacol. 2009 May 15;77(10):1642-54. doi: 10.1016/j.bcp.2009.02.020. Epub 2009 Mar 10. [Article]
  2. Brandon EF, Meijerman I, Klijn JS, den Arend D, Sparidans RW, Lazaro LL, Beijnen JH, Schellens JH: In-vitro cytotoxicity of ET-743 (Trabectedin, Yondelis), a marine anti-cancer drug, in the Hep G2 cell line: influence of cytochrome P450 and phase II inhibition, and cytochrome P450 induction. Anticancer Drugs. 2005 Oct;16(9):935-43. [Article]
  3. Machiels JP, Staddon A, Herremans C, Keung C, Bernard A, Phelps C, Khokhar NZ, Knoblauch R, Parekh TV, Dirix L, Sharma S: Impact of cytochrome P450 3A4 inducer and inhibitor on the pharmacokinetics of trabectedin in patients with advanced malignancies: open-label, multicenter studies. Cancer Chemother Pharmacol. 2014 Oct;74(4):729-37. doi: 10.1007/s00280-014-2554-1. Epub 2014 Aug 7. [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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Brandon EF, Meijerman I, Klijn JS, den Arend D, Sparidans RW, Lazaro LL, Beijnen JH, Schellens JH: In-vitro cytotoxicity of ET-743 (Trabectedin, Yondelis), a marine anti-cancer drug, in the Hep G2 cell line: influence of cytochrome P450 and phase II inhibition, and cytochrome P450 induction. Anticancer Drugs. 2005 Oct;16(9):935-43. [Article]
  3. Lee JK, Leslie EM, Zamek-Gliszczynski MJ, Brouwer KL: Modulation of trabectedin (ET-743) hepatobiliary disposition by multidrug resistance-associated proteins (Mrps) may prevent hepatotoxicity. Toxicol Appl Pharmacol. 2008 Apr 1;228(1):17-23. doi: 10.1016/j.taap.2007.11.020. Epub 2007 Dec 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Lee JK, Leslie EM, Zamek-Gliszczynski MJ, Brouwer KL: Modulation of trabectedin (ET-743) hepatobiliary disposition by multidrug resistance-associated proteins (Mrps) may prevent hepatotoxicity. Toxicol Appl Pharmacol. 2008 Apr 1;228(1):17-23. doi: 10.1016/j.taap.2007.11.020. Epub 2007 Dec 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Lee JK, Leslie EM, Zamek-Gliszczynski MJ, Brouwer KL: Modulation of trabectedin (ET-743) hepatobiliary disposition by multidrug resistance-associated proteins (Mrps) may prevent hepatotoxicity. Toxicol Appl Pharmacol. 2008 Apr 1;228(1):17-23. doi: 10.1016/j.taap.2007.11.020. Epub 2007 Dec 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Lee JK, Leslie EM, Zamek-Gliszczynski MJ, Brouwer KL: Modulation of trabectedin (ET-743) hepatobiliary disposition by multidrug resistance-associated proteins (Mrps) may prevent hepatotoxicity. Toxicol Appl Pharmacol. 2008 Apr 1;228(1):17-23. doi: 10.1016/j.taap.2007.11.020. Epub 2007 Dec 3. [Article]

Drug created at October 21, 2007 22:23 / Updated at March 18, 2024 16:48