Romidepsin

Identification

Summary

Romidepsin is a histone deacetylase (HDAC) inhibitor used to treat cutaneous and peripheral T-cell lymphoma.

Brand Names
Istodax
Generic Name
Romidepsin
DrugBank Accession Number
DB06176
Background

Romidepsin is a selective inhibitor of histone deacetylase, approved in the US in 2009 for the treatment of cutaneous T-cell lymphoma (CTCL) or/and peripheral T-cell lymphoma (PTCL) in patients who have received at least one prior systemic therapy. These indications are based on response rate. Clinical benefit such as improvement in overall survival has not been demonstrated.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 540.69
Monoisotopic: 540.207627243
Chemical Formula
C24H36N4O6S2
Synonyms
  • Romidepsin
  • Romidepsina
  • Romidepsine
  • Romidepsinum
External IDs
  • FK 228
  • FK-228
  • FK228
  • FR 901228
  • FR-901228
  • FR901228
  • NSC 630176
  • NSC-630176
  • NSC630176

Pharmacology

Indication

For the treatment of cutaneous T-cell lymphoma (CTCL) or/and peripheral T-cell lymphoma (PTCL) in patients who have received at least one prior systemic therapy. These indications are based on response rate. Clinical benefit such as improvement in overall survival has not been demonstrated.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Romidepsin is a prodrug, where it becomes active once taken up into the cell. The active metabolite has a free thiol group, which interacts with zinc ions in the active site of class 1 and 2 HDAC enzymes, resulting in inhibition of its enzymatic activity. Certain tumors have over expressed HDACs and downregulated/mutated histone acetyltransferases. This imbalance of HDAC relative to histone acetyltransferase can lead to a decrease in regulatory genes, ensuing tumorigenesis. Inhibition of HDAC may restore normal gene expression in cancer cells and result in cell cycle arrest and apoptosis.

TargetActionsOrganism
AHistone deacetylase 1
antagonist
inhibitor
Humans
AHistone deacetylase 2
antagonist
inhibitor
Humans
NHistone deacetylase 4
inhibitor
Humans
NHistone deacetylase 6
inhibitor
Humans
UMultidrug resistance-associated protein 1Not AvailableHumans
Absorption

Romidepsin exhibited linear pharmacokinetics at standard doses.

Volume of distribution

44.5L

Protein binding

Highly protein bound in plasma (92%-94%)

Metabolism

Romidepsin undergoes extensive hepatic metabolism in vitro primarily by CYP3A4 with minor contribution from CYP3A5, CYP1A1, CYP2B6 and CYP2C19.

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Route of elimination

Not Available

Half-life

Approximately 3 hours

Clearance

8.4L/h

Adverse Effects
Medicalerrors
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Toxicity

Risk factor D in pregnancy. It is not known if romidepsin is excreted in breast milk. Due to the potential for serious adverse reactions in the nursing infant, the manufacturer recommends a decision be made whether to discontinue nursing or to discontinue the drug, taking into account the importance of treatment to the mother. The majority of patients receiving romidepsin experience nausea, vomiting, and anorexia.

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 Romidepsin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Romidepsin can be increased when combined with Abatacept.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Romidepsin.
AbirateroneThe metabolism of Romidepsin can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Romidepsin can be decreased when combined with Acalabrutinib.
AcebutololThe risk or severity of QTc prolongation can be increased when Acebutolol is combined with Romidepsin.
AcenocoumarolRomidepsin may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenThe metabolism of Romidepsin can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Romidepsin can be decreased when combined with Acetazolamide.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Romidepsin.
Interactions
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Food Interactions
  • Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of romidepsin.
  • Avoid St. John's Wort. This herb induces CYP3A4 metabolism, which may reduce serum levels of romidepsin.

Products

Products
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International/Other Brands
Chromadax / Istodax
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IstodaxKit10 mg/2mLIntravenousCelgene Corporation2010-01-04Not applicableUS flag
IstodaxKit10 mg/2mLIntravenousCelgene Corporation2010-01-042016-07-27US flag
IstodaxKit10 mg/2mLIntravenousGloucester Pharmaceuticals, Inc.2009-11-052010-05-28US flag
IstodaxKit; Powder, for solution10 mg / vialIntravenousCelgene2014-02-05Not applicableCanada flag
RomidepsinInjection, solution, concentrate5 mg/1mLIntravenousTeva Parenteral Medicines, Inc.2020-04-14Not applicableUS flag
RomidepsinInjection, solution, concentrate5 mg/1mLIntravenousTeva Parenteral Medicines, Inc.2020-04-14Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RomidepsinKit10 mg/2mLIntravenousTeva Parenteral Medicines, Inc.2018-07-312021-10-31US flag
RomidepsinKit10 mg/2mLIntravenousPfizer Laboratories Div Pfizer Inc2010-01-042021-03-31US flag

Categories

ATC Codes
L01XX39 — Romidepsin
Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
CX3T89XQBK
CAS number
128517-07-7
InChI Key
OHRURASPPZQGQM-GCCNXGTGSA-N
InChI
InChI=1S/C24H36N4O6S2/c1-6-16-21(30)28-20(14(4)5)24(33)34-15-9-7-8-10-35-36-12-17(22(31)25-16)26-23(32)19(13(2)3)27-18(29)11-15/h6-7,9,13-15,17,19-20H,8,10-12H2,1-5H3,(H,25,31)(H,26,32)(H,27,29)(H,28,30)/b9-7+,16-6-/t15-,17-,19-,20+/m1/s1
IUPAC Name
(1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-bis(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone
SMILES
C\C=C1/NC(=O)[C@H]2CSSCC\C=C\[C@H](CC(=O)N[C@H](C(C)C)C(=O)N2)OC(=O)[C@@H](NC1=O)C(C)C

References

Synthesis Reference

Ueda H, Nakajima H, Hori Y, Fujita T, Nishimura M, Goto T, Okuhara M: FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. I. Taxonomy, fermentation, isolation, physico-chemical and biological properties, and antitumor activity. J Antibiot (Tokyo). 1994 Mar;47(3):301-10. Pubmed.

General References
  1. VanderMolen KM, McCulloch W, Pearce CJ, Oberlies NH: Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma. J Antibiot (Tokyo). 2011 Aug;64(8):525-31. doi: 10.1038/ja.2011.35. Epub 2011 May 18. [Article]
  2. Valdez BC, Brammer JE, Li Y, Murray D, Liu Y, Hosing C, Nieto Y, Champlin RE, Andersson BS: Romidepsin targets multiple survival signaling pathways in malignant T cells. Blood Cancer J. 2015 Oct 16;5:e357. doi: 10.1038/bcj.2015.83. [Article]
KEGG Drug
D06637
PubChem Compound
57515973
PubChem Substance
310264861
ChemSpider
10122002
BindingDB
19151
RxNav
877510
ChEBI
61080
ChEMBL
CHEMBL343448
ZINC
ZINC000003935130
PharmGKB
PA166161306
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Romidepsin
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (610 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Active Not RecruitingTreatmentPeripheral T-Cell Lymphoma (PTCL)1
3Active Not RecruitingTreatmentRefractory Angioimmunoblastic T-cell Lymphoma / Relapsed Angioimmunoblastic T-Cell Lymphoma1
3CompletedTreatmentRefractory Peripheral T-cell Lymphoma Unspecified / Relapsed Peripheral T-Cell Lymphoma1
3RecruitingTreatmentT-cell type lymphoma1
3WithdrawnOtherLymphoma, T-Cell, Peripheral1
2Active Not RecruitingTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Anaplastic Large-Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Hepatosplenic T-Cell Lymphoma / Peripheral T-Cell Lymphoma (PTCL) / Stage I Cutaneous T-cell Non-Hodgkin Lymphoma / Stage IA Mycosis Fungoides/Sezary Syndrome / Stage IB Mycosis Fungoides/Sezary Syndrome / Stage II Cutaneous T-cell Non-Hodgkin Lymphoma / Stage IIA Mycosis Fungoides/Sezary Syndrome / Stage IIB Mycosis Fungoides/Sezary Syndrome / Stage III Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage IIIA Mycosis Fungoides/Sezary Syndrome / Stage IIIB Mycosis Fungoides/Sezary Syndrome / Stage IV Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage IVA Mycosis Fungoides/Sezary Syndrome / Stage IVB Mycosis Fungoides/Sezary Syndrome1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAdult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Promyelocytic Leukemia (M3) / Recurrent Adult Acute Myeloid Leukemia1
2CompletedTreatmentAdult Alveolar Soft-part Sarcoma / Adult Angiosarcoma / Adult Epithelioid Sarcoma / Adult Extraskeletal Chondrosarcoma / Adult Extraskeletal Osteosarcoma / Adult Fibrosarcoma / Adult Leiomyosarcoma / Adult Liposarcoma / Adult Malignant Fibrous Histiocytoma / Adult Malignant Hemangiopericytoma / Adult Malignant Mesenchymoma / Adult Neurofibrosarcoma / Adult Rhabdomyosarcoma / Adult Synovial Sarcoma / Gastrointestinal Stromal Tumors / Metastatic Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Recurrent Adult Soft Tissue Sarcoma / Recurrent Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Stage III Adult Soft Tissue Sarcoma / Stage IV Adult Soft Tissue Sarcoma1
2CompletedTreatmentColorectal Cancers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitIntravenous10 mg/2mL
Kit; powder, for solutionIntravenous10 mg / vial
Injection, solution, concentrateIntravenous5 mg/1mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7611724No2009-11-032021-08-22US flag
US7608280No2009-10-272021-08-22US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0209 mg/mLALOGPS
logP1.95ALOGPS
logP1.08ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.67ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.7 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity142.09 m3·mol-1ChemAxon
Polarizability54.55 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
General Function
Transcription regulatory region sequence-specific dna binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC1
Uniprot ID
Q13547
Uniprot Name
Histone deacetylase 1
Molecular Weight
55102.615 Da
References
  1. VanderMolen KM, McCulloch W, Pearce CJ, Oberlies NH: Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma. J Antibiot (Tokyo). 2011 Aug;64(8):525-31. doi: 10.1038/ja.2011.35. Epub 2011 May 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
General Function
Transcription factor binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC2
Uniprot ID
Q92769
Uniprot Name
Histone deacetylase 2
Molecular Weight
55363.855 Da
References
  1. VanderMolen KM, McCulloch W, Pearce CJ, Oberlies NH: Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma. J Antibiot (Tokyo). 2011 Aug;64(8):525-31. doi: 10.1038/ja.2011.35. Epub 2011 May 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC4
Uniprot ID
P56524
Uniprot Name
Histone deacetylase 4
Molecular Weight
119038.875 Da
References
  1. VanderMolen KM, McCulloch W, Pearce CJ, Oberlies NH: Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma. J Antibiot (Tokyo). 2011 Aug;64(8):525-31. doi: 10.1038/ja.2011.35. Epub 2011 May 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC6
Uniprot ID
Q9UBN7
Uniprot Name
Histone deacetylase 6
Molecular Weight
131418.19 Da
References
  1. VanderMolen KM, McCulloch W, Pearce CJ, Oberlies NH: Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma. J Antibiot (Tokyo). 2011 Aug;64(8):525-31. doi: 10.1038/ja.2011.35. Epub 2011 May 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Xiao JJ, Foraker AB, Swaan PW, Liu S, Huang Y, Dai Z, Chen J, Sadee W, Byrd J, Marcucci G, Chan KK: Efflux of depsipeptide FK228 (FR901228, NSC-630176) is mediated by P-glycoprotein and multidrug resistance-associated protein 1. J Pharmacol Exp Ther. 2005 Apr;313(1):268-76. Epub 2005 Jan 5. [Article]

Enzymes

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. Iwamoto FM, Lamborn KR, Kuhn JG, Wen PY, Yung WK, Gilbert MR, Chang SM, Lieberman FS, Prados MD, Fine HA: A phase I/II trial of the histone deacetylase inhibitor romidepsin for adults with recurrent malignant glioma: North American Brain Tumor Consortium Study 03-03. Neuro Oncol. 2011 May;13(5):509-16. doi: 10.1093/neuonc/nor017. Epub 2011 Mar 3. [Article]
  2. Shiraga T, Tozuka Z, Ishimura R, Kawamura A, Kagayama A: Identification of cytochrome P450 enzymes involved in the metabolism of FK228, a potent histone deacetylase inhibitor, in human liver microsomes. Biol Pharm Bull. 2005 Jan;28(1):124-9. [Article]
  3. Woo S, Gardner ER, Chen X, Ockers SB, Baum CE, Sissung TM, Price DK, Frye R, Piekarz RL, Bates SE, Figg WD: Population pharmacokinetics of romidepsin in patients with cutaneous T-cell lymphoma and relapsed peripheral T-cell lymphoma. Clin Cancer Res. 2009 Feb 15;15(4):1496-503. doi: 10.1158/1078-0432.CCR-08-1215. [Article]
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. Shiraga T, Tozuka Z, Ishimura R, Kawamura A, Kagayama A: Identification of cytochrome P450 enzymes involved in the metabolism of FK228, a potent histone deacetylase inhibitor, in human liver microsomes. Biol Pharm Bull. 2005 Jan;28(1):124-9. [Article]
  2. Woo S, Gardner ER, Chen X, Ockers SB, Baum CE, Sissung TM, Price DK, Frye R, Piekarz RL, Bates SE, Figg WD: Population pharmacokinetics of romidepsin in patients with cutaneous T-cell lymphoma and relapsed peripheral T-cell lymphoma. Clin Cancer Res. 2009 Feb 15;15(4):1496-503. doi: 10.1158/1078-0432.CCR-08-1215. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-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
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
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
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Romidepsin FDA Label [File]
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

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Woo S, Gardner ER, Chen X, Ockers SB, Baum CE, Sissung TM, Price DK, Frye R, Piekarz RL, Bates SE, Figg WD: Population pharmacokinetics of romidepsin in patients with cutaneous T-cell lymphoma and relapsed peripheral T-cell lymphoma. Clin Cancer Res. 2009 Feb 15;15(4):1496-503. doi: 10.1158/1078-0432.CCR-08-1215. [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. Woo S, Gardner ER, Chen X, Ockers SB, Baum CE, Sissung TM, Price DK, Frye R, Piekarz RL, Bates SE, Figg WD: Population pharmacokinetics of romidepsin in patients with cutaneous T-cell lymphoma and relapsed peripheral T-cell lymphoma. Clin Cancer Res. 2009 Feb 15;15(4):1496-503. doi: 10.1158/1078-0432.CCR-08-1215. [Article]

Drug created on March 19, 2008 16:15 / Updated on May 15, 2021 12:14