Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1438)
Drug Name
Romidepsin
Prodrug Info Romidepsin is the prodrug of Romidepsin metabolite M1
Synonyms
Romidepsin; FK 228; FK-228; FK228; FR 901228; FR-901228; FR901228; NSC 630176; NSC-630176; NSC630176; NSC754143; (1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-di(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; (1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone; 128517-07-7; C24H36N4O6S2; CHEBI:61080; CHEMBL343448; Antibiotic FR 901228; Chromadax; Depsipeptide; Istodax; UNII-CX3T89XQBK
Indication Cutaneous T-cell lymphoma [ICD11: 2B01] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 540.7 Topological Polar Surface Area 193
Heavy Atom Count 36 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
5352062
PubChem SID
494874 ; 8139716 ; 11650994 ; 12014448 ; 14763476 ; 14763478 ; 35018633 ; 46519185 ; 47208288 ; 47721651 ; 47944836 ; 48394948 ; 50062237 ; 50260193 ; 53788098 ; 57361456 ; 87226502 ; 103393180 ; 104222481 ; 113905898 ; 127325932 ; 127325933 ; 131408687 ; 134338801 ; 134338973 ; 134340279 ; 137156420 ; 139110210 ; 152159610 ; 163620827 ; 163686155 ; 164233439 ; 175266198 ; 176484649 ; 178103585 ; 184816960 ; 198992824 ; 224274473 ; 226087966 ; 226972555 ; 251894761 ; 252430794 ; 252450287 ; 252473284
ChEBI ID
CHEBI:61080
CAS Number
128517-07-7
TTD Drug ID
D0L7LC
Formula
C24H36N4O6S2
Canonical SMILES
CC=C1C(=O)NC(C(=O)OC2CC(=O)NC(C(=O)NC(CSSCCC=C2)C(=O)N1)C(C)C)C(C)C
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
InChIKey
OHRURASPPZQGQM-GCCNXGTGSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Romidepsin metabolite M1 DM006128
9828788
Reduction - Reduction 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006596 Romidepsin Romidepsin metabolite M1 Reduction - Reduction CYP2C19 ... [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Romidepsin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 FDA Label of Romidepsin. The 2020 official website of the U.S. Food and Drug Administration.
4 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.
5 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.

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