ROMIDEPSIN

Search structure
Trade Names:
Synonyms:
Status: Approved (2009)
Entry Type: Protein
Molecule Category: UNKNOWN Prodrug
ATC: L01XH02
UNII: CX3T89XQBK

Structure
InChI Key OHRURASPPZQGQM-GCCNXGTGSA-N
Smile 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](C(C)C)NC1=O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H36N4O6S2
Molecular Weight 540.71
AlogP 1.43
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 2.0
Polar Surface Area 142.7
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 36.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Histone deacetylase inhibitor DailyMed Wikipedia Wikipedia
Primary Target
histone deacetylase 1
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Epigenetic regulator Eraser Histone deacetylase HDAC class I
36000 0-1050 - 0-0 36
Epigenetic regulator Eraser Histone deacetylase HDAC class IIa
- 510-8670 - 1100-1100 22
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- 80-14000 - 10-300 45
Epigenetic regulator Eraser Histone deacetylase HDAC class IV
- 4-250 - - -
Epigenetic regulator Reader Bromodomain
- 36 - - -
Epigenetic regulator Writer Histone acetyltransferase SRC family
- - - 0 -
Unclassified protein
- 3-147 - 25 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Lymphoma, T-Cell, Peripheral 4 D016411 ClinicalTrials
Lymphoma, T-Cell, Cutaneous 4 D016410 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Immunoblastic Lymphadenopathy 3 D007119 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Leukemia, Promyelocytic, Acute 2 D015473 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 2 D016403 ClinicalTrials
Adenocarcinoma, Follicular 2 D018263 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Small Cell Lung Carcinoma 2 D055752 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Breast Neoplasms, Male 2 D018567 ClinicalTrials
Lymphoma, Mantle-Cell 2 D020522 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Urinary Bladder Neoplasms 2 D001749 ClinicalTrials
Urethral Neoplasms 2 D014523 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Mycosis Fungoides 1 D009182 ClinicalTrials
Liposarcoma 1 D008080 ClinicalTrials
Leukemia 1 D007938 ClinicalTrials
Astrocytoma 1 D001254 ClinicalTrials
Gliosarcoma 1 D018316 ClinicalTrials
Carcinoma, Pancreatic Ductal 1 D021441 ClinicalTrials
Pancreatic Neoplasms 1 D010190 ClinicalTrials
Hodgkin Disease 1 D006689 ClinicalTrials
Triple Negative Breast Neoplasms 1 D064726 ClinicalTrials
Lymphoma, Non-Hodgkin 1 D008228 ClinicalTrials
Oligodendroglioma 1 D009837 ClinicalTrials
Sezary Syndrome 1 D012751 ClinicalTrials
Inflammatory Breast Neoplasms 1 D058922 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 85.5
General disorders and administration site conditions Asthenia 77.1
General disorders and administration site conditions Fatigue 77.1
General disorders and administration site conditions Asthenia 76.6
General disorders and administration site conditions Fatigue 76.6
Gastrointestinal disorders Nausea 74.5
Blood and lymphatic system disorders Anaemia 72.3
Blood and lymphatic system disorders Thrombocytopenia 72.3
Blood and lymphatic system disorders Neutropenia 66.0
Blood and lymphatic system disorders Thrombocytopenia 65.1
Blood and lymphatic system disorders Anaemia 61.7
Gastrointestinal disorders Nausea 58.8
Blood and lymphatic system disorders Lymphopenia 56.6
Blood and lymphatic system disorders Neutropenia 56.6
Gastrointestinal disorders Nausea 55.9
Blood and lymphatic system disorders Leukopenia 55.3
General disorders and administration site conditions Asthenia 55.0
General disorders and administration site conditions Fatigue 55.0
General disorders and administration site conditions Decreased appetite 54.2
Infections and infestations Infection 54.2
General disorders and administration site conditions Asthenia 52.9
General disorders and administration site conditions Fatigue 52.9
Metabolism and nutrition disorders Hypocalcaemia 51.8
Gastrointestinal disorders Vomiting 51.8
Endocrine disorders Hyperglycaemia 50.6
Hepatobiliary disorders Hypoalbuminaemia 48.2
Investigations Body temperature increased 46.8
Blood and lymphatic system disorders Neutropenia 46.8
Infections and infestations Infection 46.1
Blood and lymphatic system disorders Leukopenia 45.8
General disorders and administration site conditions Decreased appetite 44.7
Blood and lymphatic system disorders Leukopenia 44.7
Blood and lymphatic system disorders Thrombocytopenia 40.5
Gastrointestinal disorders Constipation 40.4
Gastrointestinal disorders Vomiting 40.4
Gastrointestinal disorders Dysgeusia 39.8
Gastrointestinal disorders Vomiting 38.9
Gastrointestinal disorders Constipation 38.6
Blood and lymphatic system disorders Lymphopenia 37.3
Gastrointestinal disorders Diarrhoea 36.2
Blood and lymphatic system disorders Thrombocytopenia 36.2
Gastrointestinal disorders Diarrhoea 35.9
Investigations Body temperature increased 35.1
Gastrointestinal disorders Vomiting 34.3
Nervous system disorders Headache 34.0
Investigations Blood uric acid increased 32.5
Metabolism and nutrition disorders Hyperuricaemia 32.5
Infections and infestations Infection 32.5
Skin and subcutaneous tissue disorders Pruritus 31.3
Gastrointestinal disorders Constipation 29.8
Blood and lymphatic system disorders Neutropenia 29.8
General disorders and administration site conditions Decreased appetite 28.2
Blood and lymphatic system disorders Anaemia 27.7
Investigations Aspartate aminotransferase increased 27.7
Gastrointestinal disorders Dysgeusia 27.7
Metabolism and nutrition disorders Hypomagnesaemia 27.7
Skin and subcutaneous tissue disorders Dermatitis 26.5
Immune system disorders Dermatitis exfoliative 26.5
Gastrointestinal disorders Diarrhoea 26.5
Metabolism and nutrition disorders Hypermagnesaemia 26.5
Metabolism and nutrition disorders Hypophosphataemia 26.5
Blood and lymphatic system disorders Neutropenia 26.5
Blood and lymphatic system disorders Anaemia 24.4
Blood and lymphatic system disorders Thrombocytopenia 24.4
Investigations Body temperature increased 22.9
Vascular disorders Hypotension 22.9
General disorders and administration site conditions Decreased appetite 22.5
Investigations Alanine aminotransferase increased 21.7
Blood and lymphatic system disorders Leukopenia 21.7
Metabolism and nutrition disorders Hypomagnesaemia 21.6
Respiratory, thoracic and mediastinal disorders Cough 21.3
Cardiac disorders Dyspnoea 21.3
Gastrointestinal disorders Dysgeusia 20.6
Metabolism and nutrition disorders Hypokalaemia 20.5
Metabolism and nutrition disorders Hyponatraemia 20.5
Blood and lymphatic system disorders Neutropenia 19.8
Investigations Body temperature increased 19.6
Gastrointestinal disorders Diarrhoea 19.6
General disorders and administration site conditions Asthenia 19.1
General disorders and administration site conditions Fatigue 19.1
Blood and lymphatic system disorders Anaemia 18.6
Respiratory, thoracic and mediastinal disorders Cough 17.6
Investigations Body temperature increased 17.0
General disorders and administration site conditions Chills 17.0
Metabolism and nutrition disorders Hypokalaemia 17.0
Blood and lymphatic system disorders Thrombocytopenia 16.7
Blood and lymphatic system disorders Anaemia 15.7
Investigations Weight decreased 14.9
Gastrointestinal disorders Dysgeusia 14.7
General disorders and administration site conditions Asthenia 14.5
General disorders and administration site conditions Fatigue 14.5
Nervous system disorders Headache 14.5
Blood and lymphatic system disorders Thrombocytopenia 14.5
Gastrointestinal disorders Abdominal pain 13.7
Gastrointestinal disorders Gastrointestinal pain 13.7
Cardiac disorders Dyspnoea 13.0
Vascular disorders Hypotension 13.0
Gastrointestinal disorders Abdominal pain 12.8
Gastrointestinal disorders Gastrointestinal pain 12.8
Blood and lymphatic system disorders Leukopenia 12.2
Gastrointestinal disorders Constipation 11.8
Investigations Alanine aminotransferase increased 11.0
Blood and lymphatic system disorders Thrombocytopenia 11.0
Infections and infestations Infection 10.8
Blood and lymphatic system disorders Neutropenia 10.8
Blood and lymphatic system disorders Anaemia 10.7
General disorders and administration site conditions Chills 10.7
Metabolism and nutrition disorders Hypokalaemia 10.7
Cardiac disorders Oedema peripheral 9.92
Gastrointestinal disorders Stomatitis 9.92
Cardiac disorders Tachycardia 9.92
Investigations Weight decreased 9.92
Metabolism and nutrition disorders Hypophosphataemia 9.64
Gastrointestinal disorders Vomiting 9.64
Cardiac disorders Dyspnoea 9.0
Gastrointestinal disorders Vomiting 8.51
Investigations Blood uric acid increased 8.43
Skin and subcutaneous tissue disorders Dermatitis 8.43
Immune system disorders Dermatitis exfoliative 8.43
Metabolism and nutrition disorders Hypermagnesaemia 8.43
Metabolism and nutrition disorders Hyperuricaemia 8.43
General disorders and administration site conditions Asthenia 8.4
General disorders and administration site conditions Fatigue 8.4
General disorders and administration site conditions Asthenia 7.84
General disorders and administration site conditions Fatigue 7.84
General disorders and administration site conditions Asthenia 7.0
Investigations Body temperature increased 7.0
General disorders and administration site conditions Fatigue 7.0
Vascular disorders Hypotension 6.86
Skin and subcutaneous tissue disorders Pruritus 6.86
Gastrointestinal disorders Nausea 6.38
Cardiac disorders Oedema peripheral 6.38
Gastrointestinal disorders Stomatitis 6.38
Blood and lymphatic system disorders Leukopenia 6.11
Metabolism and nutrition disorders Hypocalcaemia 6.02
Gastrointestinal disorders Nausea 6.02
Skin and subcutaneous tissue disorders Pruritus 6.02
Blood and lymphatic system disorders Neutropenia 6.0
Metabolism and nutrition disorders Hypokalaemia 5.88
Investigations Body temperature increased 5.34
General disorders and administration site conditions Oedema 5.0
Gastrointestinal disorders Vomiting 5.0
Gastrointestinal disorders Vomiting 4.58
Cardiac disorders Dyspnoea 4.26
Investigations Alanine aminotransferase increased 4.0
Cardiac disorders Dyspnoea 4.0
Investigations Body temperature increased 3.92
Skin and subcutaneous tissue disorders Dermatitis 3.92
Immune system disorders Dermatitis exfoliative 3.92
Metabolism and nutrition disorders Hypocalcaemia 3.92
Blood and lymphatic system disorders Leukopenia 3.92
Blood and lymphatic system disorders Lymphopenia 3.92
Blood and lymphatic system disorders Neutropenia 3.92
Investigations Aspartate aminotransferase increased 3.61
General disorders and administration site conditions Decreased appetite 3.61
Hepatobiliary disorders Hypoalbuminaemia 3.61
Vascular disorders Hypotension 3.61
Gastrointestinal disorders Abdominal pain 3.0
Investigations Body temperature increased 3.0
Gastrointestinal disorders Gastrointestinal pain 3.0
Investigations Alanine aminotransferase increased 2.94
Blood and lymphatic system disorders Anaemia 2.94
Investigations Aspartate aminotransferase increased 2.94
Hepatobiliary disorders Hypoalbuminaemia 2.94
Vascular disorders Hypotension 2.94
Gastrointestinal disorders Nausea 2.94
Investigations Alanine aminotransferase increased 2.41
Metabolism and nutrition disorders Hypokalaemia 2.41
Metabolism and nutrition disorders Hyponatraemia 2.41
Gastrointestinal disorders Abdominal pain 2.29
Gastrointestinal disorders Diarrhoea 2.29
Cardiac disorders Dyspnoea 2.29
Gastrointestinal disorders Gastrointestinal pain 2.29
Metabolism and nutrition disorders Hypokalaemia 2.29
Gastrointestinal disorders Nausea 2.29
Gastrointestinal disorders Abdominal pain 2.13
Gastrointestinal disorders Constipation 2.13
General disorders and administration site conditions Decreased appetite 2.13
Gastrointestinal disorders Diarrhoea 2.13
Gastrointestinal disorders Gastrointestinal pain 2.13
Nervous system disorders Headache 2.13
Metabolism and nutrition disorders Hypokalaemia 2.13
Metabolism and nutrition disorders Dehydration 2.0
Gastrointestinal disorders Constipation 1.96
Endocrine disorders Hyperglycaemia 1.96
General disorders and administration site conditions Decreased appetite 1.53
Investigations Body temperature increased 1.2
Gastrointestinal disorders Constipation 1.2
Gastrointestinal disorders Diarrhoea 1.2
Endocrine disorders Hyperglycaemia 1.2
General disorders and administration site conditions Decreased appetite 0.98
Skin and subcutaneous tissue disorders Dermatitis 0.98
Immune system disorders Dermatitis exfoliative 0.98
Gastrointestinal disorders Diarrhoea 0.98
Hepatobiliary disorders Hypoalbuminaemia 0.98
Metabolism and nutrition disorders Hypomagnesaemia 0.98
Metabolism and nutrition disorders Hyponatraemia 0.98
Gastrointestinal disorders Vomiting 0.98
General disorders and administration site conditions Chills 0.763
Gastrointestinal disorders Constipation 0.763
Cardiac disorders Oedema peripheral 0.763

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
14.31
Blood and lymphatic system disorders
13.63
Gastrointestinal disorders
10.39
Investigations
6.74
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
6.7
Infections and infestations
6.28
Vascular disorders
6.13
Cardiac disorders
5.71
Respiratory, thoracic and mediastinal disorders
4.99
Skin and subcutaneous tissue disorders
4.49
Nervous system disorders
4.26
Metabolism and nutrition disorders
3.96
Injury, poisoning and procedural complications
2.7
Musculoskeletal and connective tissue disorders
2.63

Cross References

Resources Reference
CAS NUMBER 128517-07-7
ChEBI 61080
ChEMBL CHEMBL343448
DrugBank DB06176
DrugCentral 4119
FDA SRS CX3T89XQBK
Guide to Pharmacology 7006
KEGG D06637
PharmGKB PA166161306
PubChem 5352062
SureChEMBL SCHEMBL677497
ZINC ZINC000003935130
CONTENTS