DOXORUBICIN HYDROCHLORIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1974)
Entry Type: Small molecule
Molecule Category: Salt
UNII: 82F2G7BL4E
Parent Compound: DOXORUBICIN

Structure
InChI Key MWWSFMDVAYGXBV-RUELKSSGSA-N
Smile COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
InChI
InChI=1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H30ClNO11
Molecular Weight 579.99
AlogP 0.0
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 6.0
Number of Rotational Bond 5.0
Polar Surface Area 206.07
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 39.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor Wikipedia FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 10
Enzyme Isomerase
- 940 - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 96910 - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Ovarian Neoplasms 4 D010051 ClinicalTrials
Ovarian Neoplasms 4 D010051 ClinicalTrials
Carcinoma 4 D002277 ClinicalTrials
Ovarian Neoplasms 4 D010051 ClinicalTrials
Osteosarcoma 4 D012516 ClinicalTrials
Sarcoma 4 D012509 ClinicalTrials
Lymphoma, Non-Hodgkin 4 D008228 ClinicalTrials
Breast Neoplasms 4 D001943 ClinicalTrials
Ovarian Neoplasms 4 D010051 ClinicalTrials
Breast Neoplasms 4 D001943 ClinicalTrials
Sarcoma 4 D012509 ClinicalTrials
Hodgkin Disease 4 D006689 ClinicalTrials
Histiocytoma 3 D051642 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Mesothelioma 3 D008654 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Neuroblastoma 3 D009447 ClinicalTrials
Uterine Neoplasms 3 D014594 ClinicalTrials
Hepatoblastoma 3 D018197 ClinicalTrials
Inflammatory Breast Neoplasms 3 D058922 ClinicalTrials
Peritoneal Neoplasms 3 D010534 ClinicalTrials
Wilms Tumor 3 D009396 ClinicalTrials
Adrenal Cortex Neoplasms 3 D000306 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Pheochromocytoma 3 D010673 ClinicalTrials
Ganglioneuroblastoma 3 D018305 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Peritoneal Neoplasms 3 D010534 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Liver Neoplasms 3 D008113 ClinicalTrials
Urethral Neoplasms 3 D014523 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Endometrial Neoplasms 3 D016889 ClinicalTrials
Lymphohistiocytosis, Hemophagocytic 3 D051359 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma 3 D054218 ClinicalTrials
Leiomyosarcoma 3 D007890 ClinicalTrials
Liposarcoma 3 D008080 ClinicalTrials
Neurilemmoma 3 D009442 ClinicalTrials
Sarcoma, Synovial 3 D013584 ClinicalTrials
Hemangiosarcoma 3 D006394 ClinicalTrials
Sarcoma, Alveolar Soft Part 3 D018234 ClinicalTrials
Mesenchymoma 3 D008637 ClinicalTrials
Fibrosarcoma 3 D005354 ClinicalTrials
Hemangiopericytoma 3 D006393 ClinicalTrials
Dermatofibrosarcoma 3 D018223 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Blast Crisis 2 D001752 ClinicalTrials
Central Nervous System Neoplasms 2 D016543 ClinicalTrials
Thyroid Carcinoma, Anaplastic 2 D065646 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Leukemia, Biphenotypic, Acute 2 D015456 ClinicalTrials
Lymphoma, T-Cell, Peripheral 2 D016411 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Uterine Cervical Neoplasms 2 D002583 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Carcinoma, Adenoid Cystic 2 D003528 ClinicalTrials
Rhabdomyosarcoma 2 D012208 ClinicalTrials
Triple Negative Breast Neoplasms 2 D064726 ClinicalTrials
Head and Neck Neoplasms 2 D006258 ClinicalTrials
Breast Neoplasms, Male 2 D018567 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 2 D016553 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Rhabdomyosarcoma, Embryonal 2 D018233 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Lymphoma, Mantle-Cell 2 D020522 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Retinoblastoma 2 D012175 ClinicalTrials
Acquired Immunodeficiency Syndrome 2 D000163 ClinicalTrials
Burkitt Lymphoma 2 D002051 ClinicalTrials
Leukemia, Biphenotypic, Acute 2 D015456 ClinicalTrials
Rhabdomyosarcoma, Alveolar 2 D018232 ClinicalTrials
Neoplasm Metastasis 1 D009362 ClinicalTrials
Sarcoma, Ewing 1 D012512 ClinicalTrials
Small Cell Lung Carcinoma 1 D055752 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 1 D054437 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 1 D002289 ClinicalTrials
Breast Carcinoma In Situ 1 D000071960 ClinicalTrials
Leukemia, Plasma Cell 1 D007952 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials

Related Entries

Scaffolds

Parent

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Blood and lymphatic system disorders
13.26
General disorders and administration site conditions
11.52
Injury, poisoning and procedural complications
9.61
Infections and infestations
8.36
Gastrointestinal disorders
7.35
Respiratory, thoracic and mediastinal disorders
6.28
Cardiac disorders
5.72
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
5.55
Nervous system disorders
5.21
Vascular disorders
4.7
Investigations
3.7
Skin and subcutaneous tissue disorders
3.56
Metabolism and nutrition disorders
3.02
Hepatobiliary disorders
2.12
Renal and urinary disorders
2.01

Cross References

Resources Reference
ChEBI 31522
ChEMBL CHEMBL359744
EPA CompTox DTXSID3030636
FDA SRS 82F2G7BL4E
Guide to Pharmacology 7069
KEGG C01661
PDB DM2
PubChem 443939
SureChEMBL SCHEMBL3242
ZINC ZINC03918087
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