doxorubicin indications/contra

Stem definitionDrug idCAS RN
antineoplastics, daunorubicin derivatives 960 23214-92-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • doxorubicin
  • hydroxydaunomycin
  • hydroxydaunorubicin
  • rubidox
  • doxorubicin hydrochloride
  • liposomal doxorubicin
  • hydroxydaunorubicin hydrochloride
  • adriamycin
  • doxorubicin HCl
  • hydroxydaunorubicin HCl
Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of DAUNORUBICIN.
  • Molecular weight: 543.53
  • Formula: C27H29NO11
  • CLOGP: 0.32
  • LIPINSKI: 3
  • HAC: 12
  • HDO: 6
  • TPSA: 206.07
  • ALOGS: -2.67
  • ROTB: 5

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
Aug. 7, 1974 FDA

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Febrile neutropenia 10229.06 48.21 2662 24014 16313 3342870
Neutropenia 6320.88 48.21 2085 24591 31301 3327882
Off label use 3840.14 48.21 1650 25026 52327 3306856
Thrombocytopenia 3096.09 48.21 1255 25421 34013 3325170
Infection 2549.71 48.21 997 25679 24405 3334778
Sepsis 2532.74 48.21 1062 25614 31311 3327872
Mucosal inflammation 2442.41 48.21 724 25952 7259 3351924
Product use issue 2273.37 48.21 811 25865 15190 3343993
Anaemia 2241.67 48.21 1143 25533 53190 3305993
Disease progression 2161.68 48.21 949 25727 31310 3327873
Acute myeloid leukaemia 1854.40 48.21 531 26145 4642 3354541
Pyrexia 1851.80 48.21 1158 25518 79957 3279226
Haematotoxicity 1765.16 48.21 427 26249 1747 3357436
Leukopenia 1697.76 48.21 653 26023 15170 3344013
Myelodysplastic syndrome 1677.17 48.21 501 26175 5146 3354037
Death 1596.63 48.21 1356 25320 150968 3208215
Hepatitis B 1459.54 48.21 375 26301 2058 3357125
Pneumonia 1340.21 48.21 897 25779 69246 3289937
Bone marrow failure 1339.83 48.21 466 26210 8021 3351162
Pancytopenia 1264.90 48.21 556 26120 18264 3340919
Neuropathy peripheral 1255.35 48.21 535 26141 16272 3342911
Vomiting 1251.27 48.21 946 25730 88585 3270598
Cardiotoxicity 1230.32 48.21 306 26370 1436 3357747
Pneumocystis jirovecii pneumonia 1210.87 48.21 356 26320 3434 3355749
Palmar-plantar erythrodysaesthesia syndrome 1164.64 48.21 393 26283 6139 3353044
Nausea 1139.71 48.21 1047 25629 128598 3230585
Diarrhoea 1063.51 48.21 917 25759 103431 3255752
Stomatitis 1038.45 48.21 423 26253 11429 3347754
Septic shock 956.23 48.21 402 26274 11782 3347401
Neutropenic sepsis 942.95 48.21 272 26404 2434 3356749

Pharmacologic Action:

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SourceCodeDescription
ATC L01DB01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES
Anthracyclines and related substances
MeSH PA D000903 Antibiotics, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D059005 Topoisomerase II Inhibitors
MeSH PA D059003 Topoisomerase Inhibitors
FDA EPC N0000175414 Anthracycline Topoisomerase Inhibitor
FDA Chemical/Ingredient N0000007530 Anthracyclines

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Acute lymphoid leukemia indication 91857003 DOID:9952
Acute myeloid leukemia, disease indication 91861009 DOID:9119
Kaposi's sarcoma indication 109385007 DOID:8632
Diffuse non-Hodgkin's lymphoma, large cell indication 109969005
Multiple myeloma indication 109989006 DOID:9538
Hodgkin's disease indication 118599009 DOID:8651
Non-Hodgkin's lymphoma indication 118601006 DOID:8675
Burkitt's lymphoma indication 118617000 DOID:8584
Small cell carcinoma of lung indication 254632001 DOID:5409
Carcinoma of breast indication 254838004 DOID:3459
Nephroblastoma indication 302849000 DOID:2154
Osteosarcoma of bone indication 307576001 DOID:3376
Follicular non-Hodgkin's lymphoma indication 308121000
Malignant tumor of lung indication 363358000
Malignant tumor of ovary indication 363443007 DOID:2394
Malignant tumor of thyroid gland indication 363478007 DOID:1781
Kaposi's sarcoma associated with AIDS indication 420524008
Neuroblastoma indication 432328008 DOID:769
Carcinoma of female breast indication 447782002
Soft or Connective Tissue Sarcoma indication
Invasive Bladder Malignancy indication
Metastatic Breast Carcinoma indication
Metastatic Gastric Cancer indication
Mycosis contraindication 3218000 DOID:1564
Bundle branch block contraindication 6374002
Hyperbilirubinemia contraindication 14783006 DOID:2741
Viral disease contraindication 34014006 DOID:934
Hyperuricemia contraindication 35885006 DOID:1920
Conduction disorder of the heart contraindication 44808001
Myocarditis contraindication 50920009 DOID:820
Heart disease contraindication 56265001 DOID:114
Hepatic failure contraindication 59927004
Heart failure contraindication 84114007 DOID:6000
Leukopenia contraindication 84828003 DOID:615
Cardiomyopathy contraindication 85898001 DOID:0050700
Bacterial infectious disease contraindication 87628006 DOID:104
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Atrioventricular block contraindication 233917008 DOID:0050820
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Myocardial infarction in recovery phase contraindication 418044006
Asymptomatic left ventricular systolic dysfunction contraindication 698592004
Protozoal Infection contraindication
Severe Cardiac Disease contraindication
Carcinoid syndrome off-label use 35868009
Ewing's sarcoma off-label use 76909002 DOID:3369
Chronic lymphoid leukemia, disease off-label use 92814006 DOID:1040
Malignant neoplasm of liver off-label use 93870000 DOID:3571
Endometrial carcinoma off-label use 254878006 DOID:2871
Malignant tumor of head and/or neck off-label use 255056009
Primary cutaneous T-cell lymphoma off-label use 400122007
Adenocarcinoma of pancreas off-label use 700423003 DOID:4074
Pancreatic Neuroendocrine Tumor off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.85 acidic
pKa2 9.21 acidic
pKa3 9.92 acidic
pKa4 11.11 acidic
pKa5 8.6 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA topoisomerase 2-alpha Enzyme INHIBITOR IC50 6 CHEMBL CHEMBL
Caspase-1 Enzyme IC50 4.91 DRUG MATRIX
Tyrosine-protein kinase Lck Kinase IC50 4.50 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.29 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 5.60 DRUG MATRIX
Multidrug resistance-associated protein 6 Transporter WOMBAT-PK
ATP-binding cassette sub-family G member 2 Transporter WOMBAT-PK
Multidrug resistance-associated protein 1 Transporter WOMBAT-PK
Canalicular multispecific organic anion transporter 1 Transporter WOMBAT-PK
Multidrug resistance protein 1 Transporter WOMBAT-PK
Telomerase reverse transcriptase Enzyme IC50 4.14 CHEMBL
DNA topoisomerase 1 Enzyme IC50 4.70 CHEMBL
Aurora kinase A Kinase IC50 7.40 CHEMBL
72 kDa type IV collagenase Enzyme IC50 5.96 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 5.43 DRUG MATRIX
5-hydroxytryptamine receptor 4 GPCR Ki 5.68 DRUG MATRIX
Arachidonate 15-lipoxygenase Enzyme IC50 4.87 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 4.81 DRUG MATRIX
Type-2 restriction enzyme HindIII Unclassified IC50 4.02 CHEMBL
Type-2 restriction enzyme ScaI Unclassified IC50 4.60 CHEMBL
Ribonuclease pancreatic Enzyme IC50 4.60 CHEMBL
Integrase Enzyme IC50 6.05 CHEMBL
ORF 73 Unclassified AC50 5.84 CHEMBL
UDP-galactopyranose mutase Unclassified AC50 4.49 CHEMBL
Reverse transcriptase Enzyme IC50 4.28 CHEMBL

External reference:

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IDSource
4019737 VUID
N0000147829 NUI
C0013089 UMLSCUI
7069 IUPHAR_LIGAND_ID
D01275 KEGG_DRUG
80168379AG UNII
3005 INN_ID
DB00997 DRUGBANK_ID
CHEMBL53463 ChEMBL_ID
3639 RXNORM
372817009 SNOMEDCT_US
68444001 SNOMEDCT_US
d00218 MMSL
4019737 VANDF
N0000006795 NDFRT
N0000147829 NDFRT
004818 NDDF
25316-40-9 SECONDARY_CAS_RN
31703 PUBCHEM_CID
CHEMBL359744 ChEMBL_ID
D004317 MESH_DESCRIPTOR_UI
C506643 MESH_SUPPLEMENTAL_RECORD_UI
CHEBI:28748 CHEBI
DM2 PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-0171 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 mg INTRAVENOUS ANDA 15 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-3030 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-3031 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-3032 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-3033 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-3034 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-4004 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-4015 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-4026 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-4030 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-4031 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-4032 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-4033 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-4034 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0069-4037 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 20 sections
Adriamycin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9275 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 mg INTRAVENOUS ANDA 18 sections
Adriamycin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9277 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 mg INTRAVENOUS ANDA 18 sections
Adriamycin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9546 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 18 sections
Adriamycin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9547 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 18 sections
Adriamycin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9548 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 18 sections
Adriamycin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9549 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 18 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0703-5040 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 19 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0703-5043 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 19 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0703-5046 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 19 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-742 INJECTABLE, LIPOSOMAL 2 mg INTRAVENOUS ANDA 19 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-856 INJECTABLE, LIPOSOMAL 2 mg INTRAVENOUS ANDA 19 sections
doxorubicin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 25021-207 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 19 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43598-283 INJECTABLE, LIPOSOMAL 2 mg INTRAVENOUS ANDA 18 sections
Doxorubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43598-541 INJECTABLE, LIPOSOMAL 2 mg INTRAVENOUS ANDA 18 sections
Doxorubicin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 45963-733 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 19 sections