RIFABUTIN

Search structure
Trade Names:
Synonyms:
Status: Approved (1992)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: J04AB04
UNII: 1W306TDA6S

Structure
InChI Key ATEBXHFBFRCZMA-VXTBVIBXSA-N
Smile CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C2=NC3(CCN(CC(C)C)CC3)NC2=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O
InChI
InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12+,20-15+,24-14-/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C46H62N4O11
Molecular Weight 847.02
AlogP 4.62
Hydrogen Bond Acceptor 14.0
Hydrogen Bond Donor 5.0
Number of Rotational Bond 4.0
Polar Surface Area 205.55
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 61.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial DNA-directed RNA polymerase inhibitor PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 26700-26700 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 15900 - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Mycobacterium avium-intracellulare Infection 4 D015270 ClinicalTrials
Tuberculosis 4 D014376 ClinicalTrials
HIV Infections 4 D015658 ClinicalTrials
Mycoses 3 D009181 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Crohn Disease 3 D003424 ClinicalTrials
Mycobacterium Infections 3 D009164 ClinicalTrials
Tuberculosis, Pulmonary 2 D014397 ClinicalTrials
Osteomyelitis 0 D010019 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Renal and urinary disorders Chromaturia 30.0
Blood and lymphatic system disorders Neutropenia 25.0
Blood and lymphatic system disorders Neutropenia
Blood and lymphatic system disorders Leukopenia 17.0
Blood and lymphatic system disorders Leukopenia
Investigations Aspartate aminotransferase increased
Investigations Alanine aminotransferase increased
Skin and subcutaneous tissue disorders Dermatitis 11.0
Skin and subcutaneous tissue disorders Rash 11.0
Investigations Alanine aminotransferase increased 9.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Rash
Blood and lymphatic system disorders Anaemia
Investigations Aspartate aminotransferase increased 7.0
Blood and lymphatic system disorders Anaemia 6.0
Renal and urinary disorders Chromaturia
Gastrointestinal disorders Nausea 6.0
Nervous system disorders Headache
Gastrointestinal disorders Nausea
Blood and lymphatic system disorders Thrombocytopenia 5.0
Gastrointestinal disorders Abdominal pain 4.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Gastrointestinal disorders Gastrointestinal pain 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Blood and lymphatic system disorders Thrombocytopenia
Gastrointestinal disorders Abdominal pain
Investigations Blood alkaline phosphatase increased
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 3.0
Gastrointestinal disorders Dysgeusia 3.0
Gastrointestinal disorders Dyspepsia 3.0
Gastrointestinal disorders Eructation 3.0
Gastrointestinal disorders Gastrointestinal pain
Nervous system disorders Headache 3.0
Gastrointestinal disorders Nausea 3.0
Gastrointestinal disorders Vomiting 3.0
Investigations Body temperature increased 2.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 2.0
Gastrointestinal disorders Flatulence 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Musculoskeletal and connective tissue disorders Myalgia 2.0
Gastrointestinal disorders Nausea
Blood and lymphatic system disorders Neutropenia 2.0
General disorders and administration site conditions Pain
Gastrointestinal disorders Vomiting
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 1.0
Investigations Blood alkaline phosphatase increased 1.0
Investigations Body temperature increased
Cardiac disorders Chest pain
Cardiac disorders Chest pain 1.0
Gastrointestinal disorders Dysgeusia
Gastrointestinal disorders Dyspepsia
Blood and lymphatic system disorders Eosinophilia
Blood and lymphatic system disorders Eosinophilia 1.0
Gastrointestinal disorders Eructation
Gastrointestinal disorders Flatulence
Nervous system disorders Insomnia
Nervous system disorders Insomnia 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
General disorders and administration site conditions Pain 1.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
10.52
Gastrointestinal disorders
9.92
Hepatobiliary disorders
8.13
Immune system disorders
7.78
Injury, poisoning and procedural complications
7.36
Nervous system disorders
6.16
Eye disorders
5.73
Skin and subcutaneous tissue disorders
5.65
Infections and infestations
5.3
Musculoskeletal and connective tissue disorders
4.7
Blood and lymphatic system disorders
4.36
Metabolism and nutrition disorders
4.02
Respiratory, thoracic and mediastinal disorders
3.93
Investigations
3.85
Vascular disorders
3.42
Psychiatric disorders
3.25
Cardiac disorders
2.31

Cross References

Resources Reference
CAS NUMBER 72559-06-9
ChEBI 45367
ChEMBL CHEMBL444633
DrugBank DB00615
DrugCentral 2376
EPA CompTox DTXSID0033960
FDA SRS 1W306TDA6S
KEGG C07235
PDB RBT
PharmGKB PA451249
PubChem 6323490
SureChEMBL SCHEMBL36043
ZINC ZINC000169621215
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