Rifabutin
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1992
- First approval year
- 1992
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Rifabutin
- Molecular weight
- 847.02
- Structure (SMILES)
- 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
- mycobutin
- Mycobutin
- rifabutin
- Rifabutin
- rifabutin component of talicia
- Rifabutin component of talicia
- 1 4 didehydro 1 deoxy 1 4 dihydro 5 2 methylpropyl 1 oxorifamycin xiv
- 1',4-DIDEHYDRO-1-DEOXY-1,4-DIHYDRO-5'-(2-METHYLPROPYL)-1-OXORIFAMYCIN XIV
- 4 deoxo 3 4 2 spiro n isobutyl 4 piperidyl 1h imidazo 2 5 dihydro rifamycin s
- 4 n isobutylspiropiperidylrifamycin s
- 4-DEOXO-3,4-(2-SPIRO-(N-ISOBUTYL-4-PIPERIDYL))-(1H)-IMIDAZO-(2,5-DIHYDRO)RIFAMYCIN S
- 4-N-ISOBUTYLSPIROPIPERIDYLRIFAMYCIN S
- ansamycin
- Ansamycin
- clarithromycin rifabutin
- lm 427
- LM 427
- LM-427
- mycobutin
- Mycobutin
- MYCOBUTIN
- rifabutin
- Rifabutin
- RIFABUTIN [EP MONOGRAPH]
- RIFABUTIN [HSDB]
- rifabutin [INN]
- RIFABUTIN [JAN]
- RIFABUTIN [MART.]
- RIFABUTIN [MI]
- RIFABUTIN [ORANGE BOOK]
- RIFABUTIN [USAN]
And 30 more, listed on the interactive page.
- ATC classification codes
- J04AB04
Sources for recorded values
- CAS registry numbers
- 72559-06-9
- ChEMBL ID
- CHEMBL444633
- InChIKey
- ATEBXHFBFRCZMA-VXTBVIBXSA-N
- PubChem compound IDs
- 6323490
- RxNorm IDs (RxCUI)
- 55672
- FDA ingredient codes (UNII)
- 1W306TDA6S
- Applicant
- PFIZER
- Approval date
- 23 Dec 1992
- Application number
- NDA050689
- Patents
- 7
- Designations
- 2
- Earliest recorded loss of exclusivity
- 27 May 2042
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- Yes
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- United States (FDA)
- Approved
- Pharmacology name
- rifabutin
- Type
- Synthetic organic
- Drug name stem
- rifa-
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Mechanism
- Bacterial DNA-directed RNA polymerase inhibitor
- Action type
- Inhibitor
- Target
- Bacterial DNA-directed RNA polymerase
- Protein identifier
- P0A7Z4
- Mechanism
- Bacterial DNA-directed RNA polymerase inhibitor
- Action type
- Inhibitor
- Target
- Bacterial DNA-directed RNA polymerase
- Protein identifier
- P0A800
- Mechanism
- Bacterial DNA-directed RNA polymerase inhibitor
- Action type
- Inhibitor
- Target
- Bacterial DNA-directed RNA polymerase
- Protein identifier
- P0A8T7
- Mechanism
- Bacterial DNA-directed RNA polymerase inhibitor
- Action type
- Inhibitor
- Target
- Bacterial DNA-directed RNA polymerase
- Protein identifier
- P0A8V2
Open Targets mechanisms
- Mechanism
- Bacterial DNA-directed RNA polymerase inhibitor
- Action type
- Inhibitor
- Target
- Bacterial DNA-directed RNA polymerase
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- rpoA|rpoZ|rpoC|rpoB
- Protein identifier
- P0A7Z4|P0A800|P0A8T7|P0A8V2
- Organism
- Escherichia coli (strain K12)
- Condition
- HIV Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000180
- Subject identifier
- D015658
- Condition
- Crohn Disease
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000384
- Subject identifier
- D003424
- Condition
- Infections
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000544
- Subject identifier
- D007239
- Condition
- HIV Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000764
- Subject identifier
- D015658
- Condition
- Osteomyelitis
- Highest recorded phase
- 0.5
- Condition identifier
- EFO:0003102
- Subject identifier
- D010019
- Condition
- Lung Diseases
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003818
- Subject identifier
- D008171
- Condition
- Mycobacterium avium-intracellulare Infection
- Highest recorded phase
- 4
- Condition identifier
- EFO:0007386
- Subject identifier
- D015270
- Condition
- Mycobacterium Infections
- Highest recorded phase
- 3
- Condition identifier
- EFO:0009429
- Subject identifier
- D009164
- Condition
- Tuberculosis, Pulmonary
- Highest recorded phase
- 2
- Condition identifier
- EFO:1000049
- Subject identifier
- D014397
- Condition
- Mycoses
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0002041
- Subject identifier
- D009181
- Condition
- Tuberculosis
- Highest recorded phase
- 4
- Condition identifier
- MONDO:0018076
- Subject identifier
- D014376
- Condition identifier
- EFO_0000180
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000384
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000544
- Condition identifier
- EFO_0000544
- Highest recorded phase
- 4
- Condition identifier
- EFO_0000764
- Condition identifier
- EFO_0003102
- Condition identifier
- EFO_0005262
- Condition identifier
- EFO_0005262
- Highest recorded phase
- 4
- Condition identifier
- EFO_0007386
- Condition identifier
- EFO_0009429
- Condition identifier
- EFO_0009429
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0000170
- Condition identifier
- MONDO_0000170
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005010
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005011
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005109
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005530
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0005866
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0006052
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0006781
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0012268
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0018076
- Condition identifier
- MONDO_0018076
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0020590
- Condition identifier
- MONDO_0020590
- Highest recorded phase
- 4
And 1 more, listed on the interactive page.
- Event
- acute hepatic failure
- Reports
- 8
- Reporting signal score
- 14.0559
- Event
- atypical mycobacterial infection
- Reports
- 10
- Reporting signal score
- 41.2917
- Event
- cerebral toxoplasmosis
- Reports
- 3
- Reporting signal score
- 10.1149
- Event
- corneal deposits
- Reports
- 8
- Reporting signal score
- 34.0879
- Event
- cytomegalovirus chorioretinitis
- Reports
- 10
- Reporting signal score
- 36.2395
- Event
- cytopenia
- Reports
- 9
- Reporting signal score
- 17.6181
- Event
- deafness
- Reports
- 8
- Reporting signal score
- 10.8485
- Event
- disseminated mycobacterium avium complex infection
- Reports
- 7
- Reporting signal score
- 44.8271
- Event
- disseminated tuberculosis
- Reports
- 7
- Reporting signal score
- 20.5302
- Event
- drug interaction
- Reports
- 45
- Reporting signal score
- 39.0527
- Event
- drug reaction with eosinophilia and systemic symptoms
- Reports
- 26
- Reporting signal score
- 49.0067
- Event
- drug resistance
- Reports
- 42
- Reporting signal score
- 106.436
- Event
- eosinophilia
- Reports
- 8
- Reporting signal score
- 9.56585
- Event
- gastritis haemorrhagic
- Reports
- 4
- Reporting signal score
- 11.7729
- Event
- gynaecological chlamydia infection
- Reports
- 4
- Reporting signal score
- 23.4887
- Event
- hepatic function abnormal
- Reports
- 12
- Reporting signal score
- 12.5268
- Event
- hepatitis cholestatic
- Reports
- 7
- Reporting signal score
- 14.1822
- Event
- hepatotoxicity
- Reports
- 28
- Reporting signal score
- 65.2022
- Event
- hyperuricaemia
- Reports
- 7
- Reporting signal score
- 17.5125
- Event
- hypopyon
- Reports
- 7
- Reporting signal score
- 26.6311
- Event
- immune reconstitution inflammatory syndrome
- Reports
- 33
- Reporting signal score
- 118.547
- Event
- immune reconstitution inflammatory syndrome associated tuberculosis
- Reports
- 9
- Reporting signal score
- 47.2497
- Event
- immune reconstitution syndrome
- Reports
- 7
- Reporting signal score
- 24.6666
- Event
- iridocyclitis
- Reports
- 16
- Reporting signal score
- 55.3038
- Event
- kidney malformation
- Reports
- 3
- Reporting signal score
- 12.1267
And 30 more, listed on the interactive page.
- NCT00000877
- NCT00002122
- NCT00004736
- NCT00646776
- NCT01231542
- NCT02138084
- NCT02184078
- NCT03149848
- NCT05458102
- NCT00001030
- NCT00001047
- NCT00001058
- NCT00002101
- NCT00598962
- NCT04630145
- NCT01341184
- NCT03891901
- NCT05766267
- NCT02099240
- NCT02256696
- NCT03009396
- NCT03164291
- NCT03709355
- NCT04310930
- NCT04672525
- Dose
- 300mg
- Route
- Oral
- How often
- Once daily
- Hydrogen bond acceptors
- 14
- Hydrogen bond donors
- 5
- Polar surface area
- 205.55
- Calculated partition coefficient (ALogP)
- 4.62
- Calculated partition coefficient (XLogP)
- 6.3
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 61
- Molecular formula
- C46H62N4O11
- Monoisotopic mass
- 846.44150881
- Natural product
- Yes
- 10135-738
- 70954-041
- 72319-010
- 73141-020
- 57841-1150
- 59762-1350
- 70518-4254
- 70518-4594
Distribution coefficient (LogD)
- Median
- 3.3
- Mean
- 3.3
- Minimum
- 3
- Maximum
- 3.6
- Unit
- unitless
- Assays
- 2
- Standard deviation
- 0.424264
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- LogD
Solubility
- Median
- 8,950
- Mean
- 8,950
- Minimum
- 200
- Maximum
- 17,700
- Unit
- ug/mL
- Assays
- 2
- Standard deviation
- 12,374.4
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- Solubility
Oral bioavailability
- Median
- 36.5
- Mean
- 36.5
- Minimum
- 20
- Maximum
- 53
- Unit
- %
- Assays
- 2
- Standard deviation
- 23.3345
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- F
Related records
Trials (65)
- A Bioavailability Study of Rifabutin and Lopinavir/Ritonavir in Healthy Adult Subjects
- A Clinical Trial of the Safety, Pharmacokinetics and Hematologic Effects of Imatinib on Myelopoiesis in Adults When Given With and Without Isoniazid and Rifabutin
- A Comparison of Three Drug Combinations Containing Clarithromycin in the Treatment of Mycobacterium Avium Complex (MAC) Disease in Patients With AIDS
- A Double-Blind Randomized Clinical Trial of a Rifabutin Regimen in the Treatment of Mycobacterium-Avium Complex (MAC) Bacteremia in Patients With AIDS
- A Drug Interaction Study Investigating the Effect of Rifabutin on the Pharmacokinetics of Maraviroc
- A Randomized Study of Daily and Intermittent Prophylactic Regimens for the Prevention of Disseminated Mycobacterium Avium Complex (MAC) and Fungal Infections in HIV-Infected Patients
- A Study of Bedaquiline Administered as Part of a Treatment Regimen With Clarithromycin and Ethambutol in Adult Patients With Treatment-refractory Mycobacterium Avium Complex-lung Disease (MAC-LD)
- A Study of Rifabutin and MK-4646 in Healthy Participants (MK-4646-004)
- A Study of Rifabutin, Used Alone or With Ethambutol in the Prevention of Mycobacterium Avium Complex (MAC) Bacteremia in Patients With AIDS
- A Study to Evaluate VH4524184 Tablet Absorption, Effects of Food, and Interactions With Other Drugs in Healthy Adults
- A Study to Explore the Pharmacokinetics of Rilpivirine With Rifabutin in Healthy Participants
- A Three-Arm Comparative Trial for the Treatment of MAC Bacteremia in AIDS: A Clarithromycin/Ethambutol Regimen Containing Rifabutin (450 Mg) or Rifabutin (300 Mg) or Placebo
- Anti-chlamydophila Antibiotic Combination Therapy in the Treatment of Patients With Coronary Heart Disease
- Assessing PA-824 for Tuberculosis (the APT Trial)
- Dosing, Safety and Pharmacokinetic Profile of Rifabutin in Children Receiving Concomitant Treatment With Kaletra
- Drug Interaction Study
- Drug Interaction Study Between Rifabutin And Lersivirine (UK-453,061)
- Drug-drug Interaction (DDI) Rifabutin
- Drug-Drug Interaction Study of Vesatolimod in Adults With HIV-1 Who Have Very Low or Undetectable Virus Levels
- EARNEST Rifabutin Pharmacokinetics (PK) Substudy
Approved for (4)
- HIV infectious disease
- Microphthalmia, isolated, with coloboma
- Mycobacterium avium complex disease
- Tuberculosis
In development for (11)
- AIDS Phase 2
- Coronary artery disorder Phase 2
- Crohn disease Phase 3
- Fungal infectious disease Phase 3
- Helicobacter pylori infectious disease Phase 3
- Lung disorder Phase 2
- Meningitis Phase 2
- Mycobacterial infectious disease Phase 3
- Opiate dependence Phase 1
- Osteomyelitis Early phase 1
- Pulmonary tuberculosis Phase 2