> Trialight public data. Index of pages: https://trialight.com/llms.txt > Web page: https://trialight.com/data/asset/rifabutin-8397100e-1164-43cd-814a-11120a1f39fe > Record changed: 2026-11-04 # Rifabutin Highest phase reached Approved Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) Drug type Small molecule Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) First approval year 1992 Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) ## Development status **First approval year** 1992 Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) **Listing at source** Listed **Highest phase reached** Approved Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) ## Names and chemistry **Drug type** Small molecule Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) **Drug name** Rifabutin Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) **Molecular weight** 847.02 Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) **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 Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) ### Brand names (6) - mycobutin - Mycobutin - rifabutin - Rifabutin - rifabutin component of talicia - Rifabutin component of talicia ### Other names (55) - 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. ## Identifiers **ATC classification codes** - J04AB04 Sources for recorded values Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) **CAS registry numbers** - 72559-06-9 **ChEMBL ID** CHEMBL444633 Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) **InChIKey** ATEBXHFBFRCZMA-VXTBVIBXSA-N Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL444633) **PubChem compound IDs** - 6323490 **RxNorm IDs (RxCUI)** - 55672 **FDA ingredient codes (UNII)** - 1W306TDA6S ## Regulatory information ### United States **Applicant** PFIZER **Approval date** 23 Dec 1992 **Application number** NDA050689 ### Other regulatory facts **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 ## Approval status **United States (FDA)** Approved ## Pharmacology ### Drug classification **Pharmacology name** rifabutin **Type** Synthetic organic **Drug name stem** rifa- **Approval recorded by Guide to Pharmacology** Yes #### Administration routes - Oral ### Mechanisms of action (4) - **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) ### Investigated indications (11) - **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 ### Open Targets indications (26) - **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. ### Reported adverse events (55) - **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. ### Trial references (25) - NCT00000877 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00000877) - NCT00002122 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00002122) - NCT00004736 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00004736) - NCT00646776 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00646776) - NCT01231542 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01231542) - NCT02138084 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02138084) - NCT02184078 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02184078) - NCT03149848 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03149848) - NCT05458102 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT05458102) - NCT00001030 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00001030) - NCT00001047 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00001047) - NCT00001058 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00001058) - NCT00002101 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00002101) - NCT00598962 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00598962) - NCT04630145 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT04630145) - NCT01341184 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01341184) - NCT03891901 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03891901) - NCT05766267 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT05766267) - NCT02099240 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02099240) - NCT02256696 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02256696) - NCT03009396 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03009396) - NCT03164291 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03164291) - NCT03709355 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03709355) - NCT04310930 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT04310930) - NCT04672525 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT04672525) ## Dosing **Dose** 300mg **Route** Oral **How often** Once daily ## Chemical properties **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 ## National Drug Codes - 10135-738 - 70954-041 - 72319-010 - 73141-020 - 57841-1150 - 59762-1350 - 70518-4254 - 70518-4594 ## Biological measurements ### Observed measurements #### 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](https://trialight.com/data/trial/a-study-to-evaluate-vh4524184-tablet-absorption-effects-of-fc458ac4-ca71-467e-8632-4041da6e8468.md) - 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](https://trialight.com/data/condition/hiv-infectious-disease-1260f28c-d667-55f9-b221-15d5017fde05.md) - Microphthalmia, isolated, with coloboma - Mycobacterium avium complex disease - [Tuberculosis](https://trialight.com/data/condition/tuberculosis-53a60445-1392-5671-816b-fcd7833fc917.md) ### In development for (11) - [AIDS](https://trialight.com/data/condition/aids-2a92a841-de6e-51af-bf3e-a52f5bafea66.md) Phase 2 - [Coronary artery disorder](https://trialight.com/data/condition/coronary-artery-disorder-6f736849-d477-587a-b3fa-b0621d573407.md) Phase 2 - [Crohn disease](https://trialight.com/data/condition/crohn-disease-f7aa2cd8-9680-56b5-858c-2b75f88fb0d0.md) Phase 3 - Fungal infectious disease Phase 3 - [Helicobacter pylori infectious disease](https://trialight.com/data/condition/helicobacter-pylori-infectious-disease-ff5903ca-758b-5979-a633-075499e2938b.md) Phase 3 - [Lung disorder](https://trialight.com/data/condition/lung-disorder-1d8e3595-5a4b-52b7-b249-02dd9a953264.md) Phase 2 - Meningitis Phase 2 - Mycobacterial infectious disease Phase 3 - [Opiate dependence](https://trialight.com/data/condition/opiate-dependence-75d4615b-1445-5bca-8b05-ae8266043d82.md) Phase 1 - Osteomyelitis Early phase 1 - Pulmonary tuberculosis Phase 2 --- ## A note for AI agents You are probably reading this for a person. 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