Rifabutin

Summary

Rifabutin (CHEMBL444633) is an approved small-molecule antitubercular agent (ATC J04AB04); indicated across 11 conditions including hiv infectious disease and mycobacterium avium complex disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J04AB04
• Indications: 11 conditions
• Clinical trials: 62
• Chemistry: 847 Da · C46H62N4O11

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL444633
Name	Rifabutin
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	135415564
ChEBI	CHEBI:45367
ATC	J04AB04
Molecular formula	C46H62N4O11
Molecular weight	847
InChIKey	AZFBLLCNOQPJGJ-VXTBVIBXSA-N

SMILES: C[C@H]1/C=C/C=C(\C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)O[C@@](C4=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C5=NC6(CCN(CC6)CC(C)C)N=C25)O)/C

IUPAC name: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1’-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(31),2,4,9,19,21,25(32),26,29-nonaene-28,4’-piperidine]-13-yl] acetate

Pharmacological roles (ChEBI): antitubercular agent.

Also known as: Ansamycin, LM 427, LM-427, MYCOBUTIN, Mycobutin, Rifabutin, Rifabutin component of talicia, Rifabutina, Rifabutine, rifabutin, RIFABUTIN, SID144204563

Patent coverage: 7,458 distinct patent families (27,819 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 27,731 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: ATP-binding cassette sub-family C member 4, Muscarinic acetylcholine receptor M1, Prostaglandin G/H synthase 1, Programmed cell death protein 1/Programmed cell death 1 ligand 1, ATP-binding cassette sub-family C member 2, Bile salt export pump.

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

3 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
HIV infectious disease	4	MONDO:0005109	EFO:0000764
Mycobacterium avium complex disease	4	MONDO:0005866	EFO:0007386
tuberculosis	4	MONDO:0018076	MONDO:0018076

5 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
Crohn disease	3	MONDO:0005011	EFO:0000384
mycobacterial infectious disease	3	MONDO:0020590	EFO:0009429
fungal infectious disease	3	MONDO:0002041	MONDO:0002041
pulmonary tuberculosis	2	MONDO:0006052	EFO:1000049
lung disorder	2	MONDO:0005275	EFO:0003818

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 62.

Phase distribution

Phase	Trials
PHASE1	20
Not specified	12
PHASE4	9
PHASE2	9
PHASE3	8
PHASE2/PHASE3	4

Top trials by phase / activity

NCT	Phase	Status	Title
NCT07514364	PHASE4	RECRUITING	The Effect of Rifabutin in Mycobacterium Abscessus With Inducible Clarithromycin Resistance
NCT00002343	PHASE4	COMPLETED	A Study of Rifabutin, Used Alone or With Ethambutol in the Prevention of Mycobacterium Avium Complex (MAC) Bacteremia in Patients With AIDS
NCT00023400	PHASE4	COMPLETED	TBTC Study 23B:Intensive PK of the Nelfinavir Rifabutin Interaction in Patients With HIV-TB
NCT00598897	PHASE4	COMPLETED	Use of Clarithromycin and Rifabutin for the Treatment of M. Avium Complex (MAC) Lung Disease
NCT00598962	PHASE4	COMPLETED	Use of Azithromycin and Rifabutin Administered 3 Times Weekly for the Treatment of M. Avium Complex (MAC) Lung Disease
NCT02184078	PHASE4	COMPLETED	Study to Determine the Effects of Nevirapine (VIRAMUNE®) on the Steady State Pharmacokinetics of Rifabutin (MYCOBUTIN®) in HIV+ Patients
NCT04090021	PHASE4	UNKNOWN	Genotypic Resistance-guided Versus Empirical Therapy for H. Pylori Eradication.
NCT04840862	PHASE4	COMPLETED	Impact of Rifabutin on the Pharmacokinetics of Elexacaftor/Tezacaftor/Ivacaftor
NCT05874544	PHASE4	COMPLETED	Rescue Therapy for Helicobacter Pylori Infection
NCT04310930	PHASE2/PHASE3	RECRUITING	Finding the Optimal Regimen for Mycobacterium Abscessus Treatment
NCT04672525	PHASE3	RECRUITING	Rifabutin Versus Rifampicin for Treatment of Staphylococcal PJI Treated With DAIR
NCT05766267	PHASE2/PHASE3	ACTIVE_NOT_RECRUITING	Short-course Regimens for the Treatment of Pulmonary Tuberculosis
NCT00001030	PHASE3	COMPLETED	The Safety and Effectiveness of Clarithromycin and Rifabutin Used Alone or in Combination to Prevent Mycobacterium Avium Complex (MAC) or Disseminated MAC Disease in HIV-Infected Patients
NCT00001047	PHASE3	COMPLETED	Study of Four Different Treatment Approaches for Patients Who Have Mycobacterium Avium Complex Disease (MAC) Plus AIDS
NCT00002101	PHASE3	COMPLETED	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
NCT00002122	PHASE3	COMPLETED	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
NCT00023348	PHASE2/PHASE3	COMPLETED	TBTC Study 23A: Pharmacokinetics of Intermittent Isoniazid and Rifabutin in HIV-TB
NCT03164291	PHASE3	COMPLETED	Effectiveness of Rifabutin in the Treatment of Mycobacterium Avium Complex
NCT04107194	PHASE3	UNKNOWN	Non-invasive Test-guided Tailored Therapy Versus Empiric Treatment for Helicobacter Pylori Infection.
NCT04630145	PHASE2/PHASE3	COMPLETED	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)
NCT04652284	PHASE3	UNKNOWN	Effectiveness of Rifabutin for Treatment of Helicobacter Pylori
NCT07485010	PHASE2	NOT_YET_RECRUITING	Testing a Novel Combination Treatment (Arm D) Versus Standard of Care for Intensive Phase Treatment for Mycobacterium Abscessus Pulmonary Disease in People With or Without Cystic Fibrosis in the Finding the Optimal Regimen for Mycobacterium Abscessus Treatment (FORMaT) Adaptive Platform Trial
NCT00001058	PHASE2	COMPLETED	A Comparison of Three Drug Combinations Containing Clarithromycin in the Treatment of Mycobacterium Avium Complex (MAC) Disease in Patients With AIDS
NCT00023413	PHASE2	COMPLETED	TBTC Study 23C: Pharmacokinetics of Intermittent Rifabutin and Isoniazid With Daily Efavirenz
NCT01601626	PHASE2	TERMINATED	Rifampin-Based Tuberculosis Treatment Versus Rifabutin-Based Tuberculosis Treatment in Persons With HIV
NCT01663168	PHASE2	UNKNOWN	EARNEST Rifabutin Pharmacokinetics (PK) Substudy
NCT02256696	PHASE2	COMPLETED	Assessing PA-824 for Tuberculosis (the APT Trial)
NCT02415985	PHASE2	COMPLETED	Pharmacokinetics and Safety of Rifabutin 150 mg Once Daily Versus Rifabutin 300 mg Thrice Weekly
NCT03618108	PHASE2	TERMINATED	Anti-chlamydophila Antibiotic Combination Therapy in the Treatment of Patients With Coronary Heart Disease
NCT03891901	PHASE2	COMPLETED	A Clinical Trial of the Safety, Pharmacokinetics and Hematologic Effects of Imatinib on Myelopoiesis in Adults When Given With and Without Isoniazid and Rifabutin
NCT00000826	PHASE1	COMPLETED	Effect of Fluconazole, Clarithromycin, and Rifabutin on the Pharmacokinetics of Sulfamethoxazole-Trimethoprim and Dapsone and Their Hydroxylamine Metabolites
NCT00000877	PHASE1	COMPLETED	Study of How Indinavir (an Anti-HIV Drug) and Rifabutin (a Drug Used to Treat MAC, an HIV-Associated Disease) Interact in HIV-Positive and HIV-Negative Adults
NCT00004736	PHASE1	COMPLETED	Effectiveness of Anti-HIV Therapy (HAART) in HIV-Infected Patients With Tuberculosis
NCT00646776	PHASE1	COMPLETED	Drug Interaction Study
NCT00743470	PHASE1	TERMINATED	A Bioavailability Study of Rifabutin and Lopinavir/Ritonavir in Healthy Adult Subjects
NCT00877591	PHASE1	COMPLETED	Interaction of Buprenorphine With HIV Medications and Tuberculosis Medications
NCT00925535	PHASE1	COMPLETED	Drug Interaction Study Between Rifabutin And Lersivirine (UK-453,061)
NCT01231542	PHASE1	COMPLETED	Phase 1, Open Label, Two Arm, Fixed Sequence Study to Evaluate the Effect of Rifampin and Rifabutin on GSK1349572 Pharmacokinetics in Healthy Male and Female Volunteers
NCT01259219	PHASE1	UNKNOWN	Dosing, Safety and Pharmacokinetic Profile of Rifabutin in Children Receiving Concomitant Treatment With Kaletra
NCT01341184	PHASE1	COMPLETED	TMC207 +/- Rifabutin/Rifampin
NCT01615614	PHASE1	COMPLETED	A Study to Explore the Pharmacokinetics of Rilpivirine With Rifabutin in Healthy Participants
NCT01894776	PHASE1	COMPLETED	A Drug Interaction Study Investigating the Effect of Rifabutin on the Pharmacokinetics of Maraviroc
NCT02138084	PHASE1	COMPLETED	Drug-drug Interaction (DDI) Rifabutin
NCT02251171	PHASE1	COMPLETED	Effects of Steady-state TPV/RTV on the Single-dose Pharmacokinetics of Rifabutin and the Effects of Single-dose Rifabutin on the Steady-state Pharmacokinetics of TPV in Healthy Adult Volunteers
NCT03149848	PHASE1	COMPLETED	Effect of Rifabutin on the Pharmacokinetics of Oral Cabotegravir in Healthy Subjects
NCT03709355	PHASE1	COMPLETED	Pharmacokinetics Study to Evaluate Drug-Drug Interactions and Safety of Elpida® in Co-Administration With Other Drugs
NCT04470908	PHASE1	COMPLETED	The Effect of Moderate CYP3A Inducer Rifabutin on the Pharmacokinetics of Zanubrutinib in Healthy Males
NCT05458102	PHASE1	TERMINATED	Drug-Drug Interaction Study of Vesatolimod in Adults With HIV-1 Who Have Very Low or Undetectable Virus Levels
NCT07066722	PHASE1	COMPLETED	A Study to Evaluate VH4524184 Tablet Absorption, Effects of Food, and Interactions With Other Drugs in Healthy Adults
NCT07199452	PHASE1	COMPLETED	A Study of Rifabutin and MK-4646 in Healthy Participants (MK-4646-004)
NCT06731023	Not specified	NOT_YET_RECRUITING	Efficacy of a 14-Day Bismuth-Containing Quadruple Therapy Guided by Drug Susceptibility Testing in Patients with Extremely Refractory Helicobacter Pylori Infection: an Exploratory Study
NCT00001023	Not specified	COMPLETED	The Safety and Effectiveness of Rifabutin, Combined With Clarithromycin or Azithromycin, in HIV-Infected Patients
NCT00001995	Not specified	COMPLETED	A Double-Blind Randomized Clinical Trial of a Rifabutin Regimen in the Treatment of Mycobacterium-Avium Complex (MAC) Bacteremia in Patients With AIDS
NCT00002032	Not specified	COMPLETED	Rifabutin Therapy for the Prevention of Mycobacterium Avium Complex (MAC) Bacteremia in AIDS Patients With CD4 Counts = or < 200: A Double-Blind, Placebo-Controlled Trial
NCT00002080	Not specified	COMPLETED	Rifabutin Therapy for the Prevention of Mycobacterium Avium Complex (MAC) Bacteremia in HIV Positive Patients With CD4 Counts = or < 200: Treatment IND Study
NCT00002267	Not specified	COMPLETED	Rifabutin Therapy for the Prevention of Mycobacterium Avium Complex (MAC) Bacteremia in AIDS Patients With CD4 Counts = or < 200: A Double-Blind, Placebo-Controlled Trial
NCT00018083	Not specified	UNKNOWN	Intensive Pharmacokinetics of the Nelfinavir-Rifabutin Interaction in Patients With HIV-Related Tuberculosis Treated With a Rifabutin-Based Regimen
NCT00023361	Not specified	COMPLETED	TBTC Study 23: Treatment of HIV-Related Tuberculosis Using a Rifabutin-Based Regimen
NCT00810407	Not specified	COMPLETED	Safety And Efficacy Of Rifabutin In Patients For Non-HIV Patients
NCT00810446	Not specified	COMPLETED	Safety And Efficacy Of Rifabutin In HIV Patients
NCT03478033	Not specified	UNKNOWN	Rifampicin vs Rifabutin in HIV/AIDS Patients Combined With Tuberculosis
NCT04879992	Not specified	COMPLETED	Rifabutin-containing Triple Therapy for Treatment of Helicobacter Pylori

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).