rifabutin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, rifamycin derivatives 2376 72559-06-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • rifabutin
  • ansamycin
  • mycobutin
  • rifabutine
A broad-spectrum antibiotic that is being used as prophylaxis against disseminated Mycobacterium avium complex infection in HIV-positive patients.
  • Molecular weight: 847.02
  • Formula: C46H62N4O11
  • CLOGP: 4.73
  • LIPINSKI: 2
  • HAC: 15
  • HDO: 5
  • TPSA: 205.55
  • ALOGS: -4.70
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.15 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.19 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 5.06 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 20 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 9.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.29 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 37 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 23, 1992 FDA PHARMACIA AND UPJOHN

FDA Adverse Event Reporting System (Female)

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
Mycobacterium avium complex infection 195.78 37.75 38 1489 2830 53344709
Uveitis 111.22 37.75 30 1497 9614 53337925
Drug resistance 105.87 37.75 34 1493 19928 53327611
Immune reconstitution inflammatory syndrome 83.87 37.75 22 1505 6324 53341215
Drug interaction 82.68 37.75 60 1467 219269 53128270
Drug reaction with eosinophilia and systemic symptoms 58.18 37.75 25 1502 32775 53314764
Iridocyclitis 56.52 37.75 13 1514 2169 53345370
Mycobacterial infection 53.95 37.75 12 1515 1723 53345816
Disseminated mycobacterium avium complex infection 43.60 37.75 6 1521 48 53347491
Tuberculosis of central nervous system 38.21 37.75 7 1520 378 53347161

FDA Adverse Event Reporting System (Male)

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
Immune reconstitution inflammatory syndrome 242.87 28.76 67 2223 9492 32501744
Mycobacterium avium complex infection 85.83 28.76 23 2267 2894 32508342
Mycobacterial infection 79.38 28.76 20 2270 1976 32509260
Drug interaction 71.66 28.76 82 2208 218103 32293133
Cytomegalovirus chorioretinitis 67.63 28.76 20 2270 3592 32507644
Atypical mycobacterial infection 67.45 28.76 15 2275 865 32510371
Drug resistance 65.34 28.76 32 2258 22933 32488303
Uveitis 64.25 28.76 22 2268 6328 32504908
Drug level decreased 48.76 28.76 18 2272 6428 32504808
Immune reconstitution inflammatory syndrome associated tuberculosis 46.45 28.76 10 2280 495 32510741
Disseminated tuberculosis 44.69 28.76 13 2277 2201 32509035
Tuberculosis 40.11 28.76 17 2273 8712 32502524
Intra-abdominal haemorrhage 40.05 28.76 12 2278 2251 32508985
Hyperuricaemia 34.58 28.76 15 2275 8126 32503110
Repetitive speech 34.21 28.76 6 2284 99 32511137
Thrombocytopenia 32.92 28.76 46 2244 148253 32362983
Hepatotoxicity 32.51 28.76 19 2271 19318 32491918
Neutropenia 31.40 28.76 44 2246 142131 32369105
Nephropathy toxic 29.10 28.76 15 2275 11931 32499305

Pharmacologic Action:

SourceCodeDescription
ATC A02BD16 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC J04AB04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Antibiotics
FDA CS M0019113 Rifamycins
FDA EPC N0000175501 Rifamycin Antimycobacterial
CHEBI has role CHEBI:33231 antitubercular
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000904 Antibiotics, Antitubercular
MeSH PA D000995 Antitubercular Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pulmonary Mycobacterium avium complex infection indication 186342000
Inactive tuberculosis off-label use 11999007
Acute tuberculosis off-label use 25629007
Tuberculosis of meninges off-label use 58437007
Pulmonary tuberculosis off-label use 154283005 DOID:2957
Acute nephropathy contraindication 58574008
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.13 acidic
pKa2 8.78 acidic
pKa3 12.55 acidic
pKa4 8.26 Basic
pKa5 2.95 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
250MG;EQ 10MG BASE;12.5MG TALICIA REDHILL N213004 Nov. 1, 2019 RX CAPSULE, DELAYED RELEASE ORAL 11135172 Feb. 12, 2034 TREATMENT OF H. PYLORI INFECTION IN ADULTS
250MG;EQ 10MG BASE;12.5MG TALICIA REDHILL N213004 Nov. 1, 2019 RX CAPSULE, DELAYED RELEASE ORAL 9050263 Feb. 12, 2034 TREATMENT OF H. PYLORI INFECTION IN ADULTS
250MG;EQ 10MG BASE;12.5MG TALICIA REDHILL N213004 Nov. 1, 2019 RX CAPSULE, DELAYED RELEASE ORAL 9498445 Feb. 12, 2034 TREATMENT OF H. PYLORI INFECTION IN ADULTS
250MG;EQ 10MG BASE;12.5MG TALICIA REDHILL N213004 Nov. 1, 2019 RX CAPSULE, DELAYED RELEASE ORAL 9603806 Feb. 12, 2034 TREATMENT OF H. PYLORI INFECTION IN ADULTS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Bacterial DNA-directed RNA polymerase Enzyme INHIBITOR CHEMBL CHEMBL
DNA-directed RNA polymerase subunit beta Enzyme Ki 8 WOMBAT-PK

External reference:

IDSource
4020770 VUID
N0000148321 NUI
D00424 KEGG_DRUG
4020770 VANDF
C0140575 UMLSCUI
CHEBI:45367 CHEBI
RBT PDB_CHEM_ID
CHEMBL444633 ChEMBL_ID
D017828 MESH_DESCRIPTOR_UI
DB00615 DRUGBANK_ID
5668 INN_ID
1W306TDA6S UNII
135398743 PUBCHEM_CID
227450 RXNORM
132500 MMSL
1985 MMSL
5423 MMSL
d01097 MMSL
004117 NDDF
108684009 SNOMEDCT_US
386893001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mycobutin HUMAN PRESCRIPTION DRUG LABEL 1 0013-5301 CAPSULE 150 mg ORAL NDA 26 sections
Mycobutin HUMAN PRESCRIPTION DRUG LABEL 1 54868-2841 CAPSULE 150 mg ORAL NDA 23 sections
Mycobutin HUMAN PRESCRIPTION DRUG LABEL 1 55695-010 CAPSULE 150 mg ORAL NDA 27 sections
Talicia HUMAN PRESCRIPTION DRUG LABEL 3 57841-1150 CAPSULE, DELAYED RELEASE 12.50 mg ORAL NDA 32 sections
Rifabutin HUMAN PRESCRIPTION DRUG LABEL 1 59762-1350 CAPSULE 150 mg ORAL NDA 26 sections
rifabutin HUMAN PRESCRIPTION DRUG LABEL 1 68180-285 CAPSULE 150 mg ORAL ANDA 22 sections
Rifabutin Human Prescription Drug Label 1 70954-041 CAPSULE 150 mg ORAL ANDA 21 sections