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 179.46 35.08 35 1332 2613 46682082
Uveitis 113.84 35.08 30 1337 8611 46676084
Drug resistance 89.07 35.08 29 1338 17339 46667356
Drug interaction 67.49 35.08 52 1315 203042 46481653
Immune reconstitution inflammatory syndrome 66.46 35.08 18 1349 5707 46678988
Mycobacterial infection 54.40 35.08 12 1355 1621 46683074
Iridocyclitis 51.98 35.08 12 1355 1988 46682707
Drug reaction with eosinophilia and systemic symptoms 50.22 35.08 22 1345 29526 46655169
Hypopyon 38.61 35.08 8 1359 803 46683892
Tuberculosis of central nervous system 38.20 35.08 7 1360 370 46684325
Disseminated mycobacterium avium complex infection 36 35.08 5 1362 42 46684653

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 220.13 30.44 61 1990 9040 29941387
Mycobacterial infection 82.90 30.44 20 2031 1701 29948726
Mycobacterium avium complex infection 78.59 30.44 21 2030 2690 29947737
Cytomegalovirus chorioretinitis 70.18 30.44 20 2031 3248 29947179
Uveitis 64.01 30.44 21 2030 5456 29944971
Drug interaction 63.86 30.44 73 1978 199495 29750932
Atypical mycobacterial infection 52.79 30.44 12 2039 786 29949641
Drug resistance 43.23 30.44 23 2028 20110 29930317
Intra-abdominal haemorrhage 41.26 30.44 12 2039 2090 29948337
Drug level decreased 39.91 30.44 15 2036 5790 29944637
Immune reconstitution inflammatory syndrome associated tuberculosis 36.98 30.44 8 2043 417 29950010
Disseminated tuberculosis 36.87 30.44 11 2040 2091 29948336
Tuberculosis 35.11 30.44 15 2036 8062 29942365
Repetitive speech 34.73 30.44 6 2045 93 29950334
Hepatotoxicity 31.43 30.44 18 2033 18127 29932300

Pharmacologic Action:

SourceCodeDescription
ATC J04AB04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Antibiotics
FDA CS M0019113 Rifamycins
FDA EPC N0000175501 Rifamycin Antimycobacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000904 Antibiotics, Antitubercular
MeSH PA D000995 Antitubercular Agents
CHEBI has role CHEBI:33231 antitubercular

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)

None

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
DB00615 DRUGBANK_ID
135398743 PUBCHEM_CID
D017828 MESH_DESCRIPTOR_UI
5668 INN_ID
1W306TDA6S UNII
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