rifabutin ๐Ÿถ Veterinary Use | 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: 4.62
  • 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 ยตM/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
Uveitis 111.74 35.53 30 1445 9280 50594369
Mycobacterium avium complex infection 109.33 35.53 23 1452 2507 50601142
Drug resistance 106.94 35.53 34 1441 18955 50584694
Immune reconstitution inflammatory syndrome 86.54 35.53 22 1453 5494 50598155
Drug interaction 84.47 35.53 59 1416 199562 50404087
Drug reaction with eosinophilia and systemic symptoms 61.20 35.53 25 1450 28399 50575250
Iridocyclitis 57.10 35.53 13 1462 2036 50601613
Hypopyon 40.18 35.53 8 1467 661 50602988
Hepatitis cholestatic 38.74 35.53 12 1463 6105 50597544
Cryptococcosis 37.92 35.53 8 1467 880 50602769
Disseminated mycobacterium avium complex infection 36.83 35.53 5 1470 35 50603614
Anticoagulation drug level decreased 36.83 35.53 5 1470 35 50603614
Labelled drug-drug interaction medication error 36.13 35.53 13 1462 10464 50593185
Hepatotoxicity 35.98 35.53 17 1458 27209 50576440

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 259.29 29.52 69 2230 7733 29564495
Drug interaction 73.47 29.52 83 2216 197302 29374926
Cytomegalovirus chorioretinitis 67.84 29.52 20 2279 3218 29569010
Drug resistance 64.28 29.52 32 2267 21508 29550720
Uveitis 63.54 29.52 22 2277 5925 29566303
Drug level decreased 51.23 29.52 19 2280 6228 29566000
Mycobacterial infection 50.24 29.52 14 2285 1842 29570386
Immune reconstitution inflammatory syndrome associated tuberculosis 47.52 29.52 10 2289 401 29571827
Atypical mycobacterial infection 47.46 29.52 11 2288 690 29571538
Mycobacterium avium complex infection 43.11 29.52 13 2286 2256 29569972
Intra-abdominal haemorrhage 39.79 29.52 12 2287 2083 29570145
Hyperuricaemia 35.57 29.52 15 2284 6874 29565354
Repetitive speech 34.74 29.52 6 2293 81 29572147
Thrombocytopenia 31.31 29.52 45 2254 134778 29437450
Hepatotoxicity 29.56 29.52 18 2281 17849 29554379

FDA Adverse Event Reporting System (Geriatric)

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 314.05 28.90 82 3374 12388 64482888
Drug interaction 150.24 28.90 136 3320 361947 64133329
Uveitis 148.78 28.90 46 3410 12662 64482614
Drug resistance 146.66 28.90 59 3397 35043 64460233
Mycobacterium avium complex infection 124.02 28.90 31 3425 3909 64491367
Immune reconstitution inflammatory syndrome associated tuberculosis 79.38 28.90 16 3440 757 64494519
Iridocyclitis 71.61 28.90 19 3437 3026 64492250
Drug reaction with eosinophilia and systemic symptoms 65.38 28.90 39 3417 54178 64441098
Hepatotoxicity 56.81 28.90 32 3424 39930 64455346
Cytomegalovirus chorioretinitis 54.16 28.90 17 3439 4895 64490381
Thrombocytopenia 48.94 28.90 60 3396 223741 64271535
Acute hepatic failure 48.56 28.90 25 3431 26087 64469189
Pancytopenia 46.05 28.90 47 3409 143262 64352014
Mycobacterial infection 44.34 28.90 13 3443 2975 64492301
Leukopenia 43.52 28.90 39 3417 101203 64394073
Neutropenia 42.60 28.90 58 3398 239566 64255710
Transplant rejection 42.30 28.90 20 3436 17381 64477895
Corneal deposits 39.88 28.90 8 3448 369 64494907
Atypical mycobacterial infection 39.69 28.90 10 3446 1298 64493978
Hyperuricaemia 38.62 28.90 16 3440 10175 64485101
Hypopyon 36.92 28.90 9 3447 1020 64494256
Neuropathy peripheral 36.75 28.90 38 3418 117487 64377789
Intra-abdominal haemorrhage 32.47 28.90 11 3445 4020 64491256
Drug level decreased 30.36 28.90 14 3442 11489 64483787

FDA Adverse Event Reporting System (Pediatric)

None

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 agents
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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
12015 IUPHAR_LIGAND_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
Rifabutin HUMAN PRESCRIPTION DRUG LABEL 1 10135-738 CAPSULE 150 mg ORAL ANDA 21 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
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