rifabutin 🐶 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 µM/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
Drug resistance 124.73 32.87 40 1812 22893 63464277
Mycobacterium avium complex infection 121.57 32.87 26 1826 3062 63484108
Uveitis 120.73 32.87 34 1818 12519 63474651
Drug interaction 90.47 32.87 65 1787 229066 63258104
Immune reconstitution inflammatory syndrome 89.20 32.87 23 1829 6061 63481109
Drug reaction with eosinophilia and systemic symptoms 66.85 32.87 28 1824 33808 63453362
Iridocyclitis 54.39 32.87 13 1839 2509 63484661
Hepatotoxicity 45.50 32.87 22 1830 37019 63450151
Hypopyon 45.44 32.87 9 1843 723 63486447
Disseminated mycobacterium avium complex infection 45.40 32.87 7 1845 128 63487042
Pathogen resistance 42.40 32.87 13 1839 6385 63480785
Hepatitis cholestatic 37.33 32.87 12 1840 6866 63480304
Deafness 35.90 32.87 15 1837 17942 63469228
Anticoagulation drug level decreased 35.81 32.87 5 1847 44 63487126
Cryptococcosis 35.80 32.87 8 1844 1149 63486021
Labelled drug-drug interaction medication error 32.99 32.87 13 1839 13386 63473784

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 260.37 27.02 70 2479 8689 34945693
Drug resistance 90.44 27.02 42 2507 25885 34928497
Drug interaction 83.85 27.02 92 2457 225854 34728528
Uveitis 82.77 27.02 28 2521 7507 34946875
Cytomegalovirus chorioretinitis 67.06 27.02 20 2529 3569 34950813
Drug level decreased 66.36 27.02 24 2525 7822 34946560
Atypical mycobacterial infection 50.69 27.02 12 2537 881 34953501
Mycobacterial infection 47.71 27.02 14 2535 2360 34952022
Immune reconstitution inflammatory syndrome associated tuberculosis 47.07 27.02 10 2539 448 34953934
Mycobacterium avium complex infection 42.63 27.02 13 2536 2498 34951884
Intra-abdominal haemorrhage 38.92 27.02 12 2537 2392 34951990
Hyperuricaemia 37.53 27.02 16 2533 8027 34946355
Thrombocytopenia 35.64 27.02 50 2499 156197 34798185
Pancytopenia 35.47 27.02 39 2510 95118 34859264
Repetitive speech 34.92 27.02 6 2543 84 34954298
Hepatotoxicity 32.57 27.02 20 2529 21465 34932917
Nephropathy toxic 30.70 27.02 16 2533 12572 34941810

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 319.55 29.91 84 3957 13757 79726590
Uveitis 175.38 29.91 55 3986 16775 79723572
Drug resistance 169.90 29.91 68 3973 42145 79698202
Drug interaction 167.77 29.91 150 3891 415033 79325314
Mycobacterium avium complex infection 135.78 29.91 34 4007 4566 79735781
Immune reconstitution inflammatory syndrome associated tuberculosis 79.02 29.91 16 4025 820 79739527
Hepatotoxicity 69.35 29.91 39 4002 51313 79689034
Iridocyclitis 68.96 29.91 19 4022 3685 79736662
Drug reaction with eosinophilia and systemic symptoms 68.85 29.91 42 3999 64202 79676145
Hypopyon 62.92 29.91 14 4027 1128 79739219
Pancytopenia 60.84 29.91 57 3984 165688 79574659
Drug level decreased 53.72 29.91 22 4019 14380 79725967
Cytomegalovirus chorioretinitis 53.23 29.91 17 4024 5473 79734874
Neutropenia 51.65 29.91 68 3973 287642 79452705
Thrombocytopenia 51.21 29.91 65 3976 265194 79475153
Mycobacterial infection 46.71 29.91 14 4027 3654 79736693
Acute hepatic failure 46.50 29.91 25 4016 30088 79710259
Leukopenia 44.51 29.91 41 4000 116472 79623875
Atypical mycobacterial infection 42.17 29.91 11 4030 1732 79738615
Transplant rejection 41.25 29.91 20 4021 19417 79720930
Hyperuricaemia 40.54 29.91 17 4024 11782 79728565
Pathogen resistance 40.54 29.91 18 4023 14324 79726023
Disseminated mycobacterium avium complex infection 38.21 29.91 7 4034 210 79740137
Corneal deposits 38.11 29.91 8 4033 490 79739857
Neuropathy peripheral 37.85 29.91 41 4000 141264 79599083
Pyrexia 33.33 29.91 92 3949 678617 79061730
Intra-abdominal haemorrhage 31.79 29.91 11 4030 4529 79735818

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 | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 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
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
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 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 68180-285 CAPSULE 150 mg ORAL ANDA 22 sections
Mycobutin HUMAN PRESCRIPTION DRUG LABEL 1 70518-3731 CAPSULE 150 mg ORAL NDA 25 sections
Rifabutin Human Prescription Drug Label 1 70954-041 CAPSULE 150 mg ORAL ANDA 21 sections