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

Stem definition	Drug id	CAS RN
antibiotics, rifamycin derivatives	2376	72559-06-9

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.15	g	O

ADMET properties:

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

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Approvals:

Date	Agency	Company	Orphan
Dec. 23, 1992	FDA	PHARMACIA AND UPJOHN

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
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
CHEBI has role	CHEBI:33231	antitubercular agents
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

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.13	acidic
pKa2	8.78	acidic
pKa3	12.55	acidic
pKa4	8.26	Basic
pKa5	2.95	Basic

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Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent 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

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Bacterial DNA-directed RNA polymerase	Enzyme		RPOA_ECOLI RPOZ_ECOLI RPOC_ECOLI RPOB_ECOLI	INHIBITOR				CHEMBL	CHEMBL
DNA-directed RNA polymerase subunit beta	Enzyme		RPOB_MYCTU		Ki	8		WOMBAT-PK

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External reference:

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ID	Source
RBT	PDB_CHEM_ID
004117	NDDF
108684009	SNOMEDCT_US
12015	IUPHAR_LIGAND_ID
132500	MMSL
1985	MMSL
1W306TDA6S	UNII
227450	RXNORM
386893001	SNOMEDCT_US
4020770	VUID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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
Mycobutin	HUMAN PRESCRIPTION DRUG LABEL	1	70518-3731	CAPSULE	150 mg	ORAL	NDA	25 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
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

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