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

Stem definition	Drug id	CAS RN
endothelin receptor antagonists	392	147536-97-8

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: bosentan hydrate bosentan monohydrate stayveer bosentan actelion tracleer bosentan anhydrous	a specific and competitive antagonist at endothelin receptor types ETA and ETB, has a slightly higher affinity for ETA receptors than for ETB receptors, indicated for the treatment of pulmonary arterial hypertension Molecular weight: 551.62 Formula: C27H29N5O6S CLOGP: 3.87 LIPINSKI: 2 HAC: 11 HDO: 2 TPSA: 145.65 ALOGS: -4.79 ROTB: 10 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

bosentan hydrate
bosentan monohydrate
stayveer
bosentan
actelion
tracleer
bosentan anhydrous

a specific and competitive antagonist at endothelin receptor types ETA and ETB, has a slightly higher affinity for ETA receptors than for ETB receptors, indicated for the treatment of pulmonary arterial hypertension

Molecular weight: 551.62
Formula: C27H29N5O6S
CLOGP: 3.87
LIPINSKI: 2
HAC: 11
HDO: 2
TPSA: 145.65
ALOGS: -4.79
ROTB: 10

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.25	g	O

ADMET properties:

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Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	6.47 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	50 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	4.10 hours	Lombardo F, Berellini G, Obach RS
CL (Clearance)	2.10 mL/min/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	2 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	0.29 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.04 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.00 mg/mL	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
May 14, 2002	EMA	Janssen-Cilag International N.V.
Nov. 20, 2001	FDA	ACTELION PHARMS LTD

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
Death	2159.01	14.10	2474	76128	371907	63038513
Dyspnoea	1459.58	14.10	2778	75824	658535	62751885
Right ventricular failure	1324.01	14.10	569	78033	16619	63393801
Aspartate aminotransferase increased	931.15	14.10	821	77781	89456	63320964
Alanine aminotransferase increased	811.07	14.10	809	77793	102961	63307459
Fluid retention	759.70	14.10	613	77989	59073	63351347
Blood alkaline phosphatase increased	641.32	14.10	485	78117	42482	63367938
Liver function test abnormal	615.43	14.10	496	78106	47685	63362735
Drug ineffective	582.40	14.10	286	78316	1044479	62365941
Pulmonary hypertension	569.44	14.10	426	78176	36697	63373723

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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
Death	702.94	17.33	1137	24862	396912	34534020
Right ventricular failure	571.69	17.33	223	25776	8561	34922371
Fluid retention	415.21	17.33	255	25744	26632	34904300
Dyspnoea	386.59	17.33	856	25143	375926	34555006
Pulmonary hypertension	254.89	17.33	171	25828	20753	34910179
Aspartate aminotransferase increased	246.35	17.33	277	25722	67506	34863426
Lung transplant	231.54	17.33	78	25921	1946	34928986
Alanine aminotransferase increased	198.10	17.33	271	25728	80544	34850388
Catheterisation cardiac	177.72	17.33	69	25930	2608	34928324
Liver function test abnormal	169.18	17.33	158	25841	30916	34900016

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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
Death	2484.91	13.14	3216	92883	563298	79084991
Right ventricular failure	1669.85	13.14	729	95370	22768	79625521
Dyspnoea	1653.20	13.14	3350	92749	853675	78794614
Fluid retention	1168.49	13.14	835	95264	68974	79579315
Aspartate aminotransferase increased	958.22	13.14	999	95100	137642	79510647
Alanine aminotransferase increased	795.20	13.14	979	95120	161591	79486698
Pulmonary hypertension	751.49	13.14	552	95547	47528	79600761
Liver function test abnormal	660.90	13.14	578	95521	63897	79584392
Blood alkaline phosphatase increased	655.13	13.14	572	95527	63092	79585197
Transfusion	546.17	13.14	333	95766	20997	79627292

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	C02KX01	CARDIOVASCULAR SYSTEM ANTIHYPERTENSIVES OTHER ANTIHYPERTENSIVES Antihypertensives for pulmonary arterial hypertension
CHEBI has role	CHEBI:35674	antihypertensive drugs
CHEBI has role	CHEBI:51451	ERA
FDA EPC	N0000175581	Endothelin Receptor Antagonist
FDA MoA	N0000175364	Endothelin Receptor Antagonists
FDA MoA	N0000185507	Cytochrome P450 2C9 Inducers
FDA MoA	N0000190118	Cytochrome P450 3A Inducers
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D065128	Endothelin Receptor Antagonists

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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 arterial hypertension	indication	11399002
Pulmonary hypertension	indication	70995007	DOID:6432
Systemic sclerosis	indication	89155008	DOID:418
Hyperbilirubinemia	contraindication	14783006	DOID:2741
Pulmonary edema	contraindication	19242006	DOID:11396
Hepatic failure	contraindication	59927004
Pulmonary veno-occlusive disease	contraindication	89420002	DOID:5453
Liver function tests abnormal	contraindication	166603001
Decompensated cardiac failure	contraindication	195111005
Disease of liver	contraindication	235856003	DOID:409

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.84	acidic
pKa2	2.87	Basic
pKa3	1.44	Basic

Orange Book patent data (new drug applications)

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
125MG	TRACLEER	ACTELION	N021290	Nov. 20, 2001	RX	TABLET	ORAL	Sept. 5, 2024	FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S)
32MG	TRACLEER	ACTELION	N209279	Sept. 5, 2017	RX	TABLET, FOR SUSPENSION	ORAL	Sept. 5, 2024	TREATMENT OF PULMONARY ARTERIAL HYPERTENSION (PAH) (WHO GROUP 1) IN PEDIATRIC PATIENTS AGED 3 YRS AND OLDER WITH IDIOPATHIC OR CONGENITAL PAH TO IMPROVE PULMONARY VASCULAR RESISTANCE (PVR), WHICH IS EXPECTED TO RESULT IN AN IMPROVEMENT IN EXERCISE ABILITY
62.5MG	TRACLEER	ACTELION	N021290	Nov. 20, 2001	RX	TABLET	ORAL	Sept. 5, 2024	FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S)

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Endothelin-1 receptor	GPCR	P25101	EDNRA_HUMAN	ANTAGONIST	Ki	8.19	CHEMBL	CHEMBL
Endothelin B receptor	GPCR	P24530	EDNRB_HUMAN	ANTAGONIST	Ki	7.10	CHEMBL	CHEMBL
Nuclear receptor subfamily 1 group I member 2	Nuclear hormone receptor	O75469	NR1I2_HUMAN				WOMBAT-PK
Bile salt export pump	Transporter	O95342	ABCBB_HUMAN		IC50	4.42	CHEMBL
Endothelin-1 receptor	GPCR		EDNRA_RAT		Ki	8.19	CHEMBL
Endothelin-1 receptor	GPCR		EDNRA_PIG		IC50	8.12	CHEMBL
Bile salt export pump	Transporter		ABCBB_RAT		IC50	4.51	CHEMBL
Endothelin B receptor	GPCR		EDNRB_RAT		IC50	7.02	CHEMBL

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External reference:

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ID	Source
009514	NDDF
104865	PUBCHEM_CID
1268952004	SNOMEDCT_US
1468845	RXNORM
157212-55-0	SECONDARY_CAS_RN
16217	MMSL
230939	MMSL
33033	MMSL
3494	IUPHAR_LIGAND_ID
385558007	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Bosentan	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0520	TABLET	62.50 mg	ORAL	ANDA	25 sections
Bosentan	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0521	TABLET	125 mg	ORAL	ANDA	25 sections
bosentan	HUMAN PRESCRIPTION DRUG LABEL	1	0591-2511	TABLET, FILM COATED	62.50 mg	ORAL	ANDA	27 sections
bosentan	HUMAN PRESCRIPTION DRUG LABEL	1	0591-2512	TABLET, FILM COATED	125 mg	ORAL	ANDA	27 sections
Bosentan	Human Prescription Drug Label	1	46708-383	TABLET, FILM COATED	62.50 mg	ORAL	ANDA	26 sections
Bosentan	Human Prescription Drug Label	1	46708-384	TABLET, FILM COATED	125 mg	ORAL	ANDA	26 sections
Bosentan	Human Prescription Drug Label	1	47335-038	TABLET, FILM COATED	62.50 mg	ORAL	ANDA	27 sections
Bosentan	Human Prescription Drug Label	1	47335-039	TABLET, FILM COATED	125 mg	ORAL	ANDA	27 sections
Bosentan	HUMAN PRESCRIPTION DRUG LABEL	1	47781-270	TABLET, FILM COATED	62.50 mg	ORAL	ANDA	27 sections
Bosentan	HUMAN PRESCRIPTION DRUG LABEL	1	47781-271	TABLET, FILM COATED	125 mg	ORAL	ANDA	27 sections

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