ISBUFYLLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H16N4O2
Molecular Weight	236.2703
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CN1C=NC2=C1C(=O)N(C)C(=O)N2C

InChI

InChIKey=WHUWQSQEVISUMC-UHFFFAOYSA-N

InChI=1S/C11H16N4O2/c1-7(2)5-15-6-12-9-8(15)10(16)14(4)11(17)13(9)3/h6-7H,5H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C11H16N4O2
Molecular Weight	236.2703
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1707621 | https://www.ncbi.nlm.nih.gov/pubmed/7511949 | https://www.ncbi.nlm.nih.gov/pubmed/7507057

Isbufylline is a xanthine derivative. This compound exhibits remarkable antibronchospastic properties both in in vitro and in vivo (after oral or intravenous administration) experimental models. Isbufylline is significantly more effective than theophylline in antagonizing bronchospasms elicited by spasmogens (capsaicin, arachidonic acid, PAF and antigen) which mainly act by a local release of biologically active substances proposed to be involved in the pathogenesis of asthma. Isbufylline, unlike theophylline, possesses little or no CNS excitatory properties. Isbufylline exerts a greater inhibitory activity than theophylline on total phosphodiesterase activity in the rat lung.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cyclic-nucleotide phosphodiesterase activity 3 Target ID: GO:0004112 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7507057	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: http://adisinsight.springer.com/drugs/800000109	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
2.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379919	12 mg/kg single, oral dose: 12 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ISBUFYLLINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.04 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379919	12 mg/kg single, intravenous dose: 12 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		ISBUFYLLINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
109.3 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379919	12 mg/kg single, oral dose: 12 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ISBUFYLLINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED
195.7 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379919	12 mg/kg single, intravenous dose: 12 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		ISBUFYLLINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
28.8 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379919	12 mg/kg single, oral dose: 12 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ISBUFYLLINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED
27.3 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379919	12 mg/kg single, intravenous dose: 12 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		ISBUFYLLINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
55% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379919	12 mg/kg single, oral dose: 12 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ISBUFYLLINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED
53% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379919	12 mg/kg single, intravenous dose: 12 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		ISBUFYLLINE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
AsisChem	R15612	https://asischem.com/catalogsearch/result/?q=R15612
BOC Sciences	90162-60-0	http://www.bocsci.com/description.asp?cas=90162-60-0
ChemBridge	6254600	http://www.hit2lead.com/screening-compounds/6254600
Chemspace	CSC046248903	https://chem-space.com/CSC046248903
Enamine	Z96531573	https://www.enaminestore.com/blog/real/Z96531573/
Frontier Scientific Services	100066361	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=100066361&type=hts
Frontier Scientific Services	600001700	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=600001700&type=hts
Lab Network	LN03090691	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN03090691
MolPort	MolPort-001-818-394	https://www.molport.com/shop/molecule-link/MolPort-001-818-394
Princeton BioMolecular Research	OSSL_391493	http://www.princetonbio.com/order_online?common_id=OSSL_391493
Vitas-M Laboratory	STK868787	http://www.vitasmlab.biz/search/STK868787
eMolecules	1065924	https://orderbb.emolecules.com/search/#?query=1065924
mcule	MCULE-3705552034	https://mcule.com/MCULE-3705552034/

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Guinea pigs: At a dose (106 umol/kg i.p.) providing complete protection against acetylcholine aerosol-induced dyspnea in the guinea pig, isbufylline inhibited platelet activating factor (PAF)- and antigen-induced eosinophil infiltration into bronchoalveolar lavage fluid 24 h after the challenge of normal and actively immunized guinea pigs, respectively. Isbufylline, 4.2 umol/kg-1 i.v., significantly inhibited PAF-induced bronchial hyper-responsiveness to i.v. histamine, without exerting evident bronchodilator activity.

Route of Administration: Other

In Vitro Use Guide

Isbufylline (10-90 uM) produced a concentration-dependent inhibition of the NANC response (EFS: 20 Hz, supramaximal voltage, 0.5 ms pulse, width for 10 s) of bronchi (IC50 = 47 uM) without affecting the cholinergic contractile response in tracheal smooth muscle (EFS: 0.5 up to 32 Hz, supramaximal voltage, 0.5 ms pulse, for 15 s every min).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:02:35 GMT 2023` Edited by `admin` on `Sat Dec 16 17:02:35 GMT 2023`
Record UNII	9C8Z5F38D0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISBUFYLLINE

Official Name

English

isbufylline [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744