PROXYPHYLLINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H14N4O3
Molecular Weight	238.2432
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=KYHQZNGJUGFTGR-UHFFFAOYSA-N

InChI=1S/C10H14N4O3/c1-6(15)4-14-5-11-8-7(14)9(16)13(3)10(17)12(8)2/h5-6,15H,4H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C10H14N4O3
Molecular Weight	238.2432
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6291318
Curator's Comment: description was created based on several sources, including http://www.ndrugs.com/?s=ephedrine/proxyphylline

Proxyphylline is a xanthine derivative that acts as a cardiac stimulant, vasodilator and bronchodilator. In combination with ephedrine it’s used for relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema. Proxyphylline is readily absorbed from the gastrointestinal tract and it’s not converted to theophylline in the body. The clinical studies are agreed with the property of proxyphylline to inhibit the cyclic nucleotide phosphodiesterases.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
3',5'-cyclic phosphodiesterase 5 Target ID: CHEMBL2363066 Sources: http://www.ncbi.nlm.nih.gov/pubmed/6291318	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Obstructive airways disease 1 Sources: http://www.ndrugs.com/?s=proxyphylline/theophylline/dyphylline	Secondary	Approved 8583	Novofilin Approved Use Unknown
Asthma 244 Sources: http://www.ndrugs.com/?s=ephedrine/proxyphylline	Secondary	Approved 8583	Unknown Approved Use Unknown
Bronchial disorders 1 Sources: http://www.ndrugs.com/?s=ephedrine/proxyphylline	Secondary	Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
6.87 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6630383/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: DYPHYLLINE	DYPHYLLINE	PROXYPHYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.946 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/730155_2229112F1033_1_011_1F.pdf#page=17	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: EPHEDRINE HYDROCHLORIDE	EPHEDRINE HYDROCHLORIDE	PROXYPHYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.588 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/730155_2229112F1033_1_011_1F.pdf#page=18	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: EPHEDRINE HYDROCHLORIDE	EPHEDRINE HYDROCHLORIDE	PROXYPHYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
59.57 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/730155_2229112F1033_1_011_1F.pdf#page=17	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: EPHEDRINE HYDROCHLORIDE	EPHEDRINE HYDROCHLORIDE	PROXYPHYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
46.38 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/730155_2229112F1033_1_011_1F.pdf#page=18	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: EPHEDRINE HYDROCHLORIDE	EPHEDRINE HYDROCHLORIDE	PROXYPHYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.69 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6630383/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: DYPHYLLINE	DYPHYLLINE	PROXYPHYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/530169_2115008F1038_1_005_1F.pdf#page=18			PROXYPHYLLINE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka_plain.cgi?n=34095	unhealthy, UNKNOWN Health Status: unhealthy Age Group: UNKNOWN Sex: M+F Food Status: UNKNOWN Sources: https://www.rad-ar.or.jp/siori/english/kekka_plain.cgi?n=34095	Sources: https://www.rad-ar.or.jp/siori/english/kekka_plain.cgi?n=34095

PubMed

Title	Date	PubMed
Synthesis, pharmacological activity and nitric oxide generation by nitrate derivatives of theophylline.	2008-05	18416941
Modifying the release of proxyphylline from PVA hydrogels using surface crosslinking.	2008-02-12	17875374
Surface crosslinking for delayed release of proxyphylline from PHEMA hydrogels.	2008-02-12	17825507
Hydrophilic molecularly imprinted poly(hydroxyethyl-methacrylate) polymers.	2006-07	16602126
The role of the discriminant factor in the assessment and treatment of alcoholic hepatitis.	2004-04-22	15100527
Minimization of initial burst in poly(vinyl alcohol) hydrogels by surface extraction and surface-preferential crosslinking.	2002-11-06	12429472
Polymer particle erosion controlling drug release. II. Swelling investigations to clarify the release mechanism.	2002-10-24	12429482
Kinetic-spectrophotometric determination of theophylline, dyphylline, and proxyphylline by use of partial least-squares regression.	2002-09	12207237
Application of micellar electrokinetic chromatography to the quality control of a pharmaceutical preparation containing three bronchodilators.	2002-02	11870768
Antianaphylactic and antiasthmatic properties of new piperazinyl 7-(beta-hydroxypropyl)-theophylline derivatives in guinea pigs.	2002-01-15	11787952
Multi-component kinetic-spectrophotometric analysis. Selection of wavelength and time ranges.	2001-07	11478649
[Effectiveness of proxyphylline in chronic obstructive pulmonary disease (author's transl)].	1980-06-20	7408664

Patents

Sample Use Guides

In Vivo Use Guide

intravenous: 29 mumol/kgsingle oral: 21 mumol/kg and multiple oral: 21 mumol/kg three times a day

Route of Administration: Other

In Vitro Use Guide

Inhibition of cAMP and cGMP hydrolysis in human lung tissue by proxyphylline and its main metabolite 1-methyl-7-(beta-hydroxypropyl)xanthine was compared with theophylline and its metabolite 3-methylxanthine. The Inhibition constant of proxyphylline was 0.06-0.7 mmol/l at low cAMP concentrations and at low and high cGMP concentrations, while it was 1.0 mmol/l at high cAMP concentrations

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:20 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:20 GMT 2025`
Record UNII	13G1DMN4P0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MONOPHYLLIN

Preferred Name

English

PROXYPHYLLINE

Official Name

English

SPASMOLYSIN

Brand Name

English

THEAN

Brand Name

English

7 BETA-HYDROXYPROPYL THEOPHYLLINE

Systematic Name

English

proxyphylline [INN]

Common Name

English

SIGOPHYL

Brand Name

English

1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-7-(2-HYDROXYPROPYL)-1,3-DIMETHYL-

Systematic Name

English

7-.BETA.-HYDROXYPROPYL THEOPHYLLINE

Systematic Name

English

THEODEN

Brand Name

English

SPANTIN

Brand Name

English

PROXYPHYLLINE [JAN]

Common Name

English

DIPROPHYLLINE IMPURITY D [EP IMPURITY]

Common Name

English

(±)-PROXYPHYLLIN

Common Name

English

R03DA03

Code

English

Proxyphylline [WHO-DD]

Common Name

English

PUROPHYLLIN

Common Name

English

PROXYPHYLLINE [EP MONOGRAPH]

Common Name

English

7-(2-HYDROXYPROPYL)THEOPHYLLINE

Systematic Name

English

OXYPROPYLTHEOPHYLLINE

Common Name

English

PROXYPHYLLINE [MART.]

Common Name

English

NSC-163343

Code

English

.BETA.-HYDROXYPROPYLTHEOPHYLLINE

Systematic Name

English

BRONTYL

Brand Name

English

PROXYPHYLLINE [MI]

Common Name

English

1,3-DIMETHYL-7-(2-HYDROXYPROPYL)XANTHINE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

R03DA03