U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry UNKNOWN
Molecular Formula C18H21NO5.ClH
Molecular Weight 367.824
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROTOKYLOL HYDROCHLORIDE

SMILES

Cl.CC(CC1=CC2=C(OCO2)C=C1)NCC(O)C3=CC(O)=C(O)C=C3

InChI

InChIKey=LOVXREQUMZKFCM-UHFFFAOYSA-N
InChI=1S/C18H21NO5.ClH/c1-11(6-12-2-5-17-18(7-12)24-10-23-17)19-9-16(22)13-3-4-14(20)15(21)8-13;/h2-5,7-8,11,16,19-22H,6,9-10H2,1H3;1H

HIDE SMILES / InChI

Description

Protokylol, a sympathomimetic drug has been utilized in general clinical practice as a bronchodilator. Protokylol (brand names Caytine, Ventaire) is a β-adrenergic receptor agonist which was used as a bronchodilator in Europe and the United States.

CNS Activity

CNS Non-penetrant
1014
Curator's Comment: Only small quantities of Protokylol pass the blood-brain barrier in rats.

Originator

Approval Year

1959
138
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
VENTAIRE

Approved Use

Respiratory-system disorders
Doses

Doses

DosePopulationAdverse events​
4 g 4 times / day multiple, oral (max)
Recommended
Dose: 4 g, 4 times / day
Route: oral
Route: multiple
Dose: 4 g, 4 times / day
Sources:
https://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDFhttps://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDF
Page: p.258
unhealthy
Health Status: unhealthy
Condition: Bronchial asthma
Sources:
https://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDFhttps://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDF
Page: p.258
Sources:
https://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDFhttps://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDF
Page: p.258
0.5 mg single, intramuscular|subcutaneous (max)
Recommended
Dose: 0.5 mg
Route: intramuscular|subcutaneous
Route: single
Dose: 0.5 mg
Sources:
https://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDFhttps://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDF
Page: p.258
unhealthy
Health Status: unhealthy
Condition: Acute bronchial asthma
Sources:
https://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDFhttps://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDF
Page: p.258
Sources:
https://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDFhttps://academic.oup.com/ajhp/article-abstract/17/4/255/5237544?redirectedFrom=PDF
Page: p.258
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
BSEP
402
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BSEP
403
 weak [IC50 >982.3 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY519699
https://www.001chemical.com/chem/136-70-9
AAA Chemistry
AR-1H9707
ABI Chem
AC1L1JBR
ABI Chem
AC1Q6ZXQ
Alfa Chemistry
136-70-9
https://www.alfa-chemistry.com/cas_136-70-9.htm
BOC Sciences
136-69-6
BOC Sciences
136-70-9
Chemieliva Pharmaceutical Co., Ltd
PBCM1167716
Molcore
MC519699
https://www.molcore.com/product/136-70-9
MuseChem
M067007
NCI Plated 2007
113490
NovoSeek
4969
Sigma Aldrich
PH013892
Sigma Aldrich
PH013892|ALDRICH
Smolecule
S540450
http://www.smolecule.com/products/s540450
THE BioTek
bt-280923
https://www.thebiotek.com/product/inhibitors/bt-280923
ZINC
ZINC000000000677
http://zinc15.docking.org/substances/ZINC000000000677
ZINC
ZINC000001704226
http://zinc15.docking.org/substances/ZINC000001704226
ZINC
ZINC000001704227
http://zinc15.docking.org/substances/ZINC000001704227
ZINC
ZINC000001704228
http://zinc15.docking.org/substances/ZINC000001704228
eMolecules
110046186
eMolecules
300976303
PubMed

PubMed

TitleDatePubMed
The resolution of dopamine and beta 1- and beta 2-adrenergic-sensitive adenylate cyclase activities in homogenates of cat cerebellum, hippocampus and cerebral cortex.
1979 Dec 28
N-Aralkyl substitution increases the affinity of adrenergic drugs for the alpha-adrenoceptor in rat liver.
1979 Jan
Patents

Patents

JP2002541233A
400

Sample Use Guides

In Vivo Use Guide
0.2-0.6 ml, aerosol
Route of Administration: Respiratory
In Vitro Use Guide
Protokylol dose-dependently (10(-6) - 10(-4) mM) induced guinea-pig trachea relaxation.
Name Type Language
PROTOKYLOL HYDROCHLORIDE
GREEN BOOK   MART.   MI   ORANGE BOOK   WHO-DD  
Common Name English
PROTOKYLOL HYDROCHLORIDE [MI]
Common Name English
PROTOKYLOL HYDROCHLORIDE [GREEN BOOK]
Common Name English
.ALPHA.-(((.ALPHA.-METHYL-3,4-METHYLENEDIOXYPHENETHYL)AMINO)METHYL)PROTOCATECHUYL ALCOHOL, HYDROCHLORIDE
Common Name English
PROTOKYLOL HYDROCHLORIDE [MART.]
Common Name English
NSC-113490
Code English
PROTOKYLOL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
PROTOKYLOL HCL
Common Name English
Protokylol hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL1201273
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-254-8
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
DRUG BANK
DBSALT001481
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
NCI_THESAURUS
C66496
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID30929210
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
CAS
136-69-6
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
MESH
C010312
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
PUBCHEM
8699
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
WIKIPEDIA
Protokylol hydrochloride
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
NSC
113490
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
FDA UNII
7U7O8Q48IO
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
SMS_ID
100000085135
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
EVMPD
SUB04113MIG
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY
MERCK INDEX
m9274
Created by admin on Fri Dec 15 15:17:23 GMT 2023 , Edited by admin on Fri Dec 15 15:17:23 GMT 2023
PRIMARY Merck Index
ACTIVE MOIETY
Structure of PROTOKYLOL
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966