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

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H22N2S
Molecular Weight 322.4689
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEQUITAZINE, (R)-

SMILES

c1ccc2c(c1)N(C[C@@]3([H])CN4CCC3CC4)c5ccccc5S2

InChI

InChIKey=HOKDBMAJZXIPGC-MRXNPFEDSA-N
InChI=1S/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2/t16-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H22N2S
Molecular Weight 322.4689
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

(R)-Mequitazine or V0162 (10-[(3R)-1-azabicyclo[2.2.2]oct-3-ylmethyl]-10H-phenothiazine) is an anticholinergic enantiomer of mequitazine, an existing oral racemic antihistamine commercialized for over 30 years. (R)-Mequitazine was found to be an antagonist at muscarinic acetylcholine receptors behaving as an inverse agonist. (R)-Mequitazine was investigated in clinical trials for the treatment of chronic obstructive pulmonary disease, asthma and urinary incontinence.

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
V0162 a new long-acting bronchodilator for treatment of chronic obstructive lung diseases: preclinical and clinical results.
2015 Jun 8
Characterization of V0162, a new long-acting antagonist at human M3 muscarinic acetylcholine receptors.
2015 Oct
Long acting muscarinic antagonists for the treatment of chronic obstructive pulmonary disease: a review of current and developing drugs.
2017 Feb
Patents

Sample Use Guides

(R)-Mequitazine (V0162) was given via inhalation route. In the healthy volunteers study, 88 subjects were enrolled: 66 received V0162 and 22 received placebo. No particular safety concerns were raised. The maximal tolerated dose was not reached and the dose escalation was stopped at 2400 μg. A total of 20 patients with chronic obstructive pulmonary disease were then enrolled. All patients received a single-dose of V0162 1600 μg and of placebo in two alternating periods.
Route of Administration: Other
(R)-Mequitazine (V0162) antagonized acetylcholine-mediated contractions in a human bronchial preparation; the pA2 values increased with the incubation time (up to 2 h). Moreover, there was a progressive increase in V0162's ability to inhibit electrically-induced contractions, which persisted after compound washout.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:45:48 UTC 2021
Edited
by admin
on Sat Jun 26 11:45:48 UTC 2021
Record UNII
05VP796JC6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEQUITAZINE, (R)-
Common Name English
V-0162
Code English
10-(((3R)-1-AZABICYCLO(2.2.2)OCTANE-3.ALPHA.-YL)METHYL)-10H-PHENOTHIAZINE
Systematic Name English
(+)-MEQUITAZINE
Common Name English
10H-PHENOTHIAZINE, 10-(1-AZABICYCLO(2.2.2)OCT-3-YLMETHYL)-, (R)-
Systematic Name English
10H-PHENOTHIAZINE, 10-((3R)-1-AZABICYCLO(2.2.2)OCT-3-YLMETHYL)-
Systematic Name English
J2.972.564K
Code English
(R)-MEQUITAZINE
Common Name English
Code System Code Type Description
FDA UNII
05VP796JC6
Created by admin on Sat Jun 26 11:45:48 UTC 2021 , Edited by admin on Sat Jun 26 11:45:48 UTC 2021
PRIMARY
CAS
147780-50-5
Created by admin on Sat Jun 26 11:45:48 UTC 2021 , Edited by admin on Sat Jun 26 11:45:48 UTC 2021
PRIMARY
PUBCHEM
3246605
Created by admin on Sat Jun 26 11:45:48 UTC 2021 , Edited by admin on Sat Jun 26 11:45:48 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER
TARGET -> INHIBITOR
S-ISOMER BINDS WITH LESS AVIDITY
IC50
Related Record Type Details
ACTIVE MOIETY