Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H22N2S |
| Molecular Weight | 322.467 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C([C@H]1CN2CCC1CC2)N3C4=C(SC5=C3C=CC=C5)C=CC=C4
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
| Molecular Formula | C20H22N2S |
| Molecular Weight | 322.467 |
| 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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 3.9 nM [Ki] | |||
Target ID: CHEMBL216 |
1.4 nM [Ki] | ||
Target ID: CHEMBL211 |
7.0 nM [Ki] | ||
Target ID: CHEMBL3759 |
1.18 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
Edited
Sat Dec 16 08:04:55 UTC 2023
by
admin
on
Sat Dec 16 08:04:55 UTC 2023
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| Record UNII |
05VP796JC6
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| Record Status |
Validated (UNII)
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RACEMATE -> ENANTIOMER | |||
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TARGET -> INHIBITOR |
S-ISOMER BINDS WITH LESS AVIDITY
IC50
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ACTIVE MOIETY |
