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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H20N2O2
Molecular Weight 236.3101
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVODROPROPIZINE

SMILES

OC[C@@H](O)CN1CCN(CC1)C2=CC=CC=C2

InChI

InChIKey=PTVWPYVOOKLBCG-ZDUSSCGKSA-N
InChI=1S/C13H20N2O2/c16-11-13(17)10-14-6-8-15(9-7-14)12-4-2-1-3-5-12/h1-5,13,16-17H,6-11H2/t13-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.rlsnet.ru/mnn_index_id_2804.htm | https://www.drugs.com/international/levodropropizine.html | https://www.ncbi.nlm.nih.gov/pubmed/26097707 | https://www.ncbi.nlm.nih.gov/pubmed/1611233

Levodropropizine is a non-opioid cough suppressant whose peripheral antitussive action may result from its modulation of sensory neuropeptide levels within the respiratory tract. Levodropropizine exerts its antitussive effect through an inhibitory action at the level of the airway sensory nerves and it has been shown to be able to inhibit in vitro the release of neuropeptides from C-fibers. Levodropropizine is an effective antitussive drug both in children and adults, showing statistically significant better outcomes vs. central antitussive drugs in terms of overall efficacy in reducing cough intensity, frequency and night awakenings. After oral administration, Levodropropizine is absorbed from the intestine, undergoes the first-pass metabolism and reaches peak plasma concentrations approximately 90 to 120 minutes after administration. Levocloperastine undergoes extensive biotransformation and is widely distributed throughout the body. Levocloperastine can cross the placental barrier (although to a moderate extent), but there is no evidence of accumulation, and is eliminated in the form of metabolites mainly in the faeces and to a lesser degree in the urine. The pharmacological effects of Levodropropizine were confirmed in large-scale clinical trials, non-blind or comparative. In the 10 trials reported here, oral Levodropropizine caused a rapid remission (after the first day of treatment) in cough symptoms (intensity and frequency of a daytime cough and disturbed night-time sleep) in all groups of patients. In children, the improved sleep quality resulted in a significant reduction in irritability and an overall improvement in their quality of life. Importantly, in adult patients with COPD, Levodropropizine reduced the frequency and intensity of dry unproductive cough without adversely influencing the beneficial effects of underlying treatment. In clinical trials, Levodropropizine was generally well tolerated, with mild and transient nausea the only adverse event reported. There was no evidence of central adverse events with Levodropropizine.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Levotuss

Approved Use

Indication: Dry non-productive cough with pharyngitis, laryngitis, acute tracheitis and tracheobronchitis, influenza, bronchopneumonia, chronic obstructive bronchitis, bronchial asthma, emphysema, lung tumor, allergic and infectious-inflammatory diseases of the respiratory tract (symptomatic treatment).
PubMed

PubMed

TitleDatePubMed
Sensitive spectrophotometric method for quantitation of guaifenesin and dropropizine in their dosage forms.
2010
An anaphylactic reaction caused by levodropropizine.
2010 Mar
Clinical expert guidelines for the management of cough in lung cancer: report of a UK task group on cough.
2010 Oct 6
Patents

Patents

Sample Use Guides

10 ml of syrup (60mg Levodropropizine) or 20 drops, preferably diluted in half a glass of water, 1-3 times a day at intervals of not less than 6 hours; Children from 2 to 12 years of age are given 1 mg / kg (syrup) 1-3 times a day until cessation ceases, but not more than a week
Route of Administration: Oral
In Vitro Use Guide
In the experiments the quasidiploid V79 Chinese hamster cells were used. Cells attached on petri dishes were exposed to Dropropizine (8000 ug/ml) Then the drug solutions were removed by aspiration, the cells were rinsed with PBS buffer and the numbers of cells in each treated group as well as in control groups were counted at 24-h intervals. Cytostatic effects lasting 24 h were observed.
Name Type Language
LEVODROPROPIZINE
EP   INN   MART.   WHO-DD  
INN  
Official Name English
(2S)-3-(4-PHENYL-1-PIPERAZINYL)-1,2-PROPANEDIOL
Systematic Name English
RAPITUX
Brand Name English
DANKA
Brand Name English
LEVODROPROPIZINE [MART.]
Common Name English
LEVODROPROPIZINE [EP MONOGRAPH]
Common Name English
1,2-PROPANEDIOL, 3-(4-PHENYL-1-PIPERAZINYL)-, (S)-
Systematic Name English
DROPROPIZINE, (S)-
Common Name English
LEVOPRONT
Brand Name English
(-)-(S)-3-(4-PHENYL-1-PIPERAZINYL)-1,2-PROPANEDIOL
Systematic Name English
Levodropropizine [WHO-DD]
Common Name English
1,2-PROPANEDIOL, 3-(4-PHENYL-1-PIPERAZINYL)-, (2S)-
Systematic Name English
LEVOTUSS
Brand Name English
(-)-DROPROPIZINE
Common Name English
LVDP
Common Name English
L-DROPROPIZINE
Common Name English
levodropropizine [INN]
Common Name English
DROPROPIZINE S-FORM [MI]
Common Name English
(S)-(-)-DROPROPIZINE
Common Name English
DIPROPIZINE, (S)-ISOMER
Common Name English
Classification Tree Code System Code
WHO-VATC QR05DB27
Created by admin on Fri Dec 15 16:15:13 GMT 2023 , Edited by admin on Fri Dec 15 16:15:13 GMT 2023
WHO-ATC R05DB27
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NCI_THESAURUS C66917
Created by admin on Fri Dec 15 16:15:13 GMT 2023 , Edited by admin on Fri Dec 15 16:15:13 GMT 2023
Code System Code Type Description
CAS
99291-25-5
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PRIMARY
RXCUI
52014
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PRIMARY RxNorm
ChEMBL
CHEMBL1288810
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PRIMARY
EVMPD
SUB12105MIG
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PRIMARY
DRUG BANK
DB12472
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PRIMARY
MERCK INDEX
m4770
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PRIMARY Merck Index
PUBCHEM
65859
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SMS_ID
100000092264
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PRIMARY
NCI_THESAURUS
C81593
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PRIMARY
MESH
C035916
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PRIMARY
FDA UNII
3O31P6T4G3
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PRIMARY
EPA CompTox
DTXSID8023210
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PRIMARY
CHEBI
82722
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PRIMARY
INN
6200
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PRIMARY
WIKIPEDIA
LEVODROPROPIZINE
Created by admin on Fri Dec 15 16:15:13 GMT 2023 , Edited by admin on Fri Dec 15 16:15:13 GMT 2023
PRIMARY
DRUG CENTRAL
1568
Created by admin on Fri Dec 15 16:15:13 GMT 2023 , Edited by admin on Fri Dec 15 16:15:13 GMT 2023
PRIMARY