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Details

Stereochemistry RACEMIC
Molecular Formula C18H29NO3
Molecular Weight 307.4278
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTAMIRATE

SMILES

CCC(C(=O)OCCOCCN(CC)CC)C1=CC=CC=C1

InChI

InChIKey=DDVUMDPCZWBYRA-UHFFFAOYSA-N
InChI=1S/C18H29NO3/c1-4-17(16-10-8-7-9-11-16)18(20)22-15-14-21-13-12-19(5-2)6-3/h7-11,17H,4-6,12-15H2,1-3H3

HIDE SMILES / InChI
Molecular Formula C18H29NO3
Molecular Weight 307.4278
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Butamirate (or brospamin) is a medicine used for the symptomatic treatment of non-productive (dry) cough. Butamirate is centrally acting cough suppressant which is neither chemically nor pharmacologically related to opium alkaloids. In addition to its antitussive effect, Butamirate also decreases the airway resistance. Butamirate is rapidly and completely absorbed after oral administration. Maximum concentration is reached within 9 hours with sustain release tablet. Butamirate is extremely protein bound and Plasma elimination half-life is about 13 hours. Butamirate is indicated in acute cough of any etiology, pre and post operative cough sedation for surgical procedure and bronchoscopy. Butamirate is well tolerated. In rare cases, skin rash, nausea, diarrhea, dizziness have been reported.They disappear after reduction of the dosage or discontinuation of the drug.

CNS Activity

Originator

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Butagan

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
932.421 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24995954/
22.5 mg 0 times / UNKNOWN single, oral
dose: 22.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PHENYLBUTYRIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2624.067 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24995954/
67.5 mg 4 times / UNKNOWN single, oral
dose: 67.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PHENYLBUTYRIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.77 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9089001/
45 mg single, oral
dose: 45 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PHENYLBUTYRIC ACID plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
14728.949 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24995954/
22.5 mg 0 times / UNKNOWN single, oral
dose: 22.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PHENYLBUTYRIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
39843.405 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24995954/
67.5 mg 4 times / UNKNOWN single, oral
dose: 67.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PHENYLBUTYRIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
49.6 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9089001/
45 mg single, oral
dose: 45 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PHENYLBUTYRIC ACID plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
28 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9089001/
45 mg single, oral
dose: 45 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
2-PHENYLBUTYRIC ACID plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
90 mg single, oral
Highest studied dose
Dose: 90 mg
Route: oral
Route: single
Dose: 90 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/24995954/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/24995954/
Other AEs: Nausea, Gastrointestinal discomfort...
Other AEs:
Nausea
Gastrointestinal discomfort
Sources:
https://pubmed.ncbi.nlm.nih.gov/24995954/
7.5 mg single, oral
Recommended
Dose: 7.5 mg
Route: oral
Route: single
Dose: 7.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23283272/
unhealthy, CHILD
Health Status: unhealthy
Age Group: CHILD
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/23283272/
Disc. AE: Cervical dystonia...
AEs leading to
discontinuation/dose reduction:
Cervical dystonia
Sources:
https://pubmed.ncbi.nlm.nih.gov/23283272/
AEs

AEs

AESignificanceDosePopulation
Gastrointestinal discomfort
90 mg single, oral
Highest studied dose
Dose: 90 mg
Route: oral
Route: single
Dose: 90 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/24995954/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/24995954/
Nausea
90 mg single, oral
Highest studied dose
Dose: 90 mg
Route: oral
Route: single
Dose: 90 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/24995954/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/24995954/
Cervical dystonia Disc. AE
7.5 mg single, oral
Recommended
Dose: 7.5 mg
Route: oral
Route: single
Dose: 7.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23283272/
unhealthy, CHILD
Health Status: unhealthy
Age Group: CHILD
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/23283272/
PubMed

PubMed

TitleDatePubMed
[The use and safety of butamirate containing drops, syrup and depot tablets in Hungary].
2005-03-27
Determination of butamyrate citrate in cough preparations by derivative UV spectrophotometry and high performance liquid chromatography.
2003-04
Patents

Patents

DE1151515
2

Sample Use Guides

In Vivo Use Guide
15 ml up to 4 times daily
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:45:13 GMT 2025
Edited
by admin
on Wed Apr 02 08:45:13 GMT 2025
Record UNII
M75MZG2236
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTAMIRATE
INN   MI   WHO-DD  
INN  
Official Name English
CODIMIN
Preferred Name English
BUTAMIRATE [MI]
Common Name English
BENZENEACETIC ACID, .ALPHA.-ETHYL-2-(2-(DIETHYLAMINO)ETHOXY)ETHYL ESTER
Common Name English
butamirate [INN]
Common Name English
2-(2-(DIETHYLAMINO)ETHOXY)ETHYL 2-PHENYLBUTYRATE
Systematic Name English
Butamirate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66917
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
WHO-VATC QR05DB13
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
WHO-ATC R05DB13
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
Code System Code Type Description
EVMPD
SUB06000MIG
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
RXCUI
19862
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID7048403
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
WIKIPEDIA
BUTAMIRATE
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
PUBCHEM
28892
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
ChEMBL
CHEMBL1332546
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
NCI_THESAURUS
C81596
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
MESH
C006841
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
DRUG BANK
DB13731
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
MERCK INDEX
m2786
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
242-005-2
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
DRUG CENTRAL
442
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
INN
2704
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
SMS_ID
100000088476
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
CAS
18109-80-3
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
FDA UNII
M75MZG2236
Created by admin on Wed Apr 02 08:45:13 GMT 2025 , Edited by admin on Wed Apr 02 08:45:13 GMT 2025
PRIMARY
Related Record Type Details
Structure of BUTAMIRATE CITRATE
SALT/SOLVATE -> PARENT
Structure of BUTAMIRATE, (S)-
ENANTIOMER -> RACEMATE
Structure of BUTAMIRATE, (R)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of BUTAMIRATE
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