BUTAMIRATE CITRATE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H29NO3.C6H8O7
Molecular Weight	499.5513
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=JVKMHUAWFDGPTF-UHFFFAOYSA-N

InChI=1S/C18H29NO3.C6H8O7/c1-4-17(16-10-8-7-9-11-16)18(20)22-15-14-21-13-12-19(5-2)6-3;7-3(8)1-6(13,5(11)12)2-4(9)10/h7-11,17H,4-6,12-15H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

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	( + / - )

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/uk/butamirate-7-5mg-5ml-syrup-leaflet.html

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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24995954	Primary		Approved 8583	Butagan Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

Title	Date	PubMed
[The use and safety of butamirate containing drops, syrup and depot tablets in Hungary].	2005-03-27	15856625
Determination of butamyrate citrate in cough preparations by derivative UV spectrophotometry and high performance liquid chromatography.	2003-04	12725392

Patents

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 `Mon Mar 31 18:48:51 GMT 2025` Edited by `admin` on `Mon Mar 31 18:48:51 GMT 2025`
Record UNII	67HP51L98R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ABBOTT 36581

Preferred Name

English

BUTAMIRATE CITRATE

Official Name

English

BUTAMIRATE CITRATE [MI]

Common Name

English

HH-197

Code

English

Butamirate citrate [WHO-DD]

Common Name

English

ABBOTT-36581

Code

English

BUTAMIRATE CITRATE [MART.]

Common Name

English

HH 197

Code

English

BENZENEACETIC ACID, .ALPHA.-ETHYL-2-(2-(DIETHYLAMINO)ETHOXY)ETHYL ESTER, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)

Common Name

English

BUTAMIRATE CITRATE [USAN]

Common Name

English

2-[2-(Diethylamino)ethoxy]ethyl 2-phenylbutyrate citrate (1:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66917