TIROPRAMIDE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C28H41N3O3
Molecular Weight	467.6434
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCN(CCC)C(=O)C(CC1=CC=C(OCCN(CC)CC)C=C1)NC(=O)C2=CC=CC=C2

InChI

InChIKey=FDBWMYOFXWMGEY-UHFFFAOYSA-N

InChI=1S/C28H41N3O3/c1-5-18-31(19-6-2)28(33)26(29-27(32)24-12-10-9-11-13-24)22-23-14-16-25(17-15-23)34-21-20-30(7-3)8-4/h9-17,26H,5-8,18-22H2,1-4H3,(H,29,32)

HIDE SMILES / InChI

Molecular Formula	C28H41N3O3
Molecular Weight	467.6434
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6114146 | http://app7.infarmed.pt/infomed/download_ficheiro.php?med_id=5292&tipo_doc=fi

Tiropramide is an antispasmodic medication. It acts by increasing cAMP concentration in smooth muscle possibly because of inhibition of cAMP catabolism. The drug is marketed worldwide for the treatment of irritable bowel syndrome, biliary dyskinesia, acute spasmodic dysphoric syndromes, and other urological and gynecological disorders.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
smooth muscle contraction 13 Target ID: GO:0006939 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1337131\|https://www.ncbi.nlm.nih.gov/pubmed/2744399	Inhibitor 8504		19.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Spastic syndromes 2 Sources: https://www.ndrugs.com/?s=tiropramide http://www.druginfosys.com/drug.aspx?drugcode=1075&type=1 https://www.codifa.it/farmaci/a/alfospas-tiropramide-cloridrato-antispastici	Primary		Approved 8583	ALFOSPAS Approved Use Painful-spastic syndromes such as acute hepatobiliary colic, abdominal different nature, kidney or ureteral. Spasms and abdominal pain originating from gastrointestinal dyskinesia, cholelithiasis, cholecystitis, post-surgical adhesions.

C_max

Value	Dose	Co-administered	Analyte	Population
106.76 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17127027/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TIROPRAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
352.81 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17127027/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TIROPRAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.07 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17127027/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TIROPRAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
300 mg 3 times / day multiple, oral Highest studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6694801/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6694801/	Sources: https://pubmed.ncbi.nlm.nih.gov/6694801/
400 mg single, oral Highest studied dose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3370360/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3370360/	Sources: https://pubmed.ncbi.nlm.nih.gov/3370360/

PubMed

Title	Date	PubMed
Pharmacokinetics of tiropramide after single doses in man.	1986-04	3718598
Mechanism of smooth muscle relaxation by tiropramide.	1981-01	6114146

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:48:17 GMT 2025` Edited by `admin` on `Mon Mar 31 18:48:17 GMT 2025`
Record UNII	R7S0904CN2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(±)-.ALPHA.-BENZAMIDO-P-(2-(DIETHYLAMINO)ETHOXY)-N,N-DIPROPYLHYDROCINNAMAMIDE

Preferred Name

English

TIROPRAMIDE

Official Name

English

Tiropramide [WHO-DD]

Common Name

English

TIROPRAMIDE [MI]

Common Name

English

DL-.ALPHA.-BENZAMIDO-P-(2-(DIETHYLAMINO)ETHOXY)-N,N-DIPROPYLHYDROCINNAMAMIDE

Common Name

English

tiropramide [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA03AC05