TRIPAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H20ClN3O3S
Molecular Weight	369.866
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NS(=O)(=O)C1=C(Cl)C=CC(=C1)C(=O)NN2C[C@H]3[C@H]4CC[C@H](C4)[C@H]3C2

InChI

InChIKey=UHLOVGKIEARANS-NIFPGPBJSA-N

InChI=1S/C16H20ClN3O3S/c17-14-4-3-11(6-15(14)24(18,22)23)16(21)19-20-7-12-9-1-2-10(5-9)13(12)8-20/h3-4,6,9-10,12-13H,1-2,5,7-8H2,(H,19,21)(H2,18,22,23)/t9-,10+,12-,13+

HIDE SMILES / InChI

Molecular Formula	C16H20ClN3O3S
Molecular Weight	369.866
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.eisai.jp/medical/products/di/EPI/NOL_T_EPI.pdf
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/6861441 and http://www.genome.jp/dbget-bin/www_bget?D01895

Tripamide is a new diuretic derived from a sulfonamide nucleus that has both antihypertensive and natriuretic properties. It is Na-K-Cl cotransporter inhibitor. The antihypertensive mechanism of tripamide is considered to be based on a mild saluretic action and a peripheral vasodilation action. Tripamide is an ingredient of Normonal in Japan, indicated for the treatment of essential hypertension.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium-(potassium)-chloride cotransporter 2 15 Target ID: CHEMBL1874 Sources: http://www.genome.jp/dbget-bin/www_bget?D01895	Inhibitor 8504
Solute carrier family 12 member 2 3 Target ID: CHEMBL1615383 Sources: http://www.genome.jp/dbget-bin/www_bget?D01895	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Essential hypertension 17 Sources: http://www.eisai.jp/medical/products/di/EPI/NOL_T_EPI.pdf	Primary		Approved 8583	NORMONAL Approved Use Essential hypertension Launch Date 1982

Doses

Dose	Population	Adverse events
100 mg 1 times / day multiple, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3527514/ https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1988.tb00515.x	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3527514/ https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1988.tb00515.x	Other AEs: Hypokalemia... Other AEs: Hypokalemia Sources: https://pubmed.ncbi.nlm.nih.gov/3527514/ https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1988.tb00515.x

AEs

AE	Significance	Dose	Population
Hypokalemia		100 mg 1 times / day multiple, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3527514/ https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1988.tb00515.x	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3527514/ https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1527-3466.1988.tb00515.x

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671199#sid=170466047	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671197#sid=170466047	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170466047	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466047	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671201#sid=170466047	yes [IC50 12.3018 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671200#sid=170466047

PubMed

Title	Date	PubMed
Antihypertensive and biochemical dose-response study of tripamide.	1986-09	3527514
Sites of action of tripamide.	1983-07	6861441
Effects of N-(4-azo-endo-tricyclo[5.2.1.0.(2.6)]-decan-4-yl)-4-chloro-3-sulfamoylbenzamide (E614; tripamide) on vascular smooth muscles.	1982	7095400

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage for oral use is 15 mg of tripamide (one tablet) once to twice daily after breakfast or after breakfast and lunch

Route of Administration: Oral

In Vitro Use Guide

In the guniea-pig mesenteric artery, Tripamide (less than 10(-6) g/ml) suppressed the spike evoked by outward current pulses in the presence of 3-5 mM TEA.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:45:59 GMT 2025` Edited by `admin` on `Mon Mar 31 17:45:59 GMT 2025`
Record UNII	G36A0E9CVT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORMONAL

Preferred Name

English

TRIPAMIDE

Official Name

English

BENZAMIDE, 3-(AMINOSULFONYL)-4-CHLORO-N-(OCTAHYDRO-4,7-METHANO-2H-ISOINDOL-2-YL)-, (3A.ALPHA.,4.ALPHA.,7.ALPHA.,7A.ALPHA.)-

Common Name

English

4-Chloro-N-(endo-hexahydro-4,7-methanoisoindolin-2-yl)-3-sulfamoylbenzamide

Common Name

English

TRIPAMIDE [JAN]

Common Name

English

ADR-033

Code

English

E-614

Code

English

TRIPAMIDE [MI]

Common Name

English

TRIPAMIDE [USAN]

Common Name

English

TRIPAMIDE [MART.]

Common Name

English

tripamide [INN]

Common Name

English

Tripamide [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C448