THIPHENAMIL HYDROCHLORIDE

First approved in 1950

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H25NOS.ClH
Molecular Weight	363.945
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CCN(CC)CCSC(=O)C(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=MZWKCFGWAWRHDY-UHFFFAOYSA-N

InChI=1S/C20H25NOS.ClH/c1-3-21(4-2)15-16-23-20(22)19(17-11-7-5-8-12-17)18-13-9-6-10-14-18;/h5-14,19H,3-4,15-16H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula	C20H25NOS
Molecular Weight	327.484
Charge	0
Count

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1528051 | https://www.ncbi.nlm.nih.gov/pubmed/1598732 https://www.ncbi.nlm.nih.gov/pubmed/1598734

Thiphenamil, an antispasmodic drug with a local anesthetic activity, inhibits contraction. The clinical trials have shown that thiphenamil could suppress upper urinary tract contractility, and was suggested to use the drug for renal colic and stone management. In addition, this drug was studied for the treatment of detrusor incontinence in patients with detrusor instability. The results showed, that the drug caused a significant decrease in problems due to loss of urine when the patient was taking the drug compared to the placebo.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
smooth muscle 2 Target ID: smooth muscle Sources: https://www.ncbi.nlm.nih.gov/pubmed/1528051	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Renal colic 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1598732	Primary		Not Provided 504	Unknown Approved Use Unknown
Detrusor incontinence 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1598734	Primary		Not Provided 504	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
400 mg 4 times / day steady, oral Recommended Dose: 400 mg, 4 times / day Route: oral Route: steady Dose: 400 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1598734/	unhealthy, 44 years n = 16 Health Status: unhealthy Condition: detrusor incontinence Age Group: 44 years Sex: M Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/1598734/	Sources: https://pubmed.ncbi.nlm.nih.gov/1598734/

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L1WJ8
Alfa Chemistry	82-99-5	https://www.alfa-chemistry.com/cas_82-99-5.htm
Ambinter	Amb1869497	http://www.ambinter.com/reference/1869497
AsisChem	G00416
Aurora Fine Chemicals LLC	K00.422.883	http://online.aurorafinechemicals.com/info?ID=K00.422.883
Chemieliva Pharmaceutical Co., Ltd	PBCM0859757
Chemspace	CSSS00025767528	https://chem-space.com/CSSS00025767528
Compound Cloud	11060
Compound Cloud	11061
IBScreen	Bio-0722
Lab Network	LN00263222
MolPort	MolPort-001-012-631
NovoSeek	11061
Princeton BioMolecular Research	OSSK_580413
Princeton BioMolecular Research	PBMR122194
Scientific Exchange	POD_31/0700
Smolecule	S572065	https://www.smolecule.com/products/s572065
Vitas-M Laboratory	STK182872
ZINC	ZINC000001957899	http://zinc15.docking.org/substances/ZINC000001957899
eMolecules	975617
mcule	MCULE-2108895058

PubMed

Title	Date	PubMed
The use of thiphenamil hydrochloride (Trocinate) to control wound contraction after radial keratotomy.	1987 Jun	3614824
Relaxation mechanisms of antispasmodics papaverine and thiphenamil on the human corpus cavernosum.	1990 Dec	2231955
Pharmacologic treatment of detrusor incontinence with thiphenamil HCl.	1992	1598734
Relaxant effect of thiphenamil HCl on upper urinary tract frequency of contraction of healthy asymptomatic volunteers.	1992	1598732

Patents

Sample Use Guides

In Vivo Use Guide

The pharmacologic effect of thiphenamil HCl on the upper urinary tract as a relaxant of renal pelvic contractions was studied. A total of 17 subjects with no known upper urinary tract abnormalities were scanned. The subject was then given a single dose of 400 mg thiphenamil HCl and visualization of contractility continued for approximately 60-90 min.

Route of Administration: Oral

In Vitro Use Guide

The relaxation mechanism of the antispasmodics, papaverine and thiphenamil on isolated human corpus cavernosum (CC) was investigated. CC tissues were obtained from 12 impotent men undergoing surgery for insertion of penile prostheses. CC preparations were mounted in a tissue bath and the isometric tension was recorded. Papaverine and thiphenamil consistently inhibited high-potassium ([K])-induced contractions in a dose-dependent manner. The pD'2 values were 4.77 +/- 0.20 for papaverine and 4.58 +/- 0.13 for thiphenamil. The results suggest that papaverine and thiphenamil relax CC tissue by the inhibition of extracellular Ca2+ influx (mainly voltage-dependent Ca2+ influx) and by the inhibition of release and/or storage of intracellular stored Ca2+.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:10:13 GMT 2023` Edited by `admin` on `Fri Dec 15 15:10:13 GMT 2023`
Record UNII	4OQ4SP44R2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIPHENAMIL HYDROCHLORIDE

Official Name

English

S-(2-(DIETHYLAMINO)ETHYL)DIPHENYLTHIOACETATE HYDROCHLORIDE

Systematic Name

English

THIPHENAMIL HCL

Common Name

English

THIPHENAMIL HYDROCHLORIDE [USAN]

Common Name

English

TIFENAMIL HYDROCHLORIDE

Common Name

English

THIPHENAMIL HYDROCHLORIDE [MI]

Common Name

English

BENZENEETHANETHIOIC ACID, .ALPHA.-PHENYL-, S-(2-(DIETHYLAMINO)ETHYL) ESTER HYDROCHLORIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704