TEMOCAPRILAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24N2O5S2
Molecular Weight	448.556
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CN1C[C@H](SC[C@H](N[C@@H](CCC2=CC=CC=C2)C(O)=O)C1=O)C3=CC=CS3

InChI

InChIKey=KZVWEOXAPZXAFB-BQFCYCMXSA-N

InChI=1S/C21H24N2O5S2/c24-19(25)12-23-11-18(17-7-4-10-29-17)30-13-16(20(23)26)22-15(21(27)28)9-8-14-5-2-1-3-6-14/h1-7,10,15-16,18,22H,8-9,11-13H2,(H,24,25)(H,27,28)/t15-,16-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H24N2O5S2
Molecular Weight	448.556
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2851680
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11686312 | https://www.ncbi.nlm.nih.gov/pubmed/19932971 | https://www.drugs.com/international/acecol.html

Temocapril is a prodrug-type angiotensin-I converting enzyme (ACE) inhibitor not approved for use in the United States but is approved in Japan and South Korea. Temocapril can also be used in hemodialysis patients without risk of serious accumulation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 94 Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2851680	Inhibitor 8504		3.6 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.pmda.go.jp/files/000153405.pdf	Primary		Approved 8583	Acecol Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
136 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9803985/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		TEMOCAPRIL HYDROCHLORIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
139 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9803985/	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		TEMOCAPRIL HYDROCHLORIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
141 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9803985/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		TEMOCAPRIL HYDROCHLORIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
140 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9803985/	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		TEMOCAPRIL HYDROCHLORIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9803985/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		TEMOCAPRIL HYDROCHLORIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9803985/	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		TEMOCAPRIL HYDROCHLORIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
40 mg 1 times / day multiple, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/	Disc. AE: Cough... Other AEs: Orthostatic hypotension, GGT increased... AEs leading to discontinuation/dose reduction: Cough (1.4%) Other AEs: Orthostatic hypotension (0.3%) GGT increased (0.3%) Bronchitis (3.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/

AEs

AE	Significance	Dose	Population
GGT increased	0.3%	40 mg 1 times / day multiple, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/
Orthostatic hypotension	0.3%	40 mg 1 times / day multiple, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/
Cough	1.4% Disc. AE	40 mg 1 times / day multiple, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/
Bronchitis	3.8%	40 mg 1 times / day multiple, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9296310/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438		inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 P-gp 1741 CYP1A2 2153 CYP2C19 2057	OATP1B1 503 PEPT1 60 P-gp 2052 BCRP 697 MRP2 252 CES1 45

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/443873#section=Biological-Test-Results Page: 6.0	inconclusive [EC50 28.1838 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/443873#section=Biological-Test-Results Page: 7.0	inconclusive [IC50 43.6486 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/443873#section=Biological-Test-Results Page: 44.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/443873#section=Biological-Test-Results Page: 118.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/443873#section=Biological-Test-Results Page: 118.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/443873#section=Biological-Test-Results Page: 106.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIxMTA2MjcifX0=	no

Drug as victim

Target	Modality	Activity	Clinical evidence
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21618543/	no
OATP1B1 503	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16678545/	weak	yes (pharmacogenomic study) Comment: The AUC of temocapril in 1b/1b carriers (12.4 /- 4.1 ng.h/mL) was 67% of that in 1a/1a carriers (18.5 /- 7.7 ng.h/mL) [P = .061] Sources: https://pubmed.ncbi.nlm.nih.gov/16678545/
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21618543/	yes
CES1 45	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19937843/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21618543/	yes
PEPT1 60	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0NjA1IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIxMTA2MjcifX0=	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/443873#section=Biological-Test-Results Page: 119.0

PubMed

Title	Date	PubMed
Effect of temocapril hydrochloride on serum lipid levels in patients with hypertensive type 2 diabetes mellitus.	2001	11686312

Patents

Sample Use Guides

In Vivo Use Guide

A tablet containing 2 mg of temocapril hydrochloride was administered once a day in the morning, and the monitoring term was for 16 weeks.

Route of Administration: Oral

In Vitro Use Guide

A force of 1.0 g was applied, and the strips were allowed to equilibrate for 90 min. Aortic strips were exposed to 30 nM of angiotensin I (AI), which produced contractions approximately equal to 90% of the maximum response. After three successive contractions of equal size had been obtained, test drugs (CS-622 diacid) was added to the bath. Contractile responses to AI in the presence of a test drug were compared with control responses before the drug was added. The concentration of the drug was increased in a cumulative manner by a ratio of 3 at a 10 min interval to construct a concentration inhibition curve. The IC50 value was determined as the concentration inhibiting by 50% the response to AI

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:30:50 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:50 GMT 2025`
Record UNII	2D6A12Q12R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEMOCAPRILAT

Official Name

English

TEMOCAPRIL DIACID

Preferred Name

English

RS-5139

Code

English

1,4-THIAZEPINE-4(5H)-ACETIC ACID, 6-((1-CARBOXY-3-PHENYLPROPYL)AMINO)TETRAHYDRO-5-OXO-2-(2-THIENYL)-, (2S- (2.ALPHA.,6.BETA.(R*)))-

Common Name

English

temocaprilat [INN]

Common Name

English

(+)-(2S,6R)-6-(((1S)-1-CARBOXY-3-PHENYLPROPYL)AMINO)TETRAHYDRO-5-OXO-2-(2-THIENYL)-1,4-THIAZEPINE-4(5H)-ACETIC ACID

Systematic Name

English

TEMOCAPRIL DIACID [MI]

Common Name

English

Temocaprilat [WHO-DD]

Common Name

English

RNH-5139

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C247