TRANDOLAPRIL HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H34N2O5.ClH
Molecular Weight	466.998
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2[C@H]3CCCC[C@@H]3C[C@H]2C(O)=O

InChI

InChIKey=QNSWMJYOGMUVGO-REWXTUPXSA-N

InChI=1S/C24H34N2O5.ClH/c1-3-31-24(30)19(14-13-17-9-5-4-6-10-17)25-16(2)22(27)26-20-12-8-7-11-18(20)15-21(26)23(28)29;/h4-6,9-10,16,18-21,25H,3,7-8,11-15H2,1-2H3,(H,28,29);1H/t16-,18+,19-,20-,21-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C24H34N2O5
Molecular Weight	430.5372
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

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: http://www.drugbank.ca/drugs/DB00519
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020528s024lbl.pdf

Trandolapril is a non-sulhydryl prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is metabolized to its biologically active diacid form, trandolaprilat, in the liver. Trandolaprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Trandolapril may be used to treat mild to moderate hypertension, to improve survival following myocardial infarction in clinically stable patients with left ventricular dysfunction, as an adjunct treatment for congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy. Trandolapril is marketed by Abbott Laboratories under the brand name Mavik.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 94 Target ID: CHEMBL1808 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020528s024lbl.pdf \| http://www.drugbank.ca/drugs/DB00519	Inhibitor 8504		15.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020528s024lbl.pdf	Primary		Approved 8583	MAVIK Approved Use Hypertension MAVIK is indicated for the treatment of hypertension. It may be used alone or in combination with other antihypertensive medication such as hydrochlorothiazide. Heart Failure Post Myocardial Infarction or Left-Ventricular Dysfunction Post Myocardial Infarction MAVIK is indicated in stable patients who have evidence of left-ventricular systolic dysfunction (identified by wall motion abnormalities) or who are symptomatic from congestive heart failure within the first few days after sustaining acute myocardial infarction. Launch Date 1996
Heart failure post myocardial infarction 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020528s024lbl.pdf	Primary		Approved 8583	MAVIK Approved Use Hypertension MAVIK is indicated for the treatment of hypertension. It may be used alone or in combination with other antihypertensive medication such as hydrochlorothiazide. Heart Failure Post Myocardial Infarction or Left-Ventricular Dysfunction Post Myocardial Infarction MAVIK is indicated in stable patients who have evidence of left-ventricular systolic dysfunction (identified by wall motion abnormalities) or who are symptomatic from congestive heart failure within the first few days after sustaining acute myocardial infarction. Launch Date 1996

C_max

Value	Dose	Analyte	Population
0.99 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANDOLAPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.3 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANDOLAPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
9 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRANDOLAPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6.2 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRANDOLAPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
19.1 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANDOLAPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.8 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TRANDOLAPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
101 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRANDOLAPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.2 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRANDOLAPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
115 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:		TRANDOLAPRILAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020528Orig1s000rev.pdf	4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered:		TRANDOLAPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9231890/	unhealthy, 55 Health Status: unhealthy Age Group: 55 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9231890/	Disc. AE: Diarrhea, Dizziness... AEs leading to discontinuation/dose reduction: Diarrhea Dizziness Elevated liver enzymes Sources: https://pubmed.ncbi.nlm.nih.gov/9231890/

AEs

AE	Significance	Dose	Population
Diarrhea	Disc. AE	8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9231890/	unhealthy, 55 Health Status: unhealthy Age Group: 55 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9231890/
Dizziness	Disc. AE	8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9231890/	unhealthy, 55 Health Status: unhealthy Age Group: 55 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9231890/
Elevated liver enzymes	Disc. AE	8 mg 1 times / day multiple, oral Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9231890/	unhealthy, 55 Health Status: unhealthy Age Group: 55 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9231890/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CES1 45 CES2 33

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CES2 33	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24141856/	no	TRANDOLAPRIL 3
CES1 45	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24141856/	yes [Km 1721 uM]	TRANDOLAPRIL 3

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1477	http://www.3bsc.com/index/pro_info.php?id=55193
Alfa Chemistry	83601-86-9	https://www.alfa-chemistry.com/cas_83601-86-9.htm
Alfa Chemistry	AP87679718	https://reagents.alfa-chemistry.com/product/trandolapril-related-compound-e-cas-87679-71-8-17686.html
BLD Pharm	BD154453	http://www.bldpharm.com/products/87679-71-8.html
ChemMol	49422350	http://www.chemmol.com/chemmol/49422350.html
Clearsynth	CS-O-08347	https://www.clearsynth.com/en/CSO08347.html
DC Chemicals	DC32672	http://www.dcchemicals.com//product_show-Trandolaprilat.html
eNovation Chemicals	D591705	https://www.enovationchem.com/ProductDetails.asp?ProductID=D591705
Excenen	EX-A4862	https://www.excenen.com/searchresultlist.php?id=EX-A4862
Glentham Life Sciences	GP7119	http://www.glentham.com/products/product/GP7119/
iChemical	EBD21706	http://www.ichemical.com/products/87679-71-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
MuseChem	R044833	https://www.musechem.com/product/R044833.html
OChem	21859	http://www.ocheminc.com/index.php?act=psearch&pid=679T718
Smolecule	S545706	http://www.smolecule.com/products/s545706
THE BioTek	bt-286404	https://www.thebiotek.com/product/inhibitors/bt-286404

PubMed

Title	Date	PubMed
[Diagnosis of and therapy for renal hypertension].	2004-03-10	15052808
[Therapeutic strategy for patients with stable-stage chronic kidney failure].	2004-03-10	15052806
Endothelial dysfunction in congestive heart failure: ACE inhibition vs. angiotensin II antagonism.	2004-03-01	14984722
Significant target organs for hypertension and cardiac hypertrophy by angiotensin-converting enzyme inhibitors.	2004-03	15080380
[Effects of angiotensin II receptor blockers, angiotensin converting enzyme inhibitors, 3-hydroxy-3-methyl glutaryl (HMG) CoA reductase inhibitors, amlodipine and epalrestat on cultured basilar artery smooth muscle cell proliferation].	2004-03	15049134
[Preventive therapy with ACE inhibitors for coronary patients].	2004-02-29	15077477
[Induction of heat shock protein 70 in failing heart].	2004-02	14745126
ACE-inhibition is superior to endothelin A receptor blockade in preventing abnormal capillary supply and fibrosis of the heart in experimental diabetes.	2004-02	14727024
Effects of bedtime vs. morning administration of the long-acting lipophilic angiotensin-converting enzyme inhibitor trandolapril on morning blood pressure in hypertensive patients.	2004-01	15055251
Effect of nolomirole on monocrotaline-induced heart failure.	2004-01	14597145
Pharmacological treatment and prevention of heart failure in the diabetic patient.	2004	15029109
A calcium antagonist vs a non-calcium antagonist hypertension treatment strategy for patients with coronary artery disease. The International Verapamil-Trandolapril Study (INVEST): a randomized controlled trial.	2003-12-03	14657064
The angiotensin converting enzyme inhibitor trandolapril has neutral effect on exercise tolerance or functional class in patients with myocardial infarction and reduced left ventricular systolic function.	2003-12	14643272
ACE inhibition limits chronic injury of kidney transplant even with treatment started when lesions are established.	2003-12	14633150
Aldosterone antagonism and myocardial infarction: from animals to man and back.	2003-11-05	14607458
Additive improvement of left ventricular remodeling and neurohormonal activation by aldosterone receptor blockade with eplerenone and ACE inhibition in rats with myocardial infarction.	2003-11-05	14607457
Differing anti-proteinuric action of candesartan and losartan in chronic renal disease.	2003-11	14714578
Submaximal dose of trandolapril in the COOPERATE trial?	2003-11	14531832
Angiotensin-converting enzyme inhibitor trandolapril does not affect C-reactive protein levels in myocardial infarction patients.	2003-10-14	14557351
Some recent randomized clinical trials in the management of atrial fibrillation.	2003-10	14574035
A study on the stereochemical purity of trandolapril and octahydro-1H-indole-2-carboxylic acid by HPLC method.	2003-09-19	13678325
Verapamil reverts acute renal functional impairment induced by angiotensin II converting enzyme inhibitors.	2003-09	14575281
Renal damage in the SHR/N-cp type 2 diabetes model: comparison of an angiotensin-converting enzyme inhibitor and endothelin receptor blocker.	2003-09	13679434
The BErgamo NEphrologic DIabetes Complications Trial (BENEDICT): design and baseline characteristics.	2003-08	12865039
ACE inhibitors and AT-1-receptor antagonists COOPERATE in non-diabetic renal disease.	2003-07	12831343
The verapamil versus amlodipine in nondiabetic nephropathies treated with trandolapril (VVANNTT) study.	2003-07	12830458
Role of L-type calcium channels in pacing-induced short-term and long-term cardiac memory in canine heart.	2003-06-10	12756152
Addition of the selective aldosterone receptor antagonist eplerenone to ACE inhibition in heart failure: effect on endothelial dysfunction.	2003-06-01	12798439
Choosing a drug from within a class.	2003-06	12833771
ACE-inhibitors but not endothelin receptor blockers prevent podocyte loss in early diabetic nephropathy.	2003-06	12802493
Inhibition of platelet activation in congestive heart failure by aldosterone receptor antagonism and ACE inhibition.	2003-06	12783115
Tick-borne encephalitis with hemorrhagic syndrome, Novosibirsk region, Russia, 1999.	2003-06	12781020
Antihypertensive therapy with verapamil SR plus trandolapril versus atenolol plus chlorthalidone on glycemic control.	2003-05	12745200
Protective effects of quinaprilat and trandolaprilat, active metabolites of quinapril and trandolapril, on hemolysis induced by lysophosphatidylcholine in human erythrocytes.	2003-05	12736518
Trandolapril and endothelin antagonist LU-135252 in the treatment of the fructose-induced hypertensive, hyperinsulinemic, hypertriglyceridemic rat.	2003-04	12670751
The COOPERATE trial.	2003-03-22	12660076
The COOPERATE trial.	2003-03-22	12660075
[The effect of analysed hypotensive drugs on certain metabolic parameters].	2003-03	12924169
Trandolapril: a newer angiotensin-converting enzyme inhibitor.	2003-03	12852701
Sustained activation of nuclear factor kappa B and activator protein 1 in chronic heart failure.	2003-03	12618236
Exercise testing in hypertensive patients taking different angiotensin-converting enzyme inhibitors.	2003-02	12640507
Combination treatment of angiotensin-II receptor blocker and angiotensin-converting-enzyme inhibitor in non-diabetic renal disease (COOPERATE): a randomised controlled trial.	2003-01-11	12531578
Trandolapril in left ventricular dysfunction after myocardial infarction: focus on the TRACE study.	2003-01	12669106
Combination treatment with an ET(A)-receptor blocker and an ACE inhibitor is not superior to the respective monotherapies in attenuating chronic transplant vasculopathy in different aorta allotransplantation rat models.	2003-01	12480961
Effect of endothelin blockade on early cardiovascular remodeling in the one-clip-two-kidney hypertension of the rat.	2003	14610336
Time-effect profile of antihypertensive agents assessed with trough/peak ratio, smoothness index and dose omission: an ambulatory blood pressure monitoring study with trandolapril vs. quinapril.	2002-12	12685514
Relative long-term effects of spironolactone in conjunction with an angiotensin-converting enzyme inhibitor on left ventricular mass and diastolic function in patients with essential hypertension.	2002-11	12484506
High-dose verapamil + trandolapril-induced thrombotic microangiopathy.	2002	12611489
[Clinical sequelae of tissue angiotensin converting enzyme inhibition: practicability of use in ischemic heart disease].	2002	12494137
Trandolapril in hypertension: overview of a new angiotensin-converting enzyme inhibitor.	1992-10-29	1414922

Patents

Sample Use Guides

In Vivo Use Guide

The recommended initial dosage of MAVIK (Trandolapril) for patients not receiving a diuretic is 1 mg once daily in non-black patients and 2 mg in black patients.

Route of Administration: Oral

In Vitro Use Guide

Trandolapril at 10(-7) mol/l, significantly increased 11beta-HSD2 activity after pretreatment for 16 or 24 h of the human epithelial colon cell line SW-620

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:00:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:31 GMT 2025`
Record UNII	3EY8XK2J4T
Record Status	`Validated (UNII)`
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Name

Type

Language

TRANDOLAPRIL HYDROCHLORIDE

Common Name

English

1H-INDOLE-2-CARBOXYLIC ACID, 1-((2S)-2-(((1S)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)OCTAHYDRO-, MONOHYDROCHLORIDE, (2S,3AR,7AS)-

Preferred Name

English

Code System Code Type Description

PUBCHEM

67422545