TRANDOLAPRIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H34N2O5
Molecular Weight	430.5372
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=VXFJYXUZANRPDJ-WTNASJBWSA-N

InChI=1S/C24H34N2O5/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)/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

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
Effect of strict blood pressure control on proteinuria in renal patients treated with different antihypertensive drugs.	2001	11369828
Effect of two antihypertensive combinations on metabolic control in type-2 diabetic hypertensive patients with albuminuria: a randomised, double-blind study.	2001 Dec	11773987
Does the electrocardiographic presence of Q waves influence the survival of patients with acute myocardial infarction?	2001 Jun	11469214
Characteristics of patients with coronary artery disease and hypertension: a report from INVEST.	2001 Nov	11712775
Effect of long-term treatment with trandolapril on Hsp72 and Hsp73 induction of the failing heart following myocardial infarction.	2001 Nov	11682444
Renal adaptive mechanisms in aged and hypertensive humans: possible effects of treatment.	2001 Nov-Dec	11687731
Dosing time-dependent effect of trandolapril on the prevention of cardiac hypertrophy in rats with aortic banding.	2001 Sep	11676204
[The effect of trandolapril, in monotherapy and associated with verapamil, on arterial pressure, albuminuria, and metabolic control in hypertensive patients with type 2 diabetes and albuminuria].	2001 Sep-Oct	11795014
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
Fixed combination trandolapril/verapamil sustained-release: a review of its use in essential hypertension.	2002	12421112
Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update.	2002	11929321
Dissociation between blood pressure reduction and fall in proteinuria in primary renal disease: a randomized double-blind trial.	2002 Apr	11910310
[Treatment of hypertension in diabetics with trandolapril, an angiotensin converting enzyme inhibitor--a multicenter study].	2002 Aug	12425199
Beneficial effects of trandolapril in uninephrectomized spontaneously hypertensive rats: role of cyclooxygenase pathway.	2002 Aug	12420798
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 Dec	12685514
Impact of age and sex on sudden cardiovascular death following myocardial infarction.	2002 Dec	12433881
Acute blood pressure response to trandolapril and captopril in patients with left ventricular dysfunction after acute myocardial infarction.	2002 Feb	11835037
Addition of spironolactone to angiotensin-converting enzyme inhibition in heart failure improves endothelial vasomotor dysfunction: role of vascular superoxide anion formation and endothelial nitric oxide synthase expression.	2002 Jan 16	11788231
Angiotensin II and trials of cardiovascular outcomes.	2002 Jan 24	11835905
Trandolapril reduces infarction area after middle cerebral artery occlusion in rats.	2002 Jul	12358145
Angiotensin-converting enzyme inhibition and endothelin antagonism for endothelial dysfunction in heart failure: mono-or combination therapy.	2002 Oct	12352322
Effect of endothelin blockade on early cardiovascular remodeling in the one-clip-two-kidney hypertension of the rat.	2003	14610336
Trandolapril and endothelin antagonist LU-135252 in the treatment of the fructose-induced hypertensive, hyperinsulinemic, hypertriglyceridemic rat.	2003 Apr	12670751
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 Dec	14643272
ACE inhibition limits chronic injury of kidney transplant even with treatment started when lesions are established.	2003 Dec	14633150
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 Dec 3	14657064
Exercise testing in hypertensive patients taking different angiotensin-converting enzyme inhibitors.	2003 Feb	12640507
Trandolapril in left ventricular dysfunction after myocardial infarction: focus on the TRACE study.	2003 Jan	12669106
Combination treatment of angiotensin-II receptor blocker and angiotensin-converting-enzyme inhibitor in non-diabetic renal disease (COOPERATE): a randomised controlled trial.	2003 Jan 11	12531578
ACE inhibitors and AT-1-receptor antagonists COOPERATE in non-diabetic renal disease.	2003 Jul	12831343
The verapamil versus amlodipine in nondiabetic nephropathies treated with trandolapril (VVANNTT) study.	2003 Jul	12830458
ACE-inhibitors but not endothelin receptor blockers prevent podocyte loss in early diabetic nephropathy.	2003 Jun	12802493
Inhibition of platelet activation in congestive heart failure by aldosterone receptor antagonism and ACE inhibition.	2003 Jun	12783115
Tick-borne encephalitis with hemorrhagic syndrome, Novosibirsk region, Russia, 1999.	2003 Jun	12781020
Addition of the selective aldosterone receptor antagonist eplerenone to ACE inhibition in heart failure: effect on endothelial dysfunction.	2003 Jun 1	12798439
Sustained activation of nuclear factor kappa B and activator protein 1 in chronic heart failure.	2003 Mar	12618236
Protective effects of quinaprilat and trandolaprilat, active metabolites of quinapril and trandolapril, on hemolysis induced by lysophosphatidylcholine in human erythrocytes.	2003 May	12736518
Differing anti-proteinuric action of candesartan and losartan in chronic renal disease.	2003 Nov	14714578
Aldosterone antagonism and myocardial infarction: from animals to man and back.	2003 Nov 5	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 Nov 5	14607457
Some recent randomized clinical trials in the management of atrial fibrillation.	2003 Oct	14574035
Renal damage in the SHR/N-cp type 2 diabetes model: comparison of an angiotensin-converting enzyme inhibitor and endothelin receptor blocker.	2003 Sep	13679434
[Induction of heat shock protein 70 in failing heart].	2004 Feb	14745126
[Preventive therapy with ACE inhibitors for coronary patients].	2004 Feb 29	15077477
Significant target organs for hypertension and cardiac hypertrophy by angiotensin-converting enzyme inhibitors.	2004 Mar	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 Mar	15049134
Endothelial dysfunction in congestive heart failure: ACE inhibition vs. angiotensin II antagonism.	2004 Mar 1	14984722
[Therapeutic strategy for patients with stable-stage chronic kidney failure].	2004 Mar 10	15052806
Pharmacological treatment and prevention of heart failure in the diabetic patient.	2004 Winter	15029109

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 18:06:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:54 GMT 2025`
Record UNII	1T0N3G9CRC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TARKA COMPONENT TRANDOLAPRIL

Preferred Name

English

TRANDOLAPRIL

Official Name

English

TRANDOLAPRIL [USP-RS]

Common Name

English

TRANDOLAPRIL [VANDF]

Common Name

English

TRANDOLAPRIL [JAN]

Common Name

English

1H-INDOLE-2-CARBOXYLIC ACID, OCTAHYDRO N-((2S)-1-ETHOXY-1-OXO-4-PHENYLBUTAN-2-YL)-1-ALANYL (2S,3AR,7AS)

Common Name

English

TRANDOLAPRIL [EP MONOGRAPH]

Common Name

English

TRANDOLAPRIL [USP MONOGRAPH]

Common Name

English

TRANDOLAPRIL [MI]

Common Name

English

(2S,3aR,7aS)-1-[(S)-N-[(S)-1-Carboxy-3-phenylpropyl]alanyl]hexahydro-2-indolinecarboxylic acid, 1-ethyl ester

Common Name

English

NSC-758939

Code

English

TRANDOLAPRIL [ORANGE BOOK]

Common Name

English

TRANDOLAPRIL [MART.]

Common Name

English

RU 44570

Code

English

MAVIK

Brand Name

English

Trandolapril [WHO-DD]

Common Name

English

trandolapril [INN]

Common Name

English

RU-44570

Code

English

Classification Tree Code System Code

WHO-VATC

QC09AA10