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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 of TRANDOLAPRIL

SMILES

[H][C@@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(=O)OCC)[C@@]1([H])CCCC2)C(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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
15.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MAVIK
Primary
MAVIK

Cmax

ValueDoseCo-administeredAnalytePopulation
0.99 ng/mL
1 mg single, oral
TRANDOLAPRILAT plasma
Homo sapiens
1.3 ng/mL
1 mg single, oral
TRANDOLAPRIL plasma
Homo sapiens
9 ng/mL
4 mg 1 times / day multiple, oral
TRANDOLAPRILAT plasma
Homo sapiens
6.2 ng/mL
4 mg 1 times / day multiple, oral
TRANDOLAPRIL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
19.1 ng × h/mL
1 mg single, oral
TRANDOLAPRILAT plasma
Homo sapiens
1.8 ng × h/mL
1 mg single, oral
TRANDOLAPRIL plasma
Homo sapiens
101 ng × h/mL
4 mg 1 times / day multiple, oral
TRANDOLAPRILAT plasma
Homo sapiens
8.2 ng × h/mL
4 mg 1 times / day multiple, oral
TRANDOLAPRIL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
115 h
4 mg 1 times / day multiple, oral
TRANDOLAPRILAT plasma
Homo sapiens
8.4 h
4 mg 1 times / day multiple, oral
TRANDOLAPRIL plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

PubMed

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
Record UNII
1T0N3G9CRC
Record Status Validated (UNII)
Record Version