Trandolapril

Trandolapril is an ACE inhibitor used to treat high blood pressure. It may also be used to treat other conditions. It is similar in structure to another ramipril but has a cyclohexane group. It is a prodrug that must be metabolized into its active form. It has a longer half-life when compared to other agents in this class.

Quick Facts Clinical data, Trade names ...

Trandolapril

Clinical data
Trade names	Mavik, others
AHFS/Drugs.com	Monograph
MedlinePlus	a697010
Routes of administration	By mouth
ATC code	C09AA10 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	Trandolapril 80% (independent of concentration) Trandolaprilat 65 to 94% (concentration-dependent)
Metabolism	Liver
Elimination half-life	6 hours (trandolapril) 10 hours (trandolaprilat)
Excretion	Fecal and Kidney
Identifiers
IUPAC name (2S,3aR,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
CAS Number	87679-37-6 Y
PubChem CID	5484727
IUPHAR/BPS	6453
DrugBank	DB00519 Y
ChemSpider	4588590 Y
UNII	1T0N3G9CRC
KEGG	D00383 Y
ChEBI	CHEBI:9649
ChEMBL	ChEMBL1519 Y
CompTox Dashboard (EPA)	DTXSID2023692
ECHA InfoCard	100.108.532
Chemical and physical data
Formula	C24H34N2O5
Molar mass	430.545 g·mol−1
3D model (JSmol)	Interactive image
Melting point	119 to 123 °C (246 to 253 °F)
SMILES O=C(OCC)[C@@H](N[C@H](C(=O)N1[C@H](C(=O)O)C[C@H]2CCCC[C@H]12)C)CCc3ccccc3
InChI 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 Y Key:VXFJYXUZANRPDJ-WTNASJBWSA-N Y
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It was patented in 1981 and approved for medical use in 1993.^[1] It is marketed by Abbott Laboratories under the brand name Mavik.

Side effects reported for trandolapril include nausea, vomiting, diarrhea, headache, dry cough, dizziness or lightheadedness when sitting up or standing, hypotension, or fatigue.

Patients also on diuretics may experience an excessive reduction of blood pressure after initiation of therapy with trandolapril. It can reduce potassium loss caused by thiazide diuretics and increase serum potassium when used alone. Therefore, hyperkalemia is a possible risk. Increased serum lithium levels can occur in patients who are also on lithium.

Main article: ACE inhibitor § Contraindications and precautions

Trandolapril is teratogenic (US: pregnancy category D) and can cause birth defects and even death of the developing fetus. The highest risk to the fetus is during the second and third trimesters. When pregnancy is detected, trandolapril should be discontinued as soon as possible. Trandolapril should not be administered to nursing mothers.

Combination therapy with paricalcitol and trandolapril has been found to reduce fibrosis in obstructive uropathy.^[2]

Trandolapril is a prodrug that is deesterified to trandolaprilat. It is believed to exert its antihypertensive effect through the renin–angiotensin–aldosterone system. Trandolapril has a half-life of about six hours, while trandolaprilat has a half life of about ten hours. Trandolaprilat has about eight times the activity of its parent drug. About one-third of trandolapril and its metabolites are excreted in the urine, and about two-thirds of trandolapril and its metabolites are excreted in the feces. Serum protein binding of trandolapril is about 80%.

Main article: ACE inhibitor

Trandolapril acts by competitive inhibition of angiotensin converting enzyme (ACE), a key enzyme in the renin–angiotensin system. which plays an important role in regulating blood pressure.