Trandolapril

Trandolapril

Clinical data
Trade names	Mavik
AHFS/Drugs.com	Monograph
MedlinePlus	a697010
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Oral
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	Hepatic
Biological half-life	6 hours (trandolapril) 10 hours (trandolaprilat)
Excretion	Fecal and renal
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
ChEMBL	CHEMBL1519 Y
ECHA InfoCard	100.108.532
Chemical and physical data
Formula	C24H34N2O5
Molar mass	430.537 g/mol
3D model (Jmol)	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

Trandolapril is an ACE inhibitor used to treat high blood pressure, it may also be used to treat other conditions. It is marketed by Abbott Laboratories under the brand name Mavik.

Trandolapril is a prodrug that is de-esterified to trandolaprilat. It is believed to exert its antihypertensive effect through the renin-angiotensin-aldosterone system. Trandolapril has a half-life of about 6 hours, and trandolaprilat has a half life of about 10 h. 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%.

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.

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 lithum levels can occur in patients who are also on lithium.

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 administed to nursing mothers.