Trandolapril Explained

Watchedfields:changed
Verifiedrevid:470612121
Iupac Name:(2S,3aR,7aS)-1-[(2''S'')-2-<nowiki/>{[(2''S'')-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
Width2:222
Tradename:Mavik, others
Pregnancy Us:D
Legal Status:Rx-only
Routes Of Administration:By mouth
Protein Bound: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
Iuphar Ligand:6453
Cas Number:87679-37-6
Atc Prefix:C09
Atc Suffix:AA10
Pubchem:5484727
Drugbank:DB00519
Chemspiderid:4588590
Unii:1T0N3G9CRC
Kegg:D00383
Chebi:9649
Chembl:1519
C:24
H:34
N:2
O:5
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
Stdinchi: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
Stdinchikey:VXFJYXUZANRPDJ-WTNASJBWSA-N
Melting Point:119
Melting High:123

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.

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

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

Possible drug interactions

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.

Contraindications and precautions

See main article: article.

Pregnancy and lactation

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.

Additional effects

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

Pharmacology

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%.

Mode of action

See main article: article and 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.

External links

Notes and References

  1. Book: Fischer J, Ganellin CR . Analogue-based Drug Discovery . 2006 . John Wiley & Sons . 9783527607495 . 469 . en.
  2. Tan X, He W, Liu Y . Combination therapy with paricalcitol and trandolapril reduces renal fibrosis in obstructive nephropathy . Kidney International . 76 . 12 . 1248–1257 . December 2009 . 19759524 . 5527548 . 10.1038/ki.2009.346 .