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Trandolapril

Antihypertensive drug of the ACE inhibitor class

Antihypertensive drug of the ACE inhibitor class

FieldValue
Watchedfieldschanged
verifiedrevid470612121
IUPAC_name(2*S*,3*aR*,7*aS*)-1-[(2*S*)-2-{[(2*S*)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydro-1*H*-indole-2-carboxylic acid
imageTrandolapril structure.svg
image_classskin-invert-image
width2222
tradenameMavik, others
Drugs.com
MedlinePlusa697010
pregnancy_USD
legal_statusRx-only
routes_of_administrationBy mouth
protein_boundTrandolapril 80%
(independent of concentration)
Trandolaprilat 65 to 94%
(concentration-dependent)
metabolismLiver
elimination_half-life6 hours (trandolapril)
10 hours (trandolaprilat)
excretionFecal and Kidney
IUPHAR_ligand6453
CAS_number_Ref
CAS_number87679-37-6
ATC_prefixC09
ATC_suffixAA10
PubChem5484727
DrugBank_Ref
DrugBankDB00519
ChemSpiderID_Ref
ChemSpiderID4588590
UNII_Ref
UNII1T0N3G9CRC
KEGG_Ref
KEGGD00383
ChEBI9649
ChEMBL_Ref
ChEMBL1519
C24H=34N=2O=5
smilesO=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_Ref
StdInChI1S/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_Ref
StdInChIKeyVXFJYXUZANRPDJ-WTNASJBWSA-N
melting_point119
melting_high123

| Drugs.com =

(independent of concentration) Trandolaprilat 65 to 94% (concentration-dependent) | elimination_half-life = 6 hours (trandolapril) 10 hours (trandolaprilat)

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. 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

:

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.

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

: 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.

References

References

  1. (2006). "Analogue-based Drug Discovery". John Wiley & Sons.
  2. (December 2009). "Combination therapy with paricalcitol and trandolapril reduces renal fibrosis in obstructive nephropathy". Kidney International.
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ace-inhibitors carboxamides carboxylic-acids drugs-developed-by-abbvie enantiopure-drugs ethyl-esters indoles prodrugs
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