View source for Trandolapril

{{Short description|Antihypertensive drug of the ACE inhibitor class}}
{{redirect-distinguish|Mavik|Mavic (disambiguation){{!}}Mavic}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 470612121
| IUPAC_name = (2''S'',3''aR'',7''aS'')-1-[(2''S'')-2-<nowiki/>{[(2''S'')-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydro-1''H''-indole-2-carboxylic acid
| image = Trandolapril structure.svg
| width2 = 222

<!--Clinical data-->
| tradename = Mavik, others
| Drugs.com = {{drugs.com|monograph|trandolapril}}
| MedlinePlus = a697010
| pregnancy_US = D
| legal_status = Rx-only
| routes_of_administration = By mouth

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = Trandolapril 80%<br />(independent of concentration)<br />Trandolaprilat 65 to 94%<br />(concentration-dependent)
| metabolism = [[Liver]]
| elimination_half-life = 6 hours (trandolapril)<br />10 hours (trandolaprilat)
| excretion = Fecal and [[Kidney]]

<!--Identifiers-->
| IUPHAR_ligand = 6453
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 87679-37-6
| ATC_prefix = C09
| ATC_suffix = AA10
| PubChem = 5484727
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00519
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4588590
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1T0N3G9CRC
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00383
| ChEBI = 9649
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1519

<!--Chemical data-->
| 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_Ref = {{stdinchicite|correct|chemspider}}
| 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VXFJYXUZANRPDJ-WTNASJBWSA-N
| melting_point = 119
| melting_high = 123
}}
<!-- Definition and medical uses -->
'''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.

<!-- Society and culture -->
It was patented in 1981 and approved for medical use in 1993.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=469 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA469 |language=en}}</ref> It is marketed by [[Abbott Laboratories]] under the brand name '''Mavik'''.

== Side effects ==
[[Side effect]]s reported for trandolapril include [[nausea]], [[vomiting]], [[diarrhea]], [[headache]], dry cough, [[dizziness]] or [[lightheadedness]] when [[orthostasis|sitting up or standing]], [[hypotension]], or [[fatigue (physical)|fatigue]].{{cn|date=February 2025}}

== Possible drug interactions ==
Patients also on [[diuretic]]s may experience an [[hypotension|excessive reduction of blood pressure]] after initiation of therapy with trandolapril. It can reduce potassium loss caused by [[thiazide diuretic]]s 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.{{cn|date=February 2025}}

== Contraindications and precautions ==
:{{main article|ACE inhibitor#Contraindications and precautions}}

==Pregnancy and lactation==
Trandolapril is [[teratogenic]] (US: [[pregnancy category]] D) and can cause [[birth defect]]s 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 [[lactation|nursing]] mothers.{{cn|date=February 2025}}

==Additional effects==
[[Combination therapy]] with [[paricalcitol]] and trandolapril has been found to reduce [[fibrosis]] in [[obstructive uropathy]].<ref>{{cite journal | vauthors = Tan X, He W, Liu Y | title = Combination therapy with paricalcitol and trandolapril reduces renal fibrosis in obstructive nephropathy | journal = Kidney International | volume = 76 | issue = 12 | pages = 1248–1257 | date = December 2009 | pmid = 19759524 | pmc = 5527548 | doi = 10.1038/ki.2009.346 }}</ref>

== Pharmacology ==
[[File:Trandolaprilat.svg|thumb|left|Trandolaprilat — the active metabolite of trandolapril]] {{clear left}}
Trandolapril is a [[prodrug]] that is de[[ester]]ified 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%.{{cn|date=February 2025}}

== Mode of action ==
:{{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.{{cn|date=February 2025}}

== References ==
{{reflist}}

== External links ==
* [http://www.rxlist.com/cgi/generic3/mavik.htm Trandolapril Information - rxlist.com] (Rxlist.com, The Internet Drug Index)

{{ACE inhibitors}}
{{Angiotensin receptor modulators}}

[[Category:ACE inhibitors]]
[[Category:Carboxamides]]
[[Category:Carboxylic acids]]
[[Category:Drugs developed by AbbVie]]
[[Category:Enantiopure drugs]]
[[Category:Ethyl esters]]
[[Category:Indoles]]
[[Category:Prodrugs]]