Trandolapril Chemical Properties

Melting point:

122-123°C

Boiling point:

626.0±55.0 °C(Predicted)

Density 

1.181±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: ≥20mg/mL

form 

white powder

pka

3.15±0.20(Predicted)

color 

White to Off-White

InChIKey

VXFJYXUZANRPDJ-WTNASJBWSA-N

SMILES

N1(C(=O)[C@@H](N[C@H](C(OCC)=O)CCC2=CC=CC=C2)C)[C@]2([H])[C@]([H])(CCCC2)C[C@H]1C(O)=O

CAS DataBase Reference

87679-37-6(CAS DataBase Reference)

Safety Information

WGK Germany 

3

RTECS 

NL6015178

HS Code 

2933995300

Hazardous Substances Data

87679-37-6(Hazardous Substances Data)

MSDS

• Language:English Provider:(2S,3aR,7aS)-1-[(2S)-2-[[(1S)-1-Ethoxycarbonyl-3-phenyl-propyl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid

Trandolapril Usage And Synthesis

Description

Trandolapril is a new ACE inhibitor that is rapidly hydrolyzed, mainly in the liver, to its biologically active form, trandolaprilat. Compared with all other ACE inhibitors, trandolaprilat is reported to have the highest lipophilicity and the most prolonged ACE inhibitory activity. In hypertensive patients, trandolapril at a dose of 2 mg reduces blood pressure consistently throughout the 24 hour period after intake, making it one of the best once a day antihypertensive drugs. It has also been demonstrated to inhibit aortic atherosclerosis in the hyperlipidemic rabbit.

Chemical Properties

White or almost white powder.

Originator

Roussel Uclaf (France)

Uses

Trandolapril has been used as an angiotensin-converting enzyme (ACE) inhibitor to study its effects on responsiveness of human retinal endothelial cells (HRECs) to vascular endothelial growth factor (VEGF).

Uses

An antihypertensive. Angiotensin converting enzyme (ACE) inhibitor

Uses

antibacterial

Definition

ChEBI: Trandolapril is a heterobicylic compound that is (2S,3aR,7aS)-1-[(2S)-2-aminopropanoyl]octahydro-1H-indole-2-carboxylic acid in which the hydrogen of the amino group is substituted by a (2R)-1-ethoxy-1-oxo-4-phenylbutan-2-yl group. It is a angiotensin-converting enzyme inhibitor and a prodrug used for the treatment of hypertension. It has a role as a prodrug, an antihypertensive agent and an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor. It is a dicarboxylic acid monoester, a dipeptide, an ethyl ester, a secondary amino compound, a tertiary carboxamide and an organic heterobicyclic compound. It is functionally related to a trandolaprilat.

brand name

Odrik; Udrik; Gopten

General Description

Trandolapril, 1-[2-(1-ethoxycarbonyl-3-phenylpropylamino)propionyl]octahydroindole-2-carboxylicacid (Mavik), is an indole-containing ACE inhibitorthat is structurally related to most of the precedingagents discussed. Enalapril is very similar to trandolapril,with the primary difference occurring in the heterocyclicsystems. The pyrrolidine of enalapril has been replacedwith an octahydroindole system. Much like enalaprilate,trandolapril must be hydrolyzed to tranolaprilate, which isthe bioactive species.

Biochem/physiol Actions

Trandolapril is an ACE inhibitor. Trandolapril differs from other ACE inhibitors in that it has a longer biological half-life and a high degree of lipophilicity.

Clinical Use

Angiotensin converting enzyme inhibitor:
Hypertension
Heat failure
After myocardial infarction

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: antagonism of hypotensive effect and increased risk of renal impairment with NSAIDs; hyperkalaemia with ketorolac and other NSAIDs.
Antihypertensives: increased risk of hyperkalaemia, hypotension and renal failure with ARBs and aliskiren.
Bee venom extract: possible severe anaphylactoid reactions when used together.
Ciclosporin: increased risk of hyperkalaemia and nephrotoxicity.
Cytotoxics: increased risk of angioedema with everolimus.
Diuretics: enhanced hypotensive effect; hyperkalaemia with potassium-sparing diuretics.
ESAs: increased risk of hyperkalaemia; antagonism of hypotensive effect.
Gold: flushing and hypotension with sodium aurothiomalate.
Lithium: reduced excretion (possibility of enhanced lithium toxicity).
Potassium salts: increased risk of hyperkalaemia.
Tacrolimus: increased risk of hyperkalaemia and nephrotoxicity.

Metabolism

Trandolapril is metabolised in the liver to the active trandolaprilat and to some inactive metabolites. About 33
% of an oral dose of trandolapril is excreted in the urine, mainly as trandolaprilat; the rest is excreted in the faeces.

Trandolapril(87679-37-6)Related Product Information

• DIETHOXYMETHANE
• PHENYL VALERATE
• 4-Ethoxyphenol
• Phenetidine
• Diethoxymethyl acetate
• Propyl butyrate
• Ethoxyquin
• Phenylhydrazine
• 2-Ethoxyphenol
• acetic acid, triethoxy-, ethyl ester
• Propyl gallate
• Trandolapril-d5
• Trandolaprilat
• ZOPICLONE OXIDE
• Zopiclone
• Trandolapril Acyl--D-glucuronide, 85%
• TRANDOLAPRIL-PHENYL-D5
• TRANDOLAPRIL IMPURITY D