Trandolapril

Identification

Summary

Trandolapril is a prodrug of an ACE inhibitor used to treat hypertension, congestive heart failure, and to improve survival following a myocardial infarction.

Brand Names

Mavik, Tarka

Generic Name

Trandolapril

DrugBank Accession Number

DB00519

Background

Trandolapril is a non-sulhydryl prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is metabolized to its biologically active diacid form, trandolaprilat, in the liver. Trandolaprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Trandolapril may be used to treat mild to moderate hypertension, to improve survival following myocardial infarction in clinically stable patients with left ventricular dysfunction, as an adjunct treatment for congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Trandolapril (DB00519)

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Weight

Average: 430.5372
Monoisotopic: 430.246772208

Chemical Formula

C₂₄H₃₄N₂O₅

Synonyms

• Trandolapril
• Trandolaprilum

External IDs

• RU 44570
• RU-44570

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Pharmacology

Indication

For the treatment of mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure (CHF), to improve survival following myocardial infarction (MI) in individuals who are hemodynamically stable and demonstrate symptoms of left ventricular systolic dysfunction or signs of CHF within a few days following acute MI, and to slow progression of renal disease in hypertensive patients with diabetes mellitus and microalbuminuria or overt nephropathy.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Symptomatic treatment of	Heart failure		••••••••••••			••••••
Used in combination to manage	High blood pressure (hypertension)		••••••••••••			••••••
Management of	High blood pressure (hypertension)		••••••••••••			••••••
Used in combination to manage	Hypertension	Combination Product in combination with: Verapamil (DB00661)	••••••••••••			••••••• •••••••• •••••••
Symptomatic treatment of	Left ventricular dysfunction		••••••••••••			••••••

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Pharmacodynamics

Trandolapril is the ethyl ester prodrug of a nonsulfhydryl ACE inhibitor, trandolaprilat. Trandolapril is deesterified in the liver to the diacid metabolite, trandolaprilat, which is approximately eight times more active as an inhibitor of ACE than its parent compound. ACE is a peptidyl dipeptidase that is part of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure via a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may further sustain the effects of trandolaprilat by causing increased vasodilation and decreased blood pressure. The blood pressure lowering effect of trandolaprilat is due to a decrease in peripheral vascular resistance, which is not accompanied by significant changes in urinary excretion of chloride or potassium or water or sodium retention.

Mechanism of action

There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Trandolaprilat, the active metabolite of trandolapril, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Trandolaprilat also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors.

Target	Actions	Organism
AAngiotensin-converting enzyme	inhibitor	Humans

Absorption

~ 40-60% absorbed; extensive first pass metabolism results in a low bioavailability of 4-14%

Volume of distribution

• 18 L

Protein binding

Serum protein binding of trandolapril is ~ 80% (independent of concentration and not saturable) while that of trandolaprilat is 65 to 94% (concentration-dependent and saturable).

Metabolism

Cleavage of the ester group of trandolapril, primarily in the liver, is responsible for conversion to trandolaprilat, the active metabolite. Seven other metabolites, including diketopiperazine and glucuronide conjugated derivatives of trandolapril and trandolaprilat, have been identified.

Hover over products below to view reaction partners

• Trandolapril
  • Diketopiperazine
  • Trandolaprilat

Route of elimination

After oral administration of trandolapril, about 33% of parent drug and metabolites are recovered in urine, mostly as trandolaprilat, with about 66% in feces.

Half-life

The elimination half lives of trandolapril and trandolaprilat are about 6 and 10 hours, respectively, but, similar to all ACE inhibitors, trandolaprilat also has a prolonged terminal elimination phase that involves a small fraction of administered drug. This likely represents drug binding to plasma and tissue ACE. The effective half life of elimination for trandolaprilat is 16-24 hours.

Clearance

• 52 L/h [After approximately 2 mg IV doses]

Adverse Effects

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Toxicity

Most likely clinical manifestations of overdose are symptoms of severe hypotension. Most common adverse effects include cough, headache and dizziness. The oral LD₅₀ of trandolapril in mice was 4875 mg/kg in males and 3990 mg/kg in females. In rats, an oral dose of 5000 mg/kg caused low mortality (1 male out of 5; 0 females). In dogs, an oral dose of 1000 mg/kg did not cause mortality and abnormal clinical signs were not observed.

Pathways

Pathway	Category
Trandolapril Action Pathway	Drug action
Trandolapril Metabolism Pathway	Drug metabolism

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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abaloparatide	The risk or severity of adverse effects can be increased when Trandolapril is combined with Abaloparatide.
Acebutolol	Trandolapril may increase the hypotensive activities of Acebutolol.
Aceclofenac	The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Trandolapril.
Acemetacin	The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Trandolapril.
Acetylsalicylic acid	The therapeutic efficacy of Trandolapril can be decreased when used in combination with Acetylsalicylic acid.

Food Interactions

• Avoid hypertensive herbs (e.g. bayberry, blue cohosh, cayenne, ephedra, and licorice).
• Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
• Limit salt intake. Salt may attenuate the antihypertensive effect.
• Take with or without food. The absorption is unaffected by food.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Trandolapril hydrochloride	3EY8XK2J4T	87725-72-2	QNSWMJYOGMUVGO-REWXTUPXSA-N

Active Moieties

Name	Kind	UNII	CAS	InChI Key
Trandolaprilat	prodrug	RR6866VL0O	87679-71-8	AHYHTSYNOHNUSH-HXFGRODQSA-N

Product Images

PreviousNext

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Mavik	Capsule	2 mg	Oral	Bgp Pharma Ulc	1998-01-14	Not applicable
Mavik	Capsule	4 mg	Oral	Bgp Pharma Ulc	2003-11-01	Not applicable
Mavik	Tablet	1 mg/1	Oral	AbbVie Inc.	1996-04-26	2017-06-30
Mavik	Capsule	1 mg	Oral	Bgp Pharma Ulc	1998-01-07	Not applicable
Mavik	Tablet	4 mg/1	Oral	AbbVie Inc.	1996-04-26	2016-04-30

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apo-trandolapril	Capsule	2 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Apo-trandolapril	Capsule	1 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Apo-trandolapril	Capsule	4 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Apo-trandolapril	Capsule	0.5 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Auro-trandolapril	Capsule	4 mg	Oral	Auro Pharma Inc	2018-09-27	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Tarka	Trandolapril (2 mg/1) + Verapamil hydrochloride (180 mg/1)	Tablet, film coated, extended release	Oral	AbbVie Inc.	1996-10-22	2021-08-14
Tarka	Trandolapril (1 mg) + Verapamil hydrochloride (240 mg)	Tablet, extended release	Oral	Abbott	2002-07-15	2010-11-12
Tarka	Trandolapril (2 mg/1) + Verapamil hydrochloride (240 mg/1)	Tablet, film coated, extended release	Oral	Physicians Total Care, Inc.	2005-05-27	Not applicable
Tarka	Trandolapril (2 mg/1) + Verapamil hydrochloride (240 mg/1)	Tablet, film coated, extended release	Oral	AbbVie Inc.	1996-10-22	2021-09-13
Tarka	Trandolapril (2 mg) + Verapamil hydrochloride (180 mg)	Tablet, extended release	Oral	Abbott	2002-07-15	2010-11-12

Categories

ATC Codes

C09AA10 — Trandolapril

• C09AA — ACE inhibitors, plain
• C09A — ACE INHIBITORS, PLAIN
• C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
• C — CARDIOVASCULAR SYSTEM

C09BB10 — Trandolapril and verapamil

• C09BB — ACE inhibitors and calcium channel blockers
• C09B — ACE INHIBITORS, COMBINATIONS
• C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
• C — CARDIOVASCULAR SYSTEM

Drug Categories

• ACE Inhibitors and Calcium Channel Blockers
• Agents Acting on the Renin-Angiotensin System
• Agents causing angioedema
• Agents causing hyperkalemia
• Angiotensin-Converting Enzyme Inhibitors
• Antihypertensive Agents
• Antihypertensive Agents Indicated for Hypertension
• Cardiovascular Agents
• Enzyme Inhibitors
• Heterocyclic Compounds, Fused-Ring
• Hypotensive Agents
• Protease Inhibitors

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Alpha amino acid esters / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Indoles and derivatives / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Aralkylamines / Fatty acid esters / Benzene and substituted derivatives / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Carboxylic acid esters / Amino acids / Dialkylamines / Carboxylic acids / Azacyclic compounds / Carbonyl compounds / Organic oxides / Organopnictogen compounds / Hydrocarbon derivatives

show 10 more

Substituents

Alpha-amino acid amide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid ester / Dicarboxylic acid or derivatives / Fatty acid ester / Fatty acyl / Hydrocarbon derivative / Indole or derivatives / Monocyclic benzene moiety / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / N-acyl-l-alpha-amino acid / N-acylpyrrolidine / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Pyrrolidine / Pyrrolidine carboxylic acid / Pyrrolidine carboxylic acid or derivatives / Secondary aliphatic amine / Secondary amine / Tertiary carboxylic acid amide

show 28 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

1T0N3G9CRC

CAS number

87679-37-6

InChI Key

VXFJYXUZANRPDJ-WTNASJBWSA-N

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

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

SMILES

[H][C@@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O

References

Synthesis Reference

Narendra Joshi, Shekhar Bhirud, Buddhavarapu Ramam, Arjun Bodkhe, "Process for the preparation of intermediates of trandolapril and use thereof for the preparation of trandolapril." U.S. Patent US20060079698, issued April 13, 2006.

US20060079698

General References

1. Berl T: Review: renal protection by inhibition of the renin-angiotensin-aldosterone system. J Renin Angiotensin Aldosterone Syst. 2009 Mar;10(1):1-8. doi: 10.1177/1470320309102747. [Article]
2. Conen H, Brunner HR: Pharmacologic profile of trandolapril, a new angiotensin-converting enzyme inhibitor. Am Heart J. 1993 May;125(5 Pt 2):1525-31. [Article]
3. Diaz A, Ducharme A: Update on the use of trandolapril in the management of cardiovascular disorders. Vasc Health Risk Manag. 2008;4(6):1147-58. [Article]
4. Guay DR: Trandolapril: a newer angiotensin-converting enzyme inhibitor. Clin Ther. 2003 Mar;25(3):713-75. [Article]
5. Jouquey S, Stepniewski JP, Hamon G: Trandolapril dose-response in spontaneously hypertensive rats: effects on ACE activity, blood pressure, and cardiac hypertrophy. J Cardiovasc Pharmacol. 1994;23 Suppl 4:S16-8. [Article]
6. Reynolds NA, Wagstaff AJ, Keam SJ: Trandolapril/verapamil sustained release: a review of its use in the treatment of essential hypertension. Drugs. 2005;65(13):1893-914. [Article]
7. Rubio-Guerra AF, Vargas-Robles H, Vargas-Ayala G, Rodriguez-Lopez L, Escalante-Acosta BA: The effect of trandolapril and its fixed-dose combination with verapamil on circulating adhesion molecules levels in hypertensive patients with type 2 diabetes. Clin Exp Hypertens. 2008 Oct;30(7):682-8. doi: 10.1080/10641960802251941. [Article]
8. Sanbe A, Tanonaka K, Kobayasi R, Takeo S: Effects of long-term therapy with ACE inhibitors, captopril, enalapril and trandolapril, on myocardial energy metabolism in rats with heart failure following myocardial infarction. J Mol Cell Cardiol. 1995 Oct;27(10):2209-22. [Article]
9. Torp-Pedersen C, Kober L: Effect of ACE inhibitor trandolapril on life expectancy of patients with reduced left-ventricular function after acute myocardial infarction. TRACE Study Group. Trandolapril Cardiac Evaluation. Lancet. 1999 Jul 3;354(9172):9-12. [Article]
10. Authors unspecified: Trandolapril: an ACE inhibitor for treatment of hypertension. Med Lett Drugs Ther. 1996 Nov 22;38(988):104-5. [Article]
11. Wiseman LR, McTavish D: Trandolapril. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in essential hypertension. Drugs. 1994 Jul;48(1):71-90. [Article]
12. Zannad F: Trandolapril. How does it differ from other angiotensin converting enzyme inhibitors? Drugs. 1993;46 Suppl 2:172-81; discussion 182. [Article]
13. FDA Approved Drug Products: Mavik (trandolapril) tablets for oral use [Link]
14. FDA Approved Drugs: Tarka® extended-release tablets [Link]

External Links

Human Metabolome Database

HMDB0014660

KEGG Drug

D00383

PubChem Compound

5484727

PubChem Substance

46508300

ChemSpider

4588590

BindingDB

50369775

RxNav

38454

ChEBI

9649

ChEMBL

CHEMBL1519

ZINC

ZINC000001853205

Therapeutic Targets Database

DAP000583

PharmGKB

PA451737

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Trandolapril

MSDS

Download (57.2 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Coronary Artery Disease (CAD) / Hypertension	1
4	Completed	Treatment	Diabetes / Hypertension	1
4	Completed	Treatment	Diabetes / Hypertension / Proteinuria	1
4	Completed	Treatment	Heart Failure / Left Ventricular Dysfunction	1
4	Completed	Treatment	Hypertension	3

Pharmacoeconomics

Manufacturers

• Abbott laboratories pharmaceutical products div
• Aurobindo pharma ltd
• Cipla ltd
• Corepharma llc
• Dr reddys laboratories ltd
• Epic pharma llc
• Invagen pharmaceuticals inc
• Lupin ltd
• Mylan pharmaceuticals inc
• Teva pharmaceuticals usa
• Watson laboratories inc

Packagers

• Abbott Laboratories Ltd.
• Arrow Pharm Malta Ltd.
• Aurobindo Pharma Ltd.
• BASF Corp.
• Cipla Ltd.
• Cobalt Pharmaceuticals Inc.
• Corepharma LLC
• DAVA Pharmaceuticals
• Doctor Reddys Laboratories Ltd.
• Glenmark Generics Ltd.
• Greenstone LLC
• InvaGen Pharmaceuticals Inc.
• Lupin Pharmaceuticals Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Physicians Total Care Inc.
• Resource Optimization and Innovation LLC
• Sandoz
• Teva Pharmaceutical Industries Ltd.
• West-Ward Pharmaceuticals

Dosage Forms

Form	Route	Strength
Capsule	Oral
Capsule	Oral	0.5 mg
Capsule	Oral	1 mg
Capsule	Oral	2 mg
Capsule	Oral	4 mg
Tablet, extended release	Oral
Tablet, film coated, extended release	Oral
Tablet, film coated	Oral
Tablet, delayed release	Oral
Capsule, coated	Oral
Tablet	Oral	1 mg/1
Tablet	Oral	2 mg/1
Tablet	Oral	4 mg/1
Capsule	Oral

Prices

Unit description	Cost	Unit
Tarka 1-240 mg Controlled Release Tabs	3.46USD	tab
Tarka 4-240 mg Controlled Release Tabs	3.4USD	tab
Tarka 1-240 mg tablet sa	3.33USD	tablet
Tarka 2-180 mg tablet sa	3.33USD	tablet
Tarka 2-240 mg Controlled Release Tabs	3.33USD	tab
Tarka 2-240 mg tablet sa	3.33USD	tablet
Tarka 4-240 mg tablet sa	3.33USD	tablet
Tarka 2-180 mg Controlled Release Tabs	3.29USD	tab
Mavik 2 mg tablet	1.61USD	tablet
Mavik 4 mg tablet	1.61USD	tablet
Mavik 1 mg tablet	1.47USD	tablet
Trandolapril 1 mg tablet	1.24USD	tablet
Trandolapril 2 mg tablet	1.23USD	tablet
Trandolapril 4 mg tablet	1.23USD	tablet
Mavik 4 mg Capsule	1.03USD	capsule
Mavik 2 mg Capsule	0.83USD	capsule
Mavik 1 mg Capsule	0.72USD	capsule
Mavik 0.5 mg Capsule	0.42USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5744496	No	1998-04-28	2015-04-28
CA2023089	No	2003-01-14	2010-08-10
CA1341206	No	2001-03-20	2018-03-20

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	119-123 °C	Not Available
logP	3.5	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0207 mg/mL	ALOGPS
logP	1.31	ALOGPS
logP	1.95	Chemaxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.8	Chemaxon
pKa (Strongest Basic)	5.21	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	95.94 Å2	Chemaxon
Rotatable Bond Count	10	Chemaxon
Refractivity	115.79 m3·mol-1	Chemaxon
Polarizability	46.96 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9303
Blood Brain Barrier	-	0.8908
Caco-2 permeable	-	0.8501
P-glycoprotein substrate	Substrate	0.7744
P-glycoprotein inhibitor I	Inhibitor	0.5527
P-glycoprotein inhibitor II	Inhibitor	0.7759
Renal organic cation transporter	Non-inhibitor	0.8336
CYP450 2C9 substrate	Non-substrate	0.8227
CYP450 2D6 substrate	Non-substrate	0.8935
CYP450 3A4 substrate	Substrate	0.5515
CYP450 1A2 substrate	Non-inhibitor	0.915
CYP450 2C9 inhibitor	Non-inhibitor	0.785
CYP450 2D6 inhibitor	Non-inhibitor	0.9018
CYP450 2C19 inhibitor	Non-inhibitor	0.796
CYP450 3A4 inhibitor	Non-inhibitor	0.5339
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.6906
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.9188
Biodegradation	Not ready biodegradable	0.9587
Rat acute toxicity	2.2048 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9811
hERG inhibition (predictor II)	Non-inhibitor	0.5531

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-001l-9134000000-c52f8386e44b6f3e4183
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0525900000-d9c0915ea98e09dcb1f2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-1124900000-5eee64e8c1e5f75edd90
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-08gi-1943200000-de24c6ad53cb95ac9a7d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00kf-6904200000-405b8d0e54d6867217cc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-06vl-4922000000-aba8aed6f26b832aed82
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-2910000000-f746a379c603b8b0333c
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	216.9686721	predicted	DarkChem Lite v0.1.0
[M-H]-	223.2352721	predicted	DarkChem Lite v0.1.0
[M-H]-	202.76476	predicted	DeepCCS 1.0 (2019)
[M+H]+	217.2796721	predicted	DarkChem Lite v0.1.0
[M+H]+	223.8521721	predicted	DarkChem Lite v0.1.0
[M+H]+	205.16034	predicted	DeepCCS 1.0 (2019)
[M+Na]+	216.6994721	predicted	DarkChem Lite v0.1.0
[M+Na]+	223.4460721	predicted	DarkChem Lite v0.1.0
[M+Na]+	211.07362	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	0.93	N/A	N/A	A27344

Details

Binding Properties1. Angiotensin-converting enzyme

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Zinc ion binding

Specific Function

Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...

Gene Name

ACE

Uniprot ID

P12821

Uniprot Name

Angiotensin-converting enzyme

Molecular Weight

149713.675 Da

References

1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
2. Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [Article]
3. Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55