This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Pinacidil
DrugBank Accession Number
DB06762
Background

Pinacidil is a cyanoguanidine drug that acts by opening ATP-sensitive potassium channels, leading to peripheral vasodilatation of arterioles and decreasing peripheral vascular resistance. The above processes result in reduced blood pressure. This drug has been discontinued by the FDA.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 245.33
Monoisotopic: 245.164045632
Chemical Formula
C13H19N5
Synonyms
  • Pinacidil
  • Pinacidil anhydrous
  • Pinacidilum
External IDs
  • P 1134
  • P-1134
  • S 1230
  • S-1230

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbametapirThe serum concentration of Pinacidil can be increased when it is combined with Abametapir.
AcebutololAcebutolol may increase the hypotensive activities of Pinacidil.
AceclofenacThe therapeutic efficacy of Pinacidil can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Pinacidil can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Pinacidil.
AlclofenacThe therapeutic efficacy of Pinacidil can be decreased when used in combination with Alclofenac.
AldesleukinAldesleukin may increase the hypotensive activities of Pinacidil.
AlfentanilAlfentanil may decrease the antihypertensive activities of Pinacidil.
AlfuzosinAlfuzosin may increase the hypotensive activities of Pinacidil.
AliskirenPinacidil may increase the hypotensive activities of Aliskiren.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pinacidil monohydrate7B0ZZH8P2W85371-64-8AFJCNBBHEVLGCZ-UHFFFAOYSA-N
International/Other Brands
Pindac (Leo Pharm)

Categories

ATC Codes
C02DG01 — PinacidilC02LX01 — Pinacidil and diuretics
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Not Available
Direct Parent
Pyridines and derivatives
Alternative Parents
Heteroaromatic compounds / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carboximidamide / Guanidine / Heteroaromatic compound / Hydrocarbon derivative / Organic 1,3-dipolar compound / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
BB4UGO5K0D
CAS number
60560-33-0
InChI Key
IVVNZDGDKPTYHK-UHFFFAOYSA-N
InChI
InChI=1S/C13H19N5/c1-10(13(2,3)4)17-12(16-9-14)18-11-5-7-15-8-6-11/h5-8,10H,1-4H3,(H2,15,16,17,18)
IUPAC Name
(Z)-N'-cyano-N-(3,3-dimethylbutan-2-yl)-N''-(pyridin-4-yl)guanidine
SMILES
CC(N\C(NC#N)=N\C1=CC=NC=C1)C(C)(C)C

References

General References
  1. Hansen PR: [Pinacidil (Pindac). A peripheral vasodilator agent with a new mechanism of action]. Ugeskr Laeger. 1989 Oct 30;151(44):2906-8. [Article]
  2. Ahnfelt-Ronne I: Pinacidil. Preclinical investigations. Drugs. 1988;36 Suppl 7:4-9. [Article]
  3. Koliopoulos K, Papadoyannis DE, Karatzas NB: Pinacidil, a new vasodilator, in the treatment of patients with moderate to severe hypertension. Eur J Clin Pharmacol. 1984;27(3):287-9. [Article]
ChemSpider
4660
BindingDB
50240750
RxNav
33717
ChEBI
91706
ChEMBL
CHEMBL1159
Wikipedia
Pinacidil

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.136 mg/mLALOGPS
logP2.3ALOGPS
logP1.94Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)16.28Chemaxon
pKa (Strongest Basic)8.16Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area73.1 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity73.04 m3·mol-1Chemaxon
Polarizability27.31 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-2790000000-b4614b7b3adabc514ad4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dj-5901100000-3131ef3fa766db3846ca

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhang Z, Li Y, Stearns RA, Ortiz De Montellano PR, Baillie TA, Tang W: Cytochrome P450 3A4-mediated oxidative conversion of a cyano to an amide group in the metabolism of pinacidil. Biochemistry. 2002 Feb 26;41(8):2712-8. [Article]

Drug created at September 14, 2010 16:21 / Updated at February 21, 2021 18:52