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Details

Stereochemistry RACEMIC
Molecular Formula C13H19N5.H2O
Molecular Weight 263.3387
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PINACIDIL

SMILES

O.CC(NC(NC1=CC=NC=C1)=NC#N)C(C)(C)C

InChI

InChIKey=AFJCNBBHEVLGCZ-UHFFFAOYSA-N
InChI=1S/C13H19N5.H2O/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);1H2

HIDE SMILES / InChI
Molecular Formula C13H19N5
Molecular Weight 245.3235
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Pinacidil is a clinically effective vasodilator used for the treatment of hypertension.

CNS Activity

CNS Non-penetrant
1040
Curator's Comment: Pinacidil does not have a high propensity for crossing the blood/brain barrier

Originator

Approval Year

1989
115
Targets

Targets

Primary TargetPharmacologyConditionPotency
Opener
34
 2.0 µM [EC50]
Agonist
2752
 260.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
PINDAC

Approved Use

Hypertension

Launch Date

1989
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
69.7 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10028374
12.5 mg 2 times / day multiple, oral
dose: 12.5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PINACIDIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
365.4 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10028374
12.5 mg 2 times / day multiple, oral
dose: 12.5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PINACIDIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10028374
12.5 mg 2 times / day multiple, oral
dose: 12.5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PINACIDIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
unhealthy, 53.1 years
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
Other AEs: Headache, Edema...
Other AEs:
Headache (9.7%)
Edema (29%)
Dizziness (9.7%)
Asthenia (3.2%)
Tachycardia (12.9%)
Palpitation (3.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
25 mg 2 times / day multiple, oral
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
Disc. AE: Edema, Tachycardia...
AEs leading to
discontinuation/dose reduction:
Edema (5.9%)
Tachycardia (3.4%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
37.5 mg 2 times / day multiple, oral
Dose: 37.5 mg, 2 times / day
Route: oral
Route: multiple
Dose: 37.5 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
Disc. AE: Edema...
AEs leading to
discontinuation/dose reduction:
Edema (18.8%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
AEs

AEs

AESignificanceDosePopulation
Tachycardia 12.9%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
unhealthy, 53.1 years
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
Edema 29%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
unhealthy, 53.1 years
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
Asthenia 3.2%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
unhealthy, 53.1 years
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
Palpitation 3.2%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
unhealthy, 53.1 years
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
Dizziness 9.7%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
unhealthy, 53.1 years
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
Headache 9.7%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
unhealthy, 53.1 years
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2466178
Tachycardia 3.4%
Disc. AE
25 mg 2 times / day multiple, oral
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
Edema 5.9%
Disc. AE
25 mg 2 times / day multiple, oral
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
Edema 18.8%
Disc. AE
37.5 mg 2 times / day multiple, oral
Dose: 37.5 mg, 2 times / day
Route: oral
Route: multiple
Dose: 37.5 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2758730
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
substrate
1193
substrate
1388

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1197

CYP2A6
626

CYP2B6
776

CYP2C8
810

CYP2C19
1119

CYP2E1
729
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1946
 major
CYP1A2
1197
 no
CYP2A6
626
 no
CYP2B6
776
 no
CYP2C19
1119
 no
CYP2C8
810
 no
CYP2C9
1193
 no
CYP2E1
729
 no
CYP2D6
1388
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY562883
https://www.001chemical.com/chem/60560-33-0
3B Scientific (Wuhan) Corp
3B3-062585
http://www.3bsc.com/index/pro_info.php?id=101708
AA Blocks
AA004OUW
https://www.aablocks.com/goods/Goods/detail?id=AA004OUW
Aaron Chemicals
AR004PMO
http://www.aaronchem.com/85371-64-8
Achemica
ACMC-20mijl
http://www.achemica.com/prodinfo/?id=205392
Achemtek
0102-012964
http://www.achemtek.com/60560-33-0
AHH Chemical co.,ltd
MT-58006
http://www.ahhchemical.com/product/MT-58006.html
AK Scientific, Inc. (AKSCI)
2657AH
http://www.aksci.com/item_detail.php?cat=2657AH
Ambinter
Amb21855945
http://www.ambinter.com/reference/21855945
Aurora Fine Chemicals LLC
K01.232.447
http://online.aurorafinechemicals.com/info?ID=K01.232.447
BLD Pharm
BD148078
http://www.bldpharm.com/products/60560-33-0.html
Boerchem
BC202316
http://www.boerchem.com/?product_33966.html
ChemMol
44001175
http://www.chemmol.com/chemmol/44001175.html
ChemMol
49422510
http://www.chemmol.com/chemmol/49422510.html
ChemMol
99119191
http://www.chemmol.com/chemmol/99119191.html
Chemspace
CSSB00020618617
https://chem-space.com/CSSB00020618617
eNovation Chemicals
D676220
https://www.enovationchem.com/ProductDetails.asp?ProductID=D676220
Finetech
FT-0630932
http://www.finetechnology-ind.com/prod/detail/pub/85371-64-8.html
Glentham Life Sciences
GP1084
http://www.glentham.com/products/product/GP1084/
mcule
MCULE-2402591602
https://mcule.com/MCULE-2402591602/
Molcore
MC562883
https://www.molcore.com/product/60560-33-0
OChem
21738
http://www.ocheminc.com/index.php?act=psearch&pid=371P648
OChem
30687
http://www.ocheminc.com/index.php?act=psearch&pid=560P330
Smolecule
S539702
http://www.smolecule.com/products/s539702
THE BioTek
bt-278368
https://www.thebiotek.com/product/inhibitors/bt-278368
Yuhao Chemical
YH89905
http://www.chemyuhao.com/85371-64-8.html
PubMed

PubMed

TitleDatePubMed
Sulphonylurea receptor 2B and Kir6.1 form a sulphonylurea-sensitive but ATP-insensitive K+ channel.
1997-03-15
A novel sulfonylurea receptor forms with BIR (Kir6.2) a smooth muscle type ATP-sensitive K+ channel.
1996-10-04
A family of sulfonylurea receptors determines the pharmacological properties of ATP-sensitive K+ channels.
1996-05
Pinacidil relaxes porcine and human coronary arteries by activating ATP-dependent potassium channels in smooth muscle cells.
1995-11
Patents

Patents

JPH01224316A
2

Sample Use Guides

In Vivo Use Guide
Adults: Oral: 12.5 mg twice daily, may increase at intervals of 1-2 weeks; maximum dose: 100-150 mg/day in divided doses
Route of Administration: Oral
In Vitro Use Guide
In murine WT ventricular cells, pinacidil (1-100uM) concentration-dependently induced an outward current and action potential shortening, effects that were blocked by glibenclamide, a K(ATP) channel blocker.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:49:38 GMT 2025
Edited
by admin
on Mon Mar 31 18:49:38 GMT 2025
Record UNII
7B0ZZH8P2W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PINACIDIL
MART.   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
PINACIDIL MONOHYDRATE
MI   WHO-DD  
Preferred Name English
PINDAC
Brand Name English
GUANIDINE, N-CYANO-N'-4-PYRIDINYL-N''-(1,2,2-TRIMETHYLPROPYL)-, MONOHYDRATE
Systematic Name English
PINACIDIL MONOHYDRATE [MI]
Common Name English
PINACIDIL [MART.]
Common Name English
PINACIDIL [JAN]
Common Name English
GUANIDINE, N''-CYANO-N-4-PYRIDINYL-N'-(1,2,2-TRIMETHYLPROPYL)-, MONOHYDRATE, (±)-
Common Name English
Pinacidil monohydrate [WHO-DD]
Common Name English
PINACIDIL [USAN]
Common Name English
PINACIDIL [VANDF]
Common Name English
NSC-759588
Code English
(±)-2-CYANO-1-(4-PYRIDINYL)-3-(1,2,2-TRIMETHYLPROPYL)GUANIDINE MONOHYDRATE
Systematic Name English
PINACIDIL [ORANGE BOOK]
Common Name English
GUANIDINE, N-CYANO-N'-4-PYRIDINYL-N''-(1,2,2-TRIMETHYLPROPYL)-, HYDRATE (1:1)
Systematic Name English
Classification Tree Code System Code
WHO-VATC QC02LX01
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
WHO-ATC C02DG01
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
WHO-VATC QC02DG01
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
WHO-ATC C02LX01
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
NCI_THESAURUS C270
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
Code System Code Type Description
FDA UNII
7B0ZZH8P2W
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
IUPHAR
2412
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID4045682
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
PUBCHEM
55329
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
CAS
85371-64-8
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
NSC
759588
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
MESH
D020110
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
MERCK INDEX
m8819
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY Merck Index
RXCUI
33717
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C66387
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
DRUG BANK
DB06762
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
WIKIPEDIA
PINACIDIL
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
DRUG CENTRAL
2173
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL1159
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
USAN
U-14
Created by admin on Mon Mar 31 18:49:38 GMT 2025 , Edited by admin on Mon Mar 31 18:49:38 GMT 2025
PRIMARY
Related Record Type Details
Structure of PINACIDIL ANHYDROUS
PARENT -> SALT/SOLVATE
Structure of PINACIDIL ANHYDROUS
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of PINACIDIL ANHYDROUS
ACTIVE MOIETY
NIH
NCATS
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