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Details

Stereochemistry RACEMIC
Molecular Formula C13H19N5.H2O
Molecular Weight 263.3392
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PINACIDIL

SMILES

CC(C(C)(C)C)NC(=NC#N)N=c1cc[nH]cc1.O

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 H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H19N5
Molecular Weight 245.324
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

CNS Activity

Curator's Comment:: Pinacidil does not have a high propensity for crossing the blood/brain barrier

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
69.7 ng/mL
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
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
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:
unhealthy, 53.1 years
n = 31
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Population Size: 31
Sources:
Other AEs: Headache, Edema...
Other AEs:
Headache (9.7%)
Edema (29%)
Dizziness (9.7%)
Asthenia (3.2%)
Tachycardia (12.9%)
Palpitation (3.2%)
Sources:
25 mg 2 times / day multiple, oral
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources:
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
Disc. AE: Edema, Tachycardia...
AEs leading to
discontinuation/dose reduction:
Edema (5.9%)
Tachycardia (3.4%)
Sources:
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:
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
Disc. AE: Edema...
AEs leading to
discontinuation/dose reduction:
Edema (18.8%)
Sources:
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:
unhealthy, 53.1 years
n = 31
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Population Size: 31
Sources:
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:
unhealthy, 53.1 years
n = 31
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Population Size: 31
Sources:
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:
unhealthy, 53.1 years
n = 31
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Population Size: 31
Sources:
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:
unhealthy, 53.1 years
n = 31
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Population Size: 31
Sources:
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:
unhealthy, 53.1 years
n = 31
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Population Size: 31
Sources:
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:
unhealthy, 53.1 years
n = 31
Health Status: unhealthy
Age Group: 53.1 years
Sex: M+F
Population Size: 31
Sources:
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:
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
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:
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
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:
unhealthy, 53.6 ± 11.0 years
Health Status: unhealthy
Age Group: 53.6 ± 11.0 years
Sex: M+F
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Pinacidil relaxes porcine and human coronary arteries by activating ATP-dependent potassium channels in smooth muscle cells.
1995 Nov
A family of sulfonylurea receptors determines the pharmacological properties of ATP-sensitive K+ channels.
1996 May
A novel sulfonylurea receptor forms with BIR (Kir6.2) a smooth muscle type ATP-sensitive K+ channel.
1996 Oct 4
Sulphonylurea receptor 2B and Kir6.1 form a sulphonylurea-sensitive but ATP-insensitive K+ channel.
1997 Mar 15
Patents

Patents

Sample Use Guides

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 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 Fri Jun 25 22:13:46 UTC 2021
Edited
by admin
on Fri Jun 25 22:13:46 UTC 2021
Record UNII
7B0ZZH8P2W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PINACIDIL
MART.   ORANGE BOOK   USAN   VANDF  
USAN  
Official 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
PINACIDIL MONOHYDRATE [WHO-DD]
Common Name English
GUANIDINE, N''-CYANO-N-4-PYRIDINYL-N'-(1,2,2-TRIMETHYLPROPYL)-, MONOHYDRATE, (+/-)
Common Name English
PINACIDIL MONOHYDRATE
MI   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 Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
WHO-ATC C02DG01
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
WHO-VATC QC02DG01
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
WHO-ATC C02LX01
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
NCI_THESAURUS C270
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
Code System Code Type Description
FDA UNII
7B0ZZH8P2W
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
IUPHAR
2412
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
EPA CompTox
85371-64-8
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
PUBCHEM
55329
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
CAS
85371-64-8
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
MESH
D020110
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
MERCK INDEX
M8819
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY Merck Index
RXCUI
33717
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C66387
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
DRUG BANK
DB06762
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
WIKIPEDIA
PINACIDIL
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
DRUG CENTRAL
2173
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL1159
Created by admin on Fri Jun 25 22:13:46 UTC 2021 , Edited by admin on Fri Jun 25 22:13:46 UTC 2021
PRIMARY
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PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY