PINACIDIL

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2434746

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

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sulfonylurea receptor 2, Kir6.2 11 Target ID: CHEMBL2095198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9692785 \| https://www.ncbi.nlm.nih.gov/pubmed/10825398 \| https://www.ncbi.nlm.nih.gov/pubmed/11118199 \| https://link.springer.com/article/10.1007/s11434-012-5035-0	Opener 34		2.0 µM [EC50]
Transient receptor potential cation channel subfamily A member 1 38 Target ID: CHEMBL6007 Sources: https://link.springer.com/article/10.1007/s11434-012-5035-0	Agonist 2678		260.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3188983 http://cursoenarm.net/UPTODATE/contents/mobipreview.htm?15/11/15548?source=HISTORY https://www.ncbi.nlm.nih.gov/pubmed/2196168	Primary		Approved 8429	PINDAC Approved Use Hypertension Launch Date 6.3080641E11

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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 n = 31 Health Status: unhealthy Age Group: 53.1 years Sex: M+F Population Size: 31 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

AE	Significance	Dose	Population
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 n = 31 Health Status: unhealthy Age Group: 53.1 years Sex: M+F Population Size: 31 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 n = 31 Health Status: unhealthy Age Group: 53.1 years Sex: M+F Population Size: 31 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 n = 31 Health Status: unhealthy Age Group: 53.1 years Sex: M+F Population Size: 31 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 n = 31 Health Status: unhealthy Age Group: 53.1 years Sex: M+F Population Size: 31 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 n = 31 Health Status: unhealthy Age Group: 53.1 years Sex: M+F Population Size: 31 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 n = 31 Health Status: unhealthy Age Group: 53.1 years Sex: M+F Population Size: 31 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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C19 991 CYP2E1 667

Drug as victim

Target	Modality	Activity
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11851418/ Page: 5.0	major
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11851418/ Page: 5.0	no
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11851418/ Page: 5.0	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11851418/ Page: 5.0	no
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11851418/ Page: 5.0	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11851418/ Page: 5.0	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11851418/ Page: 5.0	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11851418/ Page: 5.0	no
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11851418/ Page: 5.0	yes

Sourcing

Vendor/Aggregator	ID	URL
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
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
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
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
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/
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
eNovation Chemicals	D676220	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676220
mcule	MCULE-2402591602	https://mcule.com/MCULE-2402591602/

PubMed

Title	Date	PubMed
Pinacidil relaxes porcine and human coronary arteries by activating ATP-dependent potassium channels in smooth muscle cells.	1995 Nov	7473155
A family of sulfonylurea receptors determines the pharmacological properties of ATP-sensitive K+ channels.	1996 May	8630239
A novel sulfonylurea receptor forms with BIR (Kir6.2) a smooth muscle type ATP-sensitive K+ channel.	1996 Oct 4	8798681
Sulphonylurea receptor 2B and Kir6.1 form a sulphonylurea-sensitive but ATP-insensitive K+ channel.	1997 Mar 15	9130167

Patents

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 `Fri Dec 15 17:37:25 UTC 2023` Edited by `admin` on `Fri Dec 15 17:37:25 UTC 2023`
Record UNII	7B0ZZH8P2W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PINACIDIL

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

GUANIDINE, N''-CYANO-N-4-PYRIDINYL-N'-(1,2,2-TRIMETHYLPROPYL)-, MONOHYDRATE, (±)-

Common Name

English

Pinacidil monohydrate [WHO-DD]

Common Name

English

PINACIDIL MONOHYDRATE

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