APRIKALIM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H16N2OS2
Molecular Weight	268.398
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(=S)[C@@]1(CCCC[S@+]1[O-])C2=CN=CC=C2

InChI

InChIKey=GKEMHVLBZNVZOI-SJKOYZFVSA-N

InChI=1S/C12H16N2OS2/c1-13-11(16)12(6-2-3-8-17(12)15)10-5-4-7-14-9-10/h4-5,7,9H,2-3,6,8H2,1H3,(H,13,16)/t12-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C12H16N2OS2
Molecular Weight	268.398
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8789792 | https://adisinsight.springer.com/drugs/800000232

Aprikalim [RP 52891, RPG 52891] is a potent, specific, and selective opener of ATP-sensitive K+ (KATP) channels. By virtue of this pharmacological property, aprikalim affords cardioprotection in experimental models of ischemia/reperfusion injury, and, at higher doses, also causes peripheral or coronary vasodilatation. It is undergoing phase II clinical trials with Aventis Pharma for the treatment of asthma; heart failure; hypertension; myocardial ischaemia.

Originator

Approval Year

PubMed

Title	Date	PubMed
Effect of subarachnoid hemorrhage on dilatation of rat basilar artery in vivo.	1996-07	8760167
In vivo reactivity of resistance arterioles to activation of ATP-sensitive K+ channels.	1993-09-21	8223932
Role of ATP-sensitive potassium channels in the basilar artery.	1993-01	8430866
Cross tolerance between cromakalim and RP49356 in the uterus of the rat in vivo and in vitro.	1992-09-04	1425963

Sample Use Guides

In Vitro Use Guide

When smooth muscle cells of the rat portal vein were clamped at -10 mV, aprikalim (3 uM) induced a slowly-developing K-current (IKCO), the noise of which gradually increased. Aprikalim (3 uM) inhibited the slowly activating, slowly inactivating delayed rectifier current, ITO.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:42:33 GMT 2025` Edited by `admin` on `Mon Mar 31 18:42:33 GMT 2025`
Record UNII	374BH4KVRG
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

APRIKALIM

Official Name

English

aprikalim [INN]

Preferred Name

English

(-)-(1R,2R)-TETRAHYDRO-N-METHYL-2-(3-PYRIDYL)THIO-2H-THIOPYRAN-2-CARBOXAMIDE 1-OXIDE

Systematic Name

English

2H-THIOPYRAN-2-CARBOTHIOAMIDE, TETRAHYDRO-N-METHYL-2-(3-PYRIDINYL)-, 1-OXIDE, (1R,2R)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C270