NAPITANE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H25NO2
Molecular Weight	335.4394
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C([C@@H]1CCCC2=C1C=CC3=C2OCO3)N4CC[C@@H](C4)C5=CC=CC=C5

InChI

InChIKey=HAEPGZUGYMHCJE-ROUUACIJSA-N

InChI=1S/C22H25NO2/c1-2-5-16(6-3-1)17-11-12-23(13-17)14-18-7-4-8-20-19(18)9-10-21-22(20)25-15-24-21/h1-3,5-6,9-10,17-18H,4,7-8,11-15H2/t17-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H25NO2
Molecular Weight	335.4394
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800005107 | https://www.ncbi.nlm.nih.gov/pubmed/8525465

Napitane [A 75200, ABT 200] is a norepinephrine uptake inhibitor and α2 adrenoceptor antagonist. It was undergoing clinical trials with Abbott in the USA as a treatment for depression. However it was discontinued later. Napitane is a potent alpha 2-adrenoceptor antagonist (Ki = 1.2 nM) with modest norepinephrine uptake-blocking activity (IC50 = 841 nM).

Originator

Approval Year

PubMed

Title	Date	PubMed
Actions of A-75200, a novel catecholamine uptake inhibitor, on norepinephrine uptake and release from bovine adrenal chromaffin cells.	1993 Mar	8450458
ABT-200, a norepinephrine uptake inhibitor, blocks Ca2+ signals in chromaffin cells.	1994 Oct 14	7851493
Effects of the putative antidepressant, ABT 200, on the clearance of exogenous norepinephrine in rat cerebellum.	1995 Sep	8525465

Sample Use Guides

In Vivo Use Guide

Rats: 30 mg/kg i.p.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Napitane is a potent alpha 2-adrenoceptor antagonist (Ki = 1.2 nM) with modest norepinephrine uptake-blocking activity (IC50 = 841 nM).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:00:38 GMT 2023` Edited by `admin` on `Fri Dec 15 17:00:38 GMT 2023`
Record UNII	5Y6TH3C053
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NAPITANE

Official Name

English

(±)-(3R*)-3-PHENYL-1-(((6R*)-6,7,8,9-TETRAHYDRONAPHTHO(1,2-D)-1,3-DIOXOL-6-YL)METHYL)PYRROLIDINE

Systematic Name

English

napitane [INN]

Common Name

English

A-75200

Code

English

PYRROLIDINE, 3-PHENYL-1-((6,7,8,9-TETRAHYDRONAPHTHO(1,2-D)-1,3-DIOXOL-6-YL)METHYL)-, (R*,R*)-(±)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713