APOREINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H17NO2.ClH
Molecular Weight	315.794
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@@]12CC3=CC=CC=C3C4=C5OCOC5=CC(CCN1C)=C24

InChI

InChIKey=SFAVZRNMTSBKPO-UQKRIMTDSA-N

InChI=1S/C18H17NO2.ClH/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17;/h2-5,9,14H,6-8,10H2,1H3;1H/t14-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H17NO2
Molecular Weight	279.3331
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/19775092 | https://www.ncbi.nlm.nih.gov/pubmed/26606133 | https://www.ncbi.nlm.nih.gov/pubmed/26426004

Aporeine (Roemerine) is an aporphine alkaloid that can be isolated from many plants such as Annona senegalensis, Turkish Papaver and Rollinialeptopetala. Aporeine has been reported to exhibit antibacterial activity. It has also been demonstrated to have certain antifungal activity. Aporeine showed selective inhibitory effect on Cox-2.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19775092	Inhibitor 8297
Staphylococcus aureus 67 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26606133	Inhibitor 8297
Candida albicans 14 Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26426004	Inhibitor 8297
Plasmodium falciparum 74 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23127648	Inhibitor 8297	17.9 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Staphylococcal infections 24 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26606133	Primary	Preclinical	Unknown Approved Use Unknown
Candida infections 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26426004	Primary	Basic research	Unknown Approved Use Unknown
Malaria 95 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23127648	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Monoterpenoid indole alkaloids from Alstonia yunnanensis.	2009 Oct	19775092
Roemerine Improves the Survival Rate of Septicemic BALB/c Mice by Increasing the Cell Membrane Permeability of Staphylococcus aureus.	2015	26606133

Patents

Sample Use Guides

In Vivo Use Guide

After bacterial challenge for 1 h, mice were randomized to receive i.p. injection of Aporeine (Roemerine) at 20 mg/kg once daily for 2 d. The survival rates for roemerine 20 mg/kg was 58.3%, the survival rate of the model group was only 8.3%.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Aporeine showed selective inhibitory effect on Cox-2, with inhibitory rate of 94% at 100 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:33:30 GMT 2023` Edited by `admin` on `Sat Dec 16 09:33:30 GMT 2023`
Record UNII	J88097HTC1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APOREINE HYDROCHLORIDE

Common Name

English

APOREINE HYDROCHLORIDE [MI]

Common Name

English

1,2-METHYLENEDIOXYAPORPHINE HYDROCHLORIDE

Systematic Name

English

(7AS)-6,7,7A,8-TETRAHYDRO-7-METHYL-5H-BENZO(G)-1,3-BENZODIOXOLO(6,5,4-DE)QUINOLINE HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

PUBCHEM

73425403

Created by admin on Sat Dec 16 09:33:30 GMT 2023 , Edited by admin on Sat Dec 16 09:33:30 GMT 2023

PRIMARY

FDA UNII

J88097HTC1

Created by admin on Sat Dec 16 09:33:30 GMT 2023 , Edited by admin on Sat Dec 16 09:33:30 GMT 2023

PRIMARY

CAS

7633-71-8

Created by admin on Sat Dec 16 09:33:30 GMT 2023 , Edited by admin on Sat Dec 16 09:33:30 GMT 2023

PRIMARY

MERCK INDEX

m2005

Created by admin on Sat Dec 16 09:33:30 GMT 2023 , Edited by admin on Sat Dec 16 09:33:30 GMT 2023

PRIMARY

Merck Index

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/19775092 | https://www.ncbi.nlm.nih.gov/pubmed/26606133 | https://www.ncbi.nlm.nih.gov/pubmed/26426004

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19775092 | https://www.ncbi.nlm.nih.gov/pubmed/26606133 | https://www.ncbi.nlm.nih.gov/pubmed/26426004