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Details

Stereochemistry RACEMIC
Molecular Formula C11H12Cl2N2O
Molecular Weight 259.132
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOFEXIDINE

SMILES

CC(OC1=C(Cl)C=CC=C1Cl)C2=NCCN2

InChI

InChIKey=KSMAGQUYOIHWFS-UHFFFAOYSA-N
InChI=1S/C11H12Cl2N2O/c1-7(11-14-5-6-15-11)16-10-8(12)3-2-4-9(10)13/h2-4,7H,5-6H2,1H3,(H,14,15)

HIDE SMILES / InChI

Molecular Formula C11H12Cl2N2O
Molecular Weight 259.132
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Lofexidine is newly FDA approved in the United States under the brand name LUCEMYRA for the treatment of opioid withdrawal symptoms in adults. Lofexidine acts as an agonist to α2 adrenergic receptors. These receptors inhibit adenylyl cyclase activity, leading to the inhibition of the second messenger, cyclic adenosine monophosphate (cAMP). The inhibition of cAMP leads to potassium efflux through calcium-activated channels, blocking calcium ions from entering the nerve terminal, resulting in suppression of neural firing, inhibition of norepinephrine release. Lofexidine replaces the opioid-driven inhibition of cAMP production and moderating the symptoms of opioid withdrawal.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Animal experiments on the safety pharmacology of lofexidine.
1982
Alcohol withdrawal syndromes: clinical management with lofexidine.
1985 Mar-Apr
Double-blind randomised controlled trial of lofexidine versus clonidine in the treatment of heroin withdrawal.
1997 Nov 25
Accelerated lofexidine treatment regimen compared with conventional lofexidine and methadone treatment for in-patient opiate detoxification.
1998 May 1
Evidence-based addiction medicine: the use of lofexidine for opioid detoxification.
2004 Nov
Lofexidine for opioid detoxification.
2005 Jan
Opioid dependence.
2009 Jul 24
A case report of inpatient detoxification after kratom (Mitragyna speciosa) dependence.
2010
A comparison of methadone, buprenorphine and alpha(2) adrenergic agonists for opioid detoxification: a mixed treatment comparison meta-analysis.
2010 Apr 1
Lofexidine, an {alpha}2-receptor agonist for opioid detoxification.
2010 Feb
The pharmacological treatment of opioid addiction--a clinical perspective.
2010 Jun
Clonidine in adults as a sedative agent in the intensive care unit.
2010 Oct
Patents

Patents

Sample Use Guides

In Vivo Use Guide
The usual LUCEMYRA starting dosage is three 0.18 mg tablets taken orally 4 times daily during the period of peak withdrawal symptoms (generally the first 5 to 7 days following last use of opioid) with dosing guided by symptoms and side effects. There should be 5 to 6 hours between each dose. The total daily dosage of LUCEMYRA should not exceed 2.88 mg (16 tablets) and no single dose should exceed 0.72 mg (4 tablets).
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Tue Mar 06 11:35:12 UTC 2018
Edited
by admin
on Tue Mar 06 11:35:12 UTC 2018
Record UNII
UI82K0T627
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOFEXIDINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
LOFEXIDINE [VANDF]
Common Name English
LOFEXIDINE [WHO-DD]
Common Name English
LOFEXIDINE [MI]
Common Name English
1H-IMIDAZOLE, 2-(1-(2,6-DICHLOROPHENOXY)ETHYL)-4,5-DIHYDRO-
Systematic Name English
2-(1-(2,6-DICHLOROPHENOXY)ETHYL)-2-IMIDAZOLINE
Systematic Name English
LOFEXIDINE [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC N07BC04
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
WHO-VATC QN07BC04
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
Code System Code Type Description
MERCK INDEX
M6885
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY Merck Index
EPA CompTox
31036-80-3
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY
NCI_THESAURUS
C87578
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY
MESH
C025655
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY
ChEMBL
CHEMBL17860
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY
EVMPD
SUB08558MIG
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY
DRUG BANK
DB04948
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY
CAS
31036-80-3
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY
PUBCHEM
30668
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY SWITZERF
INN
3766
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY
RXCUI
28863
Created by admin on Tue Mar 06 11:35:12 UTC 2018 , Edited by admin on Tue Mar 06 11:35:12 UTC 2018
PRIMARY RxNorm
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY