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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
A placebo-controlled study of lofexidine in the treatment of children with tic disorders and attention deficit hyperactivity disorder.
2004 Jun
Evidence-based addiction medicine: the use of lofexidine for opioid detoxification.
2004 Nov
QT interval increased after single dose of lofexidine.
2004 Nov 6
Alpha2 adrenergic agonists for the management of opioid withdrawal.
2004 Oct 18
A comparison of buprenorphine and lofexidine for community opiate detoxification: results from a randomized controlled trial.
2005 Dec
Lofexidine for opioid detoxification.
2005 Jan
Is clonidine useful for treatment of clozapine-induced sialorrhea?
2005 Jul
Induction of patients with moderately severe methadone dependence onto buprenorphine.
2005 Jun
Role of alpha-2 adrenoceptors in stress-induced reinstatement of alcohol seeking and alcohol self-administration in rats.
2005 May
Cognitive function during early abstinence from opioid dependence: a comparison to age, gender, and verbal intelligence matched controls.
2006 Feb 24
Opioid antagonists with minimal sedation for opioid withdrawal.
2006 Jan 25
Opiate addiction in China: current situation and treatments.
2006 May
The place of detoxification in treatment of opioid dependence.
2006 May
Pharmacologic treatments for opioid dependence: detoxification and maintenance options.
2007
In-patient detoxification procedures, treatment retention, and post-treatment opiate use: comparison of lofexidine + naloxone, lofexidine + placebo, and methadone.
2007 Apr 17
Hemodynamic and cognitive effects of lofexidine and methadone coadministration: a pilot study.
2007 Aug
The Leeds Evaluation of Efficacy of Detoxification Study (LEEDS) prisons project pilot study: protocol for a randomised controlled trial comparing dihydrocodeine and buprenorphine for opiate detoxification.
2007 Jan 8
Buprenorphine versus dihydrocodeine for opiate detoxification in primary care: a randomised controlled trial.
2007 Jan 8
Opioid dependence.
2007 Jun 1
Effects of lofexidine on stress-induced and cue-induced opioid craving and opioid abstinence rates: preliminary findings.
2007 Mar
A comparative clinical study of the effects of the traditional Chinese medicine Jinniu capsules and lofexidine on acute heroin withdrawal symptoms.
2008
Clinical pharmacokinetics of lofexidine, the alpha 2-adrenergic receptor agonist, in opiate addicts plasma using a highly sensitive liquid chromatography tandem mass spectrometric analysis.
2008
Tai-Kang-Ning, a Chinese herbal medicine formula, alleviates acute heroin withdrawal.
2008
Effects of THC and lofexidine in a human laboratory model of marijuana withdrawal and relapse.
2008 Mar
Agenda for specialty section in addiction medicine.
2008 Oct
Functional neuroanatomy of the noradrenergic locus coeruleus: its roles in the regulation of arousal and autonomic function part II: physiological and pharmacological manipulations and pathological alterations of locus coeruleus activity in humans.
2008 Sep
A Phase 3 placebo-controlled, double-blind, multi-site trial of the alpha-2-adrenergic agonist, lofexidine, for opioid withdrawal.
2008 Sep 1
A study on Fu-Yuan Pellet, a traditional chinese medicine formula for detoxification of heroin addictions.
2009
Urine and plasma pharmacokinetics of lofexidine after oral delivery in opiate-dependent patients.
2009
Pharmacotherapy for cannabis dependence: how close are we?
2009
Norepinephrine and stimulant addiction.
2009 Apr
Alpha2-adrenergic agonists for the management of opioid withdrawal.
2009 Apr 15
The Leeds Evaluation of Efficacy of Detoxification Study (LEEDS) prisons project: a randomised controlled trial comparing dihydrocodeine and buprenorphine for opiate detoxification.
2009 Feb 5
Pharmacokinetics of lofexidine hydrochloride in healthy volunteers.
2009 Jan
The Leeds Evaluation of Efficacy of Detoxification Study (LEEDS) Prisons Project Study: protocol for a randomised controlled trial comparing methadone and buprenorphine for opiate detoxification.
2009 Jul 14
Opioid dependence.
2009 Jul 24
Buprenorphine for the management of opioid withdrawal.
2009 Jul 8
Electrocardiographic effects of lofexidine and methadone coadministration: secondary findings from a safety study.
2009 May
Opioid antagonists with minimal sedation for opioid withdrawal.
2009 Oct 7
Alpha2-receptor agonists for treatment and prevention of iatrogenic opioid abstinence syndrome in critically ill patients.
2009 Sep
A double-blind, randomized, parallel group study to compare the efficacy, safety and tolerability of slow-release oral morphine versus methadone in opioid-dependent in-patients willing to undergo detoxification.
2009 Sep
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