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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H30N2O4
Molecular Weight 398.4953
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHOLCODINE

SMILES

[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3OCCN6CCOCC6

InChI

InChIKey=GPFAJKDEDBRFOS-FKQDBXSBSA-N
InChI=1S/C23H30N2O4/c1-24-7-6-23-16-3-4-18(26)22(23)29-21-19(5-2-15(20(21)23)14-17(16)24)28-13-10-25-8-11-27-12-9-25/h2-5,16-18,22,26H,6-14H2,1H3/t16-,17+,18-,22-,23-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.phadia.com/Global/ImmunoCAP%20Allergens/Product%20Leaflets/Product_Leaflet_c261_Pholcodine.pdf http://www.ncbi.nlm.nih.gov/pubmed/23773349

Pholcodine is an opioid that has been widely used worldwide since 1950 for the treatment of non-productive cough in children and adults. Illicit drug. Additionally Pholcodine is a marker for sensitization to neuromuscular blocking agents (NMBA) and is intended for use as a diagnostic tool in NMBA-induced anaphylaxis.

CNS Activity

Originator

Chabrier, P. et al.
6
Sources: Chabrier, P., Guidicelli, R. & Thuillier, J. (1950) Etude chimique, pharmacologique et clinique d’un nouveau skdatif de la toux: la morpholyethyimorphine (M.E.M.). Annales Pharmaceutiques Francais. 8, 26 1-273.
Curator's Comment: Reference was retrieved from: http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2710.1988.tb00502.x/epdf

Approval Year

Unknown
127998
Targets

Targets

Primary TargetPharmacologyConditionPotency
Mu-type opioid receptor
61
Target ID: P33535|||Q64064
Gene ID: 25601.0
Gene Symbol: Oprm1
Target Organism: Rattus norvegicus (Rat)
Agonist
2637
Mu-type opioid receptor
61
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
Agonist
2637
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
Pholcodine Linctus B.P.

Approved Use

Cough
Diagnostic
Approved
8307
ImmunoCAP® Allergen c261

Approved Use

Anaphylaxis to neuromuscular blocking agents
PubMed

PubMed

TitleDatePubMed
Angle closure risk from proprietary medicines.
2001 Apr
Comparison of eight commercial on-site screening devices for drugs-of-abuse testing.
2001 Jul
The toxicity of opiates and their metabolites in HepG2 cells.
2003 Oct 25
Allergy to pholcodine: first case documented by oral challenge.
2005 Apr
Automated multiple development thin-layer chromatography for separation of opiate alkaloids and derivatives.
2005 Jul 8
Comparative efficacy and tolerability of pholcodine and dextromethorphan in the management of patients with acute, non-productive cough : a randomized, double-blind, multicenter study.
2006
Pholcodine stimulates a dramatic increase of IgE in IgE-sensitized individuals. A pilot study.
2006 Jan
Site-specific acid-base properties of pholcodine and related compounds.
2006 Nov
Immunoglobulin E antibodies to rocuronium: a new diagnostic tool.
2007 Aug
Pholcodine exposure raises serum IgE in patients with previous anaphylaxis to neuromuscular blocking agents.
2007 Dec
IgE-mediated anaphylactic reactions to neuromuscular blocking agents: can they be prevented?
2008 Sep
The pholcodine story.
2009 Aug
Suspected anaphylactic reactions associated with anaesthesia.
2009 Feb
[Anaphylaxis during anaesthesia].
2010 Mar 11

Sample Use Guides

In Vivo Use Guide
Syrup (1mg/ml pholcodine) Two 5 ml spoonfuls 3 or 4 times a day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
PHOLCODINE
INN   MI   WHO-DD  
INN  
Official Name English
MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-3-(2-(4-MORPHOLINYL)ETHOXY)-, (5.ALPHA.,6.ALPHA.)-
Systematic Name English
HIBERNYL
Common Name English
GALENPHOL
Common Name English
Pholcodine [WHO-DD]
Common Name English
PHOLTEX
Common Name English
pholcodine [INN]
Common Name English
CODYLIN
Common Name English
GLYCODINE
Common Name English
TUSSOKON
Common Name English
MEMINE
Common Name English
PHOLCODINE [MI]
Common Name English
HOMOCODEINE
Common Name English
DEA NO. 9314
Code English
WEIFACODINE
Common Name English
ETHNINE
Common Name English
MORPHOLINYLETHYLMORPHINE
Common Name English
BIOCALYPTOL
Common Name English
3-(2-(4-MORPHOLINYL)ETHYL)MORPHINE
Common Name English
FOLCODINE
Common Name English
NEOCODINE
Common Name English
IDS-NP-011(SECT.2)
Code English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
DEA NO. 9314
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
WHO-ATC R05DA08
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
WHO-VATC QR05DA08
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
Code System Code Type Description
INN
272
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
CAS
509-67-1
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
MESH
C008872
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
FDA UNII
LPP64AWZ7L
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
EPA CompTox
DTXSID70198923
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
DRUG BANK
DB09209
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
CHEBI
53579
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
MERCK INDEX
M8711
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY Merck Index
ChEMBL
CHEMBL2105224
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
NCI_THESAURUS
C87365
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
WIKIPEDIA
PHOLCODINE
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
EVMPD
SUB09795MIG
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
ECHA (EC/EINECS)
208-102-9
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
PUBCHEM
5311356
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
RXCUI
33431
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY RxNorm
DRUG CENTRAL
2154
Created by admin on Fri Dec 16 16:58:00 UTC 2022 , Edited by admin on Fri Dec 16 16:58:00 UTC 2022
PRIMARY
ACTIVE MOIETY
Structure of PHOLCODINE
SALT/SOLVATE (PARENT)
Structure of PHOLCODINE HYDROCHLORIDE
SALT/SOLVATE (PARENT)
Structure of PHOLCODINE CITRATE
SALT/SOLVATE (PARENT)
Structure of PHOLCODINE DITARTRATE
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