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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
139594
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
2678
Mu-type opioid receptor
61
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Pholcodine Linctus B.P.

Approved Use

Cough
Diagnostic
Approved
8429
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
Comparative biotransformation of morphine, codeine and pholcodine in rat hepatocytes: identification of a novel metabolite of pholcodine.
2002 Dec
Impurity profiling of pholcodine by liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS).
2002 Jan
Interpretation of GC-MS opiate results in the presence of pholcodine.
2002 Jun 25
Enzyme immunoassay validation for the detection of buprenorphine in urine.
2003 Mar
The toxicity of opiates and their metabolites in HepG2 cells.
2003 Oct 25
Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens.
2004 Jul 16
Prevalence of IgE antibodies to morphine. Relation to the high and low incidences of NMBA anaphylaxis in Norway and Sweden, respectively.
2005 Apr
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
Validated toxicological determination of 30 drugs of abuse as optimized derivatives in oral fluid by long column fast gas chromatography/electron impact mass spectrometry.
2005 Jun
Pholcodine stimulates a dramatic increase of IgE in IgE-sensitized individuals. A pilot study.
2006 Jan
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
Hypersensitivity reactions to neuromuscular blocking agents.
2008
Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.
2008 Jun
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
Determination of opiates and cocaine in urine by high pH mobile phase reversed phase UPLC-MS/MS.
2009 Feb 1
On the origin and specificity of antibodies to neuromuscular blocking (muscle relaxant) drugs: an immunochemical perspective.
2009 Mar
Pholcodine caused anaphylaxis in Sweden 30 years ago.
2009 May
Cholinergic and oxidative stress mechanisms in sudden infant death syndrome.
2009 Nov
National pholcodine consumption and prevalence of IgE-sensitization: a multicentre study.
2010 Apr
[Anaphylaxis during anaesthesia].
2010 Mar 11
Clinical expert guidelines for the management of cough in lung cancer: report of a UK task group on cough.
2010 Oct 6

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 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
DEA NO. 9314
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
WHO-ATC R05DA08
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
WHO-VATC QR05DA08
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
Code System Code Type Description
INN
272
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
CAS
509-67-1
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
MESH
C008872
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
FDA UNII
LPP64AWZ7L
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID70198923
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
DRUG BANK
DB09209
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
CHEBI
53579
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
MERCK INDEX
m8711
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL2105224
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
SMS_ID
100000092419
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
NCI_THESAURUS
C87365
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
WIKIPEDIA
PHOLCODINE
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
EVMPD
SUB09795MIG
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-102-9
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
PUBCHEM
5311356
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
RXCUI
33431
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
2154
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
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
NIH
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