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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H30N2O4.2C4H6O6
Molecular Weight 698.669
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHOLCODINE DITARTRATE

SMILES

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

InChI

InChIKey=GZJIYWTVLNYQGH-MNNIXRQBSA-N
InChI=1S/C23H30N2O4.2C4H6O6/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;2*5-1(3(7)8)2(6)4(9)10/h2-5,16-18,22,26H,6-14H2,1H3;2*1-2,5-6H,(H,7,8)(H,9,10)/t16-,17+,18-,22-,23-;2*1-,2-/m011/s1

HIDE SMILES / InChI
Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C23H30N2O4
Molecular Weight 398.4953
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens.
2004 Jul 16
Allergy to pholcodine: first case documented by oral challenge.
2005 Apr
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
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
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:44:17 GMT 2023
Edited
by admin
on Sat Dec 16 10:44:17 GMT 2023
Record UNII
4F1CY0O7OD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHOLCODINE DITARTRATE
Common Name English
O3-(.BETA.-MORPHOLINOETHYL)MORPHINE DITARTRATE
Systematic Name English
MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-3-(2-(4-MORPHOLINYL)ETHOXY)-, (5.ALPHA.,6.ALPHA.)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:2) (SALT)
Systematic Name English
PHOLCODINE TARTRATE
Common Name English
MORPHINE, O3-(2-MORPHOLINOETHYL)-, DITARTRATE
Systematic Name English
MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-3-(2-(4-MORPHOLINYL)ETHOXY)-, (5.ALPHA.,6.ALPHA.)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:2) (SALT)
Systematic Name English
Code System Code Type Description
CAS
7369-11-1
Created by admin on Sat Dec 16 10:44:18 GMT 2023 , Edited by admin on Sat Dec 16 10:44:18 GMT 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
4F1CY0O7OD
Created by admin on Sat Dec 16 10:44:18 GMT 2023 , Edited by admin on Sat Dec 16 10:44:18 GMT 2023
PRIMARY
CAS
124107-36-4
Created by admin on Sat Dec 16 10:44:18 GMT 2023 , Edited by admin on Sat Dec 16 10:44:18 GMT 2023
PRIMARY
PUBCHEM
86278259
Created by admin on Sat Dec 16 10:44:18 GMT 2023 , Edited by admin on Sat Dec 16 10:44:18 GMT 2023
PRIMARY
Related Record Type Details
Structure of PHOLCODINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PHOLCODINE
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