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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

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.

Originator

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P33535|||Q64064
Gene ID: 25601.0
Gene Symbol: Oprm1
Target Organism: Rattus norvegicus (Rat)
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Pholcodine Linctus B.P.

Approved Use

Cough
Diagnostic
ImmunoCAP® Allergen c261

Approved Use

Anaphylaxis to neuromuscular blocking agents
PubMed

PubMed

TitleDatePubMed
Interpretation of GC-MS opiate results in the presence of pholcodine.
2002 Jun 25
Prevalence of IgE antibodies to morphine. Relation to the high and low incidences of NMBA anaphylaxis in Norway and Sweden, respectively.
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
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
Pholcodine caused anaphylaxis in Sweden 30 years ago.
2009 May
[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

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 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