PHOLCODINE MONOHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H30N2O4.H2O
Molecular Weight	416.5106
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=VOMHFFCEDKOLBR-RNFKYSJUSA-N

InChI=1S/C23H30N2O4.H2O/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;1H2/t16-,17+,18-,22-,23-;/m0./s1

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3283158
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu-type opioid receptor 61 Target ID: P33535\|\|\|Q64064 Gene ID: 25601.0 Gene Symbol: Oprm1 Target Organism: Rattus norvegicus (Rat) Sources: http://www.ncbi.nlm.nih.gov/pubmed/1851921	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) Sources: http://www.ebi.ac.uk/chebi/searchId.do?chebiId=53579	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: https://www.medicines.org.uk/emc/PIL.25373.latest.pdf	Primary		Approved 8429	Pholcodine Linctus B.P. Approved Use Cough
Anaphylaxis to neuromuscular blocking agents 6 Sources: http://www.phadia.com/Global/ImmunoCAP%20Allergens/Product%20Leaflets/Product_Leaflet_c261_Pholcodine.pdf	Diagnostic		Approved 8429	ImmunoCAP® Allergen c261 Approved Use Anaphylaxis to neuromuscular blocking agents

PubMed

Title	Date	PubMed
Angle closure risk from proprietary medicines.	2001 Apr	11339612
Impurity profiling of pholcodine by liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS).	2002 Jan	11829134
Interpretation of GC-MS opiate results in the presence of pholcodine.	2002 Jun 25	12098537
Enzyme immunoassay validation for the detection of buprenorphine in urine.	2003 Mar	12670004
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	17154678
Site-specific acid-base properties of pholcodine and related compounds.	2006 Nov	17004059
Pholcodine exposure raises serum IgE in patients with previous anaphylaxis to neuromuscular blocking agents.	2007 Dec	17983379
The pholcodine story.	2009 Aug	19563989
Suspected anaphylactic reactions associated with anaesthesia.	2009 Feb	19143700
On the origin and specificity of antibodies to neuromuscular blocking (muscle relaxant) drugs: an immunochemical perspective.	2009 Mar	19187323
Pholcodine caused anaphylaxis in Sweden 30 years ago.	2009 May	19210354

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 MONOHYDRATE

Common Name

English

PHOLCODINE MONOHYDRATE [EP MONOGRAPH]

Common Name

English

MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-3-(2-(4-MORPHOLINYL)ETHOXY)-, MONOHYDRATE, (5.ALPHA.,6.ALPHA.)-

Systematic Name

English

PHOLCODINE [MART.]

Common Name

English

MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-3-(2-(4-MORPHOLINYL)ETHOXY)-, HYDRATE (1:1), (5.ALPHA.,6.ALPHA.)-

Systematic Name

English

MORPHINAN-6.ALPHA.-OL, 7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-17-METHYL-3-(2-MORPHOLINOETHOXY)-, HYDRATE

Systematic Name

English

PHOLCODINE MONOHYDRATE [MI]

Common Name

English

PHOLCODINE [EP IMPURITY]

Common Name

English

3-(2-MORPHOLINOETHYL)MORPHINE MONOHYDRATE

Systematic Name

English

Code System Code Type Description

MERCK INDEX

m8711