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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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
Comparison of eight commercial on-site screening devices for drugs-of-abuse testing.	2001 Jul	11465347
Enzyme immunoassay validation for the detection of buprenorphine in urine.	2003 Mar	12670004
Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens.	2004 Jul 16	15240036
Prevalence of IgE antibodies to morphine. Relation to the high and low incidences of NMBA anaphylaxis in Norway and Sweden, respectively.	2005 Apr	15777289
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
Hypersensitivity reactions to neuromuscular blocking agents.	2008	18991700
On the origin and specificity of antibodies to neuromuscular blocking (muscle relaxant) drugs: an immunochemical perspective.	2009 Mar	19187323
Cholinergic and oxidative stress mechanisms in sudden infant death syndrome.	2009 Nov	19706020

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 10:03:31 UTC 2023` Edited by `admin` on `Sat Dec 16 10:03:31 UTC 2023`
Record UNII	538VG8KNRX
Record Status	`Validated (UNII)`
Record Version

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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