Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H30N2O4.C6H8O7 |
| Molecular Weight | 590.6188 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC(O)(CC(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=YQRMJBKLKRYXSC-RNFKYSJUSA-N
InChI=1S/C23H30N2O4.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h2-5,16-18,22,26H,6-14H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t16-,17+,18-,22-,23-;/m0./s1
| 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 |
| Molecular Formula | C6H8O7 |
| Molecular Weight | 192.1235 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Pholcodine Linctus B.P. Approved UseCough |
|||
| Diagnostic | ImmunoCAP® Allergen c261 Approved UseAnaphylaxis to neuromuscular blocking agents |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparative biotransformation of morphine, codeine and pholcodine in rat hepatocytes: identification of a novel metabolite of pholcodine. | 2002 Dec |
|
| 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 |
|
| 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 |
|
| Site-specific acid-base properties of pholcodine and related compounds. | 2006 Nov |
|
| 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 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:48:11 GMT 2023
by
admin
on
Sat Dec 16 10:48:11 GMT 2023
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| Record UNII |
K7Z9OPE11S
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| Record Status |
Validated (UNII)
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| Record Version |
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70545035
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14053-60-2
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K7Z9OPE11S
Created by
admin on Sat Dec 16 10:48:11 GMT 2023 , Edited by admin on Sat Dec 16 10:48:11 GMT 2023
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