CODEINE

US Approved OTC

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H21NO3.H2O
Molecular Weight	317.3795
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@H]5N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3OC

InChI

InChIKey=WRRSFOZOETZUPG-FFHNEAJVSA-N

InChI=1S/C18H21NO3.H2O/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;/h3-6,11-13,17,20H,7-9H2,1-2H3;1H2/t11-,12+,13-,17-,18-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C18H21NO3
Molecular Weight	299.3642
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

Description
Sources: https://online.lexi.com/lco/medguides/622452.pdf | https://www.ncbi.nlm.nih.gov/pubmed/7885194

Codeine is an opiate used to manage mild to moderate pain severe enough to require an opioid. Codeine is a selective agonist for the mu opioid receptor and has an affinity to delta and kappa-opioid receptors. In some countries, this drug is regulated under various narcotic control laws, because its chronic use can cause physical dependence. In others, it is available without a medical prescription in combination with paracetamol.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194 \| \|https://adisinsight.springer.com/drugs/800042774	Agonist 2678	6.1 µM [EC50]
Kappa-type opioid receptor 60 Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194	Agonist 2678
Delta-type opioid receptor 45 Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://online.lexi.com/lco/medguides/622452.pdf	Primary		Approved 8429	CAPITAL AND CODEINE Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1Q4DTD
AN PharmaTech	AN-23899
Alfa Chemistry	170301
Alfa Chemistry	ACM52453040
Angene	AGN-PC-0U9ZUU
Aurora Fine Chemicals LLC	A17.876.233	http://online.aurorafinechemicals.com/info?ID=A17.876.233
Avantor Inc	75835-236	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
Changzhou Highassay Chemical Co., Ltd	my_sub1415
ChemMol	30101025	http://www.chemmol.com/chemmol/30101025.html
ChemMol	49416695	http://www.chemmol.com/chemmol/49416695.html
ChemMol	99138769	http://www.chemmol.com/chemmol/99138769.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0821173
Clearsynth	CS-T-56966	http://www.clearsynth.com/en/CST56966.html
Compound Cloud	21155870
Compound Cloud	24892867
Compound Cloud	5284371
Compound Cloud	5362471
Compound Cloud	6321303
Hangzhou APIChem Technology	AC-11114
HongKong Chemhere	SCA54117
IBScreen	BB_NC-00138
IBScreen	STOCK1N-42851
LGC Standards	LGCAMP0004.10-01	https://www.lgcstandards.com/US/en/p/LGCAMP0004.10-01
LGC Standards	LGCAMP0004.10-02	https://www.lgcstandards.com/US/en/p/LGCAMP0004.10-02
LGC Standards	LGCFOR0004.10	https://www.lgcstandards.com/US/en/p/LGCFOR0004.10
LGC Standards	MM0004.10	https://www.lgcstandards.com/US/en/p/MM0004.10
Parchem	87121	https://www.parchem.com/chemical-supplier-distributor/Codeine-Alkaloid-087121.aspx
Parchem	87123	https://www.parchem.com/chemical-supplier-distributor/Codeine-USP-087123.aspx
Sigma Aldrich	C1653\|SIAL
Sigma Aldrich	C3539\|SIAL
Sigma Aldrich	C5901\|SIAL
Sigma Aldrich	Y0000722
Sigma Aldrich	Y0000722\|SIAL
Sigma-Aldrich	C-006_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/c006?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C1653_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/c1653?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	Y0000722_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/y0000722?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S627560	https://www.smolecule.com/products/s627560
Tetrahedron	TS63993
Tetrahedron	TS80953
Toronto Research Chemicals	C634075
Toronto Research Chemicals	C634080
Toronto Research Chemicals	KIT0410
Toronto Research Chemicals	KIT2460
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-1498A
ZINC	ZINC000003806721	http://zinc15.docking.org/substances/ZINC000003806721
eMolecules	193733897
mcule	MCULE-4129237460
mcule	MCULE-6243921692

PubMed

Title	Date	PubMed
Analgesic abuse, ureteric obstruction, and retroperitoneal fibrosis.	1975 Apr 12	1131554
Dystonia as acute adverse reaction to cough suppressant in a 3-year-old girl.	2001	11587381
Pharmacological control of cough.	2001 Apr	11411376
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
The diagnosis and treatment of cough.	2001 Apr 5	11291670
Sticky business: patterns of procurement and misuse of prescription cough syrup in Houston.	2001 Apr-Jun	11476259
Randomized placebo controlled trial of lofexidine hydrochloride for chronic pelvic pain in women.	2001 Aug	11473971
Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC.	2001 Aug	11451638
[Paracetamol-codeine induced hepatic colic].	2001 Aug-Sep	11481075
LC method for the analysis of paracetamol, caffeine and codeine phosphate in pharmaceutical preparations.	2001 Dec	11600297
Effect of penicillin on postoperative endodontic pain and swelling in symptomatic necrotic teeth.	2001 Feb	11491635
Effect of prophylactic amoxicillin on endodontic flare-up in asymptomatic, necrotic teeth.	2001 Jan	11487166
Opiate-sensitivity: clinical characteristics and the role of skin prick testing.	2001 Jul	11467991
Contribution of dihydrocodeine and dihydromorphine to analgesia following dihydrocodeine administration in man: a PK-PD modelling analysis.	2001 Jul	11453888
Head-column field-amplified sample stacking in presence of siphoning. Application to capillary electrophoresis-electrospray ionization mass spectrometry of opioids in urine.	2001 Jul 27	11521903
Use of beta-cyclodextrin in the capillary zone electrophoretic separation of the components of clandestine heroin preparations.	2001 Jul 27	11521902
Are cannabinoids an effective and safe treatment option in the management of pain? A qualitative systematic review.	2001 Jul 7	11440935
Heroin use by motorists in Sweden confirmed by analysis of 6-acetylmorphine in urine.	2001 Jul-Aug	11499891
Laboratory analysis of remotely collected oral fluid specimens for opiates by immunoassay.	2001 Jul-Aug	11499883
[Chronic pain in geriatrics].	2001 Jun	11488082
Effect of apical trephination on postoperative pain and swelling in symptomatic necrotic teeth.	2001 Jun	11487138
Successful withdrawal from analgesic abuse in a group of youngsters with chronic daily headache.	2001 Jun	11417614
[Information on preparations containing codeine].	2001 Jun 20	11488191
Codeine phosphate in paediatric medicine.	2001 Mar	11573533
Codeine phosphate in children: time for re-evaluation?	2001 Mar	11573519
Expression and activity of cell-wall-degrading enzymes in the latex of opium poppy, Papaver somniferum L.	2001 Mar	11414615
Myocardial Infarction associated with methadone and/or dihydrocodeine.	2001 Mar	11316924
GC-MS determination of heroin metabolites in meconium: evaluation of four solid-phase extraction cartridges.	2001 Mar	11300513
Quantitation of morphine and codeine in human urine using high-filed asymmetric waveform ion mobility spectrometry (FAIMS) with mass spectrometric detection.	2001 Mar	11300511
Acetylcodeine as a marker of illicit heroin in human hair: method validation and results of a pilot study.	2001 Mar	11300501
Opiate use to control bowel motility may induce chronic daily headache in patients with migraine.	2001 Mar	11264692
Evaluation of urinary dihydrocodeine excretion in human by gas chromatography-mass spectrometry.	2001 Mar 5	11254193
Effect of an enteric-release formulation of naloxone on intestinal transit in volunteers taking codeine.	2001 May	11328255
The analgesic effect of codeine as compared to imipramine in different human experimental pain models.	2001 May	11323149
Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations.	2001 May-Jun	11417630
Nutritional effects of surgical and medical treatment for short bowel syndrome.	2001 Nov-Dec	11688937
Novel dynamic polymer coating for capillary electrophoresis in nonaqueous methanolic background electrolytes.	2001 Oct	11699922
Analysis of morphine and codeine in samples adulterated with Stealth.	2001 Oct	11599602
Detection of opiate use in a methadone maintenance treatment population with the CEDIA 6-acetylmorphine and CEDIA DAU opiate assays.	2001 Oct	11599593
Drug contamination of US paper currency.	2001 Oct 1	11566423
Spontaneous reports on drug-induced pancreatitis in Denmark from 1968 to 1999.	2001 Sep	11699619
Community pharmacists' experience of over-the-counter medicine misuse in Scotland.	2001 Sep	11688306
Cetirizine inhibits skin reactions but not mediator release in immediate and developing late-phase allergic cutaneous reactions. A double-blind, placebo-controlled study.	2001 Sep	11591187
Tramadol/acetaminophen combination tablets and codeine/acetaminophen combination capsules for the management of chronic pain: a comparative trial.	2001 Sep	11589258
Blind trials of an onsite saliva drug test for marijuana and opiates.	2001 Sep	11569567
[Weak opioids].	2001 Sep	11554054
[Strong opioids].	2001 Sep	11554052
Concentration ratios of codeine-to-morphine in plasma after a single oral dose (100 mg) of codeine phosphate.	2001 Sep	11550826
Detection of non-prescription heroin markers in urine with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.	2001 Sep	11550816
Can standard open pediatric urological procedures be performed on an outpatient basis?	2001 Sep	11490300

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:04:29 GMT 2023` Edited by `admin` on `Fri Dec 15 15:04:29 GMT 2023`
Record UNII	Q830PW7520
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CODEINE

Common Name

English

LEAN

Common Name

English

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

Systematic Name

English

CODEINUM

Common Name

English

CODEINUM MONOHYDRICUM [WHO-IP LATIN]

Common Name

English

CODEINE [MART.]

Common Name

English

7,8-Didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol monohydrate

Systematic Name

English

CODEINE [USP MONOGRAPH]

Common Name

English

CODEINE MONOHYDRATE [EP MONOGRAPH]

Common Name

English

CODEINE COMPONENT OF TUZISTRA

Brand Name

English

TUZISTRA COMPONENT OF CODEINE

Brand Name

English

DEA NO. 9050

Common Name

English

CODEINE MONOHYDRATE [WHO-IP]

Common Name

English

CODEINE MONOHYDRATE

Common Name

English

CODEINE [VANDF]

Common Name

English

CODEINUM [HPUS]

Common Name

English

Codeine monohydrate [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N02AA79