CODEINE ANHYDROUS

US Approved OTC

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H21NO3
Molecular Weight	299.3642
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3OC

InChI

InChIKey=OROGSEYTTFOCAN-DNJOTXNNSA-N

InChI=1S/C18H21NO3/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/t11-,12+,13-,17-,18-/m0/s1

HIDE SMILES / InChI

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
Determination of opiates in serum, saliva and hair addicted persons.	2001	11450354
Pharmacological control of cough.	2001 Apr	11411376
The use of compound 48/80 and codeine phosphate as positive controls for intradermal skin testing in dogs.	2001 Apr	11360343
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
LC method for the analysis of acetylsalicylic acid, caffeine and codeine phosphate in pharmaceutical preparations.	2001 Apr	11274862
LC method for the analysis of paracetamol, caffeine and codeine phosphate in pharmaceutical preparations.	2001 Dec	11600297
Opioids for chronic nonmalignant pain. Attitudes and practices of primary care physicians in the UCSF/Stanford Collaborative Research Network. University of California, San Francisco.	2001 Feb	11219563
Inhibition by glucocorticoids of the mast cell-dependent weal and flare response in human skin in vivo.	2001 Jan	11156588
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg.	2001 Jan 10	11231885
Contribution of dihydrocodeine and dihydromorphine to analgesia following dihydrocodeine administration in man: a PK-PD modelling analysis.	2001 Jul	11453888
Time of drug elimination in chronic drug abusers. Case study of 52 patients in a "low-step" detoxification ward.	2001 Jun 15	11376991
[Information on preparations containing codeine].	2001 Jun 20	11488191
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
GC-MS determination of heroin metabolites in meconium: evaluation of four solid-phase extraction cartridges.	2001 Mar	11300513
Evaluation of urinary dihydrocodeine excretion in human by gas chromatography-mass spectrometry.	2001 Mar 5	11254193
Capillary electrophoresis-electrospray ionization ion trap mass spectrometry for analysis and confirmation testing of morphine and related compounds in urine.	2001 May 4	11382295
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
Detection of opiate use in a methadone maintenance treatment population with the CEDIA 6-acetylmorphine and CEDIA DAU opiate assays.	2001 Oct	11599593
Ropivacaine with or without clonidine improves pediatric tonsillectomy pain.	2001 Oct	11587610
Drug contamination of US paper currency.	2001 Oct 1	11566423
Blind trials of an onsite saliva drug test for marijuana and opiates.	2001 Sep	11569567
Concentration ratios of codeine-to-morphine in plasma after a single oral dose (100 mg) of codeine phosphate.	2001 Sep	11550826
Pain control in medical abortion.	2001 Sep	11543752
Engineering novel biocatalytic routes for production of semisynthetic opiate drugs.	2001 Sep	11535415
Can standard open pediatric urological procedures be performed on an outpatient basis?	2001 Sep	11490300
Experience with urine drug testing by the Correctional Service of Canada.	2001 Sep 15	11516882

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

Name

Type

Language

CODEINE ANHYDROUS

Common Name

English

MYTUSSIN

Common Name

English

ETHYLMORPHINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]

Common Name

English

IDS-NC-005(SECT.-2)

Code

English

CODEINE [HSDB]

Common Name

English

CODEINE [MI]

Common Name

English

SS85U8K5ZN

Common Name

English

KODELAK FITO

Common Name

English

MORPHINE MONOMETHYL ETHER

Common Name

English

HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY C [EP IMPURITY]

Common Name

English

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

Systematic Name

English

O3-METHYLMORPHINE

Common Name

English

CODICEPT

Common Name

English

DIHYDROCODEINE HYDROGEN TARTRATE IMPURITY A [EP IMPURITY]

Common Name

English

Codeine [WHO-DD]

Common Name

English

METHYLMORPHINE

Common Name

English

CODUCEPT

Common Name

English

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

Systematic Name

English

MORPHINE SULFATE IMPURITY A [EP IMPURITY]

Common Name

English

MORPHINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175690