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
Long-term codeine use is associated with depressive symptoms.	1999 Aug	10440467
Mimicking gene defects to treat drug dependence.	2000	10911933
Codeine analgesia is due to codeine-6-glucuronide, not morphine.	2000 Jul-Aug	11092114
[Pharmacokinetic and toxicokinetic parameters of some drugs of abuse].	2001	11450374
[Guillain-Barre syndrome as a result of poisoning with a mixture of "kompot"(Polish heroin) and drugs].	2001	11450369
Determination of opiates in serum, saliva and hair addicted persons.	2001	11450354
The use of compound 48/80 and codeine phosphate as positive controls for intradermal skin testing in dogs.	2001 Apr	11360343
Angle closure risk from proprietary medicines.	2001 Apr	11339612
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
[Paracetamol-codeine induced hepatic colic].	2001 Aug-Sep	11481075
Detection of acetylcodeine in urine as an indicator of illicit heroin use: method validation and results of a pilot study.	2001 Feb	11159779
Dose-related effects of controlled release dihydrocodeine on oro-cecal transit and pupillary light reflex. A study in human volunteers.	2001 Jan	11215327
Successful use of propranolol in migraine associated with electroconvulsive therapy.	2001 Jan	11168610
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg.	2001 Jan 10	11231885
Laboratory analysis of remotely collected oral fluid specimens for opiates by immunoassay.	2001 Jul-Aug	11499883
Myth: codeine is a powerful and effective analgesic.	2001 Jun	11381016
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 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
Audit of pain management at home following tonsillectomy in children.	2001 Mar	11244527
Effect of an enteric-release formulation of naloxone on intestinal transit in volunteers taking codeine.	2001 May	11328255
Capillary electrophoresis-electrospray ionization ion trap mass spectrometry for analysis and confirmation testing of morphine and related compounds in urine.	2001 May 4	11382295
Regional block and mexiletine: the effect on pain after cancer breast surgery.	2001 May-Jun	11359221
Seizures with intravenous codeine phosphate.	2001 Oct	11675848
Drug contamination of US paper currency.	2001 Oct 1	11566423
Predictors for completing an inpatient detoxification program among intravenous heroin users, methadone substituted and codeine substituted patients.	2001 Oct 1	11543987
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
[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
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

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

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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