CODEINE ANHYDROUS

US Approved OTC

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H21NO3
Molecular Weight	299.3649
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CC[C@@]23[C@@]4([H])C=C[C@@]([H])([C@]2([H])Oc5c(ccc(C[C@]41[H])c53)OC)O

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

Molecular Formula	C18H21NO3
Molecular Weight	299.3649
Charge	0
Count

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

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 205 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194 \| \|https://adisinsight.springer.com/drugs/800042774	Agonist 2470	6.1 µM [EC50]
Kappa-type opioid receptor 56 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 2470
Delta-type opioid receptor 42 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 2470

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 580 Sources: https://online.lexi.com/lco/medguides/622452.pdf	Primary		Approved 8043	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
Over-the-counter medications for acute cough in children and adults in ambulatory settings.	2001	11686998
Dystonia as acute adverse reaction to cough suppressant in a 3-year-old girl.	2001	11587381
Results of a phase-I/II randomized, masked, placebo-controlled trial of recombinant human interleukin-11 (rhIL-11) in the treatment of subjects with active rheumatoid arthritis.	2001	11438043
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
Prescribing limitations.	2001 Aug 11	11523877
Precipitated withdrawal following codeine administration is dependent on CYP genotype.	2001 Aug 17	11513833
[Paracetamol-codeine induced hepatic colic].	2001 Aug-Sep	11481075
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
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
Myth: codeine is a powerful and effective analgesic.	2001 Jun	11381016
Oral ibuprofen versus paracetamol plus codeine for analgesia after ambulatory surgery.	2001 Jun	11375827
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
Dextromethorphan is an effective cough suppressant.	2001 May	11394377
Capillary electrophoresis-electrospray ionization ion trap mass spectrometry for analysis and confirmation testing of morphine and related compounds in urine.	2001 May 4	11382295
From codeine to transdermal fentanyl for cancer pain control: a safety and efficacy clinical trial.	2001 May-Jun	11501851
Scalp nerve blocks decrease the severity of pain after craniotomy.	2001 Nov	11682413
Concentration ratios of morphine to codeine in blood of impaired drivers as evidence of heroin use and not medication with codeine.	2001 Nov	11673366
Seizures with intravenous codeine phosphate.	2001 Oct	11675848
Incorporation of selegiline metabolites into hair after oral selegiline intake.	2001 Oct	11599606
Analysis of morphine and codeine in samples adulterated with Stealth.	2001 Oct	11599602
Ropivacaine with or without clonidine improves pediatric tonsillectomy pain.	2001 Oct	11587610
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
Endogenous morphine and codeine. Possible role as endogenous anticonvulsants.	2001 Oct 12	11595204
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
Rofecoxib versus codeine/acetaminophen in postoperative dental pain: a double-blind, randomized, placebo- and active comparator-controlled clinical trial.	2001 Sep	11589259
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
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

Substance Class	Chemical Created by `admin` on `Sat Jun 26 06:25:49 UTC 2021` Edited by `admin` on `Sat Jun 26 06:25:49 UTC 2021`
Record UNII	UX6OWY2V7J
Record Status	`Validated (UNII)`
Record Version

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Related Record	Type

Name

Type

Language

CODEINE ANHYDROUS

Common Name

English

MYTUSSIN

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

O3-METHYLMORPHINE

Common Name

English

CODICEPT

Common Name

English

CODEINE [WHO-DD]

Common Name

English

METHYLMORPHINE

Common Name

English

MORPHINE SULFATE IMPURITY A [EP]

Common Name

English

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

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

DIHYDROCODEINE HYDROGEN TARTRATE SPECIFIED IMPURITY A [EP]

Common Name

English

7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-3-METHOXY-17-METHYLMORPHINAN-6.ALPHA.-OL

Systematic Name

English

Classification Tree Code System Code

NDF-RT

N0000175690