CODEINE ANHYDROUS

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

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

Molecular Formula	C18H21NO3
Molecular Weight	299.3642
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Agonist 2,678	6.1 µM [EC50]
Kappa-type opioid receptor 60	Agonist 2,678
Delta-type opioid receptor 45	Agonist 2,678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614	Primary		Approved 8,429	CAPITAL AND CODEINE

C_max

Value	Dose	Analyte	Population
66.9 ng/mL	30 mg single, oral	CODEINE plasma	Homo sapiens
145 ng/mL	60 mg single, oral	CODEINE plasma	Homo sapiens
229 ng/mL	60 mg single, intramuscular	CODEINE plasma	Homo sapiens
93 ng/mL	60 mg single, oral	CODEINE plasma	Homo sapiens
242 ng/mL	60 mg single, intramuscular	CODEINE plasma	Homo sapiens
53.5 ng/mL	30 mg single, oral	MORPHINE-3-GLUCURONIDE plasma	Homo sapiens
66.9 ng/mL	30 mg single, oral	CODEINE plasma	Homo sapiens
968 ng/mL	30 mg single, oral	CODEINE-6-GLUCURONIDE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
0.61 μM × h	30 mg single, oral	CODEINE plasma	Homo sapiens
466 ng × h/mL	60 mg single, oral	CODEINE plasma	Homo sapiens
849 ng × h/mL	60 mg single, intramuscular	CODEINE plasma	Homo sapiens
467 ng × h/mL	60 mg single, oral	CODEINE plasma	Homo sapiens
937 ng × h/mL	60 mg single, intramuscular	CODEINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.47 h	30 mg single, oral	CODEINE plasma	Homo sapiens
2.8 h	60 mg single, oral	CODEINE plasma	Homo sapiens
2.8 h	60 mg single, intramuscular	CODEINE plasma	Homo sapiens
2.7 h	60 mg single, oral	CODEINE plasma	Homo sapiens
2.9 h	60 mg single, intramuscular	CODEINE plasma	Homo sapiens
1.71 h	30 mg single, oral	MORPHINE-3-GLUCURONIDE plasma	Homo sapiens
1.47 h	30 mg single, oral	CODEINE plasma	Homo sapiens
2.75 h	30 mg single, oral	CODEINE-6-GLUCURONIDE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
75%	15 mg single, oral		CODEINE plasma	Homo sapiens

Doses

Doses

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Dose	Population	Adverse events
360 mg 1 times / day multiple, oral Highest recorded dose	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587	inhibitor 1,767	substrate 1,217 inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512 UGT2B7 146 CYP19A1 60 CYP1A2 1,524	UGT2B7 389 UGT1A3 422 UGT1A1 418 UGT1A4 347 OCT1 327 UGT2B4 249 UGT1A8 283 UGT1A10 291 P-gp 1,537 UGT2B15 203

Drug as perpetrator

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Target	Modality	Activity
CYP2D6 1,891	inhibitor 3,277	inconclusive [IC50 35.7774 uM]
CYP19A1 60	inhibitor 3,277	no
CYP1A2 1,692	inhibitor 3,277	no
CYP2C9 1,819	inhibitor 3,277	no
CYP3A4 1,925	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity
UGT2B4 249	substrate 3,367	major
UGT2B7 389	substrate 3,367	major
P-gp 1,537	substrate 3,367	no
UGT1A10 291	substrate 3,367	no
UGT1A3 422	substrate 3,367	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ABI Chem	AC1Q4DTD
Alfa Chemistry	170301
Alfa Chemistry	ACM52453040
AN PharmaTech	AN-23899
Angene	AGN-PC-0U9ZUU

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PubMed

Show entries

Title	Date	PubMed
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
Saliva testing after single and chronic administration of dihydrocodeine.	2001	11296884
Precipitated withdrawal following codeine administration is dependent on CYP genotype.	2001 Aug 17	11513833
LC method for the analysis of paracetamol, caffeine and codeine phosphate in pharmaceutical preparations.	2001 Dec	11600297