DIHYDROCODEINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H23NO3
Molecular Weight	301.3801
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC1=C2O[C@H]3[C@@H](O)CC[C@H]4[C@H]5CC(C=C1)=C2[C@@]34CCN5C

InChI

InChIKey=RBOXVHNMENFORY-DNJOTXNNSA-N

InChI=1S/C18H23NO3/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,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1

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Description

Dihydrocodeine is an opioid analgesic used as an alternative or adjunct to codeine to treat moderate to severe pain, severe dyspnea, and cough. It is semi-synthetic, and was developed in Germany in 1908 during an international search to find a more effective antitussive agent to help reduce the spread of airborne infectious diseases such as tuburculosis. It was marketed in 1911. Dihydrocodeine is metabolized to dihydromorphine -- a highly active metabolite with a high affinity for mu opioid receptors. Dihydrocodeine is used for the treatment of moderate to severe pain, including post-operative and dental pain. It can also be used to treat chronic pain, breathlessness and coughing. In heroin addicts, dihydrocodeine has been used as a substitute drug, in doses up to 2500mg/day to treat addiction.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 231	Agonist 2,752		0.3 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619	Palliative		Approved 8,583	SYNALGOS-DC

C_max

Value	Dose	Analyte	Population
487 pmol/g	60 mg 2 times / day multiple, oral	DIHYDROCODEINE serum	Homo sapiens
4.7 pmol/g	60 mg single, oral	DIHYDROMORPHINE serum	Homo sapiens
341 nM	60 mg single, oral	DIHYDROCODEINE serum	Homo sapiens
8.7 nM	60 mg 1 times / day multiple, oral	DIHYDROMORPHINE serum	Homo sapiens
739 nM	90 mg 1 times / day multiple, oral	DIHYDROCODEINE serum	Homo sapiens
918 nM	120 mg 1 times / day multiple, oral	DIHYDROCODEINE serum	Homo sapiens
18 nM	120 mg 1 times / day multiple, oral	DIHYDROMORPHINE serum	Homo sapiens
13 nM	90 mg 1 times / day multiple, oral	DIHYDROMORPHINE serum	Homo sapiens
60.089 ng/mL	20 mg single, oral	DIHYDROCODEINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
3367 nM × h	60 mg 2 times / day multiple, oral	DIHYDROCODEINE serum	Homo sapiens
70 nM × h	60 mg single, oral	DIHYDROMORPHINE serum	Homo sapiens
3415 nM × h	60 mg single, oral	DIHYDROCODEINE serum	Homo sapiens
65 nM × h	60 mg 1 times / day multiple, oral	DIHYDROMORPHINE serum	Homo sapiens
5118 nM × h	90 mg 1 times / day multiple, oral	DIHYDROCODEINE serum	Homo sapiens
6566 nM × h	120 mg 1 times / day multiple, oral	DIHYDROCODEINE serum	Homo sapiens
132 nM × h	120 mg 1 times / day multiple, oral	DIHYDROMORPHINE serum	Homo sapiens
99 nM × h	90 mg 1 times / day multiple, oral	DIHYDROMORPHINE serum	Homo sapiens
301.643 ng × h/mL	20 mg single, oral	DIHYDROCODEINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.146 h	20 mg single, oral		DIHYDROCODEINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
32 mg 6 times / day multiple, oral Recommended	unhealthy, > 18 years	Other AEs: Respiratory depression...
240 mg 2 times / day multiple, oral Overdose	unhealthy	Other AEs: Hypercapnic respiratory failure...

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AEs

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AE	Significance	Dose	Population
Respiratory depression	grade 5	32 mg 6 times / day multiple, oral Recommended	unhealthy, > 18 years
Hypercapnic respiratory failure		240 mg 2 times / day multiple, oral Overdose	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946	substrate 1,193	substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1,197 CYP2A6 626 CYP2C19 1,119 UGT2B7 456

Drug as victim

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Target	Modality	Activity
CYP1A2 1,197	substrate 4,014	likely
CYP2A6 626	substrate 4,014	likely
CYP2C19 1,119	substrate 4,014	likely
CYP2C9 1,193	substrate 4,014	likely
CYP2D6 1,388	substrate 4,014	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
BioSynth	D-3270
Compound Cloud	46174078
Compound Cloud	5284543
Compound Cloud	5492624
Compound Cloud	5493302

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PubMed

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Title	Date	PubMed
Time of drug elimination in chronic drug abusers. Case study of 52 patients in a "low-step" detoxification ward.	2001 Jun 15	11376991
Myocardial Infarction associated with methadone and/or dihydrocodeine.	2001 Mar	11316924
Important drugs for cough in advanced cancer.	2001 Nov	11762966
The role of tramadol in cancer pain treatment--a review.	2005 Jan	15668743
Simple and sensitive determination of free and total morphine in human liver and kidney using gas chromatography-mass spectrometry.	2006 Jan 18	16311082