DIHYDROCODEINE PHOSPHATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H23NO3.H3O4P
Molecular Weight	399.3753
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=HFBYLYCMISIEMM-FFHNEAJVSA-N

InChI=1S/C18H23NO3.H3O4P/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;1-5(2,3)4/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3;(H3,1,2,3,4)/t11-,12+,13-,17-,18-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	H3O4P
Molecular Weight	97.9952
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H23NO3
Molecular Weight	301.3801
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

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
ECG abnormalities in co-proxamol (paracetamol/dextropropoxyphene) poisoning.	2005	16035201
Simultaneous analysis of thebaine, 6-MAM and six abused opiates in postmortem fluids and tissues using Zymark automated solid-phase extraction and gas chromatography-mass spectrometry.	2005 Aug 5	15993661
Clinical urinalysis of drugs and alcohol in instances of suspected surreptitious administration ("spiked drinks").	2005 Jul-Sep	16438340
The effect of non-steroidal anti-inflammatory drugs on medical abortion with mifepristone and misoprostol at 13-22 weeks gestation.	2005 Nov	16055455
Evaluation of buprenorphine CEDIA assay versus GC-MS and ELISA using urine samples from patients in substitution treatment.	2005 Nov-Dec	16356333

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Patents

Sample Use Guides

In Vivo Use Guide

The usual dose of dihydrocodeine is 1 tablet every 4 to 6 hours

Route of Administration: Oral

In Vitro Use Guide

Dihydrocodeine inhibited paracetamol glucuronidation with Ki value 4.02 mmol/l in human liver microsomes

Substance Class	Chemical
Record UNII	5D9XI60ASE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIHYDROCODEINE PHOSPHATE

Common Name

English

4,5-ALPHA-EPOXY-3-METHOXY-17-MORPHINAN-6-OL PHOSPHATE (1:1)

Preferred Name

English

MORPHINAN-6-OL, 4,5-EPOXY-3-METHOXY-17-METHYL-, (5.ALPHA.,6.ALPHA.)-, PHOSPHATE (1:1) (SALT)

Systematic Name

English

DIHYDROCODEINE PHOSPHATE [MART.]

Common Name

English

Dihydrocodeine phosphate [WHO-DD]

Common Name

English

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Code System

Code

Type

Description

CAS

24204-13-5

PRIMARY

EVMPD

SUB01706MIG

PRIMARY

FDA UNII

5D9XI60ASE

PRIMARY

PUBCHEM

5493302

PRIMARY

SMS_ID

100000087486

PRIMARY

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Related Record

Type

Details


					N9I9HDB855

DIHYDROCODEINE

PARENT -> SALT/SOLVATE

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Related Record

Type

Details


					N9I9HDB855

DIHYDROCODEINE

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2