HYDROCOTARNINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H15NO3
Molecular Weight	221.2524
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2OCOC2=CC3=C1CN(C)CC3

InChI

InChIKey=XXANNZJIZQTCBP-UHFFFAOYSA-N

InChI=1S/C12H15NO3/c1-13-4-3-8-5-10-12(16-7-15-10)11(14-2)9(8)6-13/h5H,3-4,6-7H2,1-2H3

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Description
Sources: http://www.merriam-webster.com/medical/hydrocotarnine
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/19252340

Hydrocotarnine is a crystalline alkaloid, obtained from opium and also formed by the reduction of cotarnine. It is a non-narcotic opium alkaloid. Hydrocotarnine is supposed to potentiate the analgesic effect of oxycodone with unknown mechanism.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19252340	Inhibitor 8297		18.4 µM [IC50]
Cytochrome P450 2D6 61 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19252340	Inhibitor 8297		6.63 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer pain 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19838028	Primary		Approved 8429	Unknown Approved Use Compound injection of oxycodone and hydrocotarnine is effective for cancer pain treatment

PubMed

Title	Date	PubMed
[Conversion ratio between intravenous oxycodone/hydrocotarnine and sustained-release oral oxycodone in patients with cancer pain].	2007 Dec	18079625
Effect of hydrocotarnine on cytochrome P450 and P-glycoprotein.	2009	19252340
[Efficacy and safety of continuous subcutaneous injection of the compound oxycodone in cancer pain management: the first 4-year audit].	2009 Oct	19838028
[Efficacy and safety of compound oxycodone injection for cancer pain relief-a multicenter survey of prescriptions].	2010 May	20495318

Patents

Sample Use Guides

In Vivo Use Guide

injections of oxycodone and hydrocotarnine contains 8 mg of oxycodone hydrochloride and 2 mg of hydrocotarnine hydrochloride.

Route of Administration: Other

In Vitro Use Guide

Hydrocotarnine (0.000388–38.8 mM) did not induce a significant change in the metabolic activities of CYP2C9, 2C19, and 2E1. Although weak inhibitory effects were observed on CYP3A4 and 2D6, the inhibition rate was less than 50% at the concentrations below 3.88 mM.

Name

Type

Language

HYDROCOTARNINE

Common Name

English

8-METHOXY-5,6-METHYLENEDIOXY-2-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE

Systematic Name

English

Hydrocotarnine [WHO-DD]

Common Name

English

HYDROCOTARNINE [MI]

Common Name

English

5,6,7,8-TETRAHYDRO-4-METHOXY-6-METHYL-1,3-DIOXOLO(4,5-G)ISOQUINOLINE

Systematic Name

English

1,3-DIOXOLO(4,5-G)ISOQUINOLINE, 5,6,7,8-TETRAHYDRO-4-METHOXY-6-METHYL-

Systematic Name

English

Code System Code Type Description

FDA UNII

G22L6JNE61