APOMORPHINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C17H17NO2.2ClH.H2O
Molecular Weight	625.582
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O.Cl.Cl.[H][C@@]12CC3=C(C(O)=C(O)C=C3)C4=C1C(CCN2C)=CC=C4.[H][C@@]56CC7=C(C(O)=C(O)C=C7)C8=C5C(CCN6C)=CC=C8

InChI

InChIKey=CXWQXGNFZLHLHQ-DPFCLETOSA-N

InChI=1S/2C17H17NO2.2ClH.H2O/c2*1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12;;;/h2*2-6,13,19-20H,7-9H2,1H3;2*1H;1H2/t2*13-;;;/m11.../s1

HIDE SMILES / InChI

Molecular Formula	C17H17NO2
Molecular Weight	267.3224
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
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	ClH
Molecular Weight	36.461
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

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

Description

Apomorphine (brand names: Apokyn, Ixense, Spontane, Uprima) is indicated for the acute, intermittent treatment of hypomobility, “off” episodes (“end-of-dose wearing off” and unpredictable “on/off” episodes) in patients with advanced Parkinson’s disease. Apomorphine has been studied as an adjunct to other medications. It is a non-ergoline dopamine agonist with high in vitro binding affinity for the dopamine D4 receptor, and moderate affinity for the dopamine D2, D3, and D5, and adrenergic α1D, α2B, α2C receptors. The precise mechanism of action as a treatment for Parkinson’s disease is unknown, although it is believed to be due to stimulation of post-synaptic dopamine D2-type receptors within the caudate-putamen in the brain.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
D2-like dopamine receptor 9	Agonist 2,678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226	Palliative		Approved 8,429	APOKYN

C_max

Value	Dose	Co-administered	Analyte	Population
47.5 pmol/mL	30 μg/kg bw single, subcutaneous		APOMORPHINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
41.7 pmol × h/mL	30 μg/kg bw single, subcutaneous		APOMORPHINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
33.6 min	30 μg/kg bw single, subcutaneous		APOMORPHINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
4 mg single, respiratory Highest studied dose	unhealthy, 30 - 90 years n = 5
1.5 mg single, respiratory Recommended	unhealthy, 30 - 90 years n = 32	Other AEs: Somnolence, Dysgeusia...
2.3 mg single, respiratory Recommended	unhealthy, 30 - 90 years n = 18
3 mg single, respiratory Recommended	unhealthy, 30 - 90 years n = 12	Other AEs: Somnolence, Yawning...
10 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 44 - 87 years n = 114	Disc. AE: Cognitive impairment, Skin reaction...

Showing 1 to 5 of 9 entries

Previous1 2Next

AEs

Show entries

AE	Significance	Dose	Population
Dizziness	1 patient	1.5 mg single, respiratory Recommended	unhealthy, 30 - 90 years n = 32
Dysgeusia	1 patient	1.5 mg single, respiratory Recommended	unhealthy, 30 - 90 years n = 32
Orthostatic hypotension	1 patient	1.5 mg single, respiratory Recommended	unhealthy, 30 - 90 years n = 32
Somnolence	1 patient	1.5 mg single, respiratory Recommended	unhealthy, 30 - 90 years n = 32
Flushing	1 patient	3 mg single, respiratory Recommended	unhealthy, 30 - 90 years n = 12

Showing 1 to 5 of 22 entries

Previous1 2 3 4 5Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2B6 810 CYP2C8 911 CYP2C19 1,478 CYP3A4/5 278 BCRP 699 BSEP 402 P-gp 1,461 MRP2 383 MRP3 157 MRP4 204 MATE1 306 MATE2 263 OATP1B1 788 OATP1B3 706 OAT1 599 OAT3 642 OCT1 512 OCT2 647	UGT 192 sulfotransferases 38 CYP2B6 664 CYP2C8 693 CYP3A4/5 85	CYP1A2 701 CYP2B6 547 OCT1 35 P-gp 257 MRP2 111 MRP3 53 OATP1B1 26 BCRP 75

Drug as perpetrator

Show entries

Target	Modality	Activity	Metabolite
BCRP 773	inducer 1,573	no
BSEP 403	inhibitor 3,277	no	apomorphine glucuronide 3
CYP1A2 1,692	inducer 1,573	no	apomorphine glucuronide 3
CYP1A2 1,692	inhibitor 3,277	no	apomorphine glucuronide 3
CYP2B6 1,001	inducer 1,573	no

Showing 1 to 5 of 33 entries

Previous1 2 3 4 5 6 7Next

Drug as victim

Show entries

Target	Modality	Activity
CYP2B6 664	substrate 3,367	yes
CYP2C8 693	substrate 3,367	yes
CYP3A4/5 85	substrate 3,367	yes
UGT 192	substrate 3,367	yes
sulfotransferases 38	substrate 3,367	yes

Showing 1 to 5 of 5 entries

Previous1Next

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:48538	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48538
ZINC	ZINC000000009073	http://zinc15.docking.org/substances/ZINC000000009073
eMolecules	901400	https://www.emolecules.com/cgi-bin/more?vid=901400

Showing 1 to 3 of 3 entries

Previous1Next

PubMed

Show entries

Title	Date	PubMed
Treatment of Parkinson's disease with aporphines. Possible role of growth hormone.	1976 Mar 11	1107835
Modulatory role of 5-HT3 receptors in mediation of apomorphine-induced aggressive behaviour in male rats.	1999 Dec	10595424
Effects of continuous exposure to light on behavioral dopaminergic supersensitivity.	1999 Jun 15	10376124
Worsening of levodopa-induced dyskinesias by motor and mental tasks.	1999 Mar	10091616
Catecholamines participate in the induction of ornithine decarboxylase gene expression in normal and hyperplastic mouse kidney.	1999 May 31	10354516

Showing 1 to 5 of 42 entries

Previous1 2 3 4 5…9Next

Patents

Sample Use Guides

In Vivo Use Guide

The recommended starting dose of is 0.2 mL (2 mg). Titrate on the basis of effectiveness and tolerance, up to a maximum recommended dose of 0.6 mL (6 mg)

Route of Administration: Other

In Vitro Use Guide

Apomorphine at concentrations of higher than 2 x 10(-5) M dramatically reduced the growth-stimulatory effect of retinal pigment epithelium (RPE) cells on the scleral chondrocytes, whereas the inhibitory effect of apomorphine on the proliferation of scleral chondrocytes without RPE cells was very little

Substance Class	Chemical
Record UNII	F39049Y068
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

APOMORPHINE HYDROCHLORIDE

Common Name

English

APOMORPHINE HYDROCHLORIDE HYDRATE

Common Name

English

TALUVIAN

Brand Name

English

APOMORPHINUM MURIATICUM [HPUS]

Common Name

English

APOMORPHINE HYDROCHLORIDE HEMIHYDRATE

Common Name

English

Showing 1 to 5 of 25 entries

Previous1 2 3 4 5Next

Show entries

Classification Tree

Code System

Code

Agent Affecting Nervous System

NCI_THESAURUS

C66884

SEXUAL DYSFUNCTIONS, PSYCHOLOGICAL

EMA ASSESSMENT REPORTS

IXENSE (WITHDRAWN: ERECTILE DYSFUNCTIONS)

Positive

EU-Orphan Drug

EU/3/06/349

Agent Affecting Nervous System

NCI_THESAURUS

C38149

Designated

FDA ORPHAN DRUG

204305

Showing 1 to 5 of 7 entries

Previous1 2Next

Show entries

Code System

Code

Type

Description

DAILYMED

F39049Y068

PRIMARY

WIKIPEDIA

Apomorphine hydrochloride

PRIMARY

CAS

41372-20-7

PRIMARY

NSC

755875

PRIMARY

EPA CompTox

DTXSID0048185

PRIMARY

Showing 1 to 5 of 17 entries

Previous1 2 3 4Next

Show entries

Related Record

Type

Details


					F39049Y068

APOMORPHINE HYDROCHLORIDE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (TITRATION)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [98.5 to 100.5] WEIGHT PERCENT (limits)


					F39049Y068

APOMORPHINE HYDROCHLORIDE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (TITRATION)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [98.5 to 101.5] WEIGHT PERCENT (limits)


					9K13MD7A0D

APOMORPHINE HYDROCHLORIDE ANHYDROUS

ANHYDROUS->SOLVATE


					N21FAR7B4S

APOMORPHINE

PARENT -> SALT/SOLVATE

Amount:

Showing 1 to 4 of 4 entries

Previous1Next

Show entries

Related Record

Type

Details


					76I7G6D29C

MORPHINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.15] PERCENT PEAK AREA (limits)

Showing 1 to 1 of 1 entries

Previous1Next

Show entries

Related Record

Type

Details


					N21FAR7B4S

APOMORPHINE

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

SMILES

InChI

CNS Activity

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator