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Economics

Properties

Spectra

Taxonomy

Apomorphine

Targets (14)Enzymes (10)Biointeractions (15)

Identification

Name

Apomorphine

Accession Number

DB00714 (APRD00531, DB05816)

Type

Small Molecule

Groups

Approved, Investigational

Description

A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.

Apomorphine was granted FDA approval on 20 April 2004.⁸

Structure

Similar Structures

Synonyms

(−)-10,11-dihydroxyaporphine
(6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
(R)-5,6,6a,7-tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol
Apomorfina
Apomorphin
Apomorphine
R-(−)-apomorphine

External IDs

APL-130277 / VR-040 / VR-400 / VR040

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Apomorphine hydrochloride	F39049Y068	41372-20-7	CXWQXGNFZLHLHQ-DPFCLETOSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Apokyn	Injection	30 mg/3mL	Subcutaneous	US WorldMeds, LLC	2004-07-02	Not applicable
Apokyn	Liquid	10 mg/1mL	Subcutaneous	Vernalis Pharmaceuticals Inc	2006-09-19	2006-09-19
Apokyn	Injection	30 mg/3mL	Subcutaneous	Tercica	2004-07-02	2011-10-31
Movapo	Solution		Subcutaneous	Paladin Labs Inc	2017-09-07	Not applicable
Movapo	Solution		Subcutaneous	Paladin Labs Inc	Not applicable	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands

Ixense (Takeda (discontinued)) / Spontane / Uprima (Abbott (discontinued))

Categories

UNII

N21FAR7B4S

CAS number

58-00-4

Weight

Average: 267.3224
Monoisotopic: 267.125928793

Chemical Formula

C₁₇H₁₇NO₂

InChI Key

VMWNQDUVQKEIOC-CYBMUJFWSA-N

InChI

InChI=1S/C17H17NO2/c1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12/h2-6,13,19-20H,7-9H2,1H3/t13-/m1/s1

IUPAC Name

(9R)-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-3,4-diol

SMILES

[H][C@]12CC3=C(C(O)=C(O)C=C3)C3=CC=CC(CCN1C)=C23

Pharmacology

Indication

For the acute, intermittent treatment of hypomobility, off episodes (end-of-dose wearing off and unpredictable on/off episodes) associated with advanced Parkinson's disease.

Associated Conditions

Mobility decreased

Pharmacodynamics

Apomorphine is a type of dopaminergic agonist, a morphine derivative which primarily affects the hypothalamic region of the brain. Drugs containing this substance are sometimes used in the treatment of Parkinson's disease or erectile dysfunction. In higher doses it is a highly effective emetic.

Mechanism of action

The precise mechanism of action of apomorphine 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 brain. Apomorphine has been shown to improve motor function in an animal model of Parkinson's disease. In particular, apomorphine attenuates the motor deficits induced by lesions in the ascending nigrostriatal dopaminergic pathway with the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in primates.

Target	Actions	Organism
ADopamine D4 receptor	agonist	Humans
ADopamine D2 receptor	agonist	Humans
ADopamine D3 receptor	agonist	Humans
UDopamine D5 receptor	agonist	Humans
UDopamine D1 receptor	agonist	Humans
UAlpha-2C adrenergic receptor	agonist	Humans
UAlpha-2B adrenergic receptor	agonist	Humans
U5-hydroxytryptamine receptor 1A	agonist	Humans
U5-hydroxytryptamine receptor 2A	agonist	Humans
U5-hydroxytryptamine receptor 2B	agonist	Humans
U5-hydroxytryptamine receptor 2C	agonist	Humans
UAlpha-2A adrenergic receptor	agonist	Humans
U5-hydroxytryptamine receptor 1D	agonist	Humans
U5-hydroxytryptamine receptor 1B	agonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

100% following subcutaneous administration

Volume of distribution

123 to 404 L

Protein binding

~50%-albumin

Metabolism

Hepatic

Route of elimination

Not Available

Half life

40 minutes (range 30 - 60 minutes)

Clearance

223 L/hr

Toxicity

LD₅₀=0.6 mmoles/kg (mice, intraperitoneal)

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Unlock Additional Data
(R)-warfarin	The risk or severity of adverse effects can be increased when Apomorphine is combined with (R)-warfarin.
(S)-Warfarin	The risk or severity of adverse effects can be increased when Apomorphine is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of serotonin syndrome can be increased when Apomorphine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Apomorphine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when Apomorphine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarin	The risk or severity of adverse effects can be increased when Apomorphine is combined with 4-hydroxycoumarin.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Apomorphine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Apomorphine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-Nitroindazole	The risk or severity of adverse effects can be increased when Apomorphine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	The risk or severity of adverse effects can be increased when Apomorphine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Avoid alcohol. Ingesting alcohol may potentiate hypotension caused by apomorphine.

References

Synthesis Reference

Narayanasamy Gurusamy, "Process for Making Apomorphine and Apocodeine." U.S. Patent US20100228032, issued September 09, 2010.

US20100228032

General References

Matsumoto K, Yoshida M, Andersson KE, Hedlund P: Effects in vitro and in vivo by apomorphine in the rat corpus cavernosum. Br J Pharmacol. 2005 Sep;146(2):259-67. [PubMed:16025145]
SCHWAB RS, AMADOR LV, LETTVIN JY: Apomorphine in Parkinson's disease. Trans Am Neurol Assoc. 1951;56:251-3. [PubMed:14913646]
Cotzias GC, Papavasiliou PS, Fehling C, Kaufman B, Mena I: Similarities between neurologic effects of L-dipa and of apomorphine. N Engl J Med. 1970 Jan 1;282(1):31-3. [PubMed:4901383]
Corsini GU, Del Zompo M, Gessa GL, Mangoni A: Therapeutic efficacy of apomorphine combined with an extracerebral inhibitor of dopamine receptors in Parkinson's disease. Lancet. 1979 May 5;1(8123):954-6. [PubMed:87620]
Chaudhuri KR, Clough C: Subcutaneous apomorphine in Parkinson's disease. BMJ. 1998 Feb 28;316(7132):641. [PubMed:9522772]
Borkar N, Mu H, Holm R: Challenges and trends in apomorphine drug delivery systems for the treatment of Parkinson's disease. Asian J Pharm Sci. 2018 Nov;13(6):507-517. doi: 10.1016/j.ajps.2017.11.004. Epub 2017 Dec 6. [PubMed:32104425]
Thomas NL, Coughtrie MW: Sulfation of apomorphine by human sulfotransferases: evidence of a major role for the polymorphic phenol sulfotransferase, SULT1A1. Xenobiotica. 2003 Nov;33(11):1139-48. doi: 10.1080/00498250310001609192. [PubMed:14660177]
FDA Approved Drug Products: Apomorphine Subcutaneous Injection [Link]
FDA Approved Drug Products: Apomorphine Sublingual Film [Link]

External Links

Human Metabolome Database: HMDB0014852
KEGG Drug: D07460
PubChem Compound: 6005
PubChem Substance: 46508653
ChemSpider: 5783
BindingDB: 29644
RxNav: 1043
ChEBI: 48538
ChEMBL: CHEMBL53
ZINC: ZINC000000009073
Therapeutic Targets Database: DAP000281
PharmGKB: PA164781163
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Apomorphine

ATC Codes

G04BE07 — Apomorphine

N04BC07 — Apomorphine

AHFS Codes

28:36.20.08 — Nonergot-derivative Dopamine Receptor Agonists
28:08.08 — Opiate Agonists

FDA label

Download (513 KB)

MSDS

Download (25.8 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Completed	Basic Science	Healthy Volunteers	1
2	Completed	Treatment	Off Episodes of Parkinson Disease / Parkinson's Disease (PD)	1
2	Completed	Treatment	Parkinson's Disease (PD)	7
2	Recruiting	Treatment	Apomorphine-induced Skin Reactions / Parkinson's Disease (PD)	1
2	Recruiting	Treatment	Disorders of Consciousness	1
2	Recruiting	Treatment	Parkinson's Disease (PD) / Visual Hallucinations	1
2	Suspended	Treatment	Injuries, Brain	1
2	Unknown Status	Basic Science	Alcohol Dependence	1
2	Withdrawn	Treatment	Parkinson's Disease (PD)	1
2, 3	Completed	Treatment	Parkinson's Disease (PD)	2
3	Active Not Recruiting	Treatment	Idiopathic Parkinson's Disease	1
3	Completed	Basic Science	Parkinson's Disease (PD)	1
3	Completed	Treatment	Idiopathic Parkinson's Disease	1
3	Completed	Treatment	Parkinson Disease, Off Episodes / Parkinson's Disease (PD)	1
3	Completed	Treatment	Parkinson's Disease (PD)	8
3	Recruiting	Treatment	Motor OFF Episodes Associated With Parkinson's Disease	1
3	Recruiting	Treatment	Parkinson's Disease (PD)	2
4	Completed	Treatment	Akinesia / Delayed Levadopa Onset / Delayed Levodopa Onset / Mobility decreased / Motor Symptoms / Parkinson's Disease (PD)	1
4	Completed	Treatment	Back Pain Lower Back Chronic	1
4	Recruiting	Treatment	Parkinson's Disease (PD)	2
4	Terminated	Supportive Care	Motor Symptoms / Parkinson's Disease (PD)	1
Not Available	Completed	Basic Science	Parkinson's Disease (PD)	1
Not Available	Recruiting	Other	Parkinson's Disease (PD)	1

Pharmacoeconomics

Manufacturers

Ipsen biopharm ltd

Packagers

Ipsen Pharmaceuticals Inc.
Tercica Inc.
Vetter Pharma Fertigung GmbH and Co. KG

Dosage forms

Form	Route	Strength
Injection	Subcutaneous	30 mg/3mL
Liquid	Subcutaneous	10 mg/1mL
Solution	Subcutaneous

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	2.0	Borkar et al, 2017

Predicted Properties

Property	Value	Source
Water Solubility	0.51 mg/mL	ALOGPS
logP	2.51	ALOGPS
logP	2.87	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	13.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.99 m³·mol^-1	ChemAxon
Polarizability	29.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9816
Blood Brain Barrier	+	0.9401
Caco-2 permeable	+	0.777
P-glycoprotein substrate	Substrate	0.8501
P-glycoprotein inhibitor I	Non-inhibitor	0.8781
P-glycoprotein inhibitor II	Non-inhibitor	0.964
Renal organic cation transporter	Inhibitor	0.6477
CYP450 2C9 substrate	Non-substrate	0.7577
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.7039
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.9146
CYP450 2D6 inhibitor	Non-inhibitor	0.9084
CYP450 2C19 inhibitor	Non-inhibitor	0.8718
CYP450 3A4 inhibitor	Non-inhibitor	0.9156
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9262
Ames test	AMES toxic	0.6775
Carcinogenicity	Non-carcinogens	0.9736
Biodegradation	Not ready biodegradable	0.8928
Rat acute toxicity	2.6446 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.6544
hERG inhibition (predictor II)	Inhibitor	0.7734

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014r-0090000000-29608efdadd8efd375a6
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-000i-0090000000-052772c02bbf103a3ef5
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00kr-0290000000-1e831a8078d43cfbdb51
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0090000000-49baaafc781fbd1a40ea
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0090000000-b2abd157ce4880c73d0b
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0090000000-b747e9bb748f801c3f50
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0090000000-1a55345a571167f3fca6

Taxonomy

Description: This compound belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
Kingdom: Organic compounds
Super Class: Alkaloids and derivatives
Class: Aporphines
Sub Class: Not Available
Direct Parent: Aporphines
Alternative Parents: Phenanthrenes and derivatives / Benzoquinolines / Naphthols and derivatives / Tetrahydroisoquinolines / Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents: Aporphine / Benzoquinoline / Phenanthrene / 2-naphthol / 1-naphthol / Naphthalene / Quinoline / Tetrahydroisoquinoline / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid
show 14 more
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: isoquinoline alkaloid, isoquinolines (CHEBI:48538)

Targets

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	1.5	N/A	N/A	17149874
EC 50 (nM)	4.3	N/A	N/A	15239663 / 17149874
Ki (nM)	8.9	N/A	N/A	17149874

Details1. Dopamine D4 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Sh3 domain binding
Specific Function: Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins ...
Gene Name: DRD4
Uniprot ID: P21917
Uniprot Name: D(4) dopamine receptor
Molecular Weight: 48359.86 Da

References

Boeckler F, Russig H, Zhang W, Lober S, Schetz J, Hubner H, Ferger B, Gmeiner P, Feldon J: FAUC 213, a highly selective dopamine D4 receptor full antagonist, exhibits atypical antipsychotic properties in behavioural and neurochemical models of schizophrenia. Psychopharmacology (Berl). 2004 Aug;175(1):7-17. Epub 2004 Mar 6. [PubMed:15007532]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
Mansbach RS, Brooks EW, Sanner MA, Zorn SH: Selective dopamine D4 receptor antagonists reverse apomorphine-induced blockade of prepulse inhibition. Psychopharmacology (Berl). 1998 Jan;135(2):194-200. [PubMed:9497025]
Melis MR, Succu S, Sanna F, Melis T, Mascia MS, Enguehard-Gueiffier C, Hubner H, Gmeiner P, Gueiffier A, Argiolas A: PIP3EA and PD-168077, two selective dopamine D4 receptor agonists, induce penile erection in male rats: site and mechanism of action in the brain. Eur J Neurosci. 2006 Oct;24(7):2021-30. [PubMed:17067298]
Sanner MA, Chappie TA, Dunaiskis AR, Fliri AF, Desai KA, Zorn SH, Jackson ER, Johnson CG, Morrone JM, Seymour PA, Majchrzak MJ, Faraci WS, Collins JL, Duignan DB, Prete Di CC, Lee JS, Trozzi A: Synthesis, SAR and pharmacology of CP-293,019: a potent, selective dopamine D4 receptor antagonist. Bioorg Med Chem Lett. 1998 Apr 7;8(7):725-30. [PubMed:9871530]
Succu S, Sanna F, Melis T, Boi A, Argiolas A, Melis MR: Stimulation of dopamine receptors in the paraventricular nucleus of the hypothalamus of male rats induces penile erection and increases extra-cellular dopamine in the nucleus accumbens: Involvement of central oxytocin. Neuropharmacology. 2007 Mar;52(3):1034-43. Epub 2006 Dec 11. [PubMed:17164075]
LeWitt PA: Subcutaneously administered apomorphine: pharmacokinetics and metabolism. Neurology. 2004 Mar 23;62(6 Suppl 4):S8-11. doi: 10.1212/wnl.62.6_suppl_4.s8. [PubMed:15037665]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	1.8	N/A	N/A	17149874
EC 50 (nM)	20	N/A	N/A	17976986
EC 50 (nM)	4	N/A	N/A	18313303
EC 50 (nM)	5.8	N/A	N/A	15239663 / 17149874
Kd (nM)	0.66	N/A	N/A	2524592
Kd (nM)	127	N/A	N/A	2524592
Kd (nM)	24	N/A	N/A	8632409
Ki (nM)	>217	N/A	N/A	8064801
Ki (nM)	0.62	N/A	N/A	20155917
Ki (nM)	244	N/A	N/A	20155917
Ki (nM)	26	N/A	N/A	8097537 / 8097538
Ki (nM)	28	N/A	N/A	7932581
Ki (nM)	3.6	N/A	N/A	17149874
Ki (nM)	32	N/A	N/A	18313931
Ki (nM)	41.6	N/A	N/A	10753471
Ki (nM)	41.9	N/A	N/A	7861413 / 8784447 / 8784448 / 11311055
Ki (nM)	50	N/A	N/A	22846798
Ki (nM)	98	N/A	N/A	18562201

Details2. Dopamine D2 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Potassium channel regulator activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name: DRD2
Uniprot ID: P14416
Uniprot Name: D(2) dopamine receptor
Molecular Weight: 50618.91 Da

References

Berlin I, de Brettes B, Aymard G, Diquet B, Arnulf I, Puech AJ: Dopaminergic drug response and the genotype (Taq IA polymorphism) of the dopamine D2 receptor. Int J Neuropsychopharmacol. 2000 Mar;3(1):35-43. [PubMed:11343576]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kim HJ, Koh PO, Kang SS, Paik WY, Choi WS: The localization of dopamine D2 receptor mRNA in the human placenta and the anti-angiogenic effect of apomorphine in the chorioallantoic membrane. Life Sci. 2001 Jan 19;68(9):1031-40. [PubMed:11212866]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988]
Lucht MJ, Kuehn KU, Schroeder W, Armbruster J, Abraham G, Schattenberg A, Gaensicke M, Barnow S, Tretzel H, Herrmann FH, Freyberger HJ: Influence of the dopamine D2 receptor (DRD2) exon 8 genotype on efficacy of tiapride and clinical outcome of alcohol withdrawal. Pharmacogenetics. 2001 Nov;11(8):647-53. [PubMed:11692072]
Yamada S: [Disruption of prepulse inhibition of acoustic startle as an animal model for schizophrenia]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2000 Oct;20(4):131-9. [PubMed:11215397]
Yamada S, Harano M, Annoh N, Nakamura K, Tanaka M: Involvement of serotonin 2A receptors in phencyclidine-induced disruption of prepulse inhibition of the acoustic startle in rats. Biol Psychiatry. 1999 Sep 15;46(6):832-8. [PubMed:10494453]
LeWitt PA: Subcutaneously administered apomorphine: pharmacokinetics and metabolism. Neurology. 2004 Mar 23;62(6 Suppl 4):S8-11. doi: 10.1212/wnl.62.6_suppl_4.s8. [PubMed:15037665]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	7	N/A	N/A	17976986
Ki (nM)	10	N/A	N/A	22846798
Ki (nM)	2.6	N/A	N/A	21666830
Ki (nM)	7.8	N/A	N/A	7932581

Details3. Dopamine D3 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: G-protein coupled amine receptor activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name: DRD3
Uniprot ID: P35462
Uniprot Name: D(3) dopamine receptor
Molecular Weight: 44224.335 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
LeWitt PA: Subcutaneously administered apomorphine: pharmacokinetics and metabolism. Neurology. 2004 Mar 23;62(6 Suppl 4):S8-11. doi: 10.1212/wnl.62.6_suppl_4.s8. [PubMed:15037665]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	14.79	N/A	N/A	12388666
Ki (nM)	363	N/A	N/A	1826762

Details4. Dopamine D5 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: G-protein coupled amine receptor activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name: DRD5
Uniprot ID: P21918
Uniprot Name: D(1B) dopamine receptor
Molecular Weight: 52950.5 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
LeWitt PA: Subcutaneously administered apomorphine: pharmacokinetics and metabolism. Neurology. 2004 Mar 23;62(6 Suppl 4):S8-11. doi: 10.1212/wnl.62.6_suppl_4.s8. [PubMed:15037665]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	52	N/A	N/A	18313303
Kd (nM)	680	N/A	N/A	8632409
Ki (nM)	290	N/A	N/A	18562201
Ki (nM)	371.54	N/A	N/A	12388666
Ki (nM)	4.6	N/A	N/A	21666830
Ki (nM)	400	N/A	N/A	9686407
Ki (nM)	650	N/A	N/A	21666830
Ki (nM)	660	N/A	N/A	22846798
Ki (nM)	680	N/A	N/A	1826762
Ki (nM)	72	N/A	N/A	19454369 / 21550699

Details5. Dopamine D1 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: G-protein coupled amine receptor activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name: DRD1
Uniprot ID: P21728
Uniprot Name: D(1A) dopamine receptor
Molecular Weight: 49292.765 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Guo H, Tang Z, Yu Y, Xu L, Jin G, Zhou J: Apomorphine induces trophic factors that support fetal rat mesencephalic dopaminergic neurons in cultures. Eur J Neurosci. 2002 Nov;16(10):1861-70. [PubMed:12453049]
Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988]
LeWitt PA: Subcutaneously administered apomorphine: pharmacokinetics and metabolism. Neurology. 2004 Mar 23;62(6 Suppl 4):S8-11. doi: 10.1212/wnl.62.6_suppl_4.s8. [PubMed:15037665]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	36.31	N/A	N/A	12388666

Details6. Alpha-2C adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein homodimerization activity
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name: ADRA2C
Uniprot ID: P18825
Uniprot Name: Alpha-2C adrenergic receptor
Molecular Weight: 49521.585 Da

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	66.07	N/A	N/A	12388666

Details7. Alpha-2B adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Epinephrine binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name: ADRA2B
Uniprot ID: P18089
Uniprot Name: Alpha-2B adrenergic receptor
Molecular Weight: 49565.8 Da

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	296	N/A	N/A	10753471 / 11311055
Ki (nM)	4929	N/A	N/A	9686407
Ki (nM)	534	N/A	N/A	1348089

Details8. 5-hydroxytryptamine receptor 1A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Serotonin receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name: HTR1A
Uniprot ID: P08908
Uniprot Name: 5-hydroxytryptamine receptor 1A
Molecular Weight: 46106.335 Da

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
LeWitt PA: Subcutaneously administered apomorphine: pharmacokinetics and metabolism. Neurology. 2004 Mar 23;62(6 Suppl 4):S8-11. doi: 10.1212/wnl.62.6_suppl_4.s8. [PubMed:15037665]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	120.23	N/A	N/A	12388666

Details9. 5-hydroxytryptamine receptor 2A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Virus receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name: HTR2A
Uniprot ID: P28223
Uniprot Name: 5-hydroxytryptamine receptor 2A
Molecular Weight: 52602.58 Da

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
LeWitt PA: Subcutaneously administered apomorphine: pharmacokinetics and metabolism. Neurology. 2004 Mar 23;62(6 Suppl 4):S8-11. doi: 10.1212/wnl.62.6_suppl_4.s8. [PubMed:15037665]

Details10. 5-hydroxytryptamine receptor 2B

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Serotonin receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
Gene Name: HTR2B
Uniprot ID: P41595
Uniprot Name: 5-hydroxytryptamine receptor 2B
Molecular Weight: 54297.41 Da

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
LeWitt PA: Subcutaneously administered apomorphine: pharmacokinetics and metabolism. Neurology. 2004 Mar 23;62(6 Suppl 4):S8-11. doi: 10.1212/wnl.62.6_suppl_4.s8. [PubMed:15037665]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	102.33	N/A	N/A	12388666

Details11. 5-hydroxytryptamine receptor 2C

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Serotonin receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name: HTR2C
Uniprot ID: P28335
Uniprot Name: 5-hydroxytryptamine receptor 2C
Molecular Weight: 51820.705 Da

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]
LeWitt PA: Subcutaneously administered apomorphine: pharmacokinetics and metabolism. Neurology. 2004 Mar 23;62(6 Suppl 4):S8-11. doi: 10.1212/wnl.62.6_suppl_4.s8. [PubMed:15037665]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	141.25	N/A	N/A	12388666

Details12. Alpha-2A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Thioesterase binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name: ADRA2A
Uniprot ID: P08913
Uniprot Name: Alpha-2A adrenergic receptor
Molecular Weight: 48956.275 Da

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1230.27	N/A	N/A	12388666

Details13. 5-hydroxytryptamine receptor 1D

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Serotonin receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name: HTR1D
Uniprot ID: P28221
Uniprot Name: 5-hydroxytryptamine receptor 1D
Molecular Weight: 41906.38 Da

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	2951.21	N/A	N/A	12388666

Details14. 5-hydroxytryptamine receptor 1B

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Serotonin receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name: HTR1B
Uniprot ID: P28222
Uniprot Name: 5-hydroxytryptamine receptor 1B
Molecular Weight: 43567.535 Da

References

Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132]

Enzymes

Details1. Catechol O-methyltransferase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: O-methyltransferase activity
Specific Function: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name: COMT
Uniprot ID: P21964
Uniprot Name: Catechol O-methyltransferase
Molecular Weight: 30036.77 Da

References

van der Geest R, van Laar T, Kruger PP, Gubbens-Stibbe JM, Bodde HE, Roos RA, Danhof M: Pharmacokinetics, enantiomer interconversion, and metabolism of R-apomorphine in patients with idiopathic Parkinson's disease. Clin Neuropharmacol. 1998 May-Jun;21(3):159-68. [PubMed:9617507]

Details2. Sulfotransferase 1A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sulfotransferase activity
Specific Function: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estroge...
Gene Name: SULT1A1
Uniprot ID: P50225
Uniprot Name: Sulfotransferase 1A1
Molecular Weight: 34165.13 Da

References

Thomas NL, Coughtrie MW: Sulfation of apomorphine by human sulfotransferases: evidence of a major role for the polymorphic phenol sulfotransferase, SULT1A1. Xenobiotica. 2003 Nov;33(11):1139-48. doi: 10.1080/00498250310001609192. [PubMed:14660177]

Details3. Sulfotransferase 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Is also responsible for the sulfonation and activation of minoxidil. Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
Specific Function: Aryl sulfotransferase activity
Gene Name: SULT1A2
Uniprot ID: P50226
Uniprot Name: Sulfotransferase 1A2
Molecular Weight: 34309.49 Da

References

Thomas NL, Coughtrie MW: Sulfation of apomorphine by human sulfotransferases: evidence of a major role for the polymorphic phenol sulfotransferase, SULT1A1. Xenobiotica. 2003 Nov;33(11):1139-48. doi: 10.1080/00498250310001609192. [PubMed:14660177]

Details4. Sulfotransferase 1A3/1A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Specific Function: Amine sulfotransferase activity
Gene Name: SULT1A3
Uniprot ID: P0DMM9
Uniprot Name: Sulfotransferase 1A3
Molecular Weight: 34195.96 Da

References

Thomas NL, Coughtrie MW: Sulfation of apomorphine by human sulfotransferases: evidence of a major role for the polymorphic phenol sulfotransferase, SULT1A1. Xenobiotica. 2003 Nov;33(11):1139-48. doi: 10.1080/00498250310001609192. [PubMed:14660177]

Details5. Estrogen sulfotransferase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sulfotransferase activity
Specific Function: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen r...
Gene Name: SULT1E1
Uniprot ID: P49888
Uniprot Name: Estrogen sulfotransferase
Molecular Weight: 35126.185 Da

References

Thomas NL, Coughtrie MW: Sulfation of apomorphine by human sulfotransferases: evidence of a major role for the polymorphic phenol sulfotransferase, SULT1A1. Xenobiotica. 2003 Nov;33(11):1139-48. doi: 10.1080/00498250310001609192. [PubMed:14660177]

Details6. Sulfotransferase family cytosolic 1B member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sulfotransferase activity
Specific Function: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulf...
Gene Name: SULT1B1
Uniprot ID: O43704
Uniprot Name: Sulfotransferase family cytosolic 1B member 1
Molecular Weight: 34898.955 Da

References

Thomas NL, Coughtrie MW: Sulfation of apomorphine by human sulfotransferases: evidence of a major role for the polymorphic phenol sulfotransferase, SULT1A1. Xenobiotica. 2003 Nov;33(11):1139-48. doi: 10.1080/00498250310001609192. [PubMed:14660177]

Details7. Cytochrome P450 2B6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2B6
Uniprot ID: P20813
Uniprot Name: Cytochrome P450 2B6
Molecular Weight: 56277.81 Da

References

FDA Approved Drug Products: Apomorphine Subcutaneous Injection [Link]

Details8. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

FDA Approved Drug Products: Apomorphine Subcutaneous Injection [Link]

Details9. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

FDA Approved Drug Products: Apomorphine Subcutaneous Injection [Link]

Details10. Cytochrome P450 3A5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP3A5
Uniprot ID: P20815
Uniprot Name: Cytochrome P450 3A5
Molecular Weight: 57108.065 Da

References

FDA Approved Drug Products: Apomorphine Subcutaneous Injection [Link]

Drug created on June 13, 2005 07:24 / Updated on May 25, 2020 09:58

Apomorphine

Identification

Structure for Apomorphine (DB00714)

Pharmacology

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Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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Enzymes

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