Apomorphine

Identification

Summary

Apomorphine is a morphine derivative D2 dopamine agonist used to treat hypomobile "off" episodes of advanced Parkinson's disease.

Brand Names

Apokyn

Generic Name

Apomorphine

DrugBank Accession Number

DB00714

Background

Apomorphine is a non-ergoline dopamine D2 agonist indicated to treat hypomobility associated with Parkinson's. It was first synthesized in 1845 and first used in Parkinson's disease in 1884.¹⁰ Apomorphine has also been investigated as an emetic, a sedative, a treatment for alcoholism, and a treatment of other movement disorders.^9,10

Apomorphine was granted FDA approval on 20 April 2004.¹¹

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Apomorphine (DB00714)

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Weight

Average: 267.3224
Monoisotopic: 267.125928793

Chemical Formula

C₁₇H₁₇NO₂

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

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Pharmacology

Indication

Apomorphine is indicated to treat acute, intermittent treatment of hypomobility, off episodes associated with advanced Parkinson's disease.^11,12

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Hypomobility		••••••••••••			••••• •••••••••

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Pharmacodynamics

Apomorphine is a dopaminergic agonist that may stimulate regions of the brain involved in motor control.^8,11,12 It has a short duration of action and a wide therapeutic index as large overdoses are necessary for significant toxicity.^11,12 Patients should be counselled regarding the risk of nausea, vomiting, daytime somnolence, hypotension, oral mucosal irritation, falls, hallucinations, psychotic-like behaviour, impulsive behaviour, withdrawal hyperpyrexia, and prolongation of the QT interval.^11,12

Given the incidence of nausea and vomiting in patients taking apomorphine, treatment with trimethobenzamide may be recommended prior to or during therapy. Antiemetic pretreatment may be started three days prior to beginning therapy with apomorphine - it should only be continued as long as is necessary and generally for no longer than two months.¹⁵

Mechanism of action

Apomorphine is a non-ergoline dopamine agonist with high binding affinity to dopamine D2, D3, and D5 receptors.^11,12 Stimulation of D2 receptors in the caudate-putamen, a region of the brain responsible for locomotor control, may be responsible for apomorphine's action.⁸ However, the means by which the cellular effects of apomorphine treat hypomobility of Parkinson's remain unknown.^11,12

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

Absorption

Apomorphine has a plasma T_max of 10-20 minutes and a cerebrospinal fluid T_max.⁴ The C_max and AUC of apomorphine vary significantly between patients, with 5- to 10-fold differences being reported.^4,6

Volume of distribution

The apparent volume of distribution of subcutaneous apomorphine is 123-404L with an average of 218L.¹¹ The apparent volume of distribution of sublingual apomorphine is 3630L.¹²

Protein binding

Apomorphine is expected to be 99.9% bound to human serum albumin, as no unbound apomorphine is detected.^3,6

Metabolism

Apomorphine is N-demethylated by CYP2B6, 2C8, 3A4, and 3A5.¹¹ It can be glucuronidated by various UGTs,¹¹ or sulfated by SULTs 1A1, 1A2, 1A3, 1E1, and 1B1.² Approximately 60% of sublingual apomorphine is eliminated as a sulfate conjugate, though the structure of these sulfate conjugates are not readily available.^2,11 The remainder of an apomorphine dose is eliminated as apomorphine glucuronide and norapomorphine glucuronide.¹¹ Only 0.3% of subcutaneous apomorphine is recovered as the unchanged parent drug.⁵

Hover over products below to view reaction partners

• Apomorphine
  • Apocodeine + Isoapocodeine
  • O-quinone
  • Apomorphine 10-glucuronide
  • Apomorphine 11-glucuronide
  • Norapomorphine

Route of elimination

Data regarding apomorphine's route of elimination is not readily available.^11,12 A study in rats has shown apomorphine is predominantly eliminated in the urine.⁷

Half-life

The terminal elimination half life of a 15mg sublingual dose of apomorphine is 1.7h,¹¹ while the terminal elimination half life of an intravenous dose is 50 minutes.¹²

Clearance

The clearance of a 15mg sublingual dose of apomorphine is 1440L/h,¹¹ while the clearance of an intravenous dose is 223L/h.¹²

Adverse Effects

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Toxicity

Patients experiencing an overdose of apomorphine may present with nausea, hypotension, and loss of consciousness.¹¹ Treat patients with symptomatic and supportive measures.

The intraperitoneal LD₅₀ in mice is 145µg/kg.¹³

Pathways

Not Available

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Interactions

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of CNS depression can be increased when Apomorphine is combined with 1,2-Benzodiazepine.
Abaloparatide	The risk or severity of adverse effects can be increased when Apomorphine is combined with Abaloparatide.
Abametapir	The serum concentration of Apomorphine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Apomorphine can be increased when combined with Abatacept.
Abiraterone	The metabolism of Apomorphine can be decreased when combined with Abiraterone.

Food Interactions

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

Products

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Product Ingredients

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

Product Images

International/Other Brands

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

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apokyn	Injection	30 mg/3mL	Subcutaneous	Tercica	2004-07-02	2011-10-31
Apokyn	Injection	30 mg/3mL	Subcutaneous	MDD US Operations, LLC	2004-07-02	Not applicable
Apokyn	Liquid	10 mg/1mL	Subcutaneous	Vernalis Pharmaceuticals Inc	2006-09-19	2006-09-19
Kynmobi	Film, soluble	10 mg/1	Sublingual	Sunovion Pharmaceuticals Inc.	2020-05-21	2023-06-30
Kynmobi	Film, soluble	30 mg / film	Sublingual	Sunovion	2020-11-17	2023-09-29

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apomorphine Hydrocloride	Injection	30 mg/3mL	Subcutaneous	Trupharma, Llc	2022-02-24	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Kynmobi	Apomorphine hydrochloride (10 mg/1) + Apomorphine hydrochloride (15 mg/1) + Apomorphine hydrochloride (20 mg/1) + Apomorphine hydrochloride (25 mg/1) + Apomorphine hydrochloride (30 mg/1)	Kit	Sublingual	Sunovion Pharmaceuticals Inc.	2020-05-21	2023-06-30
Kynmobi	Apomorphine hydrochloride (10 mg/1) + Apomorphine hydrochloride (15 mg/1) + Apomorphine hydrochloride (20 mg/1) + Apomorphine hydrochloride (25 mg/1) + Apomorphine hydrochloride (30 mg/1)	Kit	Sublingual	Sunovion Pharmaceuticals Inc.	2020-05-21	2023-06-30
Kynmobi	Apomorphine hydrochloride (10 mg/1) + Apomorphine hydrochloride (15 mg/1) + Apomorphine hydrochloride (20 mg/1) + Apomorphine hydrochloride (25 mg/1) + Apomorphine hydrochloride (30 mg/1)	Kit	Sublingual	Sunovion Pharmaceuticals Inc.	2020-05-21	2023-06-30
Kynmobi	Apomorphine hydrochloride (10 mg/1) + Apomorphine hydrochloride (15 mg/1) + Apomorphine hydrochloride (20 mg/1) + Apomorphine hydrochloride (25 mg/1) + Apomorphine hydrochloride (30 mg/1)	Kit	Sublingual	Sunovion Pharmaceuticals Inc.	2020-05-21	2023-06-30
Kynmobi	Apomorphine hydrochloride (10 mg/1) + Apomorphine hydrochloride (15 mg/1) + Apomorphine hydrochloride (20 mg/1) + Apomorphine hydrochloride (25 mg/1) + Apomorphine hydrochloride (30 mg/1)	Kit	Sublingual	Sunovion Pharmaceuticals Inc.	2020-05-21	2023-06-30

Categories

ATC Codes

G04BE07 — Apomorphine

• G04BE — Drugs used in erectile dysfunction
• G04B — UROLOGICALS
• G04 — UROLOGICALS
• G — GENITO URINARY SYSTEM AND SEX HORMONES

N04BC07 — Apomorphine

• N04BC — Dopamine agonists
• N04B — DOPAMINERGIC AGENTS
• N04 — ANTI-PARKINSON DRUGS
• N — NERVOUS SYSTEM

Drug Categories

• Alkaloids
• Anti-Parkinson Agents (Dopamine Agonist)
• Anti-Parkinson Drugs
• Antidepressive Agents
• Aporphines
• Autonomic Agents
• Benzylisoquinolines
• Central Nervous System Agents
• Central Nervous System Depressants
• COMT Substrates
• Cytochrome P-450 CYP2B6 Substrates
• Cytochrome P-450 CYP2C8 Substrates
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 Substrates
• Dopamine Agents
• Dopamine Agonists
• Drugs Used in Erectile Dysfunction
• Emetics
• Gastrointestinal Agents
• Genito Urinary System and Sex Hormones
• Heterocyclic Compounds, Fused-Ring
• Hypotensive Agents
• Isoquinolines
• Nervous System
• Neurotransmitter Agents
• Nonergot-derivative Dopamine Receptor Agonists
• Opiate Agonists
• Peripheral Nervous System Agents
• Potential QTc-Prolonging Agents
• QTc Prolonging Agents
• Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
• Serotonin Agents
• Serotonin Receptor Antagonists
• Urologicals

Chemical TaxonomyProvided by Classyfire

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 / Organooxygen compounds / Hydrocarbon derivatives

show 2 more

Substituents

1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 1-naphthol / 2-naphthol / Amine / Aporphine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoquinoline / Hydrocarbon derivative / Naphthalene / Organic nitrogen compound / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenanthrene / Quinoline / Tertiary aliphatic amine / Tertiary amine / Tetrahydroisoquinoline

show 14 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid, isoquinolines (CHEBI:48538)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

N21FAR7B4S

CAS number

58-00-4

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[7.7.1.0^{2,7}.0^{13,17}]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

References

Synthesis Reference

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

US20100228032

General References

1. 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. [Article]
2. 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. [Article]
3. Fanali G, Rampoldi V, di Masi A, Bolli A, Lopiano L, Ascenzi P, Fasano M: Binding of anti-Parkinson's disease drugs to human serum albumin is allosterically modulated. IUBMB Life. 2010 May;62(5):371-6. doi: 10.1002/iub.317. [Article]
4. Jenner P, Katzenschlager R: Apomorphine - pharmacological properties and clinical trials in Parkinson's disease. Parkinsonism Relat Disord. 2016 Dec;33 Suppl 1:S13-S21. doi: 10.1016/j.parkreldis.2016.12.003. Epub 2016 Dec 13. [Article]
5. 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. [Article]
6. 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. [Article]
7. Haberzettl R, Fink H, Bert B: The murine serotonin syndrome - evaluation of responses to 5-HT-enhancing drugs in NMRI mice. Behav Brain Res. 2015 Jan 15;277:204-10. doi: 10.1016/j.bbr.2014.04.033. Epub 2014 Apr 27. [Article]
8. Costall B, Naylor RJ, Nohria V: Hyperactivity response to apomorphine and amphetamine in the mouse: the importance of the nucleus accumbens and caudate-putamen. J Pharm Pharmacol. 1979 Apr;31(4):259-61. doi: 10.1111/j.2042-7158.1979.tb13494.x. [Article]
9. Riegel F, Boehm R: Investigation into the Action of Apomorphin as an Emetic in Its Physiological and Therapeutic Relations. Glasgow Med J. 1872 May;4(3):362-377. [Article]
10. Auffret M, Drapier S, Verin M: The Many Faces of Apomorphine: Lessons from the Past and Challenges for the Future. Drugs R D. 2018 Jun;18(2):91-107. doi: 10.1007/s40268-018-0230-3. [Article]
11. FDA Approved Drug Products: Apomorphine Subcutaneous Injection [Link]
12. FDA Approved Drug Products: Apomorphine Sublingual Film [Link]
13. Cayman Chemical: Apomorphine MSDS [Link]
14. FDA Approved Drug Products: APOKYN® (apomorphine hydrochloride) injection, for subcutaneous use [Link]
15. FDA Approved Drug Products: KYNMOBI® (apomorphine hydrochloride) sublingual film 2022 [Link]

External Links

Human Metabolome Database

HMDB0014852

KEGG Drug

D07460

PubChem Compound

6005

PubChem Substance

46508653

ChemSpider

5783

BindingDB

50001955

RxNav

1043

ChEBI

48538

ChEMBL

CHEMBL53

ZINC

ZINC000000009073

Therapeutic Targets Database

DAP000281

PharmGKB

PA164781163

Guide to Pharmacology

GtP Drug Page

PDBe Ligand

OR9

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Apomorphine

PDB Entries

7jvq

FDA label

Download (513 KB)

MSDS

Download (25.8 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Parkinson's Disease (PD)	1
4	Completed	Treatment	Akinesia / Delayed Levodopa Onset / Mobility decreased / Motor Symptoms / Parkinson's Disease (PD)	1
4	Completed	Treatment	Chronic Lower Back Pain (CLBP)	1
4	Not Yet Recruiting	Treatment	Restless Legs Syndrome (RLS)	1
4	Recruiting	Treatment	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
Solution		10 mg/1ml
Solution	Subcutaneous	5 mg/ml
Injection, solution	Parenteral	10 mg/ml
Injection	Subcutaneous	5 mg/ml
Injection, solution	Parenteral	50 MG/5ML
Injection, solution	Parenteral; Subcutaneous	30 MG/3ML
Injection, solution	Subcutaneous	20 mg/2ml
Injection, solution	Subcutaneous	50 mg/5ml
Solution	Subcutaneous	10 mg
Injection	Subcutaneous	30 mg/3mL
Liquid	Subcutaneous	10 mg/1mL
Tablet	Sublingual	2 mg
Solution	Parenteral
Injection, solution		10 MG/ML
Injection, solution		5 MG/ML
Solution	Subcutaneous	50.00 mg
Solution	Parenteral	5 mg/ml
Solution	Subcutaneous	5 mg
Solution	Subcutaneous	1000000 mg
Injection, solution
Injection, solution		20 mg/2ml
Injection, solution		30 mg/3ml
Injection, solution		50 mg/5ml
Tablet	Sublingual
Film, soluble	Sublingual	10 mg/1
Film, soluble	Sublingual	10 mg / film
Film, soluble	Sublingual	15 mg/1
Film, soluble	Sublingual	15 mg / film
Film, soluble	Sublingual	20 mg/1
Film, soluble	Sublingual	20 mg / film
Film, soluble	Sublingual	25 mg/1
Film, soluble	Sublingual	25 mg / film
Film, soluble	Sublingual	30 mg/1
Film, soluble	Sublingual	30 mg / film
Kit	Sublingual
Solution	Subcutaneous	10 mg / mL
Injection	Subcutaneous	20 mg/2ml
Injection	Subcutaneous	50 mg/5ml

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8603514	No	2013-12-10	2024-04-03
US9855221	No	2018-01-02	2022-02-14
US9931305	No	2018-04-03	2022-02-14
US8765167	No	2014-07-01	2024-02-20
US8414922	No	2013-04-09	2031-12-16
US9669021	No	2017-06-06	2030-06-11
US9669019	No	2017-06-06	2030-06-11
US8846074	No	2014-09-30	2031-12-16
US9283219	No	2016-03-15	2030-06-11
US10420763	No	2019-09-24	2030-06-11
US9326981	No	2016-05-03	2030-06-11
US10449146	No	2019-10-22	2036-04-19
US8663687	No	2014-03-04	2023-02-02
US9044475	No	2015-06-02	2030-06-11
US10821074	No	2020-11-03	2029-08-07
US10888499	No	2021-01-12	2022-02-14
US10959943	No	2021-03-30	2036-04-19
US11077068	No	2021-08-03	2022-02-14
US11419769	No	2011-12-16	2031-12-16

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	2.88	Chemaxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.26	Chemaxon
pKa (Strongest Basic)	7.72	Chemaxon
Physiological Charge	1	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	splash10-0gb9-0190000000-4a508d96ec3f544ad0a5
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-0090000000-290421b2593b6ec1f059
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0090000000-09ed226472fa75b4de64
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-0090000000-79bd45b691caf9b7bf6f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0090000000-3da7831b7e8cd76e1a62
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-06du-0390000000-4eaaa8062302ab04a8a2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0190000000-c78e197d2aecab6080b2
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	169.0546528	predicted	DarkChem Lite v0.1.0
[M-H]-	162.9794	predicted	DeepCCS 1.0 (2019)
[M+H]+	169.2649528	predicted	DarkChem Lite v0.1.0
[M+H]+	165.33739	predicted	DeepCCS 1.0 (2019)
[M+Na]+	169.1359528	predicted	DarkChem Lite v0.1.0
[M+Na]+	171.72026	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	4.3	N/A	N/A	A28833 / A28834
EC 50 (nM)	1.5	N/A	N/A	A28834
Ki (nM)	8.9	N/A	N/A	A28834

Details

Binding Properties1. 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

1. 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. [Article]
2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
3. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [Article]
4. 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. [Article]
5. 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. [Article]
6. 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. [Article]
7. 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. [Article]
8. 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. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	5.8	N/A	N/A	A28833 / A28834
EC 50 (nM)	1.8	N/A	N/A	A28834
EC 50 (nM)	20	N/A	N/A	A27509
EC 50 (nM)	4	N/A	N/A	A28192
Kd (nM)	127	N/A	N/A	A28835
Kd (nM)	0.66	N/A	N/A	A28835
Kd (nM)	24	N/A	N/A	A28825
Ki (nM)	41.9	N/A	N/A	A28836 / A28838 / A28839 / A28832
Ki (nM)	28	N/A	N/A	A28463
Ki (nM)	>217	N/A	N/A	A28086
Ki (nM)	26	N/A	N/A	A28332 / A28837
Ki (nM)	41.6	N/A	N/A	A28831
Ki (nM)	3.6	N/A	N/A	A28834
Ki (nM)	32	N/A	N/A	A28840
Ki (nM)	98	N/A	N/A	A28826
Ki (nM)	244	N/A	N/A	A27829
Ki (nM)	0.62	N/A	N/A	A27829
Ki (nM)	50	N/A	N/A	A28830

Details

Binding Properties2. 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

1. 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. [Article]
2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
3. 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. [Article]
4. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [Article]
5. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [Article]
6. 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. [Article]
7. 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. [Article]
8. 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. [Article]
9. 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. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	7	N/A	N/A	A27509
Ki (nM)	7.8	N/A	N/A	A28463
Ki (nM)	2.6	N/A	N/A	A28829
Ki (nM)	10	N/A	N/A	A28830

Details

Binding Properties3. 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

1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
2. 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. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	363	N/A	N/A	A27892
Ki (nM)	14.79	N/A	N/A	A18213

Details

Binding Properties4. 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

1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
2. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [Article]
3. 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. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	52	N/A	N/A	A28192
Kd (nM)	680	N/A	N/A	A28825
Ki (nM)	680	N/A	N/A	A27892
Ki (nM)	400	N/A	N/A	A18178
Ki (nM)	371.54	N/A	N/A	A18213
Ki (nM)	290	N/A	N/A	A28826
Ki (nM)	72	N/A	N/A	A28827 / A28828
Ki (nM)	650	N/A	N/A	A28829
Ki (nM)	4.6	N/A	N/A	A28829
Ki (nM)	660	N/A	N/A	A28830

Details

Binding Properties5. 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

1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
2. 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. [Article]
3. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [Article]
4. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [Article]
5. 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. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	36.31	N/A	N/A	A18213

Details

Binding Properties6. 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

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

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	66.07	N/A	N/A	A18213

Details

Binding Properties7. 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

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

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	534	N/A	N/A	A28437
Ki (nM)	4929	N/A	N/A	A18178
Ki (nM)	296	N/A	N/A	A28831 / A28832

Details

Binding Properties8. 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

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

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	120.23	N/A	N/A	A18213

Details

Binding Properties9. 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

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

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

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

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	102.33	N/A	N/A	A18213

Details

Binding Properties11. 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

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

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	141.25	N/A	N/A	A18213

Details

Binding Properties12. 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

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

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1230.27	N/A	N/A	A18213

Details

Binding Properties13. 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

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

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	2951.21	N/A	N/A	A18213

Details

Binding Properties14. 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

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

×

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Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:54