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Showing metabocard for Apomorphine (HMDB0014852)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (15) Show 15 proteinsXML
enzymes (15) Show 15 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:27 UTC
HMDB IDHMDB0014852
Secondary Accession Numbers
  • HMDB14852
Metabolite Identification
Common NameApomorphine
DescriptionApomorphine, also known as uprima or apomorfin, 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. Apomorphine is a drug which is used 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. Apomorphine is a very strong basic compound (based on its pKa). Apomorphine is a potentially toxic compound. 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. Apomorphine has been shown to improve motor function in an animal model of Parkinson's disease. It is a powerful emetic and has been used for that effect in acute poisoning. In higher doses it is a highly effective emetic.
Structure
Data?1582753227
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-10,11-DihydroxyaporphineChEBI
(6AR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diolChEBI
(R)-5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diolChEBI
ApomorphinChEBI
R-(-)-ApomorphineChEBI
UprimaKegg
ApomorfinHMDB
Apomorphine hydrochloride hemihydrateHMDB
Apomorphinium chloride hemihydrateHMDB
ApormorphineHMDB
L-ApomorphineHMDB
VR-040HMDB
VR-400HMDB
VR004HMDB
Anhydrous apomorphine hydrochlorideHMDB
Apomorphin-teclapharmHMDB
Britannia brand OF apomorphine hydrochlorideHMDB
Hemihydrate apomorphine hydrochlorideHMDB
Apomorphine hydrochloride, hemihydrateHMDB
BritajectHMDB
Chloride, apomorphineHMDB
Hydrochloride, apomorphineHMDB
Aguettant brand OF apomorphine hydrochlorideHMDB
ApokinonHMDB
Apomorphine hydrochloride, anhydrousHMDB
Hydrochloride, anhydrous apomorphineHMDB
Teclapharm brand OF apomorphine hydrochlorideHMDB
Anhydrous, apomorphine hydrochlorideHMDB
Apomorphin teclapharmHMDB
ApomorphinTeclapharmHMDB
Apomorphine chlorideHMDB
Apomorphine hydrochlorideHMDB
Apomorphine hydrochloride anhydrousHMDB
Hydrochloride anhydrous, apomorphineHMDB
Hydrochloride, hemihydrate apomorphineHMDB
Chemical FormulaC17H17NO2
Average Molecular Weight267.3224
Monoisotopic Molecular Weight267.125928793
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
Traditional Nameapomorphine
CAS Registry Number41372-20-7
SMILES
[H][C@]12CC3=C(C(O)=C(O)C=C3)C3=CC=CC(CCN1C)=C23
InChI Identifier
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
InChI KeyVMWNQDUVQKEIOC-CYBMUJFWSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassNot Available
Direct ParentAporphines
Alternative Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • 2-naphthol
  • 1-naphthol
  • Naphthalene
  • Quinoline
  • Tetrahydroisoquinoline
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.51 g/LNot Available
LogP3.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP2.51ALOGPS
logP2.87ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)6.58ChemAxon
pKa (Strongest Basic)13.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area43.7 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.99 m³·mol⁻¹ChemAxon
Polarizability29.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gb9-0190000000-4a508d96ec3f544ad0a5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01vt-1119000000-110790047aaa5266ec7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014r-0090000000-29608efdadd8efd375a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-052772c02bbf103a3ef5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kr-0290000000-1e831a8078d43cfbdb51Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-49baaafc781fbd1a40eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-b2abd157ce4880c73d0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-b747e9bb748f801c3f50Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-1a55345a571167f3fca6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-0329e43d2073db5426bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0190000000-4dc4f5ea615d9b0a78e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05xu-1950000000-298a2d8a85a241732677Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-8dcf24a32f1f7baba7c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-734acff31070eb2a5a84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-2190000000-5a6e0c712dad2d12eaa9Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00714 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00714 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00714
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5783
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkApomorphine
METLIN IDNot Available
PubChem Compound6005
PDB IDNot Available
ChEBI ID48538
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Cotzias GC, Papavasiliou PS, Fehling C, Kaufman B, Mena I: Similarities between neurologic effects of L-dopa and of apomorphine. N Engl J Med. 1970 Jan 1;282(1):31-3. [PubMed:4901383 ]
  3. Chaudhuri KR, Clough C: Subcutaneous apomorphine in Parkinson's disease. BMJ. 1998 Feb 28;316(7132):641. [PubMed:9522772 ]
  4. SCHWAB RS, AMADOR LV, LETTVIN JY: Apomorphine in Parkinson's disease. Trans Am Neurol Assoc. 1951;56:251-3. [PubMed:14913646 ]
  5. 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 ]

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Alpha-2A adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
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. [PubMed:18691132 ]
Enzyme Details
2. Alpha-2B adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
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. [PubMed:18691132 ]
Enzyme Details
3. D(2) dopamine receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
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. [PubMed:11343576 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  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. [PubMed:11212866 ]
  4. 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 ]
  5. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
  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. [PubMed:11692072 ]
  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. [PubMed:11215397 ]
  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. [PubMed:10494453 ]
Enzyme Details
4. 5-hydroxytryptamine receptor 2B
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular weight:
54297.4
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. [PubMed:18691132 ]
Enzyme Details
5. 5-hydroxytryptamine receptor 1B
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
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. [PubMed:18691132 ]
Enzyme Details
6. D(4) dopamine receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD4
Uniprot ID:
P21917
Molecular weight:
48359.9
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. [PubMed:15007532 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. 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 ]
  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. [PubMed:9497025 ]
  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. [PubMed:17067298 ]
  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. [PubMed:9871530 ]
  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. [PubMed:17164075 ]
Enzyme Details
7. 5-hydroxytryptamine receptor 1A
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
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. [PubMed:18691132 ]
Enzyme Details
8. 5-hydroxytryptamine receptor 2A
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
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. [PubMed:18691132 ]
Enzyme Details
9. 5-hydroxytryptamine receptor 2C
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular weight:
51820.7
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. [PubMed:18691132 ]
Enzyme Details
10. 5-hydroxytryptamine receptor 1D
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1D
Uniprot ID:
P28221
Molecular weight:
41906.4
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. [PubMed:18691132 ]

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters