(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

• ChemBase ID: 595
• Molecular Formular: C17H17NO2
• Molecular Mass: 267.32238
• Monoisotopic Mass: 267.12592879
• SMILES: Oc1c2c3c4[C@H](N(CCc4ccc3)C)Cc2ccc1O
• Canonical SMILES: CN1CCc2c3[C@H]1Cc1ccc(c(c1c3ccc2)O)O
• 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
• InChIKey: VMWNQDUVQKEIOC-CYBMUJFWSA-N

NAMES AND DATABASE IDS

Names

• 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; (9R)-10-methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaene-3,4-diol
• IUPAC Traditional name: apomorphine
• Brand Name: Uprima; Ixense; Apokyn
• Synonyms: Apomorfin; Apomorphine Hydrochloride Hemihydrate; Apomorphinium Chloride Hemihydrate; Apormorphine; L-Apomorphine; apomorphine; VR004; VR-040; VR-400; Apomorphine Hydrochloride; Apomorphine

Database IDs

• CAS Number: 41372-20-7
• PubChem SID: 160964058; 46508653
• PubChem CID: 6005
• CHEBI ID: 48538
• ATC CODE: N04BC07; G04BE07
• CHEMBL: 53
• Chemspider ID: 5783
• DrugBank ID: DB00714
• IUPHAR ligand ID: 33
• KEGG ID: D07460
• Unique Ingredient Identifier: F39049Y068
• Wikipedia Title: Apomorphine
• Medline Plus: a604020

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.5761385
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.9807055
• LogD (pH = 7.4): 2.013494
• Log P: 2.054109
• Molar Refractivity: 79.9881 cm^3
• Polarizability: 31.638338 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.51
• LOG S: -2.72
• Solubility (Water): 5.10e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1.66E+004 mg/L
• Hydrophobicity(logP): 3.1

Pharmacology Properties

• Admin Routes: Oral, SC
• Bioavailability: 100% following sc injection
• Half Life: 40 minutes (range 30-60 minutes)
• Metabolism: Hepatic
• Protein Bound: ~50%
• Legal Status: Rx-only
• Pregnancy Category: C

DETAILS

DrugBank - DB00714

• Drug 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. [PubChem]
• 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.
• Pharmacology: 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.
• Toxicity: LD₅₀=0.6 mmoles/kg (mice, intraperitoneal)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 100% following subcutaneous administration
• Half Life: 40 minutes (range 30 - 60 minutes)
• Protein Binding: ~50%-albumin
• Distribution: * 123 to 404 L
• Clearance: * 223 L/hr
• 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] ; SCHWAB RS, AMADOR LV, LETTVIN JY: Apomorphine in Parkinson's disease. Trans Am Neurol Assoc. 1951;56:251-3. [Pubmed] ; 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] ; 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] ; Chaudhuri KR, Clough C: Subcutaneous apomorphine in Parkinson's disease. BMJ. 1998 Feb 28;316(7132):641. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

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
• SCHWAB RS, AMADOR LV, LETTVIN JY: Apomorphine in Parkinson's disease. Trans Am Neurol Assoc. 1951;56:251-3. Pubmed
• 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
• 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
• Chaudhuri KR, Clough C: Subcutaneous apomorphine in Parkinson's disease. BMJ. 1998 Feb 28;316(7132):641. Pubmed