Home > Compound List > Compound details
41372-20-7 molecular structure
click picture or here to close

(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 and InChIs

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

Cite this record

CBID:595 http://www.chembase.cn/molecule-595.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[7.7.1.02,7.013,17]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
CAS Number
41372-20-7
PubChem SID
46508653
160964058
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 6.5761385  H Acceptors
H Donor LogD (pH = 5.5) 0.9807055 
LogD (pH = 7.4) 2.013494  Log P 2.054109 
Molar Refractivity 79.9881 cm3 Polarizability 31.638338 Å3
Polar Surface Area 43.7 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.51  LOG S -2.72 
Solubility (Water) 5.10e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
1.66E+004 mg/L expand Show data source
Hydrophobicity(logP)
3.1 expand Show data source
Admin Routes
Oral, SC expand Show data source
Bioavailability
100% following sc injection expand Show data source
Half Life
40 minutes (range 30-60 minutes) expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
~50% expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
C expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00714 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle