Human Metabolome Database Version 3.5

Showing metabocard for Olanzapine (HMDB05012)

Record Information
Version 3.5
Creation Date 2006-10-16 07:00:12 -0600
Update Date 2013-02-08 17:13:46 -0700
HMDB ID HMDB05012
Secondary Accession Numbers None
Metabolite Identification
Common Name Olanzapine
Description Olanzapine was the third atypical antipsychotic to gain approval by the Food and Drug Administration (FDA) and has become one of the most commonly used atypical antipsychotics. Olanzapine has been approved by the FDA for the treatment of schizophrenia, acute mania in bipolar disorder, agitation associated with schizophrenia and bipolar disorder, and as maintenance treatment in bipolar disorder and psychotic depression. It has also been established in treating depression off-label because of its mood-stabilizing properties and its ability to increase the efficacy of antidepressants. Olanzapine is manufactured and marketed by the pharmaceutical company Eli Lilly and Company. It is available as a pill that comes in the strengths of 2.5 mg, 5 mg, 7.5 mg, 10 mg, 15 mg, and 20 mg and as as Zydis orally disintegrating tablets in the strengths of 5 mg, 10 mg, 15 mg, and 20 mg. It is also available as a rapid-acting intramuscular injection for short term acute use. Olanzapine (oh-LAN-za-peen, sold as Zyprexa, Zydis, or in combination with fluoxetine, as Symbyax) was the third atypical antipsychotic to gain approval by the Food and Drug Administration (FDA) and has become one of the most commonly used atypical antipsychotics. Olanzapine has been approved by the FDA for the treatment of schizophrenia, acute mania in bipolar disorder, agitation associated with schizophrenia and bipolar disorder, and as maintenance treatment in bipolar disorder and psychotic depression.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Lanzac
  2. Olanzapine
  3. Zyprexa
  4. Zyprexa Intramuscular
  5. Zyprexa Zydis
Chemical Formula C17H20N4S
Average Molecular Weight 312.432
Monoisotopic Molecular Weight 312.14086735
IUPAC Name 5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),5,8,11,13-hexaene
Traditional IUPAC Name 5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),5,8,11,13-hexaene
CAS Registry Number 132539-06-1
SMILES CN1CCN(CC1)C1=NC2=CC=CC=C2NC2=C1C=C(C)S2
InChI Identifier InChI=1S/C17H20N4S/c1-12-11-13-16(21-9-7-20(2)8-10-21)18-14-5-3-4-6-15(14)19-17(13)22-12/h3-6,11,19H,7-10H2,1-2H3
InChI Key KVWDHTXUZHCGIO-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Benzodiazepines
Sub Class N/A
Other Descriptors
  • N-arylpiperazine(ChEBI)
  • N-methylpiperazine(ChEBI)
  • benzodiazepine(ChEBI)
Substituents
  • Carboxylic Acid Amidine
  • Para Diazepine
  • Piperazine
  • Tertiary Aliphatic Amine (Trialkylamine)
  • Thiophene
Direct Parent Benzodiazepines
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.094 g/L ALOGPS
LogP 3.61 ALOGPS
LogP 3.39 ChemAxon
LogS -3.52 ALOGPS
pKa (strongest acidic) 14.17 ChemAxon
pKa (strongest basic) 7.24 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 30.87 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 93.87 ChemAxon
Polarizability 35.28 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Liver
  • Brain
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023585
KNApSAcK ID Not Available
Chemspider ID 10442212 Link_out
KEGG Compound ID C07322 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Olanzapine Link_out
NuGOwiki Link HMDB05012 Link_out
Metagene Link HMDB05012 Link_out
METLIN ID Not Available
PubChem Compound Not Available
PDB ID Not Available
ChEBI ID 7735 Link_out
References
Synthesis Reference Patel, Hiren V.; Ray, Anup K.; Patel, Pramod B.; Patel, Mahendra R. Process of preparation of olanzapine form I. PCT Int. Appl. (2003), 16 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Cerdan LF, Guevara MA, Sanz A, Amezcua C, Ramos-Loyo J: Brain electrical activity changes in treatment refractory schizophrenics after olanzapine treatment. Int J Psychophysiol. 2005 Jun;56(3):237-47. Pubmed: 15866327 Link_out
  2. Horak EL, Jenkins AJ: Postmortem tissue distribution of olanzapine and citalopram in a drug intoxication. J Forensic Sci. 2005 May;50(3):679-81. Pubmed: 15932107 Link_out
  3. Yamada K, Isotani T, Irisawa S, Yoshimura M, Tajika A, Yagyu T, Saito A, Kinoshita T: EEG Global Field Power spectrum changes after a single dose of atypical antipsychotics in healthy volunteers. Brain Topogr. 2004 Summer;16(4):281-5. Pubmed: 15379228 Link_out
  4. Mortimer A, Martin S, Loo H, Peuskens J: A double-blind, randomized comparative trial of amisulpride versus olanzapine for 6 months in the treatment of schizophrenia. Int Clin Psychopharmacol. 2004 Mar;19(2):63-9. Pubmed: 15076013 Link_out
  5. Merrick TC, Felo JA, Jenkins AJ: Tissue distribution of olanzapine in a postmortem case. Am J Forensic Med Pathol. 2001 Sep;22(3):270-4. Pubmed: 11563738 Link_out

Enzymes
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D(2) dopamine receptor
Reactions: Not Available
Gene Name: DRD2
Uniprot ID: P14416 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D(4) dopamine receptor
Reactions: Not Available
Gene Name: DRD4
Uniprot ID: P21917 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 2A
Reactions: Not Available
Gene Name: HTR2A
Uniprot ID: P28223 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 2C
Reactions: Not Available
Gene Name: HTR2C
Uniprot ID: P28335 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Histamine H1 receptor
Reactions: Not Available
Gene Name: HRH1
Uniprot ID: P35367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-1B adrenergic receptor
Reactions: Not Available
Gene Name: ADRA1B
Uniprot ID: P35368 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D(3) dopamine receptor
Reactions: Not Available
Gene Name: DRD3
Uniprot ID: P35462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M3
Reactions: Not Available
Gene Name: CHRM3
Uniprot ID: P20309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D(1A) dopamine receptor
Reactions: Not Available
Gene Name: DRD1
Uniprot ID: P21728 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M1
Reactions: Not Available
Gene Name: CHRM1
Uniprot ID: P11229 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M2
Reactions: Not Available
Gene Name: CHRM2
Uniprot ID: P08172 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M4
Reactions: Not Available
Gene Name: CHRM4
Uniprot ID: P08173 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M5
Reactions: Not Available
Gene Name: CHRM5
Uniprot ID: P08912 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA