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Showing NP-Card for Olanzapine (NP0334567)

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Record Information
Version2.0
Created at2024-09-10 18:56:17 UTC
Updated at2024-09-10 18:56:17 UTC
NP-MRD IDNP0334567
Secondary Accession NumbersNone
Natural Product Identification
Common NameOlanzapine
DescriptionOlanzapine, also known as zyprexa or lanzac, belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms). Olanzapine is a very strong basic compound (based on its pKa). Olanzapine is a potentially toxic compound. Olanzapine was first documented in 2001 (PMID: 11563738). A benzodiazepine that is 10H-thienobenzodiazepine substituted by a methyl group at position 2 and a 4-methylpiperazin-1-yl group at position 4 (PMID: 15932107) (PMID: 15866327) (PMID: 15379228) (PMID: 15076013).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334567 (Olanzapine)


  Mrv0541 04191212112D          

 22 25  0  0  0  0            999 V2000
    0.8062   -0.5677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313   -0.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0438   -1.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189   -1.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2229   -1.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055   -1.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -2.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978   -2.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -2.2926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8302   -2.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677   -1.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221   -2.5285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632   -2.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2147    0.0157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9601   -2.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0011    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0116   -0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5845    1.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949    0.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814    1.1824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9648    1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
 11 10  1  0  0  0  0
 10  4  1  0  0  0  0
  8  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7  9  2  0  0  0  0
  9  8  1  0  0  0  0
 11 13  1  0  0  0  0
  3 11  2  0  0  0  0
 12  3  1  0  0  0  0
 13 14  1  0  0  0  0
 12 14  2  0  0  0  0
  2 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
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3D MOL for NP0334567 (Olanzapine)

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3D SDF for NP0334567 (Olanzapine)

  Mrv0541 04191212112D          

 22 25  0  0  0  0            999 V2000
    0.8062   -0.5677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313   -0.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0438   -1.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189   -1.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2229   -1.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055   -1.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -2.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978   -2.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -2.2926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8302   -2.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677   -1.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221   -2.5285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632   -2.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2147    0.0157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9601   -2.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0011    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0116   -0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5845    1.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949    0.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814    1.1824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9648    1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
 11 10  1  0  0  0  0
 10  4  1  0  0  0  0
  8  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7  9  2  0  0  0  0
  9  8  1  0  0  0  0
 11 13  1  0  0  0  0
  3 11  2  0  0  0  0
 12  3  1  0  0  0  0
 13 14  1  0  0  0  0
 12 14  2  0  0  0  0
  2 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334567

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C17H20N4S

> <MOLECULAR_WEIGHT>
312.432

> <EXACT_MASS>
312.14086735

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.37184031437682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),5,8,10,12-hexaene

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
3.3884950820000004

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.174461666971585

> <JCHEM_PKA_STRONGEST_BASIC>
7.242439871833076

> <JCHEM_POLAR_SURFACE_AREA>
30.870000000000005

> <JCHEM_REFRACTIVITY>
93.87369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zyprexa

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0334567 (Olanzapine)
Download
PDB for NP0334567 (Olanzapine)
HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  N   UNK     0       1.505  -1.060   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.045  -1.060   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.815  -2.393   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.595  -3.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.416  -2.149   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.029  -1.393   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.250  -2.331   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.626  -4.447   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.049  -3.858   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.929  -4.280   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.416  -3.881   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.353  -2.313   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0       4.708  -4.720   0.000  0.00  0.00           S+0
HETATM   14  C   UNK     0       5.905  -3.751   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.134   0.029   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       7.392  -4.149   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.735   1.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.622  -0.369   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.824   2.606   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.710   0.720   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       6.312   2.207   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       7.401   3.296   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2   11   12                                                  
CONECT    4   10    8    5                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    4    9                                                       
CONECT    9    7    8                                                       
CONECT   10   11    4                                                       
CONECT   11   10   13    3                                                  
CONECT   12    3   14                                                       
CONECT   13   11   14                                                       
CONECT   14   13   12   16                                                  
CONECT   15    2   17   18                                                  
CONECT   16   14                                                            
CONECT   17   15   19                                                       
CONECT   18   15   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   21                                                       
CONECT   21   20   19   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

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3D PDB for NP0334567 (Olanzapine)
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SMILES for NP0334567 (Olanzapine)
CN1CCN(CC1)C1=NC2=CC=CC=C2NC2=C1C=C(C)S2
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INCHI for NP0334567 (Olanzapine)
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
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View in JSmol
Synonyms
ValueSource
OlanzapinaChEBI
OlanzapinumChEBI
ZyprexaChEBI
LanzacHMDB
Zyprexa intramuscularHMDB
Zyprexa zydisHMDB
ZolafrenHMDB
2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno(2,3-b)(1,5)benzodiazepineHMDB
Olanzapine pamoateHMDB
Chemical FormulaC17H20N4S
Average Mass312.4320 Da
Monoisotopic Mass312.14087 Da
IUPAC Name5-methyl-8-(4-methylpiperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),5,8,10,12-hexaene
Traditional Namezyprexa
CAS Registry NumberNot Available
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 KeyKVWDHTXUZHCGIO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzodiazepines  
Sub ClassNot Available
Direct ParentBenzodiazepines  
Alternative Parents
Substituents
  • Benzodiazepine
    • 

  • Thieno-para-diazepine
    • 

  • 2,3,5-trisubstituted thiophene
    • 

  • Para-diazepine
    • 

  • N-methylpiperazine
    • 

  • N-alkylpiperazine
    • 

  • N-arylated-2-aminothiophene
    • 

  • 1,4-diazinane
    • 

  • Piperazine
    • 

  • 2-aminothiophene
    • 

  • Benzenoid
    • 

  • Imidolactam
    • 

  • Heteroaromatic compound
    • 

  • Thiophene
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Azacycle
    • 

  • Secondary amine
    • 

  • Amidine
    • 

  • Carboxylic acid amidine
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Organopnictogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.61ALOGPS
logP3.39ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.17ChemAxon
pKa (Strongest Basic)7.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area30.87 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity93.87 m³·mol⁻¹ChemAxon
Polarizability35.37 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0005012  
DrugBank IDDB00334  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023585  
KNApSAcK IDNot Available
Chemspider ID10442212  
KEGG Compound IDC07322  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOlanzapine  
METLIN IDNot Available
PubChem Compound135398745  
PDB IDNot Available
ChEBI ID7735  
Good Scents IDNot Available
References
General References
  1. 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  ] 
  2. 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. doi: 10.1016/j.ijpsycho.2004.12.008. [PubMed:15866327  ] 
  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. doi: 10.1023/b:brat.0000032866.20058.5c. [PubMed:15379228  ] 
  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. doi:  10.1097/00004850-200403000-00002. [PubMed:15076013  ] 
  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. doi:  10.1097/00000433-200109000-00014. [PubMed:11563738  ]