NP-MRD: Showing NP-Card for Zolpidem (NP0334571)

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Record Information

Version

2.0

Created at

2024-09-10 18:57:16 UTC

Updated at

2024-09-10 18:57:16 UTC

NP-MRD ID

NP0334571

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Zolpidem

Description

Zolpidem, also known as sanval or ambien, belongs to the class of organic compounds known as phenylimidazoles. These are polycyclic aromatic compounds containing a benzene ring linked to an imidazole ring through a CC or CN bond. Zolpidem is a very strong basic compound (based on its pKa). Zolpidem is a potentially toxic compound. Zolpidem was first documented in 1999 (PMID: 10517569). An imidazopyridine compound having a 4-tolyl group at the 2-position, an N,N-dimethylcarbamoylmethyl group at the 3-position and a methyl substituent at the 6-position (PMID: 10383565) (PMID: 12469329).

Structure

MOL SDF PDB SMILES InChI

425
  Mrv0541 02231214402D          

 23 25  0  0  0  0            999 V2000
    3.4722    0.5743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -1.9816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5358    1.5287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8305    0.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795    0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932   -2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932   -0.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5307   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182   -2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182   -0.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9848    2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3431    1.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2  5  1  0  0  0  0
  2  7  1  0  0  0  0
  2 10  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4 13  1  0  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 15  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  2  0  0  0  0
 11 14  1  0  0  0  0
 11 17  1  0  0  0  0
 12 14  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334571

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N3O/c1-13-5-8-15(9-6-13)19-16(11-18(23)21(3)4)22-12-14(2)7-10-17(22)20-19/h5-10,12H,11H2,1-4H3

> <INCHI_KEY>
ZAFYATHCZYHLPB-UHFFFAOYSA-N

> <FORMULA>
C19H21N3O

> <MOLECULAR_WEIGHT>
307.3895

> <EXACT_MASS>
307.168462309

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.06322364459639

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.0176268213333337

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.653587740811252

> <JCHEM_POLAR_SURFACE_AREA>
37.61000000000001

> <JCHEM_REFRACTIVITY>
93.58370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zolpidem

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 425                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.481   1.072   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.081  -1.690   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.538  -3.699   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.467   2.854   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.538  -1.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.437  -2.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -3.230   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.017   0.243   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.977  -2.460   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -0.920   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -4.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.988   1.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -3.230   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.747  -3.793   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.747  -1.126   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -0.920   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.057  -2.460   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.287  -3.793   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.287  -1.126   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.438   4.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.974   3.171   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.597  -2.460   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2    5    7   10                                                  
CONECT    3    6    7                                                       
CONECT    4   13   21   22                                                  
CONECT    5    2    6    8                                                  
CONECT    6    3    5    9                                                  
CONECT    7    2    3   12                                                  
CONECT    8    5   13                                                       
CONECT    9    6   15   16                                                  
CONECT   10    2   11                                                       
CONECT   11   10   14   17                                                  
CONECT   12    7   14                                                       
CONECT   13    1    4    8                                                  
CONECT   14   11   12                                                       
CONECT   15    9   19                                                       
CONECT   16    9   20                                                       
CONECT   17   11                                                            
CONECT   18   19   20   23                                                  
CONECT   19   15   18                                                       
CONECT   20   16   18                                                       
CONECT   21    4                                                            
CONECT   22    4                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine-3-acetamide	ChEBI
Zolpidemum	ChEBI
Sanval	Kegg
Ambien	HMDB
Hypnogen	HMDB
Myslee	HMDB
Stilnoct	HMDB
Stilnox	HMDB
Zolpidem ambien	HMDB
Zolpidem tartrate	HMDB
Bikalm	HMDB
Zolpidem 1a pharma	HMDB
N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2a)pyridine-3-acetamide hemitartrate	HMDB
Zolpidem abz	HMDB
Amsic	HMDB
Dalparan	HMDB
Zolpinox	HMDB
Zodormdura	HMDB
Zoldem	HMDB
Zolirin	HMDB
Zolpi-lich	HMDB
Zolpimist	HMDB
Zolpidem hemitartrate	HMDB
Zolpi lich	HMDB

Chemical Formula

C₁₉H₂₁N₃O

Average Mass

307.3895 Da

Monoisotopic Mass

307.16846 Da

IUPAC Name

N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide

Traditional Name

zolpidem

CAS Registry Number

Not Available

SMILES

CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1

InChI Identifier

InChI=1S/C19H21N3O/c1-13-5-8-15(9-6-13)19-16(11-18(23)21(3)4)22-12-14(2)7-10-17(22)20-19/h5-10,12H,11H2,1-4H3

InChI Key

ZAFYATHCZYHLPB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylimidazoles. These are polycyclic aromatic compounds containing a benzene ring linked to an imidazole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Phenylimidazoles

Alternative Parents

Substituents

5-phenylimidazole
4-phenylimidazole
Imidazopyridine
Imidazo[1,2-a]pyridine
Toluene
Methylpyridine
Monocyclic benzene moiety
N-substituted imidazole
Pyridine
Benzenoid
Tertiary carboxylic acid amide
Heteroaromatic compound
Carboxamide group
Carboxylic acid derivative
Azacycle
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazopyridine (CHEBI:10125 )

Physical Properties

State

Not Available

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
logP	3.15	ALOGPS
logP	3.02	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	5.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.58 m³·mol⁻¹	ChemAxon
Polarizability	35.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0005023

DrugBank ID

DB00425

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023594

KNApSAcK ID

Not Available

Chemspider ID

5530

KEGG Compound ID

C07219

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zolpidem

METLIN ID

3071

PubChem Compound

5732

PDB ID

Not Available

ChEBI ID

10125

Good Scents ID

Not Available

References

General References

Gock SB, Wong SH, Nuwayhid N, Venuti SE, Kelley PD, Teggatz JR, Jentzen JM: Acute zolpidem overdose--report of two cases. J Anal Toxicol. 1999 Oct;23(6):559-62. doi: 10.1093/jat/23.6.559. [PubMed:10517569 ]
Von Moltke LL, Greenblatt DJ, Granda BW, Duan SX, Grassi JM, Venkatakrishnan K, Harmatz JS, Shader RI: Zolpidem metabolism in vitro: responsible cytochromes, chemical inhibitors, and in vivo correlations. Br J Clin Pharmacol. 1999 Jul;48(1):89-97. doi: 10.1046/j.1365-2125.1999.00953.x. [PubMed:10383565 ]
von Moltke LL, Weemhoff JL, Perloff MD, Hesse LM, Harmatz JS, Roth-Schechter BF, Greenblatt DJ: Effect of zolpidem on human cytochrome P450 activity, and on transport mediated by P-glycoprotein. Biopharm Drug Dispos. 2002 Dec;23(9):361-7. doi: 10.1002/bdd.329. [PubMed:12469329 ]

Showing NP-Card for Zolpidem (NP0334571)

MOL for NP0334571 (Zolpidem)

3D MOL for NP0334571 (Zolpidem)

3D SDF for NP0334571 (Zolpidem)

3D-SDF for NP0334571 (Zolpidem)

PDB for NP0334571 (Zolpidem)

3D PDB for NP0334571 (Zolpidem)

SMILES for NP0334571 (Zolpidem)

INCHI for NP0334571 (Zolpidem)

Structure for NP0334571 (Zolpidem)

3D Structure for NP0334571 (Zolpidem)