NP-MRD: Showing NP-Card for 5H-Dibenz[b,f]azepine-5-carboxamide (NP0138380)

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Record Information

Version

1.0

Created at

2022-05-31 17:57:05 UTC

Updated at

2022-05-31 17:57:05 UTC

NP-MRD ID

NP0138380

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5H-Dibenz[b,f]azepine-5-carboxamide

Description

Carbamazepine, also known as tegretol or carnexiv, belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. Carbamazepine is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, carbamazepine participates in a number of enzymatic reactions. In particular, carbamazepine can be converted into 3-hydroxycarbamazepine through its interaction with the enzymes cytochrome P450 3A4, cytochrome P450 2B6, and cytochrome P450 3A7. In addition, carbamazepine can be converted into carbamazepine-10,11-epoxide; which is catalyzed by the enzymes cytochrome P450 2C8, cytochrome P450 3A4, cytochrome P450 3A5, cytochrome P450 3A7, and cytochrome P450 2C19. In humans, carbamazepine is involved in carbamazepine metabolism pathway. Carbamazepine is a potentially toxic compound. It was first documented in 1999 (PMID: 10411478). A dibenzoazepine that is 5H-dibenzoazepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant (PMID: 15292462) (PMID: 18088268) (PMID: 11071486) (PMID: 11129121).

Structure

MOL SDF PDB SMILES InChI

564
  Mrv1652305271900052D          

 18 20  0  0  0  0            999 V2000
    4.5536   -1.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8677   -0.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1818   -1.2161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1540    0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637    1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1774   -0.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5580   -0.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421    1.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933    1.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8677   -0.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9676   -0.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678   -0.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1512    0.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    0.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  2  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2 14  1  0  0  0  0
  3 14  1  0  0  0  0
  4  6  1  0  0  0  0
  4 10  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  2  0  0  0  0
  6  8  1  0  0  0  0
  6 12  2  0  0  0  0
  7  9  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  2  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0138380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)

> <INCHI_KEY>
FFGPTBGBLSHEPO-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O

> <MOLECULAR_WEIGHT>
236.2686

> <EXACT_MASS>
236.094963016

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.002490841556707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.7660303863333335

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.958359453242029

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7540181335527305

> <JCHEM_POLAR_SURFACE_AREA>
46.33

> <JCHEM_REFRACTIVITY>
71.88800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 564                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       8.500  -2.270   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.220  -0.052   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.939  -2.270   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.552   0.589   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.887   0.589   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.881   2.031   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.559   2.031   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.959   3.187   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.481   3.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.664  -0.475   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.775  -0.475   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.345   2.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.094   2.507   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.220  -1.531   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.140  -0.033   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.300  -0.033   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.482   1.469   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.957   1.469   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2    4    5   14                                                  
CONECT    3   14                                                            
CONECT    4    2    6   10                                                  
CONECT    5    2    7   11                                                  
CONECT    6    4    8   12                                                  
CONECT    7    5    9   13                                                  
CONECT    8    6    9                                                       
CONECT    9    7    8                                                       
CONECT   10    4   15                                                       
CONECT   11    5   16                                                       
CONECT   12    6   17                                                       
CONECT   13    7   18                                                       
CONECT   14    1    2    3                                                  
CONECT   15   10   17                                                       
CONECT   16   11   18                                                       
CONECT   17   12   15                                                       
CONECT   18   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
5-Carbamoyl-5H-dibenz(b,F)azepine	ChEBI
5-Carbamoyl-5H-dibenz[b,F]azepine	ChEBI
5-Carbamoyl-5H-dibenzo(b,F)azepine	ChEBI
5-Carbamyl-5H-dibenzo(b,F)azepine	ChEBI
5H-Dibenz(b,F)azepine-5-carboxamide	ChEBI
Carbamazepen	ChEBI
Carbamazepina	ChEBI
Carbamazepinum	ChEBI
Carnexiv	ChEBI
Equetro	Kegg
Tegretol	Kegg
Carbamezepine	HMDB
Neurotol	HMDB
Amizepine	HMDB
Carbamazepine acetate	HMDB
Carbamazepine anhydrous	HMDB
Carbamazepine dihydrate	HMDB
Carbamazepine hydrochloride	HMDB
Carbamazepine phosphate	HMDB
Epitol	HMDB
Finlepsin	HMDB
Carbamazepine L-tartrate (4:1)	HMDB
Carbamazepine sulfate (2:1)	HMDB
Carbazepin	HMDB

Chemical Formula

C₁₅H₁₂N₂O

Average Mass

236.2686 Da

Monoisotopic Mass

236.09496 Da

IUPAC Name

2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

Traditional Name

2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

CAS Registry Number

1318852-41-3

SMILES

NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)

InChI Key

FFGPTBGBLSHEPO-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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 dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Dibenzazepines

Direct Parent

Dibenzazepines

Alternative Parents

Substituents

Dibenzazepine
Azepine
Benzenoid
Urea
Carbonic acid derivative
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ureas (CHEBI:3387 )
dibenzoazepine (CHEBI:3387 )

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	2.1	ALOGPS
logP	2.77	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.96	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.33 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.89 m³·mol⁻¹	ChemAxon
Polarizability	25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014704

DrugBank ID

DB00564

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2457

KEGG Compound ID

C06868

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carbamazepine

METLIN ID

Not Available

PubChem Compound

2554

PDB ID

Not Available

ChEBI ID

3387

Good Scents ID

Not Available

References

General References

Staines AG, Coughtrie MW, Burchell B: N-glucuronidation of carbamazepine in human tissues is mediated by UGT2B7. J Pharmacol Exp Ther. 2004 Dec;311(3):1131-7. Epub 2004 Aug 3. [PubMed:15292462 ]
Sisodiya SM, Goldstein DB: Drug resistance in epilepsy: more twists in the tale. Epilepsia. 2007 Dec;48(12):2369-70. [PubMed:18088268 ]
Benes J, Parada A, Figueiredo AA, Alves PC, Freitas AP, Learmonth DA, Cunha RA, Garrett J, Soares-da-Silva P: Anticonvulsant and sodium channel-blocking properties of novel 10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide derivatives. J Med Chem. 1999 Jul 15;42(14):2582-7. doi: 10.1021/jm980627g. [PubMed:10411478 ]
Genton P, Gelisse P, Thomas P, Dravet C: Do carbamazepine and phenytoin aggravate juvenile myoclonic epilepsy? Neurology. 2000 Oct 24;55(8):1106-9. doi: 10.1212/wnl.55.8.1106. [PubMed:11071486 ]
Tremont-Lukats IW, Megeff C, Backonja MM: Anticonvulsants for neuropathic pain syndromes: mechanisms of action and place in therapy. Drugs. 2000 Nov;60(5):1029-52. doi: 10.2165/00003495-200060050-00005. [PubMed:11129121 ]

Showing NP-Card for 5H-Dibenz[b,f]azepine-5-carboxamide (NP0138380)

MOL for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)

3D MOL for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)

3D SDF for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)

3D-SDF for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)

PDB for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)

3D PDB for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)

SMILES for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)

INCHI for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)

Structure for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)

3D Structure for NP0138380 (5H-Dibenz[b,f]azepine-5-carboxamide)