NP-MRD: Showing NP-Card for Carbadox (NP0338122)

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Record Information

Version

2.0

Created at

2024-09-11 13:56:01 UTC

Updated at

2024-09-11 13:56:01 UTC

NP-MRD ID

NP0338122

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carbadox

Description

Carbadox, also known as mecadox or fortigro, belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring. In 2004, carbadox was banned by the Canadian government as a livestock feed additive and for human consumption. In animal models, carbadox has been shown to be carcinogenic and to induce birth defects. Carbadox is an extremely weak basic (essentially neutral) compound (based on its pKa). In 2016, the United States Food and Drug Administration moved to ban its use in pork, citing a potential cancer risk to humans. Australia forbids the use of carbadox in food producing animals. The Food and Drug Administration's Center for Veterinary Medicine has questioned the safety in light of its possible carcinogenicity. Carbadox is indicated for control of swine dysentery (vibrionic dysentery, bloody scours, or hemorrhagic dysentery); control of bacterial swine enteritis (salmonellosis or necrotic enteritis caused by Salmonella enterica); aid in the prevention of migration and establishment of large roundworm (Ascaris suum) infections; aid in the prevention of establishment of nodular worm (Oesophagostomum) infections. The European Union also forbids the use of carbadox at any level. Carbadox is a veterinary drug that combats infection in swine, particularly swine dysentery. Carbadox is approved in the United States only for use in swine and may not be used within 42 days of slaughter or used in pregnant animals. It was first documented in 2000 (PMID: 10730338). However, as of August 2018, FDA had indefinitely stayed its withdrawal of approval and carbadox remains available.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 03191307072D          

 19 20  0  0  0  0            999 V2000
    0.0000   -6.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.3035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.1286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.3035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -4.8910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.8911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
  1  6  2  0  0  0  0
  8  1  1  0  0  0  0
  7  8  2  0  0  0  0
  9 10  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 17  2  0  0  0  0
  9 18  2  0  0  0  0
 14 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0338122

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N\N=C\C1=N(=O)C2=C(C=CC=C2)N(=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10N4O4/c1-19-11(16)13-12-6-8-7-14(17)9-4-2-3-5-10(9)15(8)18/h2-7H,1H3,(H,13,16)/b12-6+

> <INCHI_KEY>
OVGGLBAWFMIPPY-WUXMJOGZSA-N

> <FORMULA>
C11H10N4O4

> <MOLECULAR_WEIGHT>
262.2215

> <EXACT_MASS>
262.070204828

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.59817971870804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N'-[(1E)-(1,4-dioxo-1λ⁵,4λ⁵-quinoxalin-2-yl)methylidene]methoxycarbohydrazide

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
-0.7063662483333331

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.596716698002085

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4190900945499356

> <JCHEM_POLAR_SURFACE_AREA>
101.60999999999999

> <JCHEM_REFRACTIVITY>
68.24199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carbadox

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-13         0                                  
HETATM    1  C   UNK     0       0.000 -11.440   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -12.210   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334 -13.750   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -14.520   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334 -13.750   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -12.210   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -9.130   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000  -9.900   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       2.667 -11.440   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.667  -9.900   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -9.130   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.335  -9.900   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       6.668  -9.130   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       8.002  -9.900   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -9.130   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -9.900   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -9.130   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001 -12.210   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002 -11.440   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    9    1                                                  
CONECT    7    8   10                                                       
CONECT    8    1    7   17                                                  
CONECT    9    6   10   18                                                  
CONECT   10    9    7   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   14                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Mecadox	Kegg
Fortigro	HMDB
Getroxel	HMDB
GS 6244	HMDB
Methyl (2-quinoxalinylmethylene)hydrazinecarboxylate N,n'-dioxide, 9ci	HMDB
Methyl 3-(2-quinoxalinylmethylene)carbazate N1,N4-dioxide, 8ci	HMDB
Fortrigo	MeSH

Chemical Formula

C₁₁H₁₀N₄O₄

Average Mass

262.2215 Da

Monoisotopic Mass

262.07020 Da

IUPAC Name

N'-[(1E)-(1,4-dioxo-1λ⁵,4λ⁵-quinoxalin-2-yl)methylidene]methoxycarbohydrazide

Traditional Name

carbadox

CAS Registry Number

Not Available

SMILES

COC(=O)N\N=C\C1=N(=O)C2=C(C=CC=C2)N(=O)=C1

InChI Identifier

InChI=1S/C11H10N4O4/c1-19-11(16)13-12-6-8-7-14(17)9-4-2-3-5-10(9)15(8)18/h2-7H,1H3,(H,13,16)/b12-6+

InChI Key

OVGGLBAWFMIPPY-WUXMJOGZSA-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 quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinoxalines

Alternative Parents

Substituents

Quinoxaline
Pyrazine
Pyrazinium
Benzenoid
Heteroaromatic compound
Carbonic acid derivative
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.04	ALOGPS
logP	-0.71	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.6	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.24 m³·mol⁻¹	ChemAxon
Polarizability	24.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031762

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008435

KNApSAcK ID

Not Available

Chemspider ID

10606106

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carbadox

METLIN ID

Not Available

PubChem Compound

135511839

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mevius DJ, Veldman KT, van der Giessen A, van Leeuwen WJ: [Preliminary results of antibiotic resistance monitoring in the Netherlands]. Tijdschr Diergeneeskd. 2000 Mar 1;125(5):143-6. [PubMed:10730338 ]

Showing NP-Card for Carbadox (NP0338122)

MOL for NP0338122 (Carbadox)

3D MOL for NP0338122 (Carbadox)

3D SDF for NP0338122 (Carbadox)

3D-SDF for NP0338122 (Carbadox)

PDB for NP0338122 (Carbadox)

3D PDB for NP0338122 (Carbadox)

SMILES for NP0338122 (Carbadox)

INCHI for NP0338122 (Carbadox)

Structure for NP0338122 (Carbadox)

3D Structure for NP0338122 (Carbadox)