NP-MRD: Showing NP-Card for Sulphadimethoxine (NP0336535)

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Record Information

Version

2.0

Created at

2024-09-11 06:45:17 UTC

Updated at

2024-09-11 06:45:17 UTC

NP-MRD ID

NP0336535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sulphadimethoxine

Description

Sulfadimethoxine, also known as abcid or agribon, belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. It is widely available in Russia as an over-the-counter drug manufactured by a number of Russian pharmaceutical companies. Sulfadimethoxine is a drug which is used for use in the treatment of infections. Sulfadimethoxine is a moderately basic compound (based on its pKa). Sulfadimethoxine (trade name Di-Methox) is a sulfonamide antibacterial. Long-acting sulfonamide, antibacterial agent. Sulfadimethoxine is used to treat many infections including treatment of respiratory, urinary tract, enteric, and soft tissue infections. It was first documented in 1959 (PMID: 13831481). Sulfadimethoxine has been shown to be effective against streptococci, klebsiella, proteus, shigella, staphylococci, escherichia, and salmonella (PMID: 11431418) (PMID: 12038137) (PMID: 13840927) (PMID: 14435331).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 12101320452D          

 21 22  0  0  0  0            999 V2000
    0.7589    2.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733    1.6141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733    0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7589    0.3766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0444    0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701    0.3766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701   -0.4484    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4951   -0.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -0.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701   -1.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0444   -1.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0444   -2.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701   -2.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701   -3.7484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3846   -2.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3846   -1.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0444    1.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7589    2.8516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4734    3.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878    0.3766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -0.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  0  0  0  0
  1  2  2  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3 20  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 17  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=NC(OC)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N4O4S/c1-19-11-7-10(14-12(15-11)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)

> <INCHI_KEY>
ZZORFUFYDOWNEF-UHFFFAOYSA-N

> <FORMULA>
C12H14N4O4S

> <MOLECULAR_WEIGHT>
310.329

> <EXACT_MASS>
310.073575646

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
29.59705034803726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-(2,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
1.2608333366666664

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.905270599396808

> <JCHEM_PKA_STRONGEST_BASIC>
1.9538476663144784

> <JCHEM_POLAR_SURFACE_AREA>
116.43

> <JCHEM_REFRACTIVITY>
77.75430000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfadimethoxine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-DEC-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-DEC-13         0                                  
HETATM    1  C   UNK     0       1.417   3.783   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.750   3.013   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.750   1.473   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.417   0.703   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.083   1.473   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.251   0.703   0.000  0.00  0.00           N+0
HETATM    7  S   UNK     0      -1.251  -0.837   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0      -2.791  -0.837   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.289  -0.837   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.251  -2.377   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.083  -3.147   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.083  -4.687   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.251  -5.457   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.251  -6.997   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.585  -4.687   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.585  -3.147   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.083   3.013   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.417   5.323   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.750   6.093   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.084   0.703   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.084  -0.837   0.000  0.00  0.00           C+0
CONECT    1   18    2   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2   20    4                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   10   15                                                       
CONECT   17    1    5                                                       
CONECT   18    1   19                                                       
CONECT   19   18                                                            
CONECT   20    3   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
2,4-Dimethoxy-6-sulfanilamido-1,3-diazine	ChEBI
2,6-Dimethoxy-4-(p-aminobenzenesulfonamido)pyrimidine	ChEBI
2,6-Dimethoxy-4-sulfanilamidopyrimidine	ChEBI
4-Amino-N-(2,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide	ChEBI
6-Sulfanilamido-2,4-dimethoxypyrimidine	ChEBI
Abcid	ChEBI
Agribon	ChEBI
N(1)-(2,6-Dimethoxy-4-pyrimidinyl)sulfanilamide	ChEBI
Sulfadimethoxinum	ChEBI
Sulfadimethoxydiazine	ChEBI
Sulfadimetoxina	ChEBI
Sulphadimethoxine	ChEBI
2,4-Dimethoxy-6-sulphanilamido-1,3-diazine	Generator
2,6-Dimethoxy-4-(p-aminobenzenesulphonamido)pyrimidine	Generator
2,6-Dimethoxy-4-sulphanilamidopyrimidine	Generator
4-Amino-N-(2,6-dimethoxy-4-pyrimidinyl)benzenesulphonamide	Generator
6-Sulphanilamido-2,4-dimethoxypyrimidine	Generator
N(1)-(2,6-Dimethoxy-4-pyrimidinyl)sulphanilamide	Generator
Sulphadimethoxinum	Generator
Sulphadimethoxydiazine	Generator
Sulphadimetoxina	Generator
Deposul	HMDB

Chemical Formula

C₁₂H₁₄N₄O₄S

Average Mass

310.3290 Da

Monoisotopic Mass

310.07358 Da

IUPAC Name

4-amino-N-(2,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide

Traditional Name

sulfadimethoxine

CAS Registry Number

Not Available

SMILES

COC1=NC(OC)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1

InChI Identifier

InChI=1S/C12H14N4O4S/c1-19-11-7-10(14-12(15-11)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)

InChI Key

ZZORFUFYDOWNEF-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 aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

Alternative Parents

Substituents

Aminobenzenesulfonamide
Benzenesulfonyl group
Aniline or substituted anilines
Alkyl aryl ether
Pyrimidine
Organosulfonic acid amide
Imidolactam
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Organoheterocyclic compound
Ether
Azacycle
Organic oxygen compound
Organic oxide
Amine
Organic nitrogen compound
Organopnictogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:32161 )
substituted aniline (CHEBI:32161 )
sulfonamide (CHEBI:32161 )
pyrimidines (CHEBI:32161 )
sulfonamide antibiotic (CHEBI:32161 )

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	1.08	ALOGPS
logP	1.26	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.91	ChemAxon
pKa (Strongest Basic)	1.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	116.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.75 m³·mol⁻¹	ChemAxon
Polarizability	29.6 Å³	ChemAxon
Number of Rings	2	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

HMDB0015621

DrugBank ID

DB06150

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010661

KNApSAcK ID

Not Available

Chemspider ID

5132

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfadimethoxine

METLIN ID

Not Available

PubChem Compound

5323

PDB ID

Not Available

ChEBI ID

32161

Good Scents ID

Not Available

References

General References

von Greyerz S, Bultemann G, Schnyder K, Burkhart C, Lotti B, Hari Y, Pichler WJ: Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones. Int Immunol. 2001 Jul;13(7):877-85. doi: 10.1093/intimm/13.7.877. [PubMed:11431418 ]
Southey AK, Sleeman DP, Gormley E: Sulfadimethoxine and rhodamine B as oral biomarkers for European badgers (Meles meles). J Wildl Dis. 2002 Apr;38(2):378-84. doi: 10.7589/0090-3558-38.2.378. [PubMed:12038137 ]
SKINNER LE: Some clinical experiences with a new lowdosage sulfonamide, sulfadimethoxine, chiefly in respiratory tract infections. Ann N Y Acad Sci. 1959 Sep 1;82:57-60. doi: 10.1111/j.1749-6632.1959.tb44878.x. [PubMed:13831481 ]
VALSECCHI A: [Use of sulfadimethoxine, a new low-dosage sulfamide, in the obstetric-gynecological field]. Minerva Ginecol. 1960 Apr 30;12:426-9. [PubMed:13840927 ]
PUPITA F: [Clinical experience with a new delayed sulfonamide: sulfadimethoxine]. Minerva Med. 1960 Apr 7;51:1235-8. [PubMed:14435331 ]

Showing NP-Card for Sulphadimethoxine (NP0336535)

MOL for NP0336535 (Sulphadimethoxine)

3D MOL for NP0336535 (Sulphadimethoxine)

3D SDF for NP0336535 (Sulphadimethoxine)

3D-SDF for NP0336535 (Sulphadimethoxine)

PDB for NP0336535 (Sulphadimethoxine)

3D PDB for NP0336535 (Sulphadimethoxine)

SMILES for NP0336535 (Sulphadimethoxine)

INCHI for NP0336535 (Sulphadimethoxine)

Structure for NP0336535 (Sulphadimethoxine)

3D Structure for NP0336535 (Sulphadimethoxine)