Identification
NameSulfamerazine
Accession NumberDB01581
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

A sulfanilamide that is used as an antibacterial agent. [PubChem]

Structure
Thumb
Synonyms
(P-Aminobenzolsulfonyl)-2-amino-4-methylpyrimidin
2-(4-Aminobenzenesulfonamido)-4-methylpyrimidine
2-(P-Aminobenzolsulfonamido)-4-methylpyrimidine
2-(Sulfanilamido)-4-methylpyrimidine
2-Sulfa-4-methylpyrimidine
4-Amino-N-(4-methyl-2-pyrimidinyl)-benzenesulfonamide
N-(4-Methyl-2-pyrimidyl)sulfanilamide
N(1)-(4-Methyl-2-pyrimidinyl)sulfanilamide
Sulfamerazina
Sulfamerazinum
Sulfamethyldiazine
Sulphamerazine
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Sulfamerazine sodiumJOV4UJY07O 127-58-2BSFJGCCAXDCMOX-UHFFFAOYSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Trisulfaminic SusSuspensionOralShepherd Pharmaceuticals Inc.1959-12-312001-04-11Canada
Trisulfaminic TabTabletOralShepherd Pharmaceuticals Inc.1959-12-312001-04-11Canada
Categories
UNIIUR1SAB295F
CAS number127-79-7
WeightAverage: 264.304
Monoisotopic: 264.068096338
Chemical FormulaC11H12N4O2S
InChI KeyQPPBRPIAZZHUNT-UHFFFAOYSA-N
InChI
InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
IUPAC Name
4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide
SMILES
CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1
Pharmacology
Indication

A sulfanilamide that is used as an antibacterial agent. It can be used to treat bronchitis, prostatitis and urinary tract infections.

Structured Indications Not Available
Pharmacodynamics

Sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis in bacteria.

Mechanism of action

Sulfamerazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamerazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.

TargetKindPharmacological actionActionsOrganismUniProt ID
Dihydropteroate synthaseProteinyes
inhibitor
Escherichia coli (strain K12)P0AC13 details
Related Articles
Absorption

Rapidly absorbed following oral administration.

Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity

Sulfamerazine may cause nausea, vomiting, diarrhea and hypersensitivity reactions. Hematologic effects such as anemia, agranulocytosis, thrombocytopenia and hemolytic anemia in patients with glucose-6-phosphate dehydrogenase deficiency may also occur. Sulfamethoxazole may displace bilirubin from albumin binding sites causing jaundice or kernicterus in newborns.

Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
BCG vaccineThe therapeutic efficacy of Bcg can be decreased when used in combination with Sulfamerazine.Investigational
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sulfamerazine.Approved
MecamylamineThe risk or severity of adverse effects can be increased when Sulfamerazine is combined with Mecamylamine.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Sulfamerazine.Approved
Food Interactions
  • Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01EE07 — Sulfamerazine and trimethoprimD06BA06 — SulfamerazineJ01ED07 — SulfamerazineG01AE10 — Combinations of sulfonamides
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72.7 KB)
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
SuspensionOral
TabletOral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)236 °CPhysProp
water solubility202 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.14HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.304 mg/mLALOGPS
logP0.44ALOGPS
logP0.52ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)2.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.97 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.79 m3·mol-1ChemAxon
Polarizability26.51 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9929
Blood Brain Barrier+0.9356
Caco-2 permeable+0.6431
P-glycoprotein substrateNon-substrate0.8687
P-glycoprotein inhibitor INon-inhibitor0.9021
P-glycoprotein inhibitor IINon-inhibitor0.9264
Renal organic cation transporterNon-inhibitor0.8526
CYP450 2C9 substrateNon-substrate0.7402
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.7559
CYP450 1A2 substrateNon-inhibitor0.9473
CYP450 2C9 inhibitorNon-inhibitor0.9175
CYP450 2D6 inhibitorNon-inhibitor0.9471
CYP450 2C19 inhibitorNon-inhibitor0.9567
CYP450 3A4 inhibitorNon-inhibitor0.9065
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8301
Ames testNon AMES toxic0.9185
CarcinogenicityNon-carcinogens0.9333
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.9134 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9294
hERG inhibition (predictor II)Non-inhibitor0.87
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Download (8.36 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0aou-1920000000-06a82249586c8821f9d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0bt9-4900000000-1429f19666bf05cae962View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentAminobenzenesulfonamides
Alternative ParentsBenzenesulfonyl compounds / Aniline and substituted anilines / Pyrimidines and pyrimidine derivatives / Primary aromatic amines / Organosulfonamides / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Organopnictogen compounds / Organic oxides
SubstituentsAminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Primary aromatic amine / Pyrimidine / Organosulfonic acid amide / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Aminosulfonyl compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorssulfonamide, pyrimidines, sulfonamide antibiotic (CHEBI:102130 )

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate (H2Pte), the immediate precursor of folate derivatives.
Gene Name:
folP
Uniprot ID:
P0AC13
Uniprot Name:
Dihydropteroate synthase
Molecular Weight:
30614.855 Da
References
  1. Hong YL, Hossler PA, Calhoun DH, Meshnick SR: Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob Agents Chemother. 1995 Aug;39(8):1756-63. [PubMed:7486915 ]
  2. Friaza V, Morilla R, Respaldiza N, de la Horra C, Calderon EJ: Pneumocystis jiroveci dihydropteroate synthase gene mutations among colonized individuals and Pneumocystis pneumonia patients from Spain. Postgrad Med. 2010 Nov;122(6):24-8. doi: 10.3810/pgm.2010.11.2219. [PubMed:21084778 ]
  3. Thijssen HH: A simplified radioassay method of dihydropteroate synthetase activity in Escherichia coli and its application for an inhibition study of p-aminobenzoi acid derivatives. Anal Biochem. 1973 Jun;53(2):579-85. [PubMed:4577373 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Uniprot Name:
Serum albumin
Molecular Weight:
69365.94 Da
References
  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. [PubMed:1031216 ]
  2. Angelakou A, Valsami G, Koupparis M, Macheras P: Use of 1-anilino-8-napthalenesulphonate as an ion probe for the potentiometric study of the binding of sulphonamides to bovine serum albumin and plasma. J Pharm Pharmacol. 1993 May;45(5):434-8. [PubMed:8099962 ]
Drug created on August 29, 2007 08:53 / Updated on September 01, 2017 10:41