Sulfamerazine

Targets (1)Carriers (1)

Identification

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Name
Sulfamerazine
Accession Number
DB01581
Type
Small Molecule
Groups
Approved, Vet approved
Description

A sulfanilamide that is used as an antibacterial agent.

Structure
Thumb
3D
Similar Structures
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
  • Sulfamerazine
  • Sulfamerazinum
  • Sulfamethyldiazine
  • Sulphamerazine
Product Ingredients
IngredientUNIICASInChI Key
Sulfamerazine sodiumJOV4UJY07O127-58-2BSFJGCCAXDCMOX-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Trisulfaminic SusSulfamerazine (167 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg) + Sulfadiazine (167 mg) + Sulfamethazine (167 mg)SuspensionOralShepherd Pharmaceuticals Inc.1959-12-312001-04-11Canada
Trisulfaminic TabSulfamerazine (167 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg) + Sulfadiazine (167 mg) + Sulfamethazine (167 mg)TabletOralShepherd Pharmaceuticals Inc.1959-12-312001-04-11Canada
Categories
UNII
UR1SAB295F
CAS number
127-79-7
Weight
Average: 264.304
Monoisotopic: 264.068096338
Chemical Formula
C11H12N4O2S
InChI Key
QPPBRPIAZZHUNT-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.

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.

TargetActionsOrganism
ADihydropteroate synthase
inhibitor
Escherichia coli (strain K12)
Absorption

Rapidly absorbed following oral administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not 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 organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Sulfamerazine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Sulfamerazine is combined with (S)-Warfarin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Sulfamerazine.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Sulfamerazine is combined with 4-hydroxycoumarin.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulfamerazine.
AcenocoumarolThe risk or severity of bleeding can be increased when Sulfamerazine is combined with Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfamerazine.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Sulfamerazine.
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be increased when used in combination with Sulfamerazine.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfamerazine.
Food Interactions
  • Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015521
KEGG Drug
D02435
PubChem Compound
5325
PubChem Substance
46505036
ChemSpider
5134
ChEBI
102130
ChEMBL
CHEMBL438
Therapeutic Targets Database
DAP001240
PharmGKB
PA164776842
Wikipedia
Sulfamerazine
ATC Codes
J01ED07 — SulfamerazineD06BA06 — SulfamerazineG01AE10 — Combinations of sulfonamidesJ01EE07 — Sulfamerazine and trimethoprim
MSDS
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Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SuspensionOral
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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)
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Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0aou-1920000000-06a82249586c8821f9d3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0bt9-4900000000-1429f19666bf05cae962

Taxonomy

Description
This compound 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
Benzenesulfonyl compounds / Aniline and substituted anilines / Pyrimidines and pyrimidine derivatives / Organosulfonamides / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
Aminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Pyrimidine / Organosulfonic acid amide / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Heteroaromatic compound / Aminosulfonyl compound / Sulfonyl
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, pyrimidines, sulfonamide antibiotic (CHEBI:102130)

Targets

Details1. Dihydropteroate synthase
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

Details1. Serum albumin
Kind
Protein
Organism
Humans
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 colloid...
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 February 21, 2019 09:23