NAV

Sulfamerazine

Identification

Summary

Sulfamerazine is an antibacterial agent used in the treatment of various bacterial infections, such as bronchitis, prostatitis, and urinary tract infections.

Generic Name
Sulfamerazine
DrugBank Accession Number
DB01581
Background

A sulfanilamide that is used as an antibacterial agent.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
3D
Similar Structures
Weight
Average: 264.304
Monoisotopic: 264.068096338
Chemical Formula
C11H12N4O2S
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
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Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAbscessesCombination Product in combination with: Sulfamethazine (DB01582), Sulfadiazine (DB00359)••••••••••••••••••••••• ••••••
Used in combination to treatConjunctivitisCombination Product in combination with: Sulfadiazine (DB00359), Sulfamethazine (DB01582)••••••••••••••••••••••• ••••••
Used in combination to treatEar infection bacterialCombination Product in combination with: Sulfadiazine (DB00359), Sulfathiazole (DB06147)••••••••••••••••••
Used in combination to treatEnteritisCombination Product in combination with: Sulfadiazine (DB00359), Sulfathiazole (DB06147)••••••••••••••••••
Used in combination to treatEye infectionsCombination Product in combination with: Sulfathiazole (DB06147), Sulfadiazine (DB00359)••••••••••••••••••
Contraindications & Blackbox Warnings
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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

Adverse Effects
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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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
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.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfamerazine.
AlogliptinThe therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfamerazine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sulfamerazine sodiumJOV4UJY07O127-58-2BSFJGCCAXDCMOX-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Trisulfaminic SusSulfamerazine (167 mg / 5 mL) + Mepyramine maleate (6.25 mg / 5 mL) + Pheniramine maleate (6.25 mg / 5 mL) + Phenylpropanolamine hydrochloride (12.5 mg / 5 mL) + Sulfadiazine (167 mg / 5 mL) + Sulfamethazine (167 mg / 5 mL)SuspensionOralShepherd Pharmaceuticals Inc.1959-12-312001-04-11Canada flag
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 flag
ซัลฟาโคSulfamerazine (167 MG/5ML) + Sulfadiazine (167 MG/5ML) + Sulfamethazine (167 MG/5ML)Suspensionบริษัท โรงงานเภสัชกรรมแหลมทองการแพทย์ จำกัด จำกัด1987-05-15Not applicableThailand flag
ไตรซัลฟาไพริมิดีนSulfamerazine (167 MG) + Sulfadiazine (167 MG) + Sulfamethazine (167 MG)Tabletบริษัท อินแพคฟาร์มา จำกัด1987-09-222020-09-29Thailand flag
ไตรซัลฟาไพริมิดีนSulfamerazine (167 MG) + Sulfadiazine (167 MG) + Sulfamethazine (167 MG)Tabletบริษัท อินแพคฟาร์มา จำกัด1987-06-192020-09-29Thailand flag

Categories

ATC Codes
J01ED07 — SulfamerazineG01AE10 — Combinations of sulfonamidesD06BA06 — SulfamerazineJ01EE07 — Sulfamerazine and trimethoprim
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonyl group / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, pyrimidines, sulfonamide antibiotic (CHEBI:102130)
Affected organisms
Not Available

Chemical Identifiers

UNII
UR1SAB295F
CAS number
127-79-7
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

References

General References
Not Available
Human Metabolome Database
HMDB0015521
KEGG Drug
D02435
PubChem Compound
5325
PubChem Substance
46505036
ChemSpider
5134
BindingDB
50238672
RxNav
10176
ChEBI
102130
ChEMBL
CHEMBL438
ZINC
ZINC000000057501
Therapeutic Targets Database
DAP001240
PharmGKB
PA164776842
Wikipedia
Sulfamerazine
MSDS
Download (72.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SuspensionOral
TabletOral
Suspension
Tablet
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)2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area97.97 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity68.79 m3·mol-1Chemaxon
Polarizability26.53 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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-9630000000-7f08d04a103b7e16f126
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0bt9-4900000000-1429f19666bf05cae962
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0aou-1920000000-06a82249586c8821f9d3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0bt9-4900000000-1429f19666bf05cae962
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0190000000-eb7713296e3fbf18121f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-7587cbc43f74c597b5bd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-066r-0690000000-18e905e2774e47414fda
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-08fr-3890000000-07a32447fea8b4807a24
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-02t9-9320000000-e3915a4869c0d099f5f9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9400000000-5496a56e8564dd09bd1f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.7414061
predicted
DarkChem Lite v0.1.0
[M-H]-172.5974061
predicted
DarkChem Lite v0.1.0
[M-H]-157.43846
predicted
DeepCCS 1.0 (2019)
[M+H]+173.7905061
predicted
DarkChem Lite v0.1.0
[M+H]+173.7316061
predicted
DarkChem Lite v0.1.0
[M+H]+159.79645
predicted
DeepCCS 1.0 (2019)
[M+Na]+172.8484061
predicted
DarkChem Lite v0.1.0
[M+Na]+173.0206061
predicted
DarkChem Lite v0.1.0
[M+Na]+165.8896
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
  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. [Article]
  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. [Article]

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. doi: 10.1159/000136629. [Article]
  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. [Article]

Drug created at August 29, 2007 14:53 / Updated at April 30, 2021 13:05