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
Structure for Sulfamerazine (DB01581)
- 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
Pharmacology
- Indication
A sulfanilamide that is used as an antibacterial agent. It can be used to treat bronchitis, prostatitis and urinary tract infections.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Abscesses Combination Product in combination with: Sulfamethazine (DB01582), Sulfadiazine (DB00359) •••••••••••• ••••••••••• •••••• Used in combination to treat Conjunctivitis Combination Product in combination with: Sulfadiazine (DB00359), Sulfamethazine (DB01582) •••••••••••• ••••••••••• •••••• Used in combination to treat Ear infection bacterial Combination Product in combination with: Sulfadiazine (DB00359), Sulfathiazole (DB06147) •••••••••••• •••••• Used in combination to treat Enteritis Combination Product in combination with: Sulfadiazine (DB00359), Sulfathiazole (DB06147) •••••••••••• •••••• Used in combination to treat Eye infections Combination Product in combination with: Sulfathiazole (DB06147), Sulfadiazine (DB00359) •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ADihydropteroate synthase inhibitorEscherichia 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfamerazine. Acenocoumarol The risk or severity of bleeding can be increased when Sulfamerazine is combined with Acenocoumarol. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfamerazine. Albiglutide The therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfamerazine. Alogliptin The therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfamerazine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Sulfamerazine sodium JOV4UJY07O 127-58-2 BSFJGCCAXDCMOX-UHFFFAOYSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Trisulfaminic Sus Sulfamerazine (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) Suspension Oral Shepherd Pharmaceuticals Inc. 1959-12-31 2001-04-11 Canada 
Trisulfaminic Tab Sulfamerazine (167 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg) + Sulfadiazine (167 mg) + Sulfamethazine (167 mg) Tablet Oral Shepherd Pharmaceuticals Inc. 1959-12-31 2001-04-11 Canada ซัลฟาโค Sulfamerazine (167 MG/5ML) + Sulfadiazine (167 MG/5ML) + Sulfamethazine (167 MG/5ML) Suspension บริษัท โรงงานเภสัชกรรมแหลมทองการแพทย์ จำกัด จำกัด 1987-05-15 Not applicable Thailand 
ไตรซัลฟาไพริมิดีน Sulfamerazine (167 MG) + Sulfadiazine (167 MG) + Sulfamethazine (167 MG) Tablet บริษัท อินแพคฟาร์มา จำกัด 1987-06-19 2020-09-29 Thailand ไตรซัลฟาไพริมิดีน Sulfamerazine (167 MG) + Sulfadiazine (167 MG) + Sulfamethazine (167 MG) Tablet บริษัท อินแพคฟาร์มา จำกัด 1987-09-22 2020-09-29 Thailand
Categories
- ATC Codes
- J01ED07 — Sulfamerazine
- J01ED — Long-acting sulfonamides
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- D06BA — Sulfonamides
- D06B — CHEMOTHERAPEUTICS FOR TOPICAL USE
- D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- Drug Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Benzene Derivatives
- Benzenesulfonamides
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Long-Acting Antibacterial Sulfonamides
- Sulfanilamides
- Sulfonamide Antibacterial
- Sulfonamides
- Sulfonamides and trimethoprim
- Sulfones
- Sulfur Compounds
- 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
- External Links
- Human Metabolome Database
- HMDB0015521
- KEGG Drug
- D02435
- PubChem Compound
- 5325
- PubChem Substance
- 46505036
- ChemSpider
- 5134
- BindingDB
- 50238672
- 10176
- ChEBI
- 102130
- ChEMBL
- CHEMBL438
- ZINC
- ZINC000000057501
- Therapeutic Targets Database
- DAP001240
- PharmGKB
- PA164776842
- Wikipedia
- Sulfamerazine
- MSDS
- Download (72.7 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suspension Oral Tablet Oral Suspension Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 236 °C PhysProp water solubility 202 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.14 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.304 mg/mL ALOGPS logP 0.44 ALOGPS logP 0.52 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 6.99 Chemaxon pKa (Strongest Basic) 2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 97.97 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 68.79 m3·mol-1 Chemaxon Polarizability 26.53 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9929 Blood Brain Barrier + 0.9356 Caco-2 permeable + 0.6431 P-glycoprotein substrate Non-substrate 0.8687 P-glycoprotein inhibitor I Non-inhibitor 0.9021 P-glycoprotein inhibitor II Non-inhibitor 0.9264 Renal organic cation transporter Non-inhibitor 0.8526 CYP450 2C9 substrate Non-substrate 0.7402 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Non-substrate 0.7559 CYP450 1A2 substrate Non-inhibitor 0.9473 CYP450 2C9 inhibitor Non-inhibitor 0.9175 CYP450 2D6 inhibitor Non-inhibitor 0.9471 CYP450 2C19 inhibitor Non-inhibitor 0.9567 CYP450 3A4 inhibitor Non-inhibitor 0.9065 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8301 Ames test Non AMES toxic 0.9185 Carcinogenicity Non-carcinogens 0.9333 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.9134 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9294 hERG inhibition (predictor II) Non-inhibitor 0.87
Spectra
- Mass Spec (NIST)
- Download (8.36 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.7414061 predictedDarkChem Lite v0.1.0 [M-H]- 172.5974061 predictedDarkChem Lite v0.1.0 [M-H]- 157.43846 predictedDeepCCS 1.0 (2019) [M+H]+ 173.7905061 predictedDarkChem Lite v0.1.0 [M+H]+ 173.7316061 predictedDarkChem Lite v0.1.0 [M+H]+ 159.79645 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.8484061 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.0206061 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.8896 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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]
- 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]
- 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
- 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
- Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
- 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