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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomySulfamerazine
Identification
- Name
- Sulfamerazine
- Accession Number
- DB01581
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Description
A sulfanilamide that is used as an antibacterial agent.
- Structure
Structure for Sulfamerazine (DB01581)
- 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
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 Trisulfaminic Sus Sulfamerazine (167 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg) + Sulfadiazine (167 mg) + Sulfamethazine (167 mg) 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 - Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Long-Acting Sulfonamides
- Sulfanilamides
- Sulfonamide Antibacterial
- Sulfonamides
- Sulfones
- Sulfur Compounds
- 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
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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.
- 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
- 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
- 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 Unlock Additional Data(R)-warfarin The risk or severity of bleeding can be increased when Sulfamerazine is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding can be increased when Sulfamerazine is combined with (S)-Warfarin. 2,4-thiazolidinedione The therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Sulfamerazine. 4-hydroxycoumarin The risk or severity of bleeding can be increased when Sulfamerazine is combined with 4-hydroxycoumarin. Acarbose 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. AICA ribonucleotide The therapeutic efficacy of AICA ribonucleotide can be increased when used in combination with Sulfamerazine. Albiglutide The therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfamerazine. Allicin The therapeutic efficacy of Allicin can be increased when used in combination with Sulfamerazine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- 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
- BindingDB
- 50238672
- ChEBI
- 102130
- ChEMBL
- CHEMBL438
- Therapeutic Targets Database
- DAP001240
- PharmGKB
- PA164776842
- Wikipedia
- Sulfamerazine
- ATC Codes
- J01ED07 — Sulfamerazine
- J01ED — Long-acting sulfonamides
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- D06BA — Sulfonamides
- D06B — CHEMOTHERAPEUTICS FOR TOPICAL USE
- D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- MSDS
- Download (72.7 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Suspension Oral Tablet Oral - 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) 2.01 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 26.51 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
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-0aou-1920000000-06a82249586c8821f9d3 MS/MS Spectrum - , positive LC-MS/MS splash10-0bt9-4900000000-1429f19666bf05cae962
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
- 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. [PubMed:7486915]
- 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]
- 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
- 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. [PubMed:1031216]
- 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 January 02, 2020 04:49