{ "id": "ep52gmqare", "slug": "sulfadicramide", "title": "Sulfadicramide", "updated": "2026-10-21", "topic_path": [ { "id": "life", "label": "Life and health", "api_url": "https://www.edgepedia.org/api/v1/topics/life" }, { "id": "life.health", "label": "Human health and medicine", "api_url": "https://www.edgepedia.org/api/v1/topics/life.health" }, { "id": "life.health.medicines", "label": "Medicines and therapeutics", "api_url": "https://www.edgepedia.org/api/v1/topics/life.health.medicines" }, { "id": "life.health.medicines.anti-infective-drugs", "label": "Anti-infective drugs and resistance", "api_url": "https://www.edgepedia.org/api/v1/topics/life.health.medicines.anti-infective-drugs" }, { "id": "life.health.medicines.anti-infective-drugs.antibacterial-drugs", "label": "Antibacterial drugs", "api_url": "https://www.edgepedia.org/api/v1/topics/life.health.medicines.anti-infective-drugs.antibacterial-drugs" }, { "id": "life.health.medicines.anti-infective-drugs.antibacterial-drugs.sulfonamides-and-related-folate-antagonists", "label": "Sulfonamides and related folate antagonists", "api_url": "https://www.edgepedia.org/api/v1/topics/life.health.medicines.anti-infective-drugs.antibacterial-drugs.sulfonamides-and-related-folate-antagonists" } ], "geo": [ { "id": "geo.weu.t1800.life.health.medicines.anti-infective-drugs", "label": "Western Europe · 1800 to 1945: Anti-infective drugs and resistance", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.weu.t1800.life.health.medicines.anti-infective-drugs", "path": [ { "id": "geo.weu", "label": "Western Europe", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.weu" }, { "id": "geo.weu.t1800", "label": "Western Europe · 1800 to 1945", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.weu.t1800" }, { "id": "geo.weu.t1800.life", "label": "Life and health", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.weu.t1800.life" }, { "id": "geo.weu.t1800.life.health", "label": "Human health and medicine", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.weu.t1800.life.health" }, { "id": "geo.weu.t1800.life.health.medicines", "label": "Medicines and therapeutics", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.weu.t1800.life.health.medicines" }, { "id": "geo.weu.t1800.life.health.medicines.anti-infective-drugs", "label": "Anti-infective drugs and resistance", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.weu.t1800.life.health.medicines.anti-infective-drugs" } ] } ], "excerpt": "Sulfadicramide (Irgamid, sulfirgamide; INN sulfadicramidum) is a sulfanilamide sulfonamide anti-infective, CAS 115-68-4, C11H14N2O3S, ATC S01AB03, used as a 15% ophthalmic ointment in some countries.", "snippet": "Sulfadicramide (Irgamid, sulfirgamide; INN sulfadicramidum) is a sulfanilamide sulfonamide anti-infective, CAS 115-68-4, C11H14N2O3S, ATC S01AB03, used as a 15% ophthalmic ointment in some countries.", "node": "life.health.medicines.anti-infective-drugs.antibacterial-drugs.sulfonamides-and-related-folate-antagonists", "markdown": "# Sulfadicramide\n\n**Sulfadicramide** is a sulfonamide anti-infective drug used as a topical ophthalmic preparation, classified in the Anatomical Therapeutic Chemical (ATC) system under S01AB03, ophthalmologicals, antiinfectives, sulfonamides.[1](https://atcddd.fhi.no/atc_ddd_index/?code=S01AB&showdescription=yes) Its International Nonproprietary Name (INN) is sulfadicramide (Latin: sulfadicramidum), and its chemical name is N1-(3,3-dimethylacroyl)sulfanilamide.[2](https://www.who.int/docs/default-source/international-nonproprietary-names-%28inn%29/rl03.pdf?download=true) The name belongs to the WHO \"sulfa-\" stem, which is used for anti-infective sulfonamide derivatives.[3](https://iris.who.int/bitstream/handle/10665/379226/9789240099388-eng.pdf?sequence=1)\n\n| Key fact | Detail |\n|---|---|\n| Drug class | Sulfonamide anti-infective; ATC code S01AB03 (ophthalmologicals, antiinfectives, sulfonamides)[1](https://atcddd.fhi.no/atc_ddd_index/?code=S01AB&showdescription=yes) |\n| Chemical identity | CAS 115-68-4; EC 204-099-3; molecular formula C11H14N2O3S[4](https://chemicalscan.com/index.php/substance/sulfadicramide-115-68-4) |\n| IUPAC name | N-(4-aminophenyl)sulfonyl-3-methylbut-2-enamide; molecular weight 254.31 g/mol[5](https://pubchem.ncbi.nlm.nih.gov/compound/8281) |\n| Synonyms | Irgamid, sulfauridin, sulfirgamid, sulfirgamide, sulfanildimethylacryloylamide[5](https://pubchem.ncbi.nlm.nih.gov/compound/8281) • [6](https://drugcentral.org/drugcard/3560) |\n| Current use | Still used in some countries as a 15% ointment for application to the eye[7](https://www.un.org/esa/coordination/CL12.pdf) |\n| Regulatory record | UNII 7WZ5EG263C (active moiety); sodium salt UNII 6Y6D6Z2GY8[8](https://precision.fda.gov/uniisearch/srs/unii/7WZ5EG263C) • [9](https://precision.fda.gov/ginas/app/ui/substances/27b61704-6534-4d04-b377-810fdbb89ad3) |\n| Approval status | DrugCentral records no drug approvals, dosage entries, or veterinary products for the compound[6](https://drugcentral.org/drugcard/3560) |\n\n## Chemistry\n\nSulfadicramide is a sulfanilamide derivative in which the sulfonamide nitrogen carries a 3,3-dimethylacryloyl group, giving the systematic name N-(4-aminophenyl)sulfonyl-3-methylbut-2-enamide.[2](https://www.who.int/docs/default-source/international-nonproprietary-names-%28inn%29/rl03.pdf?download=true) • [5](https://pubchem.ncbi.nlm.nih.gov/compound/8281) The molecule is achiral, with no defined stereocenters.[5](https://pubchem.ncbi.nlm.nih.gov/compound/8281) Computed properties include a molecular weight of 254.31 g/mol, an acidic pKa of 5.63 and a basic pKa of 1.98, a CLOGP of 0.40, and a topological polar surface area of 89.26 Ų.[5](https://pubchem.ncbi.nlm.nih.gov/compound/8281) • [6](https://drugcentral.org/drugcard/3560) A sodium salt is registered in the FDA Global Substance Registration System as SULFADICRAMIDE SODIUM, formula C11H13N2O3S·Na, molecular weight 276.29, with sulfadicramide listed as the active moiety.[9](https://precision.fda.gov/ginas/app/ui/substances/27b61704-6534-4d04-b377-810fdbb89ad3)\n\n## Pharmacology\n\nSulfadicramide belongs to the sulfonamide class of antibacterial agents. Sulfonamides are bacteriostatic drugs that inhibit bacterial synthesis of dihydrofolic acid by preventing the condensation of [pteridine](https://www.edgepedia.org/pteridine) with aminobenzoic acid through competitive inhibition of the enzyme dihydropteroate synthetase.[10](https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fae0c19a-2177-4aa7-9266-320b8502065e) Bacteria must synthesize folate themselves, whereas mammals obtain it from the diet, which is the basis of the selective toxicity of this class.[11](https://stagetestdomain3.nih.gov/news-events/nih-research-matters/how-sulfa-drugs-work)\n\n## Clinical use and history\n\nThe compound was introduced under the trade name Irgamid and evaluated as an eye ointment in the 1950s. A 1953 study in *Medicinski arhiv* by V. Cavka and S. Miletic assessed irgamide ointment in ophthalmology.[12](https://pubmed.ncbi.nlm.nih.gov/13144111/) A German-language paper in *Ophthalmologica* described the use of Irgamid, described there as a new sulfanilamide derivative, in eye medicine.[13](https://karger.com/oph/article-abstract/101/4/193/247043/Ueber-Anwendung-von-Irgamid-einem-neuen?redirectedFrom=fulltext) In 1955, F. H. Theodore published a report in the *American Journal of Ophthalmology* on the use of sulfirgamide, a synonym of the same compound, in external diseases of the eyes.[14](https://pubmed.ncbi.nlm.nih.gov/13248907/)\n\nA United Nations listing of pharmaceutical trade names records the product under the names Ingamid, Ingamid ophtal, and Irgamid, and states that sulfadicramide is still used in some countries as a 15% ointment for application to the eye.[7](https://www.un.org/esa/coordination/CL12.pdf) The Council of Europe lists sulfadicramide among controlled substances in Schedule I of its pharmaceutical classification.[15](https://rm.coe.int/native/09000016804d24d4)\n\n## Regulatory status\n\nIn the European Union regulatory system, sulfadicramide is registered with CAS number 115-68-4 and EC number 204-099-3; it is not on the SVHC Candidate List, does not require authorization, and is not specifically restricted or banned.[4](https://chemicalscan.com/index.php/substance/sulfadicramide-115-68-4) DrugCentral records no FDA or EMA approvals, no Orange Book patent or exclusivity data, and no FDA Adverse Event Reporting System entries for the compound, and lists no pharmaceutical products.[6](https://drugcentral.org/drugcard/3560) The FDA substance registration system notes that UNII availability does not imply any regulatory review or approval.[8](https://precision.fda.gov/uniisearch/srs/unii/7WZ5EG263C)\n\n## References\n\n1. [ATC/DDD Index, S01AB Sulfonamides, WHO Collaborating Centre](https://atcddd.fhi.no/atc_ddd_index/?code=S01AB&showdescription=yes)\n2. [Recommended International Nonproprietary Names list, World Health Organization](https://www.who.int/docs/default-source/international-nonproprietary-names-%28inn%29/rl03.pdf?download=true)\n3. [Use of stems in the selection of INN, WHO](https://iris.who.int/bitstream/handle/10665/379226/9789240099388-eng.pdf?sequence=1)\n4. [Sulfadicramide, ChemicalScan](https://chemicalscan.com/index.php/substance/sulfadicramide-115-68-4)\n5. [Sulfadicramide CID 8281, PubChem](https://pubchem.ncbi.nlm.nih.gov/compound/8281)\n6. [Sulfadicramide drug card 3560, DrugCentral](https://drugcentral.org/drugcard/3560)\n7. [Pharmaceuticals (Trade Names), Twelfth Issue, United Nations](https://www.un.org/esa/coordination/CL12.pdf)\n8. [SULFADICRAMIDE UNII 7WZ5EG263C, FDA UNII Search Service](https://precision.fda.gov/uniisearch/srs/unii/7WZ5EG263C)\n9. [SULFADICRAMIDE SODIUM, FDA Global Substance Registration System](https://precision.fda.gov/ginas/app/ui/substances/27b61704-6534-4d04-b377-810fdbb89ad3)\n10. [Sulfacetamide Sodium ophthalmic solution label, DailyMed](https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fae0c19a-2177-4aa7-9266-320b8502065e)\n11. [How Sulfa Drugs Work, NIH Research Matters](https://stagetestdomain3.nih.gov/news-events/nih-research-matters/how-sulfa-drugs-work)\n12. [Cavka V, Miletic S (1953). Evaluation of irgamide ointment and irgapyrine in ophthalmology. Medicinski arhiv 7(6):105-15, PubMed](https://pubmed.ncbi.nlm.nih.gov/13144111/)\n13. [Ueber Anwendung von Irgamid, einem neuen Sulfanilamidderivat, in der Augenheilkunde, Ophthalmologica, Karger](https://karger.com/oph/article-abstract/101/4/193/247043/Ueber-Anwendung-von-Irgamid-einem-neuen?redirectedFrom=fulltext)\n14. [Theodore FH (1955). The use of sulfirgamide in external diseases of the eyes. American Journal of Ophthalmology 40(3):406-11, PubMed](https://pubmed.ncbi.nlm.nih.gov/13248907/)\n15. [Council of Europe pharmaceutical substance schedule listing](https://rm.coe.int/native/09000016804d24d4)\n\n---\n*Topic: Encyclopedia › Life and health › Human health and medicine › Medicines and therapeutics › Anti-infective drugs and resistance › Antibacterial drugs › Sulfonamides and related folate antagonists*\n\n*Initially written Oct 21, 2026*\n\n*Copyright 2026 EdgeChat AI, a subsidiary of Biostate AI.*\n\nLicense: Edgepedia Community License 1.0, https://www.edgepedia.org/edgepedia/license\n", "same_as": [], "url": "https://www.edgepedia.org/sulfadicramide", "markdown_url": "https://www.edgepedia.org/sulfadicramide.md", "license": { "name": "Edgepedia Community License 1.0", "url": "https://www.edgepedia.org/edgepedia/license", "summary": "Free with credit, commercial use included. AI training is open to everyone. For other uses, organizations over USD 100M in revenue or 100M monthly users license separately.", "spdx": "LicenseRef-Edgepedia-Community-1.0" }, "credit": "\"Sulfadicramide\", Edgepedia (EdgeChat), https://www.edgepedia.org/sulfadicramide. Edgepedia Community License 1.0.", "credit_md": "\"[Sulfadicramide](https://www.edgepedia.org/sulfadicramide)\", Edgepedia (EdgeChat), [https://www.edgepedia.org/sulfadicramide](https://www.edgepedia.org/sulfadicramide). [Edgepedia Community License 1.0](https://www.edgepedia.org/edgepedia/license).", "credit_html": "\"Sulfadicramide\", Edgepedia (EdgeChat), https://www.edgepedia.org/sulfadicramide. Edgepedia Community License 1.0.", "speakable": "Sulfadicramide is a sulfanilamide sulfonamide anti-infective, CAS 115-68-4, C11H14N2O3S, ATC S01AB03, used as a 15% ophthalmic ointment in some countries." }