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chlortetracycline
Sign in to saveAlso known as 7-Chlorotetracycline
Chlortetracycline (trade name Aureomycin, Lederle Laboratories) is a tetracycline antibiotic, the first tetracycline to be identified. It was discovered in 1945 at Lederle Laboratories under the supervision of Yellapragada Subbarow and Benjamin Minge Duggar. They were helped by Louis T. Wright, a surgeon who conducted this medication's first human trials. Duggar identified the antibiotic as the product of an actinomycete he cultured from the soil of Sanborn Field at the University of Missouri. The organism was named Streptomyces aureofaciens and the isolated drug, Aureomycin, because of the mo
Chemical data
- Formula
- C22H23ClN2O8
- Molecular weight
- 478.9 g/mol
- IUPAC name
- (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
- SMILES
- C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O
- InChIKey
- DHPRQBPJLMKORJ-XRNKAMNCSA-N
- XLogP
- -1.3
- Polar surface area
- 182 Ų
- H-bond donors
- 6
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 478.1143
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₂H₂₃ClN₂O₈
- subject has role
- bactericide
- World Health Organisation international non-proprietary name
- chlortetracycline
- isomeric SMILES
- C[C@]1(C2=C(C=CC(=C2C(=O)C3=C([C@]4([C@@H](C[C@@H]31)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)Cl)O
- canonical SMILES
- CC1(C2=C(C=CC(=C2C(=O)C3=C(C4(C(CC31)C(C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)Cl)O
- defined daily dose
- 1
- Commons category
- Chlortetracycline
via Wikidata · CC0
~2 min read
Encyclopedic overview
7 sectionsContents
- Medical uses
- Contraindications
- Adverse effects
- Interactions
- Pharmacology
- Mechanism of action
- References
Chlortetracycline (trade name Aureomycin, Lederle Laboratories) is a tetracycline antibiotic, the first tetracycline to be identified. It was discovered in 1945 at Lederle Laboratories under the supervision of Yellapragada Subbarow and Benjamin Minge Duggar. They were helped by Louis T. Wright, a surgeon who conducted this medication's first human trials. Duggar identified the antibiotic as the product of an actinomycete he cultured from the soil of Sanborn Field at the University of Missouri. The organism was named Streptomyces aureofaciens and the isolated drug, Aureomycin, because of the molecule's intense golden-yellow color.
It is on the World Health Organization's List of Essential Medicines.
Excerpted from Wikipedia’s “chlortetracycline” article, available under the CC BY-SA 4.0 licence.