Chlortetracycline

Chlortetracycline
Systematic (IUPAC) name


(4S,4aS,5aS,6S,12aS,Z)-2-[amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydrotetracene-1,3,12(2H,4H,12aH)-trione
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral, IV, topical
Pharmacokinetic data
Bioavailability	30%
Protein binding	50 to 55%
Metabolism	Hepatic (75%)
Biological half-life	5.6 to 9 hours
Excretion	Renal and biliary
Identifiers
CAS Number	57-62-5^Y
ATC code	A01AB21 (WHO) D06AA02 J01AA03 S01AA02 QG51AA08 QJ51AA03
ChemSpider	10469370^Y
UNII	WCK1KIQ23Q^Y
KEGG	D07689^Y
ChEMBL	CHEMBL456066^N
Chemical data
Formula	C₂₂H₂₃ClN₂O₈
Molar mass	478.88 g/mol
SMILES CN(C)[C@@H]2C(\O)=C(\C(N)=O)C(=O)[C@@]3(O)C(/O)=C4/C(=O)c1c(O)ccc(Cl)c1[C@@](C)(O)[C@H]4C[C@@H]23
InChI InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1^Y Key:CYDMQBQPVICBEU-XRNKAMNCSA-N^Y
^NY (what is this?) (verify)

Chlortetracycline (trade name Aureomycin, Lederle) is a tetracycline antibiotic, the first tetracycline to be identified. It was discovered in 1945 by Benjamin Minge Duggar working at Lederle Laboratories under the supervision of Yellapragada Subbarow. Duggar identified the antibiotic as the product of an actinomycete he cultured from a soil sample collected from Sanborn Field at the University of Missouri.^[1] The organism was named Streptomyces aureofaciens and the isolated drug, Aureomycin, because of their golden color.

In veterinary medicine, chlortetracycline is commonly used to treat conjunctivitis in cats.^[2]

References

↑ Jukes, Thomas H. Some historical notes on chlortetracycline. Reviews of Infectious Diseases 7(5):702-707 (1985).
↑ Merck Veterinary Manual.

Stomatological preparations (A01)

Caries prophylaxis	Dectaflur Olaflur Sodium fluoride Sodium monofluorophosphate Stannous fluoride

Infection and antiseptics	Amphotericin B Benzoxonium chloride Chlorhexidine Chlortetracycline Clotrimazole Cetylpyridinium chloride Domiphen bromide Doxycycline Eugenol Hexetidine Hydrogen peroxide Mepartricin Metronidazole Miconazole Minocycline Natamycin Neomycin Oxyquinoline Polynoxylin Sodium perborate Tetracycline Tibezonium iodide

Corticosteroids (Glucocorticoids)	Dexamethasone Hydrocortisone Triamcinolone

Other	Amlexanox Acetylsalicylic acid Becaplermin Benzydamine Epinephrine/Adrenalone

Antibiotics and chemotherapeutics for dermatological use (D06)

Antibiotics

Tetracycline and derivatives	Demeclocycline Chlortetracycline Oxytetracycline Tetracycline

Others	Amphenicol: Chloramphenicol Aminoglycosides: Neomycin Gentamicin Amikacin Quinolone: Nadifloxacin Streptogramin: Virginiamycin Rifamycin: Rifaximin other: Fusidic acid Bacitracin Tyrothricin Mupirocin

Chemotherapeutics

Sulfonamides	Silver sulfadiazine Sulfathiazole Mafenide Sulfamethizole Sulfanilamide Sulfamerazine

Antivirals	Aciclovir Penciclovir Idoxuridine Edoxudine Imiquimod Resiquimod Podophyllotoxin Docosanol Tromantadine Inosine Lysozyme Ibacitabine Lysine

Other	Ingenol mebutate Metronidazole

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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