U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H23ClN2O8
Molecular Weight 478.88
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORTETRACYCLINE

SMILES

[H][C@@]12C[C@@]3([H])C(C(=O)C4=C(C(Cl)=CC=C4O)[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C

InChI

InChIKey=CYDMQBQPVICBEU-XRNKAMNCSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H23ClN2O8
Molecular Weight 478.88
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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. The organism was named Streptomyces aureofaciens and the isolated drug, Aureomycin, because of their golden color. Chlortetracycline inhibits cell growth by inhibiting translation. It binds to the 16S part of the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. In veterinary medicine, chlortetracycline is commonly used to treat conjunctivitis in cats.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Aureomycin
Curative
Aureomycin
Curative
Aureomycin

Cmax

ValueDoseCo-administeredAnalytePopulation
1560.8 ng/mL
10 mg/kg single, oral
CHLORTETRACYCLINE plasma
Gallus gallus domesticus

AUC

ValueDoseCo-administeredAnalytePopulation
13415.51 ng × h/mL
10 mg/kg single, oral
CHLORTETRACYCLINE plasma
Gallus gallus domesticus

T1/2

ValueDoseCo-administeredAnalytePopulation
30.59 h
10 mg/kg single, oral
CHLORTETRACYCLINE plasma
Gallus gallus domesticus

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
10 mg/kg single, oral
CHLORTETRACYCLINE plasma
Gallus gallus domesticus

PubMed

Sample Use Guides

In Vivo Use Guide
Cattle: 0.1-10 mg per lb body wt per day; Swine: 10 mg per lb body wt per day; Turkeys: 25 mg per lb body wt per day;
Route of Administration: Oral
In Vitro Use Guide
Chlortetracycline activity was determined against 37 Mycoplasma putrefaciens isolates. Chlortetracycline was tested at concentrations ranged from 4 to 0.03 mg/ml/ The MIC was defined as the lowest concentration in which there was no bacterial growth, as evidenced by a lack of pH color change at the time the drug-free growth control showed a color change. This change of color was evident after 24 h of incubation.
Substance Class Chemical
Record UNII
WCK1KIQ23Q
Record Status Validated (UNII)
Record Version