Chlortetracycline

US Approved OTC

First approved in 1948

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 Search

SMILES

CN(C)[C@H]1[C@@H]2C[C@H]3C(C(=O)C4=C(C(Cl)=CC=C4O)[C@@]3(C)O)=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O

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

Description
Sources: https://www.drugs.com/vet/aureomycin-50-granular.html
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17638695 | https://www.ncbi.nlm.nih.gov/pubmed/6404649

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 Target	Pharmacology	Condition	Potency
translation 13 Target ID: GO:0006412 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6404649	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Control of bacterial pneumonia associated with shipping fever 4 Sources: https://www.drugs.com/vet/aureomycin-50-granular.html	Curative	Approved 8583	Aureomycin Approved Use Unknown
Anaplasmosis caused by Anaplasma marginale 4 Sources: https://www.drugs.com/vet/aureomycin-50-granular.html	Curative	Approved 8583	Aureomycin Approved Use Unknown
Leptospirosis (reducing the incidence of abortion and shedding of leptospirae) caused by Leptospira pomona 4 Sources: https://www.drugs.com/vet/aureomycin-50-granular.html	Curative	Approved 8583	Aureomycin Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1560.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32988509/	10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		CHLORTETRACYCLINE plasma	Gallus gallus domesticus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
13415.51 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32988509/	10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		CHLORTETRACYCLINE plasma	Gallus gallus domesticus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
30.59 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32988509/	10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		CHLORTETRACYCLINE plasma	Gallus gallus domesticus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
50% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32988509/	10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		CHLORTETRACYCLINE plasma	Gallus gallus domesticus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1139	http://www.3bsc.com/index/pro_info.php?id=54855
AA Blocks	AA00JPV7	https://www.aablocks.com/goods/Goods/detail?id=AA00JPV7
abcr GmbH	AB483493	http://www.abcr.com/shop/en/AB483493
AHH Chemical co.,ltd	MT-49188	http://www.ahhchemical.com/product/MT-49188.html
AK Scientific, Inc. (AKSCI)	S042	http://www.aksci.com/item_detail.php?cat=S042
Alichem	449038864	http://www.alichem.com/en/products/57-62-5.html
BioSynth	Q-200843	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-200843.html
Chem Scene	CS-0013541	http://www.chemscene.com/57-62-5.html
ChemMol	49425898	http://www.chemmol.com/chemmol/49425898.html
ChemMol	99111245	http://www.chemmol.com/chemmol/99111245.html
Chemspace	CSSB00020617855	https://chem-space.com/CSSB00020617855
Glentham Life Sciences	GA4273	http://www.glentham.com/products/product/GA4273/
Hairui	HR132296	http://www.hairuichem.com/en/product/57-62-5.html
Lab Network	LN01343738	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343738
mcule	MCULE-9900766267	https://mcule.com/MCULE-9900766267/
MedChem Express	HY-B1327A	https://www.medchemexpress.com/chlortetracycline.html
MolPort	MolPort-002-509-899	https://www.molport.com/shop/molecule-link/MolPort-002-509-899
OChem	6559	http://www.ocheminc.com/index.php?act=psearch&pid=864C876
Parchem	87029	https://www.parchem.com/chemical-supplier-distributor/Chlortetracycline-087029.aspx
Smolecule	S523565	http://www.smolecule.com/products/s523565
THE BioTek	bt-264223	https://www.thebiotek.com/product/inhibitors/bt-264223

PubMed

Title	Date	PubMed
Evaluation of pilot-scale microencapsulation of probiotics and product effect on broilers.	2015-10	26523573
Efficacy of chlortetracycline treatment on vulvar non-neoplastic epithelial disorders.	2015	26054119

Patents

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.

Name

Type

Language

7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide

Preferred Name

English

Chlortetracycline

Official Name

English

Chlortetracycline [VANDF]

Common Name

English

Chlortetracycline [EP IMPURITY]

Common Name

English

LYMECYCLINE IMPURITY G [EP IMPURITY]

Common Name

English

Chlortetracycline [GREEN BOOK]

Common Name

English

Chlorotetracycline

Common Name

English

(4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

Systematic Name

English

chlortetracycline [INN]

Common Name

English

Chlortetracycline [MI]

Common Name

English

Chlortetracycline [MART.]

Common Name

English

Chlortetracycline [WHO-DD]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.445