(-)-Tetracycline

444.44

444.43

200-481-9

F8VB5M810T

DTXSID7023645

C865

YELLOW CRYSTALLINE POWDER|Yellow, crystalline powder

D06AA04|A - Alimentary tract and metabolism|D - Dermatologicals|J - Antiinfectives for systemic use|S - Sensory organs

29413000

182

-1.37

yellow to yellow orange

1.6±0.1 g/cm3

5-170 °C

790.6±60.0 °C at 760 mmHg

432.0±32.9 °C

1.741

Limited solubility in water. soluble in 1M HCl with heating.95% ethanol: soluble 12.5mg/mL

2-8°C

LD50 in rats, mice (mg/kg): 807, 808 orally (Goldenthal)

D25 -257.9° (0.1N HCl); D25 -239° (methanol)

Odorless

3.0-7.0 /saturated solution/

3.3(at 25 °C)

7.68|3.3 (at 25 °C)|pKa= 3.30

198.48 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|212.5 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|200.93 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|197.3 Ų [M+H]+ [CCS Type: TW]|196.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|207.1 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|199.24 Ų [M-H]-|200.2 Ų [M-H]-

Crystals...Becomes anhydr by drying in vacuo at 60 °C for 8 hrs. /Trihydrate/|YELLOW CRYSTALLINE POWDER /HYDROCHLORIDE/|YELLOW FINE CRYSTALLINE POWDER /PHOSPHATE COMPLEX/|Stable in neutral and in alkaline soln. Soly at about 28 deg: 1.7 mg/ml water; >20 mg/l methanol. /Trihydrate/|For more Other Experimental Properties (Complete) data for TETRACYCLINE (9 total), please visit the HSDB record page.

NONH for all modes of transport

3

22-36/37/38

22-36-26

QI8750000

Xn,Xi

IN CONTRAST TO CHLORTETRACYCLINE, TETRACYCLINE IS QUITE STABLE IN NEUTRAL & ALKALINE SOLN /TRIHYDRATE/

P264, P270, P301+P312, P330, P501

H302

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

DHHS/NTP; Toxicology & Carcinogenesis Studies of Tetracycline Hydrochloride in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 344 (1989) NIH Publication No. 89-2600 /Tetracycline hydrochloride/

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 49 companies from 2 notifications to the ECHA C&L Inventory.

Dampen spilled material with water to avoid dust /generation/, then transfer material to a suitable container. Use absorbent paper dampened with water to pick up remaining material. Wash surfaces with soap and water. Seal all wastes in vapor-tight plastic bags for eventual disposal. /Tetracycline hydrochloride/

Leave contaminated area immediately. ... Flood all areas of the body that have contacted the substance with water. Remove the contaminated clothing under the water stream. Use soap to help assure removal. Isolate contaminated clothing /after removal/. ...

Skin irritant. /Tetracycline hydrochloride/

LD50=808mg/kg (orally in mice)

TETRACYCLINE ITSELF HAS BEEN SHOWN TO HAVE DIRECT, PH-DEPENDENT EFFECT ON RAT INTESTINE, RESULTING IN INCR ABSORPTION OF SULFANILIC ACID.|ORAL ADMIN OF FERROUS SULFATE (200-600 MG) INTERFERES WITH ABSORPTION OF TETRACYCLINE FROM GI TRACT & VICE VERSA, LEADING TO DECR SERUM LEVELS OF ANTIBIOTIC & IRON SALT, RESPECTIVELY. ... OTHER SALTS OF IRON SUCH AS FERROUS FUMARATE & FERROUS GLUCONATE HAVE BEEN SHOWN TO INTERACT WITH TETRACYCLINE.|BILIARY EXCRETION OF TETRACYCLINE ... IS INCR IN RATS BY TWO NEW CHOLERETIC AGENTS ALPHA,ALPHA-DIETHYL-1-NAPHTHYLACETIC ACID (DA 808) & ALPHA-METHYL-ALPHA-(2-MORPHOLINOETHYL)-1-NAPHTHYLACETIC ACID (DA 1627). ... AS DA 808 & DA 1627 CAUSE NO DECR IN TETRACYCLINE ... CONCN IN BILE, THEY APPEAR TO ACT AS TRUE CHOLERETICS. ...|ABSORPTION OF THESE AGENTS IS IMPAIRED BY CONCURRENT INGESTION OF DAIRY PRODUCTS; ALUMINUM HYDROXIDE GELS; CALCIUM, MAGNESIUM, & IRON OR ZINC SALTS; AND BISMUTH SUBSALICYLATE . MECHANISMS RESPONSIBLE FOR DECR ABSORPTION APPEAR TO BE CHELATION OF DIVALENT AND TRIVALENT CATIONS. /TETRACYCLINES/|For more Interactions (Complete) data for TETRACYCLINE (22 total), please visit the HSDB record page.

LD50 Rat oral 807 mg/kg|LD50 Mouse oral 678 mg/kg|LD50 Guinea pig oral 1875 mg/kg

... Toxicology and carcinogenesis studies of tetracycline hydrochloride (USP grade, 91% pure) were conducted by feeding diets containing tetracycline hydrochloride to groups of F344/N rats and B6C3F1 mice of each sex for ... 2 years. ... The 2 yr studies of tetracycline hydrochloride were conducted by feeding diets containing 0, 12,500, or 25,000 ppm tetracycline hydrochloride to groups of 50 rats and 50 mice of each sex for 103 wk. Conclusions: Under the condltlons of these 2 yr feed studies, there was no evidence of carcinogenic activity of tetracycline hydrochloride for male or female F344/N rats and B6C3F1 mice fed diets containing 12,500 or 25,000 ppm. Tetracycline hydrochloride dosed female rats and male mice had greater survival rates than the respective controls during these studies. Dosed mice had lower body weight than controls, and dosed female mice had no hepatocellular adenomas or carcinomas. /Tetracycline hydrochloride/

Young women given tetracycline and vitamin A in combination for acne may be at special risk and should be kept under surveillance.

20 - 67% protein bound

Used to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever, rickettsialpox and Brill-Zinsser disease. May be used to treat infections caused by Chlamydiae spp., B. burgdorferi (Lyme disease), and upper respiratory infections caused by typical (S. pneumoniae, H. influenzae, and M. catarrhalis) and atypical organisms (C. pneumoniae, M. pneumoniae, L. pneumophila). May also be used to treat acne. Tetracycline may be an alternative drug for people who are allergic to penicillin.

Antibiotics, Tetracycline; Protein Synthesis Inhibitors|Tetracycline hydrochloride ointment is used in the prophylaxis of minor bacterial skin infections and in the treatment of dermal ulcer. /Tetracycline hydrochloride; NOT included in US product labeling/|Tetracycline hydrochloride ointment is indicated in the topical treatment of minor skin infections caused by streptococci, staphylococci, and other susceptible organisms. /Tetracycline hydrochloride; Included in US product labeling/|Tetracycline hydrochloride for topical solution is indicated for the topical treatment of acne vulgaris. It may be effective in grades II and III acne, which are characterized by inflammatory lesions such as papules and pustules. /Tetracycline hydrochloride; Included in US product labeling/|For more Therapeutic Uses (Complete) data for TETRACYCLINE (37 total), please visit the HSDB record page.

EXCEPT FOR LOCAL USE IN EYE, TOPICAL USE OF TETRACYCLINES IS NOT RECOMMENDED. /TETRACYCLINES/|MICROORGANISMS THAT HAVE BECOME INSENSITIVE TO ONE TETRACYCLINE FREQUENTLY EXHIBIT RESISTANCE TO OTHERS. /TETRACYCLINES/|CROSS-SENSITIZATION AMONG VARIOUS TETRACYCLINES IS COMMON . /TETRACYCLINES/|... NAUSEA, VOMITING, POLYURIA, POLYDIPSIA, PROTEINURIA, ACIDOSIS, GLYCOSURIA, & GROSS AMINOACIDURIA, A FORM OF FANCONI SYNDROME, HAS BEEN OBSERVED IN PT INGESTING OUTDATED, & DEGRADED TETRACYCLINE.|For more Drug Warnings (Complete) data for TETRACYCLINE (31 total), please visit the HSDB record page.

Tetracycline is a short-acting antibiotic that inhibits bacterial growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. It also binds to some extent to the 50S ribosomal subunit. This binding is reversible in nature. Additionally tetracycline may alter the cytoplasmic membrane of bacteria causing leakage of intracellular contents, such as nucleotides, from the cell.

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

Bioavailability is less than 40% when administered via intramuscular injection, 100% intravenously, and 60-80% orally (fasting adults). Food and/or milk reduce GI absorption of oral preparations of tetracycline by 50% or more.|They are concentrated by the liver in the bile and excreted in the urine and feces at high concentrations in a biologically active form.|ALL TETRACYCLINES ARE ADEQUATELY BUT INCOMPLETELY ABSORBED FROM GI TRACT. MOST ABSORPTION TAKES PLACE FROM STOMACH & UPPER SMALL INTESTINE & IS GREATEST IN FASTING STATE. /TETRACYCLINES/|... /TETRACYCLINE IS/ VERY INCOMPLETELY ABSORBED. AFTER SINGLE ORAL DOSE PEAK PLASMA CONCN ARE ATTAINED IN 2-4 HR. ... ADMIN OF 250 MG EVERY 6 HR PRODUCES PEAK PLASMA CONCN OF APPROX 2-2.5 UG/ML.|THE PRIMARY ROUTE OF ELIMINATION FOR MOST TETRACYCLINES IS THE KIDNEY, ALTHOUGH THEY ARE ALSO CONCENTRATED IN THE LIVER AND EXCRETED BY ... BILE, INTO INTESTINE, FROM WHICH THEY ARE PARTIALLY REABSORBED. /TETRACYCLINES/|ELIMINATION FROM INTESTINAL TRACT OCCURS EVEN WHEN DRUGS ARE GIVEN PARENTERALLY, AS RESULT OF EXCRETION IN BILE. /TETRACYCLINES/|For more Absorption, Distribution and Excretion (Complete) data for TETRACYCLINE (16 total), please visit the HSDB record page.

Not metabolized

6-12 hours|/IT HAS HALF-LIFE/ IN RANGE OF 6-12 HR...|Tetracycline was encapsulated in erythrocytes by a dialysis technique. On encapsulation of (14)C sucrose and (3)H tetracycline, the drug concn (0.2 mg/ml of erythrocytes) decreased the tetracycline encapsulation, but not (14)C sucrose. Carrier erythrocytes containing tetracycline reinjected in calves were studied for their pharmacokinetic constants. the drug half-life was 6.7 hr with an overall elimination constant of 0.104 hr.|The serum half-life...is 6-12 hr in adults with normal renal funtion and is reported to be 57-120 hr in patients with severe renal impairment.

Tetracycline passively diffuses through porin channels in the bacterial membrane and reversibly binds to the 30S ribosomal subunit, preventing binding of tRNA to the mRNA-ribosome complex, and thus interfering with protein synthesis.|TETRACYCLINES ARE THOUGHT TO INHIBIT PROTEIN SYNTH BY BINDING SPECIFICALLY TO 30 S RIBOSOMES AND PREVENTING ACCESS OF AMINOACYL TRNA TO... MRNA-RIBOSOME COMPLEX. /TETRACYCLINES/|... IT IS POSSIBLE THAT REVERSIBLY BOUND ANTIBIOTIC IS RESPONSIBLE FOR ANTIBACTERIAL ACTION. /TETRACYCLINES/|TETRACYCLINE COMBINES WITH CELLULAR & INTRACELLULAR MATERIAL TO FORM A FLUOROPHORE WHICH UNDER UV LIGHT GLOWS WITH YELLOW-GOLD FLUORESCENCE. THE FLUOROPHORE REMAINS IN BONE FOR MANY MO.|PHOTOALLERGIC REACTIONS ARE BELIEVED TO RESULT FROM LIGHT ENERGY ACTING ON OR ALTERING DRUG & SKIN PROTEINS IN SUCH MANNER AS TO FORM AN ANTIGEN. THESE ERUPTIONS REQUIRE PREVIOUS CONTACT WITH OFFENDING SUBSTANCE, ARE NOT DOSE-RELATED, & EXHIBIT CROSS-SENSITIVITY WITH CHEM RELATED COMPD. /TETRACYCLINES/|For more Mechanism of Action (Complete) data for TETRACYCLINE (6 total), please visit the HSDB record page.

Eye contact: remove any contact lenses at once. Flush eyes well with copious quantities of water or normal saline for at least 20-30 minutes. ... /Tetracycline hydrochloride/

LONG-TERM THERAPY WITH TETRACYCLINES MAY PRODUCE CHANGES IN PERIPHERAL BLOOD. LEUKOCYTOSIS, ATYPICAL LYMPHOCYTES, TOXIC GRANULATION OF GRANULOCYTES & THROMBOPENIC PURPURA HAVE BEEN OBSERVED. /TETRACYCLINES/|CHILDREN RECEIVING LONG OR SHORT TERM THERAPY WITH A TETRACYCLINE MAY DEVELOP BROWN DISCOLORATIONS OF TEETH. LARGER THE DOSE ... RELATIVE TO BODY WT, MORE INTENSE THE DISCOLORATION OF ENAMEL. DURATION OF THERAPY APPEARS TO BE LESS IMPORTANT THAN TOTAL ... /AMT/ ANTIBIOTIC ADMIN. /TETRACYCLINES/|A case is reported in which a 43- year old man developed intravascular hemolysis with hemoglobinemia, hemoglobinuria, thrombocytopenia, hypofibrinogenemia, and transient renal impairment on at least two occasions after oral use of tetracycline. The patient's serum contained an IgG antibody that reacted only with red cells exposed either in vivo or in vitro to tetracycline.|A case report of a 24-year old man who developed esophageal ulceration after a 7-day treatment of a chest infection with 250 mg tetracycline hydrochloride. /Tetracycline hydrochloride/|For more Human Toxicity Excerpts (Complete) data for TETRACYCLINE (8 total), please visit the HSDB record page.

4 Epitetracycline

ESSENTIALLY 100% AS A BROAD SPECTRUM ANTIBIOTIC (1976)

... TETRACYCLINE HYDROCHLORIDE, USP (ACHROMYCIN, PANMYCIN, STECLIN, SUMYCIN, TETRACHEL, TETRACYN) ... /IS/ AVAIL IN WIDE VARIETY OF FORMS FOR ORAL, TOPICAL & PARENTERAL ADMIN. ... USUAL CONCN OF TETRACYCLINE FOR OPHTHALMIC USE IS 0.5 TO 1%.|Cyclopar 250 & Cyclopar 500: 250 and 500 mg of tetracycline hydrochloride. /Tetracycline hydrochloride/|Achromycin: Ophthalmic suspension sterile contains 10 mg of tetracycline hydrochloride per ml with Plastibage 50W and light mineral oil. /Tetracycline hydrochloride/|Achromycin: Intramuscular solution contains 100 mg/vial of tetracycline hydrochloride, procaine HCl: 40 mg/vial; magnesium chloride: 46.84 mg/vial; ascorbic acid: 250 mg/vial. Sterile tetracycline hydrochloride for injection: 250 mg tetracycline hydrochloride with 625 mg ascorbic acid. /Tetracycline hydrochloride/|For more Formulations/Preparations (Complete) data for TETRACYCLINE (10 total), please visit the HSDB record page.

US PATENTS FOR PREPN & PURIFICATION: 2,699, 054 TO CONOVER (1955); 2,712,517 & 2,886,595 (1955 & 1959 TO BRISTOL LAB); 3,005,023 & 3,019,173 (1961 & 1962 TO AM CYANAMID); 3,301,899 (1967 TO BRYSTOL-MYERS); & 3,053,892 (1962 TO AM CYANAMID).|This review includes a discussion of the structural requirements for biological activity. A section on the total synthesis covers the more important synthetic efforts in the field. The variables in the manufacturing process, ie, choice of strains of microorganism and choice of medium are described as well as the actual fermentation process and subsequent isolation and purification procedures. The elucidation of the biosynthetic mechanism is detailed including the important contributions of the blocked mutant and co-synthesis approach.|The tetracyclines are derivatives of the polycyclic naphthacene-carboxamides and include tetracycline, chlortetracycline, demeclocycline, oxytetracycline, and minocycline.|Various tetracycline formulations provided different degradation patterns after 2 months storage at 50 deg. ... Ointments, due to inhomogeneity of mixing, varied significantly. This was not so with capsules. Syrups, however, were the most unstable formulations; the content decreased rapidly with a corresponding increase in the content of anhydrotetracycline. Of various systems studied, tetracycline was most stable in citrate-borate buffer when no other ingredients were present in the sample. However, when it was formulated as a syrup, phosphate buffer conferred the greatest ... stability. This may be due to other ingredients present in syrup causing instability of tetracycline. Therefore, tetracycline capsules can be formulated in citrate-borate buffer because no other ingredients are present in the capsules.|For more General Manufacturing Information (Complete) data for TETRACYCLINE (6 total), please visit the HSDB record page.

... Tetracycline, oxytetracycline, and chlorotetracycline were analyzed, using an ODS-cartridge extraction device and high performance thin chromatography followed by densitometry. Recoveries of the tetracyclines from fish samples fortified at ppm level were 60.2 to 78.6%.|Tetracycline detection: meat, fish: liquid chromatography|AOAC 988.08. Antimicrobial Drugs in Milk. Microbial Receptor Assay. Scintillation counter. DL for tetracycline = 3 ng/ml. /Antibiotics/

TISSUE; FLUORESCENCE ANALYSIS: KOHN KW, ANAL CHEM (33) 862, 1961.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Veterinary Drug -> ANTIMICROBIAL_AGENT; -> JECFA Functional Classes|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Veterinary Drug -> ANTIMICROBIAL_AGENT;