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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H24N2O8
Molecular Weight 444.4346
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRACYCLINE

SMILES

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

InChI

InChIKey=OFVLGDICTFRJMM-WESIUVDSSA-N
InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H24N2O8
Molecular Weight 444.4346
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

Discovered as natural products from actinomycetes soil bacteria, the tetracyclines were first reported in the scientific literature in 1948. They were noted for their broad spectrum antibacterial activity and were commercialized with clinical success beginning in the late 1940s to the early 1950s. By catalytic hydrogenation of Aureomycin, using palladium metal and hydrogen, the C7 deschloro derivative was synthesized, producing a compound of higher potency, a better solubility profile, and favorable pharmacological activity; it was subsequently named tetracycline. Tetracyclines are primarily bacteriostatic and exert their antimicrobial effect by the inhibition of protein synthesis by binding to the 30S ribosomal subunit. Tetracycline is active against a broad range of gram-negative and gram-positive organisms. Tetracycline is indicated in the treatment of infections caused by susceptible strains. To reduce the development of drug-resistant bacteria and maintain the effectiveness of tetracycline hydrochloride and other antibacterial drugs, tetracycline hydrochloride should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TETRACYCLINE HYDROCHLORIDE

Cmax

ValueDoseCo-administeredAnalytePopulation
2.5 μg/mL
300 mg single, oral
TETRACYCLINE plasma
Homo sapiens
2.6 μg/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
2.7 μg/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
2 μg/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
4.1 μg/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
4.5 μg/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
4.5 μg/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
26.91 μg × h/mL
300 mg single, oral
TETRACYCLINE plasma
Homo sapiens
27.27 μg × h/mL
300 mg 2 times / day steady-state, oral
TETRACYCLINE plasma
Homo sapiens
27 μg × h/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
31.7 μg × h/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
25.5 μg × h/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
74.7 μg × h/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
55.7 μg × h/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
56.6 μg × h/mL
500 mg single, oral
TETRACYCLINE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.85 h
300 mg single, oral
TETRACYCLINE plasma
Homo sapiens
5.6 h
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
6.2 h
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
7.2 h
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
8.1 h
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
6.7 h
500 mg single, oral
TETRACYCLINE serum
Homo sapiens
6.1 h
500 mg single, oral
TETRACYCLINE serum
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
TETRACYCLINE HYDROCHLORIDE - tetracycline hydrochloride capsule Adults: Usual daily dose, 1 gram as 500 mg twice a day or 250 mg four times a day. Higher doses such as 500 mg four times a day may be required for severe infections or for those infections which do not respond to the smaller doses. For pediatric patients above eight years of age: Usual daily dose, 10 mg/lb to 20 mg/lb (25mg/kg to 50 mg/kg) body weight divided in four equal doses. TETRACYCLINE VISION 10 mg/g eye ointment Adults and children: depending on the severity of condition, a strip of the eye ointment with length of 1 – 1.5 cm is inserted into the conjunctival fold of the lower eyelid 3 - 4 times daily and in more severe cases, up to 6 times daily.
Route of Administration: Other
In Vitro Use Guide
Standard tetracycline powders should provide the following range of Minimal Inhibitory Concentration values: Enterococcus faecalis ATCC 29212 8 - 32 mcg/mL Escherichia coli ATCC 25922 0.5 - 2 mcg/mL Haemophilus influenzae ATCC 49247 4 - 32 mcg/mL Mycoplasma pneumoniae ATCC 29342 0.06-0.5 mcg/mL Staphylococcus aureus ATCC 29213 0.12 - 1 mcg/mL Streptococcus pneumoniae ATCC 49619 0.06 - 0.5 mcg/mL
Substance Class Chemical
Record UNII
F8VB5M810T
Record Status Validated (UNII)
Record Version