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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C22H24N2O8.C2H6O.2ClH.H2O
Molecular Weight 1025.875
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXYCYCLINE HYCLATE

SMILES

O.Cl.Cl.CCO.[H][C@@]12[C@@H](C)C3=CC=CC(O)=C3C(=O)C1=C(O)[C@]4(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]4([H])[C@H]2O.[H][C@@]56[C@@H](C)C7=CC=CC(O)=C7C(=O)C5=C(O)[C@]8(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]8([H])[C@H]6O

InChI

InChIKey=HALQELOKLVRWRI-VDBOFHIQSA-N
InChI=1S/2C22H24N2O8.C2H6O.2ClH.H2O/c2*1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29;1-2-3;;;/h2*4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);3H,2H2,1H3;2*1H;1H2/t2*7-,10+,14+,15-,17-,22-;;;;/m00..../s1

HIDE SMILES / InChI

Molecular Formula C22H24N2O8
Molecular Weight 444.4346
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C2H6O
Molecular Weight 46.0684
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Doxycycline hyclate (Vibramycin, Periostat, Vibra-Tabs) is salt of tetracycline antibiotic Doxycycline, that used to treat many kinds of infections, like dental, skin, respiratory, and urinary tract infections. It also treats acne, Lyme disease, malaria, and certain sexually transmitted diseases. Doxycycline hyclate is a light-yellow crystalline powder which is soluble in water, while doxycycline monohydrate is very slightly soluble in water. Doxycycline is bacteriostatic, inhibiting bacterial protein synthesis due to disruption of transfer RNA and messenger RNA at ribosomal sites. Doxycycline hyclate is indicated for use in the treatment of chronic adult periodontitis for a gain in clinical attachment, reduction in probing depth, and reduction in bleeding on probing.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
VIBRAMYCIN
Curative
VIBRAMYCIN
Primary
VIBRAMYCIN
Curative
VIBRAMYCIN
Curative
VIBRAMYCIN
Curative
Periostat
Curative
VIBRAMYCIN
Curative
VIBRAMYCIN

Cmax

ValueDoseCo-administeredAnalytePopulation
3.17 μg/mL
200 mg 1 times / day multiple, oral
DOXYCYCLINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
32 μg × h/mL
200 mg 1 times / day multiple, oral
DOXYCYCLINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10.5 h
200 mg 1 times / day multiple, oral
DOXYCYCLINE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
The usual dose of oral doxycycline is 200 mg on the first day of treatment (administered 100 mg every 12 hours) followed by a maintenance dose of 100 mg/day. In the management of more severe infections (particularly chronic infections of the urinary tract), 100 mg every 12 hours is recommended.
Route of Administration: Oral
In Vitro Use Guide
PC3 cells were incubated with LPS (0.5 μg/mL) for 24 h in the presence or absence of doxycycline (5 μg/mL). The effects of LPS and doxycycline on the expressions of MMP-2, MMP-8, MMP-9, MMP-10, NF-κB/p65, IκB-α, p-IκB-α, IKK-β were examined by Western blotting and immunohistochemistry in PC3 cells. LPS increased expression and activity of MMP-9 and expression of MMP-8, MMP-10, NF-κB /p65, p-IκB-α, IKK-β and doxycycline down-regulated its effects with the exception of MMP-10 expression.
Substance Class Chemical
Record UNII
19XTS3T51U
Record Status Validated (UNII)
Record Version