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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 is an antibacterial drug synthetically derived from oxytetracycline and used to treat a wide variety of bacterial infections, including those that cause acne. Doxycycline is used for bacterial pneumonia, acne, chlamydia infections, early Lyme disease, cholera, and syphilis. It is also useful for the treatment of malaria when used with quinine and for the prevention of malaria. Common side effects include diarrhea, nausea, vomiting, a red rash, and an increased risk of a sunburn. If used during pregnancy or in young children may result in permanent problems with the teeth including changes in their color. Its use during breastfeeding is probably safe. Like other tetracycline antibiotics, Doxycycline is protein synthesis inhibitors, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex by binding to the 30S ribosomal subunit in the mRNA translation complex.

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

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Periostat (Doxycycline hyclate) 20 mg twice daily as an adjunct following scaling and root planing may be administered for up to 9 TM months. Safety beyond 12 months and efficacy beyond 9 months have not been established. Periostat should be administered at least one hour prior to morning and evening meals
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