Doxycycline hyclate Chemical Properties

Melting point:

206-209?C (dec.)

alpha 

D25 -110° (c = 1 in 0.01N methanolic HCl)

RTECS 

QI8925000

storage temp. 

2-8°C

solubility 

H2O: soluble50mg/mL

form 

Yellow to yellow-green crystalline solid

color 

yellow to greenish-yellow

Water Solubility 

Soluble in water to 50mg/ml. May require warming.Soluble in water, methanol. Sparingly soluble in ethanol. Insoluble in chloroform and ether.

Merck 

14,3440

BRN 

5702728

InChI

InChI=1/C22H24N2O8.C2H6O.ClH/c1-7-8-5-4-6-9(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;/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);3H,2H2,1H3;1H/t7-,10+,14+,15-,17-,22-;;/s3

InChIKey

HALQELOKLVRWRI-VDBOFHIQSA-N

SMILES

C(O)C.O[C@@]12C(C(C(=O)N)=C(O)[C@@H](N(C)C)[C@]1([H])[C@H]([C@]1([H])[C@H](C3C=CC=C(O)C=3C(=O)C1=C2O)C)O)=O.Cl |&1:4,12,16,18,19,21,r|

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29413000

Toxicity

LD50 i.p. in rats: 262 mg/kg (Goldenthal)

Doxycycline hyclate Usage And Synthesis

Description

Doxycycline Hyclate is the hyclate salt form of doxycycline, is a broad-spectrum tetracycline antibiotic. It inhibits bacterial protein synthesis by binding to ribosomes. Doxycycline also selectively inhibits human matrix metalloproteinase-8 (MMP-8) and MMP-13 over MMP-1 with 50, 60, and 5% inhibition, respectively, when used at a concentration of 30 μM. It can be used as a regulator for inducible gene expression systems where expression depends on either the presence (Tet-On) or absence (Tet-Off) of doxycycline. Formulations containing doxycycline have been used in the treatment of bacterial infections and the prevention of malaria.

Chemical Properties

Doxycycline hyclate is a yellow, hygroscopic crystalline powder, freely soluble in water and in methanol, sparingly soluble in ethanol (96 per cent), it dissolves in solutions of alkali hydroxides and carbonates.

Uses

Doxycycline hyclate is a member of the tetracycline antibiotics group, and is commonly used to treat a variety of infections. It is used in the treatment of chlamydia, rickettsia, mycoplasma and some spirochete infections. It is also used to inhibit matrix metalloproteinases at subantimicrobial doses. Inhibits matrix metalloproteinases at subantimicrobial doses.

Definition

ChEBI: The hemiethanolate hemihydrate of doxycycline hydrochloride. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chroni obstructive pulmonary disease (COPD), and adult periodontitis.

Application

Doxycycline hyclate is a synthetic oxytetracycline derivative with similar antimicrobial activity. It has been used to eliminate Borrelia burgdorferi and Anaplasma phagocytophilum in rodent reservoirs and to eliminate Ixodes scapularis ticks. It is a broad spectrum inhibitor used to inhibit matrix metalloproteinases(MMP), such as type 1 collagenase in studies on wound healing and tissue remodeling. Doxycycline hyclate has also been used for the induction of glioma cells and human embryonic kidney 293T cells (HEK293T).

brand name

Atridox (QLT); Doryx (Faulding); Doryx (Warner Chilcott); Doxy (Abraxis); Doxychel Hyclate (Rachelle); Periostat (CollaGenex); Vibramycin (Pfizer);Abadox;Bassado;Bio-tab;Clisemina;Cloran;Cyclidox;Diocimex;Docostyl;Dosil;Dotur;Doxatet;Doxi sergo;Doxicento;Doxifin;Doxilen;Doximycin;Doxiten bio;Doxivis;Doxy-100;Doxy-basan;Doxybiocin;Doxycyl;Doxy-diolan;Doxydyn;Doxyfim;Doxygram;Doxylag;Doxylan;Doxylar;Doxylets;Doxymycin;Doxy-p;Doxytem;Doxy-wolff;Dumoxin;Duradoxal;Esadoxi;Farmodoxi;Ghimadox;Gram-val;Granudoxy;Helvedoclyn;Icladox;Miraclin;Monocline;Monodoxin;Novelciclina;Philcociclina;Roxyne;Semelciclina;Sigadoxin;Solupen;Stamicina;Supracyclin;Tetrasan;Unacil;Vibracina;Vibramicina;Vibramycin hyclate;Vibraveineuse;Vibravenosa;Ximicina;Zadorin.

World Health Organization (WHO)

Doxycycline, a semi-synthetic tetracycline derivative, was first introduced into medicine in 1960 for the treatment of bacterial, rickettsial and amoebic infections. Although allergic manifestations are uncommon, injectable preparations have occasionally resulted in severe anaphylactoid reactions. Clinical features and the fact that asthmatic patients seemed to be particularly at risk lead to suspect a sulfite preservative in the formulation more than doxycycline itself. Rapid administration may also be a factor. Injectable preparations of doxycycline hyclate are included in the WHO Model List of Essential Drugs.

General Description

Doxycycline hyclate belongs to the second generation of tetracycline antibiotics family. Doxycycline hyclate shows minimal side effects upon usage. It is effective for the treatment of recurrent aphthous stomatitis (RAS) and promotes speedy recovery.

Biochem/physiol Actions

Doxycycline hyclate inhibits the inflammatory response to the Lyme Disease Spirochete Borrelia burgdorferi. It is a broad spectrum inhibitor of matrix metalloproteinases in vivo.

storage

+4°C

Mode of action

Tetracycline antimicrobials bind to the bacterial 30S ribosomal subunit interfering with tRNA/mRNA interaction, ultimately inhibiting protein synthesis. Tetracyclines can inhibit the MMP enzyme family and inhibit mitochondrial biogenesis.

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