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24390-14-5

24390-14-5 Structure

24390-14-5 Structure
IdentificationBack Directory
[Name]

Doxycycline hyclate
[CAS]

24390-14-5
[Synonyms]

WC2031
DoxycycL
ine hycL
Doxycycline API
Doxycycline Hc1
oxycyclinehyclate
Doxycycline hyclate
DOXYCYCLINE HYDRATE
DoxycyclineHyclate>
Doxycycline hyclate, BP
Doxycline Hydrochloride
Doxycycline hyclate CRS
Doxycycline hyclate COS
Doxycycline Hyclate/HCL
Doxycycline Hyclate USP
Doxycycline Hydrochlocide
Doxycycline hyclate, ≥98%
Doxycycline hyclate, ≥94%
Doxycycline Hydrochloride?I
Doxycycline hyclate USP/EP/BP
Doxycycline Hyclate (200 mg)
DOXYCYCLINE HYCLATE USP GRADE
DOXYCYCLINE HYCLATE, =98% (HPLC)
Doxycycline Hyclate / Monohydrate
Doxycycline for system suitability
Doxycycline Hyclate Soluble Powder
DOXYCYCLINE HYDROCHLORIDE, VETRANAL
Doxycycline hyclate Solution, 100ppm
Doxycycline for system suitability CRS
Hydrochloride hemiethanolate hemihydrate
Doxycycline hydrochloride hemiethanolate
Doxycycline monohydrate BP2000/Ph Eur 4/USP25
Doxycycline Hyclate (200 mg)J0E174859ug/mg(ai)
Doxycycline HCl DISCONTINUED Replaced by D5897
Doxycycline, Hyclate - CAS 24390-14-5 - Calbiochem
Doxycycline hydrochloride hemiethanolate hemihydrate, Antibiotic for Culture Media Use Only
4-(Dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydr
4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-2-NA
(4S,4aR,5S,5aR,6R,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro -3,5,10,12,12a-pentahydroxy-6-Methyl-1,11-dioxo-
4-(DIMETHYLAMINO)-1,4,4 ALPHA,5,5 ALPHA,6,11,12 ALPHA-OCTAHYDRO-3,5,10,12,12 ALPHA-PENTAHYDROXY-6-METHYL-1,11-DIOXO-2-NAPHTHACENECARBOXAMIDE, MONOHYDRATE
(2E,4S,4aR,5S,5aR,6R,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione
(4S,4aR,5S,5aR,6R,12aS)-4-(Dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamidehydrochloride
2-(Amino-hydroxy-methylidene)-4-dimethylamino-5,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione hydrochloride hemiethanolate
(4S,4aR,5S,5aR,6R,12aS)-4-(Dimethylamino)- 3,5,10,12,12a-pentahydroxy- 6-methyl- 1,11-dioxo- 1,4,4a,5,5a,6,11,12a-octahydrotetracene- 2-carboxamide hydrochloride hemiethanolate hemihydrate
(4S,4aR,5S,5aR,6R,12aS)-4-(Dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide compound with ethanol (2:1) dihydrochloride hydrate
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, hydrochloride, (4S,4aR,5S,5aR,6R,12aS)-, compd. with ethanol, hydrate (2:2:1:1)
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, monohydrochloride, (4S,4aR,5S,5aR,6R,12aS)-, compd. with ethanol (2:1), monohydrate
[EINECS(EC#)]

2017-001-1
[Molecular Formula]

C22H26N2O9
[MDL Number]

MFCD02682958
[MOL File]

24390-14-5.mol
[Molecular Weight]

462.45
Chemical PropertiesBack Directory
[Melting point ]

206-209?C (dec.)
[alpha ]

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

QI8925000
[storage temp. ]

Store at +4°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
[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 DataBack Directory
[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)
Hazard InformationBack Directory
[Description]

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]

Yellow Solid
[Uses]

Tetracycline antibacterial.
[Uses]

tetracycline antibiotics group
[Application]

Doxycycline hyclate has been used for the induction of glioma cells and human embryonic kidney 293T cells (HEK293T).
Doxycycline hyclate is a synthetic oxytetracycline derivative. 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.
[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.
[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.
[Biological Activity]

Broad spectrum antibiotic and bacteriostatic. Shows antiprotozoal properties. Potent inhibitor of MMPs (matrix metalloproteinases) in vivo. Inhibits collagen synthesis. Increases and promotes smooth muscle cell adhesion. Inhibits proliferation and migration. Protects microvasculature by inhibiting plasminogen systems.
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

Doxycycline hyclate(24390-14-5)1HNMR
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