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564-25-0

564-25-0 structure
564-25-0 structure
  • Name: Doxycycline
  • Chemical Name: doxycycline
  • CAS Number: 564-25-0
  • Molecular Formula: C22H24N2O8
  • Molecular Weight: 444.435
  • Catalog: API Antibiotics Tetracycline
  • Create Date: 2018-05-13 08:00:00
  • Modify Date: 2026-07-23 04:46:49
  • Doxycycline, an antibiotic, is an orally active and broad-spectrum metalloproteinase (MMP) inhibitor[1].
Name doxycycline
Synonyms Monodox
azudoxat
Doxycen
2-naphthacenecboxamide,4-alpha-s-(dimethylamino)-1,4,4a-alpha-5,5a-alpha,6,1
doxiciclina
Doxycycline Base & Hyclate
doxocycline
doryx
2-Naphthacenecboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4,5S,5,6R,12aS)
doxitard
Doxycyclin hyclate
2-Naphthacenecboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo- (6CI, 8CI)
5-hydroxy-alpha-6-deoxytetracycline
Oxytetracycline, 6-deoxy
(2E,4S,5S,5,6R,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione hydrate
doxy-tabs
doxy-caps
investin
Ronaxan
5-Hydroxy-6-deoxytetracycline
5-hydroxy-alpha-6-deoxytetracyclinemonohydrate
liviatin
Unidox
(2Z,4S,4aR,5S,5aR,6R,12aS)-2-[Amino(hydroxy)methylene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
spanor
Doxivetin
Doxycycline Hydrochloride Hemiethanolat
10,12,12a-pentahydroxy-6-methyl,1,11-dioxo-,(45-(4alpha,4aalpha,5alpha,5aalpha
6-deoxy-oxytetracyclin
vibramycin
(4S,4,5S,5,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-cboxamide
Doxycycline (base and/or unspecified salts)
MFCD02682958
Doxycycline,Doxitd,Gibidox,Liomycin
6alpha,12aalpha))
alpha-doxycycline
4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-(dimethylamino)-4
doxy-puren
doxitd
2-Naphthacenecboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, [4S-(4α,4aα,5α,5aα,6α,12aα)]
alpha-6-deoxyoxytetracycline
methyl-1,11-dioxo-2-naphthacenecboxamidemonohydrate
DOXCYCLINEANHYDROUS
vibravenos
EINECS 209-271-1
(4S,4,5S,5,6R,12aS)- 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro -3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecboxamide Hyclate
6-alpha-deoxy-5-oxytetracycline
DOXYCYCLINE,ANHYDROUS
1,12a-octahydro-3,5-alpha,10,12,12a-alpha-pentahydroxy-6-alpha-methyl-1,11-dio
6-deoxy-5-hydroxytetracycline
alpha-6-tetracyclinemonohydrate
alpha-6-deoxyoxytetracyclinemonohydrate
doxytetracycline
gs-3065
(2Z,4S,4aR,5S,5aR,6R,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
(2Z,4S,4aR,5S,5aR,6R,12aS)-2-[Amino(hydroxy)methylene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-4a,5a,6,12a-tetrahydro-1,3,12(2H,4H,5H)-tetracenetrione
(4S,4,5S,5,6R,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecboxamide
DOXYCYCLINE, ANHYDROUS
Tolexine
4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecboxamide
6- Deoxy-5-hydroxytetracycline, 6-Deoxyoxytetracycline, Doxytetracycline, GS 3065, HydraMycin, MedeoMycin, VibraMycin
DoxycyclineBp93
6-Deoxyoxytetracycline
Deoxymykoin
Doxinyl
6-deoxytetracycline
Description Doxycycline, an antibiotic, is an orally active and broad-spectrum metalloproteinase (MMP) inhibitor[1].
Related Catalog
In Vitro Doxycycline affects growth of glioma cells only under high concentrations[2]. Doxycycline decreases MT-CO1 protein content with concentrations of 1 µg/mL and higher in SVG cells[2]. Cell Proliferation Assay[2] Cell Line: LNT-229, G55, and U343 glioma cells Concentration: 0.01, 0.1, 1, or 10 µg/mL Incubation Time: 4 days Result: Affected growth of glioma cells only under high concentrations. Western Blot Analysis[2] Cell Line: SVG cells Concentration: 0.01, 0.1, 1, or 10 µg/mL Incubation Time: 24 hours Result: Decreaseed MT-CO1 protein content with concentrations of 1 µg/mL and higher.
In Vivo Doxycycline (oral; 200 or 800 mg/kg/day; for 3 months) reduces active MMP-9 in untreated HT mice in a dose-dependent manner[1]. Animal Model: 6-month-old female Heterozygous Col3a1-deficient (HT) mice[1] Dosage: 200 or 800 mg/kg Administration: Oral; per day; for 3 months Result: Reduced active MMP-9 in a dose-dependent manner.
References

[1]. Briest W, et al. Doxycycline ameliorates the susceptibility to aortic lesions in a mouse model for the vascular type of Ehlers-Danlos syndrome. J Pharmacol Exp Ther. 2011 Jun;337(3):621-7.

[2]. Luger AL, et al. Doxycycline Impairs Mitochondrial Function and Protects Human Glioma Cells from Hypoxia-Induced Cell Death: Implications of Using Tet-Inducible Systems. Int J Mol Sci. 2018 May 17;19(5).
Density 1.6±0.1 g/cm3
Boiling Point 685.2±55.0 °C at 760 mmHg
Melting Point 206-209ºC
Molecular Formula C22H24N2O8
Molecular Weight 444.435
Flash Point 368.2±31.5 °C
Exact Mass 444.153259
PSA 181.62000
LogP 1.36
Vapour Pressure 0.0±2.2 mmHg at 25°C
Index of Refraction 1.737
Storage condition 2-8C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QI8650000
CHEMICAL NAME :
2-Naphthacenecarboxamide, 4-alpha-S-(dimethylamino)-1,4,4a-alpha-5,5a-alpha,6,1 1,12a- octahydro-3,5-alpha,10,12,12a-alpha-pentahydroxy-6-al pha-methyl-1,11-dioxo-
CAS REGISTRY NUMBER :
564-25-0
LAST UPDATED :
199609
DATA ITEMS CITED :
15
MOLECULAR FORMULA :
C22-H24-N2-O8
MOLECULAR WEIGHT :
444.48
WISWESSER LINE NOTATION :
L E6 C666 BV FV CU GUTTT&J DQ GVZ HQ IN1&1 KQ MQ M1 RQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
68 mg/kg/24D-I
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
378 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
228 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1870 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
410 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
241 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
750 mg/kg
SEX/DURATION :
female 2 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
3750 ug/L
REFERENCE :
BCPHBM British Journal of Clinical Pharmacology. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1974- Volume(issue)/page/year: 16,127,1983 *** REVIEWS *** TOXICOLOGY REVIEW PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 2,305,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84744 No. of Facilities: 641 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 1281 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84744 No. of Facilities: 450 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 22055 (estimated) No. of Female Employees: 18813 (estimated)
HS Code 3004909090
HS Code 3004909090
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