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Key Documents

D1822

Sigma-Aldrich

Doxycycline monohydrate

Synonym(s):

6-Deoxy-5-oxytetracycline monohydrate, Doxycycline

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About This Item

Empirical Formula (Hill Notation):
C22H24N2O8 · H2O
CAS Number:
Molecular Weight:
462.45
MDL number:
UNSPSC Code:
51284030
PubChem Substance ID:
NACRES:
NA.85

form

powder or crystals

Quality Level

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycoplasma
parasites

Mode of action

protein synthesis | interferes

storage temp.

−20°C

SMILES string

O.C[C@@H]1[C@H]2[C@H](O)[C@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C2C(=O)c4c(O)cccc14

InChI

1S/C22H24N2O8.H2O/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;/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);1H2/t7-,10+,14+,15-,17-,22-;/m0./s1

InChI key

XQTWDDCIUJNLTR-CVHRZJFOSA-N

Gene Information

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Application

  • In yeast cells, doxycycline has been used in doxycycline-inducible system for overexpression of methyltransferase Hmt1 (hnRNP methyltransferase 1).
  • It has been used in the doxycycline-inducible IFITM (interferon-induced transmembrane) cell lines.
  • It has also been used as an antimicrobial agent.

Biochem/physiol Actions

Doxycycline is a semisynthetic tetracycline that is active against bacteria, mycoplasma and protozoan parasites. It inhibits the bacterial protein synthesis by inhibiting the interaction of aminoacyl-tRNA and the bacterial ribosome.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The IFITM proteins inhibit HIV-1 infection.
Lu J, et al.
Journal of Virology, 85, 2126-2137 (2011)
In vitro antimicrobial susceptibility testing of bacterial enteropathogens causing traveler's diarrhea in four geographic regions.
Gomi H, et al.
Antimicrobial Agents and Chemotherapy, 45, 212-216 (2001)
Uninterpretable cerebrospinal fluid absorbance scan caused by doxycycline therapy.
Jan Miller
Annals of clinical biochemistry, 56(5), 619-622 (2019-06-07)
Andi Dian Permana et al.
Pharmaceutics, 11(7) (2019-07-20)
Conventional oral administration of antifilariasis drugs results in nonspecific targeting of the drugs and the intradermal delivery of nanoparticles with sizes of <100 nm could be used to improve lymphatic uptake. This study investigated the combination of nanosuspension and dissolving
Yeast Hmt1 catalyses asymmetric dimethylation of histone H3 arginine 2 in vitro.
Li HT, et al.
The Biochemical Journal, 467, 507-515 (2015)

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