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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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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)
The IFITM proteins inhibit HIV-1 infection.
Lu J, et al.
Journal of Virology, 85, 2126-2137 (2011)
Yeast Hmt1 catalyses asymmetric dimethylation of histone H3 arginine 2 in vitro.
Li HT, et al.
The Biochemical Journal, 467, 507-515 (2015)
I Chopra et al.
Microbiology and molecular biology reviews : MMBR, 65(2), 232-60 (2001-05-31)
Tetracyclines were discovered in the 1940s and exhibited activity against a wide range of microorganisms including gram-positive and gram-negative bacteria, chlamydiae, mycoplasmas, rickettsiae, and protozoan parasites. They are inexpensive antibiotics, which have been used extensively in the prophlylaxis and therapy
Uninterpretable cerebrospinal fluid absorbance scan caused by doxycycline therapy.
Jan Miller
Annals of clinical biochemistry, 56(5), 619-622 (2019-06-07)

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