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Demeclocycline

CAT: 0804-HY-121268-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-121268-01Size:5 mg
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Description
Demeclocycline is an orally active tetracycline antibiotic. Demeclocycline impairs protein synthesis by binding to the 30S ribosomal subunit to inhibit binding of aminoacyl tRNA. Demeclocycline shows anti-bacterial activitise to a wide variety of bacterial infections[1][2].
CAS Number
127-33-3
UNSPSC
12352005
Target
Antibiotic; Bacterial
Type
Reference compound
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/demeclocycline.html
Purity
98.0
Solubility
DMSO : 25 mg/mL (ultrasonic) |H2O : 40 mg/mL (ultrasonic)
Smiles
O=C(C(C1=O)=C(O)[C@@H](N(C)C)[C@]2([H])C[C@]3([H])[C@H](O)C4=C(C(C3=C(O)[C@@]21O)=O)C(O)=CC=C4Cl)N
Molecular Formula
C21H21ClN2O8
Molecular Weight
464.85
References & Citations
[1]I Chopra, et al. Tetracyclines, molecular and clinical aspects. J Antimicrob Chemother. 1992 Mar;29 (3) :245-77.|[2]D Schnappinger, et al. Tetracyclines: antibiotic action, uptake, and resistance mechanisms. Arch Microbiol. 1996 Jun;165 (6) :359-69.|[3]Marleen L A Kortenoeven, et al. Demeclocycline attenuates hyponatremia by reducing aquaporin-2 expression in the renal inner medulla. Am J Physiol Renal Physiol. 2013 Dec 15;305 (12) :F1705-18.|[4]Susobhan Sarkar, et al. Demeclocycline Reduces the Growth of Human Brain Tumor-Initiating Cells: Direct Activity and Through Monocytes. Front Immunol. 2020 Feb 21;11:272.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
Tetracycline
Citation 01
J Hazard Mater Adv. 2025 Nov 12;20:100939.|J Photoch Photobio A. 2020 May. |Chemosphere. 2019 Jun:225:378-387.|Mol Syst Biol. 2022 Sep;18 (9) :e11081.|Patent. US20230014181.

Chemical Information

Demeclocycline

Demeclocycline is tetracycline which lacks the methyl substituent at position 7 and in which the hydrogen para- to the phenolic hydroxy group is substituted by chlorine. Like tetracycline, it is an antibiotic, but being excreted more slowly, effective blood levels are maintained for longer. It is used (mainly as the hydrochloride) for the treatment of Lyme disease, acne and bronchitis, as well as for hyponatraemia (low blood sodium concentration) due to the syndrome of inappropriate antidiuretic hormone (SIADH) where fluid restriction alone has been ineffective. It has a role as a geroprotector, an aquaretic and an antibacterial drug.

CAS Number127-33-3
PubChem CID54680690
IUPAC Name(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
Molecular FormulaC21H21ClN2O8
Molecular Weight464.9
XLogP0.7
Topological Polar Surface Area182
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count2
Heavy Atom Count32
Formal Charge0
Complexity961
SMILES
CN(C)[C@H]1[C@@H]2C[C@@H]3[C@@H](C4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O
InChI
InChI=1S/C21H21ClN2O8/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31/h3-4,6-7,14-15,25-27,30,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1
InChIKey
GUXHBMASAHGULD-SEYHBJAFSA-N
Chemical Structure
2D Structure
2D structure of Demeclocycline
CAS: 127-33-3
CID: 54680690
Formula: C21H21ClN2O8
MW: 464.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight464.9
XLogP30.7
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count2
Exact Mass464.0986433
Monoisotopic Mass464.0986433
Topological Polar Surface Area182 Ų
Heavy Atom Count32
Formal Charge0
Complexity961
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BA1062-10Demeclocycline
007918Demeclocycline Hydrochloride
MBS3840270-01Demeclocycline HCl
TRC-C230725-25MGDemeclocycline Oxide

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